Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🗣 Stop Self-Editing Before You Even Start

I’m a big fan of dictation, and here’s why: when you dictate something, you speak a lot more freely.

You talk about what’s top of mind immediately. But when you type? You start to self-edit. You take your thoughts and run them through another medium—text—and simplify before you even get your full ideas out.

I use Wispr Flow to dictate my ideas freely, then use its built-in polish function to help organize and edit my message into something that’s publish-ready in minutes.

I use it for:

• Slack messages to my team

• First drafts of emails

• Brainstorming and dictating content ideas

• Polishing raw thoughts into structured lists

👉 Give Wispr Flow a try and stop self-editing before your ideas even make it out.

Try Wispr Flow Free

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🗓 What Does Month 3️⃣ as a New Chief of Staff REALLY Look Like?

This issue is guest authored by Claire Podulka, a strategic executive with 20+ years of experience across tech, education, and consulting. She is currently the Chief of Staff at Crisis Prevention Institute, the global leader in crisis prevention and de-escalation training. Previously, she spent nearly a decade at TXI, a boutique digital product consultancy. She writes and speaks on topics at the intersection of culture, operations, and strategy, with a particular focus on prioritization, both organizational and personal.

Just after my first board meeting, I hit 9️⃣ 0️⃣ days in my new Chief of Staff role.

And I had done a lot.

I had helped establish a much cleaner executive operating rhythm. We had moved from a collection of departmental roadmaps toward one cohesive organizational strategy and gone into the board meeting aligned around it. Our new global Town Halls were starting to feel less like an experiment and more like standard operating procedure. I had met and started building relationships with not just the executive team but most of our senior leaders and other influential staff members. I knew who did what, where some of the friction lived, and who I could call when I needed to understand something quickly.

📨 So I sat down to continue my new favorite personal ritual: every 90 days, I write and schedule-send an email to my future self.

And in that email, I admitted something I was almost embarrassed to think:

Is there going to be enough for me to do here long-term? 👀

(Hubris? General idiocy? Not sure. All I can say is, it felt true on that train ride home from the board meeting.)

By the time that email arrived in my inbox 90 days later, I was up to my eyeballs in entirely new problems.

I had made the classic mistake of getting to the top of a hill and assuming I had reached the top of the hill.

What I couldn’t see yet was the mountain range beyond it. ⛰

🔮 Day 90 Gives You Perspective, Not Omniscience

Clara frames days 61–90 as the point when a Chief of Staff begins driving strategic impact: launching high-impact projects, refining operating systems, and thinking beyond the initial onboarding period. That framing is right.

But there’s another shift happening around the same time.

🖼️ You finally have enough dots to start drawing meaningful lines between them and seeing pictures emerge.

In your first month, you’re gathering information: this team owns this, that leader cares deeply about that, these two functions have some friction, this process seems harder than it should be.

By 90 days, patterns start emerging.

You see that two issues you thought were unrelated actually have the same root cause. You notice the same dynamic showing up in three different meetings. You start understanding not just the org chart, but the informal organization underneath it: who trusts whom, where information flows easily, where it gets stuck, and which habits are reinforcing the outcomes everyone says they want to change.

One pattern I began to understand more deeply was the extent of our organizational silos.

I knew when I joined that functions had historically operated fairly independently. What took longer to understand was how much that history had shaped individual behaviors and relationships. Reaching across organizational boundaries, inviting someone into a conversation, sharing work in progress — behaviors that had felt routine in environments I’d worked in before — didn’t always feel routine here.

🌐 That wasn’t something I could have diagnosed in my first two weeks. I needed enough individual data points to recognize it as a system.

But recognizing a pattern does not mean immediately launching a project to fix it.

That’s another trap.

❌ The question isn’t, “What problems can I see now?”

✅ It’s, “Which of these patterns will most get in the way of where we’re trying to go?”

🎯 Or, just as importantly: “Which positive pattern, if we reinforce it, could help us get there faster?”

🧑‍🏫 THEORY: By 90 days, you understand the organization well enough to act strategically.

💡 REALITY: By 90 days, you understand the organization well enough to start recognizing the patterns that matter. You still need to connect those patterns to priorities before you act.

🎯 Strategic Impact Isn’t Enough. Aim for Sustainable Impact

At 90 days, I also had a review conversation with my CEO.

The good news was most of the feedback was positive. I was making progress on the priorities we’d agreed to, I had earned her trust relatively quickly, and she was comfortable giving me significant independence.

She also gave me feedback I needed to hear. 🙏

I needed to have more empathy for people who had been in the organization longer than I had. I needed, sometimes, to slow down. Soften my tone. Spend more time bringing people along.

Some of the same qualities that had helped me get traction quickly — urgency, clarity, a willingness to question established practices — could also work against me if I didn’t calibrate them.

From my vantage point as a newcomer, some changes felt obviously necessary and positive.

But organizations are made of humans with nervous systems, and most humans do not experience change as a tidy logic problem.

Existing ways of working may represent familiarity, expertise, status, safety, identity, or relationships built over years. Even people who agree intellectually that something needs to change may have an emotional response when it actually does.

That helped evolve how I thought about impact.

Strategic impact matters. But sustainable impact matters more. 🎯

And no impact is sustainable if you ignore the people who actually have to make it happen.

They need context. They need time. They need support. Sometimes they need space to be frustrated about a change even when you remain convinced that the change itself is right. This is something I’m still working on, even though I’m nearly a year in now, because this process is gradual and non-linear.

Clara recommends using the end of the 90-day period to reflect honestly on feedback, what worked, and how you want to grow in the role. Mine gave me a pretty clear developmental assignment: don’t lose the urgency, but get better at bringing people with you.

🧑‍🏫 THEORY: By day 90, prove that you can drive strategic impact.

💡 REALITY: The next level is learning how to make that impact sustainable. Good execution gets something done. Sustainable execution helps the organization absorb it.

🏆 Some of Your Biggest Wins Won’t Look Like Wins Yet

If you asked me to name my single biggest accomplishment from my first 90 days, I’m not sure I could.

There were certainly tangible ones. Documented KPIs and quarterly roadmaps. A successful board meeting. Steering committees having their first meetings to guide our strategic initiatives. All good and necessary things.

But the things I’m most grateful for from that period are harder to put on a 90-day scorecard.

🤝 I had begun building relationships that would support me for months afterward.

🤝 I knew more of “my people” — the people I could call for context, a candid read, history, or help getting something unstuck.

Some of my early reads would turn out to be wrong, of course. People I didn’t immediately click with became trusted partners once we had more time together. Others I thought I understood early on turned out to be more complicated.

That’s part of the point.

At 90 days, your network is becoming useful. It is not finished.

And I had built enough trust with my Principal that she was comfortable letting me handle a lot independently. That trust would make much of the work that came next possible.

🧑‍🏫 THEORY: By 90 days, you should be able to point to 1–2 high-impact wins.

💡 REALITY: Do that if you can. But don’t underestimate the infrastructure you’re building underneath the visible work: trust, relationships, judgment, credibility, and a network that helps you understand and move the organization.

🏞️ The Landscape is Changing While You’re Learning It

There’s one more problem with treating the first 90 days as a neat onboarding period: your organization does not politely stand still while you learn it.

Mine certainly didn’t.

I joined during a period of significant transformation. New leaders were joining. Priorities were shifting. Work that looked like mine in January belonged somewhere else by spring.

At one point I was leading one of our three largest strategic initiatives, focused on go-to-market metrics. As we hired new commercial leaders, the right thing to do was hand that work to them.

Meanwhile, another major initiative around product innovation became larger than anticipated. Our Senior Project Manager needed to focus almost entirely on stewarding that work, so I stepped into project management on a third strategic initiative focused on streamlining our ordering process.

None of that was in my original 90-day plan.

It wasn’t “more of the same,” either.

The landscape had changed.

This has continued throughout my tenure. New leaders begin their own first 90 days. A new tool or process changes how teams work. Someone leaves and responsibilities get reshuffled.

💡 One example: during my first 90 days, I built a useful working rhythm with our data governance lead. Then business needs changed and his priorities had to shift. The cadence we had carefully established no longer made sense.

That didn’t mean the work was wasted. I still had the context I had learned and the relationship we had built.

But the work changed, so the relationship had to change with it.

That’s why the hills-to-mountains metaphor has stuck with me. ⛰

You keep climbing, and each peak gives you a better view. But the terrain is also changing around you.

You never fully “acclimate” and switch to autopilot.

🧑‍🏫 THEORY: Your first 90 days establish the systems that will support the rest of your tenure.

💡 REALITY: Your first 90 days establish the first version of those systems. Then the organization changes, you change, and you keep adapting.

📅 Day 91 is Just Tuesday

There are two ways I think Chiefs of Staff can arrive at day 90.

😵‍💫 You may feel overwhelmed because you haven’t done enough. You haven’t fixed the operating model. You haven’t built every relationship. You’re still discovering things you somehow missed during your listening tour. You’re looking at someone else’s perfectly polished 30-60-90 plan and wondering why you don’t feel nearly that settled.

😌 Or you may feel more like I did. You took care of the obvious low-hanging fruit. You wrestled the big hairy problem that was sitting right in front of you. You built the first systems you knew the organization needed.

And now you’re wondering: What’s next?

Those feelings look opposite, but I think they come from the same place.

By 90 days, you have enough perspective and grounding to see the organization much more clearly than you did when you arrived.

But you’re still new.

You’re still unsure of some of your reads. You’re still learning what good looks like here. You’re still proving your judgment and delivering value.

Ninety days is a useful milestone because it gives you an excuse to stop for a minute, look back down the hill, and notice how far you’ve climbed.

Do that.

Then look around.

There are probably a lot more hills than you could see from the bottom.

And whether you’re panicking because you haven’t done “enough” yet or wondering whether you’ve already taken care of the biggest things, remember:

☀️ Tomorrow is just another day at work.

Nothing magically appears on day 91.

Nothing magically disappears, either.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

September 10th: First Impressions — Ace the First 5 Seconds in Interviews, Presentations, and Networking Calls

September 11th: Building Culture on High-Growth Teams (Co-hosted with Offsite)

September 15th: The Chief of Staff Playbook for Making AI Work Across the Business

September 17th: Peer Resume Review

September 22nd: From Connection to Collaboration: An Icebreaker Workshop for Chiefs of Staff

👋 In-Person Events

September 3rd: Chiefs of Staff In The Age of AI (NYC)

September 5th: San Francisco Chief of Staff Community Dinner (Member Exclusive)

September 22nd: Ask a Chief of Staff x Industrious: NYC Chief of Staff Co-Working Day

October 20th: Ask a Chief of Staff x Industrious: NYC Chief of Staff Co-Working Day

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

THANK YOU for being a premium subscriber to Ask a Chief of Staff 💜

📹 Member Exclusive Recording - This is a previously recorded workshop from our archive, available exclusively to paid members. Free subscribers can preview the content below, then upgrade to watch the full workshop.

You’re crushing it at work. You’re also snapping at your partner over the dishwasher, lying awake at 2am running tomorrow’s agenda, and checking Slack on vacation “just in case.” Sound familiar? That’s not a productivity problem you can fix with a better calendar app. That’s your nervous system waving a white flag.

This workshop with Carrie McMahon (2x Chief of Staff who’s lived through her own burnout) skips the woo-woo and delivers three science-backed breathing techniques you can start using today. You’ll learn why energy management matters more than time management, how to spot your personal early warning signs before you crash, and how to actually shift out of “always on” mode. Perfect if your current strategy is “push through until the weekend.” 😵‍💫

🧑‍🏫 About the Speaker

Carrie McMahon is a 2x Chief of Staff in tech, Top 100 PLG Operator, trauma-informed yoga teacher (RYT 200), and Somatic Experiencing® student. After her own burnout in 2023, she built the ALIGN Method and founded Ground & Regulate, where she helps tech leaders regulate their nervous systems and operate sustainably. She's lived both sides: the pressure and the recovery.

📚 About the Workshop

This isn’t a productivity seminar. It’s a hands-on, reflective session built around the real-world scenarios Chiefs of Staff face every day: constant context-switching, decision fatigue, and the pressure of always being “on.”

Carrie walks through three breath work techniques with guided practice for each, then coaches attendees through recognizing their own energy patterns and early warning signs. The Q&A dives into practical scenarios like how to regulate yourself during a triggering meeting (without anyone noticing) using somatic tracking and orienting techniques.

💡 Key Takeaways You’ll Learn:

Energy Management > Time Management

• Why a color-coded calendar can’t outrun a dysregulated nervous system

• The two modes you’re always running in (execute vs. reflect) and why most of us are stuck in one

• Sustainable vs. borrowed energy, and why the interest on borrowed energy compounds fast

Three Techniques You Can Start Using Today

• Morning Anchor – A 90-second grounding practice before you touch your phone

• Box Breathing – Your between-meetings reset (used by the military and first responders)

• Alternate Nostril Breathing – The end-of-day signal that tells your body work is over

Spotting Your Warning Signs Before You Crash

• The three buckets to watch: physical, mental, and emotional

• Why running hot has probably become your baseline (and how to reset it)

• The one small shift that beats any lifestyle overhaul

Regulating Yourself in Real Time

• Somatic tracking and orienting techniques you can do mid-meeting

• The subtle breathing pattern that calms you while you’re actively listening

• How to build awareness so you catch dysregulation before it hijacks your day

👀 Curious To See What’s Behind The Community Curtain?

Our Ask a Chief of Staff paid community is now open for a 3️⃣ 0️⃣-day free trial. Full Slack access, workshops, mentors, the works. I built this room for exactly the Chief of Staff reading this email because I know this role can be isolating. But it doesn't have to be.

We’re now 6️⃣ 0️⃣ 0️⃣ ➕ members strong, helping Chiefs of Staff navigate their careers through:

💬 Members-only Slack workspace for peer support & real-time question answering
🖥 Exclusive workshops & events (virtual & in-person)
🤝 A supportive network of peers facing similar challenges
🧑‍💼 Direct access to experienced Chiefs of Staff and mentors
🌟 Curated job opportunities from leading companies
🙌 Resources and frameworks for immediate impact

Come see for yourself if these are your people 👇

Start Your 30-Day Free Trial

Read more

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🤓 The Smartest Chiefs of Staff Aren’t Doing It All Alone

As a Chief of Staff, your leverage multiplies when the right people are handling the right work. Oceans Talent connects you with AI-fluent, rigorously vetted remote operators — EAs, marketing specialists, finance support — matched to your business in 24 hours and placed in 2️⃣ weeks.

What makes them different:

🌊 Top 1% talent, trained on the AI tools your business actually runs on

🌊 60–80% less than equivalent US hires

🌊 86% of first matches stick — they do the homework so you don’t have to

🌊 Dedicated account management so you manage the work, not the people

6️⃣ 0️⃣ 0️⃣ ➕ companies trust Oceans Talent to scale their teams without compromising on quality.

Explore Oceans Talent

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🗓 What Does Month 2️⃣ as a New Chief of Staff REALLY Look Like?

This issue is guest authored by Claire Podulka, a strategic executive with 20+ years of experience across tech, education, and consulting. She is currently the Chief of Staff at Crisis Prevention Institute, the global leader in crisis prevention and de-escalation training. Previously, she spent nearly a decade at TXI, a boutique digital product consultancy. She writes and speaks on topics at the intersection of culture, operations, and strategy, with a particular focus on prioritization, both organizational and personal.

You’ll see the advice, from Clara among others, that the 30-60 day window as a new Chief of Staff is when you begin to own and implement — the shift from listening to doing.

As I wrote in part one of this series, if you can go a full 30 days without putting your hands on an oar, lucky you. The reality is, there are often items you’ll have to jump in and own on day one or two. But by your second month, you’ll absolutely be owning some streams of work.

But what that work looked like for me was a surprise 👀

The workstreams I owned in month two, by and large, weren’t new to the organization. They built on foundations that already existed. That’s the part of the advice we’ve got to dig into more, because it flips the pressure of “own and implement” into something much more sustainable.

🛞 Do You Really Need to Invent Something New?

There’s a metaphor I learned from Rodney Evans at The Ready that gets at the heart of inventing vs. iterating.

If your work serves external customers, user research is a given before you launch anything new. But if you serve internal customers, and especially if you’re new and eager to prove your unique value, it’s very easy to walk into work one day and, without asking questions or making thorough observations, say, “You know what would make things better here? A cake.” 🎂 (Don’t get distracted by hunger — this is a metaphorical cake.)

You get this impulse, right? It feels more valuable to jump in with a shiny new idea than to observe closely, get clear on the problem and the existing solutions, and take a less splashy action. So, because you are a proactive problem solver, you run into the kitchen, whip up a favorite recipe you’ve made a dozen times before, or a new one that looked good on Instagram, and march into the next team meeting to present your beautiful delicious cake to a room full of people who did not ask for cake.

❓ The point is: ask. Talk to your teams. Read their recipe books. Check how much old cake wound up in the compost bin. Then, and only then, decide what to bake — if anyone should bake anything at all.

Because you’re a great Chief of Staff and did thorough research in your first month (and continue to do research throughout your tenure) you’re not going to waste time or effort on an initiative no one wants. You’re going to understand the most meaningful problems and what existing solutions you can build on. In my own second month, the streams I took ownership of were all versions of this:

• Producing our first Global Virtual Town Hall, transitioning from weekly HR-driven, North America–only touchbases to a monthly, global session focused on strategic direction, progress, alignment, and transparency.

• Bringing disparate functional roadmaps into a cohesive organizational strategy we share consistently across all levels of the business. Seven months in, we’re still focused on the same goals (although the tactics have shifted plenty).

• Taking control of the exec operating rhythm, moving from variable times, days, and agendas that no longer served their purpose into a consistent cadence with a living agenda.

• Stepping in to temporarily own go-to-market metrics and data governance initiatives, which my CEO had been leading but was not where her time should be spent.

None of these were invented from scratch. They were all iterations of something the organization was already doing (or trying to do).

🧑‍🏫 THEORY: Take ownership of 2–3 core processes based on the insights from your listening tour.

💡 REALITY: The processes worth owning might already exist in some form. You're not inventing; you're refining. Look for the wheel that needs to be a little rounder.

🪤 Perfection is a Trap

Just as there’s an impulse to jump in and create something new to solve a problem, there’s also pressure — almost always internal pressure — to get it right the first time.

Don’t fall for that. Clara encourages you to set up the operational infrastructure that will support your work going forward, and she’s right. But the thing she doesn’t say out loud is: you’ll always be tinkering with that infrastructure. You’ll learn more, and you’ll adjust.

The first board deck I put together was extensively detailed, with a ton of text on each slide, because I’d been given explicit instruction from our operating partner on what the board expected to see. I didn’t know the board yet, so I went with it. But after the first meeting, I realized we had leeway to adjust. The expectations were more like preferences, and we could change things to better share the narrative and drive the discussion. No two board decks I’ve built since then look exactly like that first one, but they all build on the templates and structures I used then.

The lesson: set up the best system you can, and then let it teach you what the next best system should be. Your first version isn’t your final version. It’s the foundation for the next iteration, which becomes the foundation for the one after that.

🧑‍🏫 THEORY: Build the operational infrastructure that will serve you for your entire tenure.

💡 REALITY: You'll be tinkering with that infrastructure forever. The goal isn't a finished system; it's a system good enough to build on.

👂 Keep Listening, Even After You Start Doing

The listening tour doesn’t end at day 30. It just changes shape. Once you’re owning things, the feedback loop is your listening tour.

Our first Global Virtual Town Hall is a good example. It was a real step forward from what existed before — global, strategic, transparent — but it was also almost entirely executives talking to the rest of the company. When I ran a post-event survey, one theme came through clearly: people wanted more celebrating and more connecting. They wanted to hear from each other, not just from leadership.

So the next version incorporated more voices from across the company — space to celebrate wins, share localized stories of success, and surface the kind of work most people would never otherwise hear about. That change didn’t come from a fresh idea I brought in from outside. It came from asking and from being willing to adjust something I had just built.

This is the version of “listen and learn” that carries you past day 30. It’s less about intelligence gathering and more about staying honest with yourself about what’s working. The moment you stop asking is the moment the cake you worked so hard on starts showing up in the trash.

🧑‍🏫 THEORY: Synthesize your listening tour findings into action by day 60.

💡 REALITY: Your listening tour never really ends. The version of it that runs alongside your work — surveys, retros, hallway conversations — is what keeps your work from stagnating.

Next up: Part 3 — the first 90 days, when you really start to see results (and, of course, more new problems to tackle).

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

August 18th: Peer Resume Review

August 27th: Optimize Your LinkedIn Profile

September 10th: First Impressions — Ace the First 5 Seconds in Interviews, Presentations, and Networking Calls

September 11th: Building Culture on High-Growth Teams

September 17th: Peer Resume Review

September 22nd: From Connection to Collaboration: An Icebreaker Workshop for Chiefs of Staff

👋 In-Person Events

August 20th: Talk Shop: Chicago Chiefs of Staff Meetup

August 26th: Ask a Chief of Staff x Industrious: NYC Chief of Staff Co-Working Day

August 27th: DC Happy Hour 🎊

September 1st: Boston Chief of Staff Co-Working Day

September 3rd: Chiefs of Staff In The Age of AI (NYC)

September 23rd: Ask a Chief of Staff x Industrious: NYC Chief of Staff Co-Working Day

October 20th: Ask a Chief of Staff x Industrious: NYC Chief of Staff Co-Working Day

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🗣️ Do You Know The Best Way To Communicate With Your CEO?

This issue is guest authored by Nicole Seawell, founder of Communication Intelligence™ and author of the forthcoming book How to Talk to Everyone. Nicole equips leaders and teams with the precise language and skills to understand how they're wired, bridge to others wired differently, and communicate more deliberately — including in the age of AI. A Cornell ILR and Penn Law graduate, she has worked with leaders at organizations including McKinsey, Shopify, Walmart, Liberty Media, TripAdvisor, and Endeavor.

As a Chief of Staff, this isn’t just a communication insight: it’s an operational reality.

Because your role sits at the intersection of strategy and execution, leadership and team, vision and alignment. And when communication breaks down, it rarely looks like “miscommunication.”

It shows up as misaligned priorities, slowed decision-making, friction across stakeholders, and eroding trust.

Most dysfunction is not a strategy problem. It’s a communication misalignment problem.

💭 You’re Not Just Managing Work — You’re Managing Interpretation

Chiefs of Staff are translators. You take executive intent, team input, and organizational priorities — and turn them into aligned action.

But every person you work with filters communication differently:

• What feels clear to one feels abrupt to another

• What feels thoughtful to one feels slow to another

• What feels supportive to one feels vague to another

Same message. Different reality.

🗣️ Enter Communication Intelligence™ (CQ) + The Enneagram

Communication Intelligence™ (CQ) is your ability to read, interpret, and adapt to communication differences in real time.

And this is where I use the Enneagram as a powerful companion tool — not as a label or a box, but as language for pivoting and connecting.

The Enneagram helps name why people show up differently across the CQ pillars:

• Why someone moves fast vs. deliberate

• Why someone avoids conflict vs. leans into it

• Why someone needs detail vs. prefers high-level

It gives you a shared, neutral vocabulary for differences — so you can move from “Why are they like this?” to “How do I work with this effectively?”

Together, CQ + the Enneagram give you clarity, precision, and adaptability.

🏛️ The CQ Pillars: Where Misalignment Happens

Here’s where CQ becomes practical. The seven pillars below are the specific spectrums where communication most often breaks down — meaning two people can say the same thing and mean something completely different. As you read, notice where you naturally sit on each one.

(Curious where you land across the pillars? Take a closer look at the CQ framework — or find your Enneagram type with a free quiz to see the connection in action.)

1️⃣ Pace: Fast → Moderate → Deliberate

2️⃣ Conflict Style: Direct → Balanced → Harmony-Oriented

3️⃣ Risk Tolerance: High → Moderate → Low

4️⃣ Detail Needs: High-Level → Moderate Detail → In-Depth Detail

5️⃣ Action Orientation: Act-First → Consider-Then-Act → Reflect-Before-Acting

6️⃣ Analytical ↔ Relational Orientation: Primarily Analytical → Balanced → Primarily Relational

7️⃣ Decision-Making Style: Independent → Consultative → Consensus-Oriented

🤝 Where This Gets Real: CEO ↔ Chief of Staff Dynamics

Many CEOs, especially founders and growth-stage leaders, skew toward Type 3 (The Achiever) or Type 8 (The Challenger) energy. That means fast pace, high action and risk orientation, direct communication, and low patience for ambiguity.

The pillars tell you what varies. The Enneagram helps explain why people land where they do. Together, you have a practical guidebook to your leader and team.

For example, a Type 8 (Challenger) CEO will almost always sit at fast pace, direct conflict style, and high risk tolerance. A Type 6 (Loyalist) Chief of Staff tends to land at deliberate pace, in-depth detail needs, and lower risk tolerance. Same conversation — completely different reality.

That’s where the Enneagram becomes a working tool. Not a personality label, but a way to predict where someone lands on the pillars before friction shows up.

Below is a breakdown of the 9 Communication Archetypes across the 7 CQ pillars.

👤 CQ Pillar Profile by Enneagram Type

All nine Enneagram types mapped across the seven CQ pillars.

👤 Type 1 · The Perfectionist

• Pace / Energy: Moderate / Deliberate

• Conflict Style: Rational & Logical

• Risk Tolerance: Low

• Detail Needs: In-Depth

• Action Orientation: Consider Then Act

• Analytical ↔ Relational: Analytical

• Control Orientation: High — to be right

👤 Type 2 · The Helper

• Pace / Energy: Moderate

• Conflict Style: Harmony-Oriented

• Risk Tolerance: Moderate

• Detail Needs: Moderate

• Action Orientation: Consider Then Act

• Analytical ↔ Relational: Relational

• Control Orientation: Moderate — people oriented

👤 Type 3 · The Achiever

• Pace / Energy: Fast

• Conflict Style: Rational & Logical

• Risk Tolerance: High / Moderate

• Detail Needs: High-Level with as needed

• Action Orientation: Consider / Act almost simultaneously

• Analytical ↔ Relational: Analytical

• Control Orientation: Moderate — progress oriented

👤 Type 4 · The Individualist

• Pace / Energy: Deliberate

• Conflict Style: Emotional Realness

• Risk Tolerance: Moderate

• Detail Needs: In-Depth

• Action Orientation: Reflect Feelings Before Acting

• Analytical ↔ Relational: Relational

• Control Orientation: Moderate — feelings based

👤 Type 5 · The Investigator

• Pace / Energy: Deliberate

• Conflict Style: Rational & Logical

• Risk Tolerance: Low

• Detail Needs: In-Depth

• Action Orientation: Reflect Info Before Acting

• Analytical ↔ Relational: Analytical

• Control Orientation: Moderate till certain, then strong

👤 Type 6 · The Loyalist

• Pace / Energy: Moderate

• Conflict Style: Emotional Realness

• Risk Tolerance: Low

• Detail Needs: Moderate — focused on safety

• Action Orientation: Consider Safety Then Act

• Analytical ↔ Relational: Balanced

• Control Orientation: High — to keep from going wrong

👤 Type 7 · The Enthusiast

• Pace / Energy: Fast

• Conflict Style: Harmony-Oriented

• Risk Tolerance: High

• Detail Needs: High-Level

• Action Orientation: Act-First

• Analytical ↔ Relational: Balanced

• Control Orientation: Low

👤 Type 8 · The Challenger

• Pace / Energy: Fast

• Conflict Style: Emotional Realness

• Risk Tolerance: High

• Detail Needs: High-Level

• Action Orientation: Act-First

• Analytical ↔ Relational: Gut Based Emotional

• Control Orientation: High — to not be controlled

👤 Type 9 · The Peacemaker

• Pace / Energy: Moderate / Deliberate

• Conflict Style: Harmony-Oriented

• Risk Tolerance: Low

• Detail Needs: Moderate — as needed for calm

• Action Orientation: Reflect Peace Before Acting

• Analytical ↔ Relational: Relational

• Control Orientation: Low

💡 Why This Matters for Chiefs of Staff

This is your edge.

When you understand both your leader’s and other key people’s default and your own communication pattern, you can bridge the gap intentionally.

Instead of reacting, you:

• Translate more effectively

• Anticipate friction before it happens

• Create alignment faster

• Reduce unnecessary stress on both sides

↔️ Let’s Practice the CQ Bridge

Below is a comparison of style differences for a Chief of Staff by each type ↔ with a leader Type 3 CEO.

The bold pillar values in each Chief of Staff profile indicate a gap with the example Type 3 CEO — the friction point where a bridge is needed. The Type 3 CEO profile below is the constant reference point for every comparison.

📏 Type 1 · The Perfectionist

Standards-driven, principled

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Moderate / Deliberate

• Conflict: Rational & Logical

• Risk: Low

• Detail: In-Depth

• Action: Consider Then Act

• A↔R: Analytical

• Control: High – to be right

↔️ Bridge Strategy

A natural alignment you might not expect: both the Type 1 and the Type 3 CEO communicate through rational, logical frameworks. The friction isn’t in how they think — it’s in pace and the definition of ‘done.’ The 1 needs to reach the right answer; the 3 needs to reach it fast. Name the standard upfront (’Here’s what right looks like for this one’), give the 1 ownership within a clear timeline, and honor the rigor they bring. Control the finish line, not the process.

🤝 Type 2 · The Helper

Relationship-first, attuned

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Moderate

• Conflict: Harmony-Oriented

• Risk: Moderate

• Detail: Moderate

• Action: Consider Then Act

• A↔R: Relational

• Control: Moderate – people oriented

↔️ Bridge Strategy

The Type 2 moves through connection; the Type 3 CEO moves through results. These aren’t opposites — relationship capital is what makes execution stick. Bridge: frame asks in terms of impact on people and outcomes together. When the 2’s harmony-oriented approach slows a conversation, translate it: ‘Your instinct to keep everyone together is protecting the rollout — let’s channel it into who needs to be in the room before we decide.’ Direct, warm, and specific on the ask.

🏆 Type 3 · The Achiever

Results-driven, fast-moving

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Fast

• Conflict: Rational & Logical

• Risk: High / Moderate

• Detail: High-Level, as needed

• Action: Consider / Act simultaneously

• A↔R: Analytical

• Control: Moderate – progress oriented

↔️ Bridge Strategy

Strongest natural alignment across every pillar. The risk is invisible: two 3s in the same orbit can outpace the room, under-communicate to everyone else, and mistake shared energy for shared alignment. Bridge: divide ownership explicitly. Build in a short check-in cadence — not to slow down, but to make sure the same pace that makes you powerful isn’t leaving the rest of the organization behind.

🙋🏻 Type 4 · The Individualist

Depth-seeking, meaning-driven

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Deliberate

• Conflict: Emotional Realness

• Risk: Moderate

• Detail: In-Depth

• Action: Reflect Feelings Before Acting

• A↔R: Relational

• Control: Moderate – feelings based

↔️ Bridge Strategy

The Type 4’s emotional realness in conflict — authentic, unfiltered, personal — can feel like a derail to a rational/logical 3. Resist the read that emotion is inefficiency. Bridge: acknowledge the feeling before moving to the logic. ‘I hear that this landed hard — here’s why the decision still needs to hold.’ Connect outcomes to meaning; give the 4 creative latitude within clear parameters. The depth a 4 brings is the thing a fast-moving 3 most often skips and most often needs.

🕵🏻‍♀️ Type 5 · The Investigator

Analytical, information-first

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Deliberate

• Conflict: Rational & Logical

• Risk: Low

• Detail: In-Depth

• Action: Reflect Info Before Acting

• A↔R: Analytical

• Control: Moderate till certain, then strong

↔️ Bridge Strategy

An underestimated partnership: the Type 5 and Type 3 CEO both operate through rational, logical thinking and analytical orientation — more common ground than most 3s realize. The friction is pace and information volume: the 5 needs more time and more data before they move with confidence. Send the analysis before the meeting, not in it. Define what ‘enough’ looks like upfront. Once a Type 5 is certain, their commitment is absolute — and their rigor is the check a fast-moving 3 needs.

👑 Type 6 · The Loyalist

Safety-oriented, loyalty-driven

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Moderate

• Conflict: Emotional Realness

• Risk: Low

• Detail: Moderate — safety focused

• Action: Consider Safety Then Act

• A↔R: Balanced

• Control: High – to keep from going wrong

↔️ Bridge Strategy

The Type 6’s emotionally real expression of risk — visceral, urgent, sometimes unfiltered — can read as irrational to a rational/logical Type 3. Reframe: the 6 is running sophisticated risk analysis through an emotional channel. Meet it with logical responses: answer the specific concern with specific information. ‘Here’s what we know; here’s the plan for what we don’t.’ The 6 moves when the logic holds and the leader is steady. Their high-control instinct and the 3’s progress drive are actually the same protective impulse — pointed at different things.

🤩 Type 7 · The Enthusiast

Ideas-first, energy-forward

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Fast

• Conflict: Harmony-Oriented

• Risk: High

• Detail: High-Level

• Action: Act-First

• A↔R: Balanced

• Control: Low

↔️ Bridge Strategy

Strong natural alignment on pace, risk, and action. The friction is subtler: a 7’s harmony-orientation in conflict means they pivot to a new idea rather than stay in the tension, which can frustrate a 3 who wants a rational resolution. Bridge: channel the 7’s generative energy toward finishing, not just starting. Name the next concrete step before the conversation ends. And when conflict shows up, frame it as a puzzle, not a confrontation — the 7 will engage a problem they find interesting.

⚔️ Type 8 · The Challenger

Direct, decisive, force of presence

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Fast

• Conflict: Emotional Realness

• Risk: High

• Detail: High-Level

• Action: Act-First

• A↔R: Analytical

• Control: High – to not be controlled

↔️ Bridge Strategy

Nearly full pillar alignment — same pace, risk, action, detail level, and analytical orientation. The rub: the Type 8’s emotional realness in conflict (intense, force-of-personality) meets the Type 3’s rational/logical approach — and both can read the other as missing something essential. The 3 may seem cold; the 8 may seem irrational. Name this directly and early. Two high-control styles also need clear lanes: establish who owns what before decisions get made, not after. Give genuine autonomy and expect the same back.

✌︎︎ Type 9 · The Peacemaker

Steady, harmony-seeking

📌 CQ Starting Place (bold = gap with Type 3 CEO)

• Pace/Energy: Moderate / Deliberate

• Conflict: Harmony-Oriented

• Risk: Low

• Detail: Moderate — as needed for calm

• Action: Reflect Peace Before Acting

• A↔R: Relational

• Control: Low

↔️ Bridge Strategy

The widest overall gap — and one of the most complementary partnerships when bridged intentionally. A rational/logical 3 can read a harmony-oriented 9 as having no position; the 9 often has a clear position they haven’t been invited to share. Ask directly, then wait. Create space before the deadline, not at it. The 9’s low-control, peace-first approach is not passivity — it’s the counterweight to everything a high-progress 3 tends to run past. Build in the pause. It will save you the rewind.

🔄 The Practical Shift

Before your next interaction with your leaders, ask:

• Where are they operating on the CQ spectrum right now?

• Where am I naturally operating?

• What adjustment creates alignment fastest?

That small shift changes everything.

💭 Final Thoughts

If reality is what the other person thinks you said...

Then your role is not just to communicate. It’s to ensure alignment in how communication is received.

When you combine Communication Intelligence with the Enneagram, you stop managing miscommunication and start engineering clarity, trust, and momentum — on purpose.

If this got you thinking about your own CQ gaps, I’m opening a small pilot training on the framework for the first 8 Chiefs of Staff who reach out to me at Info@SailorsSweetLife.com with the subject line “Me - Chief of Staff CQ”

LinkedIn: Nicole Elias Seawell | Website: sailorssweetlife.com

© 2026 Sailor’s Sweet Life™, LLC · Communication Intelligence™

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

August 13th: The Alignment Gap: Why Employees Don’t Understand Leadership Priorities (and What to Do About It)

September 11th: Webinar | Building Culture on High-Growth Teams

👋 In-Person Events

August 20th: Talk Shop: Chicago Chiefs of Staff Meetup

August 26th: Ask a Chief of Staff x Industrious: NYC Chief of Staff Co-Working Day

🔒 Member-Only Events

August 11th: TeachMe: Capturing Your AI Proficiency in One Page (Member-Only)

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

THANK YOU for being a premium subscriber to Ask a Chief of Staff 💜

📹 Member Exclusive Recording - This is a previously recorded workshop from our archive, available exclusively to paid members. Free subscribers can preview the content below, then upgrade to watch the full workshop.

71% of senior managers say meetings are unproductive. And when you’re the one running them? That reflects on you: your leadership, your judgment, your ability to move things forward. As Chiefs of Staff, we run meetings all day: 1:1s with our Principal, cross-functional syncs, stakeholder alignment sessions, board prep. Getting them right isn’t optional.

This workshop with executive communication coach Eloïse Eonnet delivers a foolproof structure for leading outcome-oriented meetings—the kind where alignment actually happens, decisions actually get made, and next steps are actually clear before people leave. You’ll walk away with a framework you can use for your very next meeting (yes, even the impromptu Slack huddle your Principal just pulled you into).

🧑‍🏫 About the Speaker

Eloïse Eonnet is the founder of Eloquence and an expert in executive presence and strategic communication. Since founding Eloquence in 2011, she has worked with leaders and emerging leaders to help them walk into any room, lead boldly, and communicate with confidence.

Her approach blends structure, mindset shifts, and practical toolkits, giving leaders the language and approaches they need to integrate into their day-to-day and make their own.

📚 About the Workshop

This interactive session breaks down a simple but powerful framework: every meeting is movement from Point A (where you are) to Point B (a decision, alignment, or clear outcome). Most meetings fail because leaders never properly establish Point A, which leaves everyone unclear on why they’re there, what needs to happen, and how they should contribute.

Eloïse walks through her three-part structure for nailing Point A with concrete examples you can copy, then coaches attendees through applying it to their own upcoming meetings. The Q&A dives into the trickiest real-world scenarios: rigid vs. flexible meeting cultures, silent stakeholders, and what to do when your CEO shows up and blows up your agenda 🫣

💡 Key Takeaways You’ll Learn:

The Point A → Point B Framework

• Why most meetings fail before they start (and how to fix it in five minutes of prep)

• The three non-negotiable elements of Point A: Agenda, Context, Objectives

• How to make “outcome-oriented” more than a buzzword

Writing Objectives That Actually Drive Action

• The “in order to” test that separates strong objectives from vague ones

• Why your objectives need to be actions taken during the meeting, not after

• How to build urgency and relevance into every meeting you lead

Handling the Hard Meeting Dynamics

• Setting meeting etiquette that gets quiet people talking and loud people listening

• Redirecting stakeholders who try to hijack the agenda

• What to do when your Principal or CEO changes everything mid-meeting

Scaling the Framework Across Your Whole Calendar

• Applying this to recurring meetings (EOS/L10, weekly syncs, 1:1s)

• Using the framework in impromptu conversations and quick huddles

• The pre-meeting email template that gets people to prepare (or opt out)

👀 Curious To See What’s Behind The Community Curtain?

Our Ask a Chief of Staff paid community is now open for a 3️⃣ 0️⃣-day free trial. Full Slack access, workshops, mentors, the works. I built this room for exactly the Chief of Staff reading this email because I know this role can be isolating. But it doesn't have to be.

We’re now 6️⃣ 0️⃣ 0️⃣ ➕ members strong, helping Chiefs of Staff navigate their careers through:

💬 Members-only Slack workspace for peer support & real-time question answering
🖥 Exclusive workshops & events (virtual & in-person)
🤝 A supportive network of peers facing similar challenges
🧑‍💼 Direct access to experienced Chiefs of Staff and mentors
🌟 Curated job opportunities from leading companies
🙌 Resources and frameworks for immediate impact

Come see for yourself if these are your people 👇

Start Your 30-Day Free Trial

Read more

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

💭 What I Think Now After 1️⃣ 0️⃣ 0️⃣ Issues

It’s Issue 1️⃣ 0️⃣ 0️⃣. The version of me who hit publish on Issue 1️⃣ wouldn’t recognize half of what I think now. And honestly that feels like the right thing to write about.

So instead of a milestone roundup, here’s a letter about what I got wrong, what’s changed, and what I believe now after almost 4️⃣ years and hundreds of conversations with Chiefs of Staff.

❌ What I got wrong

I assumed Chiefs of Staff would show up for the tactics 📋

Templates, frameworks, the board prep example you could steal on Monday. That’s how I described the role to myself when I was doing it, so I built for the version of me who wanted ROI by Friday.

What actually pulled people in was belonging 👩🏾‍🤝‍👨🏼

The most common reaction I get from members isn’t “I learned something new.” It’s “I didn’t know other people felt this way.” The tactical stuff is the doorway. The reason they stay is that this is the first room they’ve been in where everyone gets it without explanation.

I should have seen this coming. The role itself is structurally lonely. You sit between layers, you hold information you can’t share inside your own company, and your peers are scattered across orgs that have no idea what you actually do.

Of course the answer is other Chiefs of Staff. I just thought the answer would look more like a course.

I started a newsletter expecting to teach. I ended up building a mirror 🪞

🔄 Where my thinking has shifted

There are also a few things I believed that weren’t necessarily wrong, but that have definitely evolved after working with so many Chiefs of Staff over the years.

🧑‍💼 Leadership rooms aren’t where answers get handed down. I used to think being a Chief of Staff meant getting a backstage pass to certainty. The first time I sat in those rooms and watched smart people argue their way through gray areas with incomplete data, it reframed the job for me. The Chief of Staff isn’t there to transcribe the answer. The Chief of Staff is part of how the answer gets made.

👣 The “18–24 month stepping stone” framing isn’t right. I bought it when I started writing. I don’t anymore. I’ve watched too many people build careers as a Chief of Staff—staying with a Principal for years, moving CoS-to-CoS, becoming the operator a company can’t function without. It’s a path, not a launchpad.

🤖 You can’t be a great Chief of Staff in 2️⃣ 0️⃣ 2️⃣ 6️⃣ without being fluent in AI. When I was in seat at Hugging Face, AI literacy wasn’t on any job description, despite the company itself being AI native. Now it’s on almost all of them. The Chief of Staff is becoming the person who decides what gets automated, what stays human, and how the org adapts to both.

💡 The moment it clicked

The turning point that crystallized everything was our first NYC Summit 🍎

5️⃣ 0️⃣ Chiefs of Staff in one room, no screens between them. I’d been telling people for years that peer-to-peer was where the real value lived. Watching it happen in person was the first time I fully believed my own pitch ✨

Every once in a while a member says it back to me in a way that makes it land harder than I ever could. Gina Ruscio dropped this in our wins channel after signing her Chief of Staff offer at a Series A:

“I found this opportunity through the Ask a Chief of Staff job postings and tailored my resume with the peer resume review workshop — this is easily the fastest value I have ever seen in a professional network.”

That’s the thing. The community isn’t a place to learn the role. It’s the shortest path between a Chief of Staff and the next chapter of their career.

After 1️⃣ 0️⃣ 0️⃣ issues, hundreds of conversations, and 4️⃣ 0️⃣➕ placements, Ask a Chief of Staff isn’t just a community anymore. It’s an aggregation of what hundreds of Chiefs of Staff have figured out the hard way. Newer members get to inherit that.

That compounding effect is the thing I didn’t see coming, and the thing I most want to protect 🫂

💜 What I’m quietly proud of

From the outside, Ask a Chief of Staff looks like a newsletter, a community, and a recruiting arm. From the inside, it’s a small team running a tight ship: monthly reporting, an onboarding sequence built to reduce 90-day attrition, an event cadence we don’t break. Most of that is invisible because it works.

I learned to run an org as a Chief of Staff, and I built this one without the operational debt I’ve watched other founders dig out of. That part isn’t glamorous, but it’s the part that lets everything else compound.

🫤 What’s been harder than I expected

The loneliness is the hardest part, honestly. I often refer to the Chief of Staff role as an island of one 🏝️

I built a community for Chiefs of Staff specifically because the role is isolating, and then I underestimated how isolating founding would be. Different shape, same problem. You hold the whole picture, you make calls with incomplete data, you can’t fully offload it to anyone. It’s the same job I left, just from a different chair.

The other hard part is the lack of a playbook. I assumed my Chief of Staff toolkit (operating cadences, decision frameworks, prioritization) would mostly carry over. It does, up to a point. Running a business means making a hundred small decisions a week with no senior person to escalate to. There’s no “right” version of this, and I’m still getting used to that.

⚠️ The part nobody warned me about: when Ask a Chief of Staff is going well, it’s invisible. When something cracks, it lands on me. That’s the Chief of Staff dynamic, too. I accidentally built a business with the exact emotional weight of the role it’s for.

🔮 What I wish someone had told me before I started

I’ve talked to hundreds of Chiefs of Staff and gained an enormous amount of perspective that I simply didn’t have when I started. Here’s the short version of what I wish someone had told me before I took the role:

1️⃣ The job is whatever your Principal needs it to be. And that will change. There’s no one-size-fits-all description. Some days you’re running board prep. Some days you’re resolving team conflict. Some days you’re reworking the hiring plan. Your calendar is a reflection of their chaos. Expect it.

2️⃣ The job will break you if you don’t set boundaries. You’ll be pulled into everything. That doesn’t mean you need to own everything. Clarify your role early. Be honest about your capacity. Otherwise you become a dumping ground for “miscellaneous leadership tasks.”

3️⃣ You’ll question your impact. Often. This is a behind-the-scenes role. You’re rarely the decision-maker. You don’t always get credit. You are the glue, the amplifier, the friction remover. It matters even when it’s invisible.

4️⃣ This role runs on emotional range. It’s 30% strategic thinking, 70% relationship management. If you can’t handle egos, resolve tension, and build trust across functions, the strategy won’t land.

5️⃣ Your Principal is figuring it out, too. Even if they’ve been a CEO for 10 years, they’re still carrying doubt. Still making bets. Still human. The sooner you realize you’re both figuring it out together, the more effective (and connected) you’ll be.

6️⃣ Find other Chiefs of Staff. This job is too ambiguous, too emotionally intense, and too high-stakes to navigate solo. Whether it’s a community, a mentor, or a DM group, find your people.

7️⃣ Write stuff down and document everything. The operating cadence. The decision criteria. The takeaways from that “quick sync.” It doesn’t need to be fancy. If you’re the memory of the org, make sure you have one.

BONUS: I tapped community members to weigh in on this exact theme earlier this year. If you missed that issue about what 🔟 Chiefs of Staff would tell their former selves, check it out here.

🎯 What I’m doubling down on

You may have already noticed this in the first half of 2️⃣ 0️⃣ 2️⃣ 6️⃣ , but I’m committed to hosting even more in-person events and AI programming to better support our community.

Ask a Chief of Staff started as a Slack community and a newsletter. Our NYC Summit earlier this year convinced me the highest-leverage version of this is in person.

🏙 We’re heading to Boston, Miami, San Francisco, and beyond this year, with more cities on the runway. If you’re a Chief of Staff in one of those cities, please join us. I’d love to meet you! 💜

🤖 The other thing is AI. The role is changing faster than any other I write about, and I want Ask a Chief of Staff to be the place where Chiefs of Staff figure out what it means to operate as a “Chief of Agents.” That shows up in workshops, content, and maybe an industry survey later this year.

💭 One last thing

If you’re new here, or if you’ve been reading for a while but never said hi: you’re not making it up. The role really is this strange, this ambiguous, this lonely, but also this important.

The single thing I want you to take from this letter is the same thing this community has given me: a room full of people who get it without explanation. Find them. By DM, by mentor, by community, by whatever channel works for you. Don’t do this job alone. It’s not built for that.

Thank you for being here for 1️⃣ 0️⃣ 0️⃣ issues! For replying to my emails. For showing up to workshops at 7am your time. For trusting me with the questions you can’t post on LinkedIn. Ask a Chief of Staff doesn’t exist without you, and I mean that literally.

Here’s to 1️⃣ 0️⃣ 0️⃣ more! 💜

Clara

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

July 23rd: From Signals to Action: A Chief of Staff Toolkit for Navigating Disruption

July 28th: Board Meetings, Reimagined: A Zeck Demo + Real-World Case Study

July 30th: From Reactive to Regulated: Energy Management Tools for Chief of Staffs

👋🏼 In-Person Events

August 4th: Ask a Chief of Staff x Offsite: NYC Community Dinner

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🫣 Did You Miss The Workshop With Edward Norton?

This special bonus issue is brought to you by Zeck, modern board management software built to make board meetings worth having. Following their recent workshop with the Ask a Chief of Staff community, Robert Wolfe, Co-Founder & CEO at Zeck, shares why a board meeting shouldn’t be a review at all, and how Chiefs of Staff can turn it into a working session actually worth having.

Robert co-founded CrowdRise, which merged with GoFundMe, and has served on corporate and nonprofit boards for over two decades. He’s often been voted the worst sleeper and has to have ice cream every night.

In case you missed it: catch the full workshop — featuring Robert and Edward Norton — below 👇

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🎭 Why Does Your Board Meeting Feel Like Theater — And How Do You Fix It?

Here’s something I’ve heard from Chiefs of Staff more times than I can count: the board meeting is the worst part of the job.

Not because it’s hard. Hard is fine. Hard is interesting.

It’s that the whole exercise often feels like it works against you. You go pencils down on everything that actually matters. (The only acceptable reason to go pencils down is a Dairy Queen run🍦Cone with sprinkles, plus a thimble of extra sprinkles on the side. I only recently learned that’s what the little cup is called, and I can’t stop thinking about it.)

You spend weeks herding edits, building slides nobody loves, integrating data from six different places into a format that was already outdated when PowerPoint shipped. And at the end of it, you sit in a room and watch someone read back a document you sent three days ago.

This is not governance. This is theater. And as the person who holds the whole production together, you know better than anyone that it doesn’t have to be.

Here’s what I think is actually going on, and what you can do about it.

🕰 The Real Problem: Your Board Meeting Is Looking Backward

Most board meetings are structured as reviews.

Management presents. The board reacts. Someone asks about a number from Q2. Someone else brings up something they didn’t understand in the materials. You go through approvals. You run out of time. You schedule a follow-up.

The whole thing is designed around the past.

And the reason is structural, not personal: the tools and habits we’ve inherited were built for accountability in the rearward-looking sense. Did you hit your numbers? Did you file the right docs? Did anything blow up?

That’s not what a board should be for.

The best board meetings I’ve ever been in are almost entirely about what’s next 🔮

What’s keeping the leadership team up at night? What decisions need to be made in the next 90 days? Where does the CEO need air cover, introductions, or a sounding board? What are the board members themselves going to do before the next meeting?

That last question is underrated. The most forward-looking thing a CEO can do is end every board meeting by asking each member to name one concrete action they’ll take before you meet again. It reframes the relationship immediately.

A board meeting isn’t a review. It’s a working session, and everyone in the room has a job.

As the Chief of Staff, you’re often the one who makes that practice stick: you build it into the agenda, track what people committed to, and quietly follow up. When board members know their commitments are being held, the dynamic in the room shifts.

🤝 Accountability Runs Both Ways

Here’s a mindset shift that can change everything: the management team isn’t the only party being evaluated in a board meeting.

Chiefs of Staff spend enormous energy preparing the right materials: complete, accurate, well-organized. But then you walk in with no idea who actually read them. Did the board member who’s about to ask a pointed question about your burn rate spend 30 seconds on the financials? Did the person who wants to debate strategy skip the section where you addressed exactly that?

You’re flying blind into a conversation that could have been much more productive.

One of the things we’ve seen at Zeck is that when management teams can see exactly how board members engaged with the materials (which sections they read, how long they spent, where they stopped) it changes the whole dynamic.

Boards read more carefully when they know you’ll know if they didn’t 👀

And management teams walk in with confidence instead of anxiety, because they’re not guessing at what people understood or missed 🎯

That’s accountability running in both directions. And it’s healthy 🤝

Something else that changes the room: knowing where the board stands before you walk in.

Implement pre-voting to get a read on key decisions ahead of the meeting. Not the official vote (that still happens live) but a pulse check that tells you whether you have rough consensus or a divided table. That changes how you prepare, what your CEO addresses first, and whether anything catches you off guard. No surprises is a prep strategy.

Ask Zeck lives entirely inside your company’s data. Not trained on anyone else’s board materials. Only yours. You can use it to tighten a section that’s running long, surface a trend across your last few meetings, or ask it something the management team often forgets to ask before hitting send: “What would a board member ask about this section?” That one is genuinely useful. It’s like a read-through from a skeptical board member before you’ve shared anything. Reassuring or humbling, depending on the draft.

📜 Your Actual Leverage: Set the Rules Before the Game Starts

The Chiefs of Staff I’ve seen navigate board dynamics best aren’t just great at prep. They’re the ones who helped their CEO set expectations upfront, often before a board member ever joined the table.

This matters more than most people realize. Too many organizations hand out board seats without defining what it actually means to hold one. Invest some money, get a seat. For life, apparently, and with no particular obligations attached. That’s a recipe for the board meetings you hate.

The alternative is setting up reciprocal expectations from day one:

🤝 What does “coming prepared” actually mean? (Reading the materials before the meeting. Not skimming. Reading.)

🤝 What is the board member expected to contribute between meetings? (Introductions? Advice? Actual work on a specific problem?)

If your organization has been operating without these norms, it’s not too late to introduce them. A new tool, a new format, or even a new board member joining creates a natural inflection point. Use it.

💭 What This Means for You

Sue Bird, a WNBA legend who won championships by making everyone around her better, didn’t just execute plays. She read the entire court, adjusted in real time, and put her teammates in position to succeed before they even knew they needed it.

That’s the Chief of Staff in a board meeting. You’re not just building the materials. You’re running the play.

The Chief of Staff is often the person who makes or breaks how a board meeting actually runs, not just logistically but culturally. You’re the one who knows whether the prep process is working. You’re the one who sees the board dynamics from close enough to know what’s broken.

That’s leverage, not just a burden.

Use it to advocate for meeting structures that respect everyone’s time. Push for materials formats that people actually want to engage with. Help your CEO set expectations with the board that creates genuine accountability on both sides.

A great board meeting doesn’t happen by accident. It gets built deliberately, in advance, by the people who understand what it takes.

Board meetings are a lot like garbage day. You know exactly when it’s coming. It’s been on the calendar forever. And yet there’s this dread that starts building a few days before. Maybe that’s just me. Actually, I’m pretty sure that’s just me. The difference is you can’t fix garbage day. You can fix the board meeting.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

July 16th: How to Build an AI-Native Company: For Chiefs of Staff and Operators Who Are Done Dabbling and Ready To Go All In

July 23rd: From Signals to Action: A Chief of Staff Toolkit for Navigating Disruption

July 28th: Board Meetings, Reimagined: A Zeck Demo + Real-World Case Study

July 30th: From Reactive to Regulated: Energy Management Tools for Chief of Staffs

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🗣 Stop Self-Editing Before You Even Start

I’m a big fan of dictation, and here’s why: when you dictate something, you speak a lot more freely.

You talk about what’s top of mind immediately. But when you type? You start to self-edit. You take your thoughts and run them through another medium—text—and simplify before you even get your full ideas out.

I use Wispr Flow to dictate my ideas freely, then use its built-in polish function to help organize and edit my message into something that’s publish-ready in minutes.

I use it for:

• Slack messages to my team

• First drafts of emails

• Brainstorming and dictating content ideas

• Polishing raw thoughts into structured lists

👉 Give Wispr Flow a try and stop self-editing before your ideas even make it out.

Try Wispr Flow Free

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

👩‍💼 What Is Executive Presence Really — And Can It Be Coached?

This week’s issue is guest-written by Gena Chieco, Ask a Chief of Staff Mentor & Coach and former Chief of Staff, attorney, and senior government official. Gena guides personal and professional transformation through integrated, embodied, conscious leadership—helping clients navigate change, face fears with compassion, align with their inner compass, and honor their unique genius and deeper purpose. For more background on Gena and ways to work together, visit her website: GenaChieco.com.

As an executive coach, I hear the same story on repeat: accomplished leaders arrive disheartened, told they lack “executive presence” or “gravitas” — no examples, no guidance. They come asking me to help them build it, as if executive presence were a template to replicate.

❓ The questions swirl: Should I speak more forcefully? Take up more space? Hide my emotions? Act more “masculine”?

Every one points in the wrong direction. The problem usually isn’t the leader. It’s that most definitions of executive presence are outdated and performative — narrow rules about what powerful leadership is allowed to look like.

And the moment we treat presence as a performance, it stops being a competency and becomes a costume. We self-monitor, chase external validation, and learn to sound like someone else. We shave off the edges that make us distinctive. The cost is subtle but profound: we become smaller versions of ourselves — not because we lack power, but because we’ve distanced ourselves from it.

When we’re told we lack executive presence, shame gremlins activate — whispering that we’re inherently deficient. But outsourcing our self-worth is like going to a dry well to quench our thirst. True confidence is an inside job.

The trap of performative leadership affects every leader. It’s especially acute for Chiefs of Staff, whose whole influence runs on presence, trust, and being believed — which is exactly why the rest of this read is worth your time. 👇

🚻 When Leadership Becomes Gendered

Executive presence has long been defined through a narrow lens, with traits that can be coded as “masculine:”

• certainty over curiosity

• emotional restraint over emotional fluency

• stoicism over expression

• volume over depth

• extroversion over reflection

• detachment over empathy

And the numbers show who they’ve rewarded. Women hold just 9% of CEO roles in S&P 500 companies, despite comprising over half the population. People of color are also significantly underrepresented, occupying only a small fraction of CEO and senior executive roles. Across boards and C-suites, this pattern remains consistent.

Leadership norms are not neutral, they are conditioned.

⚖️ When Bias Undermines Leadership Potential

Executive presence is also shaped by cultural bias, privileging white, Western norms of communication and leadership.

Leaders from marginalized racial and ethnic backgrounds often receive feedback influenced by bias rather than leadership deficiencies; what is seen as a lack of executive presence is often an equally valid yet different expression of leadership. They are being asked not simply to develop as leaders, but to assimilate and leave their rich heritage at the door.

Asian professionals, for example, are often told to be more vocal or visible — despite research showing that humility, reflection, and attentive listening are themselves impactful leadership traits.

Black women face particularly challenging double binds. Studies have shown that behaviors often praised in white leaders as decisive, direct, or confident may be interpreted very differently when exhibited by Black women, who are disproportionately subjected to stereotypes that label them as “aggressive” or “intimidating.”

😣 They are expected to navigate an impossible balancing act: be assertive, but not too assertive; be confident, but not too confident; speak up, but not in a way that makes others uncomfortable.

When feedback about executive presence is filtered through conscious or unconscious biases, leaders can find themselves working endlessly to correct perceived shortcomings that are either not theirs to carry or were never shortcomings to begin with.

🎯 Why This Matters for Chiefs of Staff

Chiefs of Staff occupy a unique leadership role.

Unlike other executives, influence rarely comes from formal authority or direct reporting lines. Instead, influence is built brick by brick upon a foundation of trust, credibility, integrity, discernment, relationship-building, presence, and strategic thinking.

Chiefs of Staff are the wizards behind the curtain, the ones who lead initiatives to success without being a public face, rarely receiving credit. Inherent in the role is a commitment to amplify others: Principals, projects, and teams, which makes it hard to intentionally develop their own authority and leadership identity.

Chiefs of Staff bring innovative, creative solutions to complex problems, drawing on their cross-organizational vantage point and valuable generalist skillset, among many other superpowers.

🫱🏼‍🫲🏾 The most effective Chiefs of Staff do not command attention because they have the loudest voice in the room, but because people trust what they have to say. Their executive presence emerges from substance rather than performance.

💡 Conscious Leadership as a Lens

Conscious leadership invites a broader question of what leadership can be.

Rather than asking leaders to conform to a narrow, inherited model, it expands what we value:

👂 Deep listening as much as eloquence

👥 Collaboration as much as command

🦉 Wisdom as much as decisiveness

💯 Authenticity as much as conformity

When we expand our definition of executive presence, we create space for leaders to be evaluated on the substance of their leadership rather than their privilege or proximity to a historically dominant norm. In doing so, we not only create more equitable workplaces, but gain access to a richer, more diverse and impactful expression of leadership itself.

We can feel the difference.

Take a moment to recall a leader who entered a room trying to appear confident, yet it felt performative, like a show. What impact did that leader have on you and the room? Now reflect on a time when a leader entered a room grounded in true, innate, effortless confidence that seemed to radiate from within. What shifted in the room—and in you? While behaviors may overlap, the energy, presence, and trust they generate are distinctly different.

The most powerful leaders ignite in their teams a desire to strive for excellence and meet the moment, driven by inspiration and an aspiration to be part of something meaningful. These leaders have a way of making each person feel valued and seen. This cannot be simulated or faked.

As Maya Angelou wisely observed, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” 💜

✨ An Alternative to Executive Presence: Embodied Confidence

From this perspective, impactful leadership is not a fixed performance or persona, but a dynamic expression of embodied confidence.

Embodied confidence is:

✨ To speak even when our voice shakes

✨ To stand in our integrity and do the right thing

✨ To say “I don’t know” with vulnerability

✨ To challenge an idea respectfully, even if it means ruffling feathers

✨ To assume good intentions when tempted to go below the line

✨ To courageously navigate rupture toward repair

✨ To be responsive more than reactive

✨ To share our perspective, accepting that not everyone will agree

Embodied confidence cannot be manufactured or performed.

It emerges from self-awareness, mindfulness, reflection, and inner alignment. It is self-trust made visible, cultivated through shedding what holds us back while embracing our unique genius, our truths, our authentic voice.

As we shift away from executive presence, we see clearly that embodied confidence is not about being the most commanding person in the room or leading by fear. It is the ability to remain deeply connected to yourself while navigating complexity. Embodied confidence is not about projecting power; it is about embodying it.

🎭 When leaders stop trying to emulate someone else’s style and begin authentically leading from their own core, they become more trustworthy, influential, and effective. Not because they have mastered a performance, but because they have stopped performing altogether.

🦁 The Courage to Lead Authentically

The process of moving from performance to embodied confidence is like building a muscle—one courageous conversation, one moment of mindfulness, one intentional choice, and one brave truth at a time.

Whenever we are trying something new with a beginner’s mindset, we can feel discomfort and grasp at control to ward off the ache of vulnerability. The invitation in learning to embrace embodied confidence is to wade into these choppy waters with self-compassion. Vulnerability is your North Star—a sign that you’re headed in the right direction.

The shift is not about becoming more polished. It is about becoming more of your true self, and honoring the life you were born to lead.

Embodied confidence is a remembrance of your gifts, of being truly present, of the wisdom and truths you hold within.

Embodied confidence is not something you perform your way into. It is something you reclaim.

🪞 Reflection Questions

• Who first taught you what “executive presence” is supposed to look like—and how might that definition be shaping you today?

• What has it cost you to adapt to dominant definitions of executive presence?

• Where might you be confusing performance with embodied confidence?

• Whose leadership style are you yearning to emulate, living or deceased? Who are some of your greatest direct sources of inspiration, who have touched you personally?

• Where are you outsourcing your sense of leadership authority instead of trusting your own inner knowing?

• Where in your body do you feel most anchored in confidence—and where do you feel yourself performing?

• What limiting beliefs, fears, or coping mechanisms need to be released in order to step into your full potential?

• What would change if your goal shifted from appearing powerful to embodying your power?

• What systems of support can you seek to help you shift to embodied confidence?

📚 Strategies and Resources for Chiefs of Staff to Embody Confidence

• Get clear on your unique genius, the constellation of strengths, talents, and innate abilities that bring you confidence and aliveness. (Free resource: Conscious Leadership Group, Genius Email Campaign)

• Seek out mentors who genuinely want to see you thrive—people who recognize your strengths, reflect your potential, and offer guidance that supports your growth. These may be colleagues, friends, former professors, or anyone with whom you’ve felt a spark of connection and psychological safety.

• Stand in your integrity, even when it’s inconvenient, uncomfortable, or not rewarded. Words and actions align. You hold an internal coherence; there’s less fragmentation between your private self and your public self. Integrity often costs something: approval, belonging, ease, or advantage, but you’re willing to tolerate that cost rather than abandon yourself. (Free resource: CLG Living a Life of Integrity, Short Video)

• Gain clarity on your values and practice aligned actions. (Free resource: Brené Brown Dare to Lead Values Worksheet)

• Honor your cultural heritage and understand how biases may infiltrate the workplace. (Resources: Ginny Clarke, Brown Girl Therapy, The Loveland Foundation)

• Heal coping mechanisms and survival strategies while developing greater self-awareness and self-confidence through therapy, coaching, and other resources. (Free resources: How Can Chiefs of Staff Overcome Impostor Phenomenon, CLG Locating Yourself Worksheet, and CLG Drama Triangle Short Video)

• Become a boundary badass, honoring your needs as valid and worthy, and communicating them from a place of awareness and intentionality. (Resource: Nedra Tawwab, Set Boundaries Find Peace )

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

July 9th: Peer Resume Review

July 16th: How to Build an AI-Native Company: For Chiefs of Staff and Operators Who Are Done Dabbling and Ready To Go All In

July 23rd: From Signals to Action: A Chief of Staff Toolkit for Navigating Disruption

July 30th: From Reactive to Regulated: Energy Management Tools for Chief of Staffs

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🫣 Did You Miss The Free 3️⃣ 0️⃣ Day Trial In Our Community?

Don’t worry, we’ve got you! I’m excited to announce that we’re extending our free 3️⃣ 0️⃣ day trial to the Ask a Chief of Staff Community.

We’re now 4️⃣ 5️⃣ 0️⃣ ➕ members strong, and here’s what you’d get access to:

💬 Members-only Slack — full access to network and knowledge-share with current Chiefs of Staff

🧑‍💼 Direct access to former Chief of Staff mentors who’ve been in your seat

🖥 Regular workshops led by SMEs, coaches, and working Chiefs of Staff (plus access to 1️⃣ 0️⃣ 0️⃣ ➕ previously recorded workshops over the years)

⭐ 1️⃣:1️⃣ career coaching sessions with me (normally $149)

📚 1️⃣ 0️⃣ 0️⃣ ➕ templates in our Resource Library

💼 Curated, exclusive job opportunities from leading companies

🤝 In-person coworking, happy hours, and networking events in major cities

💰 Thousands of dollars in exclusive software and product discounts

Email Clara

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🗓 What Does the First 3️⃣ 0️⃣ Days as a New Chief of Staff REALLY Look Like?

This issue is guest authored by Claire Podulka, a strategic executive with 20+ years of experience across tech, education, and consulting. She is currently the Chief of Staff at Crisis Prevention Institute, the global leader in crisis prevention and de-escalation training. Previously, she spent nearly a decade at TXI, a boutique digital product consultancy. She writes and speaks on topics at the intersection of culture, operations, and strategy, with a particular focus on prioritization, both organizational and personal.

Every piece of advice about starting a new leadership role includes some version of the same instruction: spend your first 3️⃣ 0️⃣ days listening.

Clara’s framing of this as “intensive reconnaissance” is one of the best I’ve heard: it captures the active, purposeful nature of that early listening. It’s not passive. You’re building a map.

And yet. When I joined a ~500-person global organization in the middle of a new CEO’s transformational push, “listen first” was a luxury I couldn’t fully afford. Amid leadership and board changes, refocusing our GTM approach, and kickstarting a new cross-functional product collaboration, I was jumping onto a raft already racing along a swift current. If I didn’t grab an oar, the raft might crash… or someone might shove me overboard.

👉 So here’s my take: Clara’s advice is the foundation. This post is about what you build on top of it when reality gets messy.

👂 The Listening Tour: The Right Structure Makes All the Difference

The listening tour, systematic 1:1s with key stakeholders, is non-negotiable. Clara’s right about that. But structure matters, and there are a few things I’d add to her framework.

I approached my listening tour through three channels:

1️⃣ Formal 1:1s with every executive. Beyond introductions, I wanted to understand why they were there, what success looked like to them, and how I could help. I ended every meeting the same way: “Who’s the next person on your team I should talk to?” I’d walk out with two or three more names every time.

2️⃣ Informal coffee chats. Even when companies arrange these, push further. Ask random people for 20-minute walks or quick calls. Some of the most useful intelligence comes from these unstructured conversations.

3️⃣ Shadow meetings. People can get nervous about this, so be explicit about why you’re there. Frame it clearly: “I’m trying to get my head around our product process. Would it be possible to sit in on one of your team’s meetings this month?” And make sure the organizer introduces you to the room so no one spends the whole meeting wondering who the silent new executive in the corner is.

🧑‍🏫 THEORY: Focus the first 3️⃣ 0️⃣ days on listening before acting. Build relationships through genuinely curious conversations.

💡 REALITY: The listening tour works, but you’ll need to run it in parallel with doing, especially if the organization is already mid-change.

💪 You Can Listen And Act at the Same Time

Clara wisely warns against the “action imperative” — the urge to prove yourself by doing things before you understand the landscape. She’s right that you should only take on tasks your Principal explicitly wants off their plate. But I’d push one step further: within that constraint, move fast.

By day 3️⃣ 0️⃣, I was facilitating the weekly executive team meetings. Over the following 3️⃣ 0️⃣ days, I made a series of adjustments based on what I’d observed and heard: setting agendas proactively with the desired outcome for each item, requesting that documents go out in advance so synchronous time could be used for discussion rather than level-setting, documenting decisions to short-circuit the tendency toward re-litigating the same conversations, and adding a Monday morning stand-up to handle tactical items so the longer team meeting could stay focused on deep discussion.

These changes landed well, partly because they weren’t random. People had flagged a lack of accountability and a tendency toward churn in my listening tour. I wasn’t inventing problems; I was solving the ones they’d already named.

🧑‍🏫 THEORY: As a starting point, take on tasks your Principal wants off their plate. Avoid creating solutions to imaginary problems.

💡 REALITY: Your listening tour will point you to which problems are the most impactful and universal. Use that intelligence to make your early wins count.

✍️ The 30-60-90 Plan: Write It, Then Let It Breathe

Clara recommends aligning with your Principal on measures of success for each phase.

Good advice, and I tried to follow it. I drafted mine and shared them with my Principal. And then, almost immediately, I fell into the swirl of the organization’s everyday needs and rarely checked back on them.

Here’s the thing: I just looked back at those original measures of success. I accomplished most of them. Plus dozens more things — large and small — that we never predicted.

So write the plan. Set the goals. And then hold them loosely, because the work will teach you what actually matters.

🧑‍🏫 THEORY: Align with your Principal on clear 30-60-90 measures of success before the work begins.

💡 REALITY: You’ll probably stop checking back on the plan. That’s OK. Write it anyway. It gives you a foundation even when the current pulls you somewhere unexpected.

📨 The Best Non-Work Thing I Did

Taking this new role was a big deal for me. I had spent nearly a decade at my previous organization, a place I’d “grown up” professionally. I was confident in my decision to make a move, but I know myself; there was a good chance that I’d get to the new company and get a big old case of imposter syndrome.

So during the downtime between roles, I wrote an email to my future self.

I reminded myself why I’d made this decision, what I was hopeful for, what I was nervous about, and above all to give myself grace and patience as I learned an entirely new company - new products, new customers, new teams, new tools, new capital structures, new norms.

Then I scheduled send for 9️⃣ 0️⃣ days after I started. It was both a helpful reflection in the moment and (it turned out) a powerful reassurance when I got it 9️⃣ 0️⃣ days later.

📌 One Thing I’d Do Differently

I work remotely and joined a majority in-person organization — over the holiday season, no less.

If I could go back, I’d find a way to spend at least a full week on-site in my first 3️⃣ 0️⃣ days.

The informal moments — the coffee before you get into the rush of the day, the sidebar after the Teams meeting ends — are where institutional knowledge actually lives. You can run a great listening tour over video. But some of the most valuable parts of onboarding happen in the margins of the day, and those are much harder to manufacture remotely.

It wasn’t practical in my situation given family needs and timing. But if you have the option, take it.

Next up: Part 2 — the first 60 days, when the real work of building systems begins 👀

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

June 30th: From Slide Decks to Shipping: What Consulting Didn’t Teach Me

July 7th: The Internal Standup w/ Thomas Knoll

July 9th: Peer Resume Review

July 30th: From Reactive to Regulated: Energy Management Tools for Chief of Staffs

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Starting a new Chief of Staff role is unlike any other transition.

There’s no standardized playbook, no clear success metrics, and no map for the first 90 days. Most new Chiefs of Staff figure it out by trial and error, which is exactly why we built this guide.

This is a comprehensive, fully designed playbook covering what you need to know about your first 3️⃣ months in the role: the break-even point mindset, how to run a listening tour, building communication rhythms with your Principal, securing early wins without overstepping, and launching your first strategic projects.

It’s practical. It’s specific. And it’s built from patterns we’ve seen across hundreds of Chiefs of Staff making this exact transition.

Whether you’re starting a new role, preparing for one, or managing someone in the seat, this is the guide we wish had existed on day one.

Paid subscribers get instant access to the guide below 👇 Not a paid subscriber yet? Start a free 7-day trial and grab it today!

Read more

THANK YOU for being a premium subscriber to Ask a Chief of Staff 💜

📹 Member Exclusive Recording - This is a previously recorded workshop from our archive, available exclusively to paid members. Free subscribers can preview the content below, then upgrade to watch the full workshop.

If you’re a Chief of Staff, you already know: you’re the glue.

You’re the one making sure the right people are talking to each other, the right systems are running, and the cracks get filled before anyone notices them. But glue work is often invisible, and that means the people doing it (you) can feel underappreciated, stretched thin, and stuck in the weeds 🫠

This workshop with executive coach Ankita Terrell offers a practical framework for stepping back and rethinking how your team actually works—from individual values, to company mission, to the world beyond.

You’ll leave with reflection prompts and tools you can use immediately to build a team that’s not just high-performing, but one people genuinely want to be part of.

🧑‍🏫 About the Speaker

​​​​​Ankita Terrell is a certified executive coach and fractional strategist who partners with operational leaders to build thriving businesses. She helps them build teams and systems that are as values-driven as they are high-performing. With an MBA and a background across VC, startups, and B Corps, Ankita blends strategic clarity with heart-centered insight. She’s the host of the top-rated podcast The Heart Led Entrepreneur.

📚 About the Workshop

This interactive session walks through Ankita’s framework for building teams that people actually want to work on, moving from the individual (each direct report’s values, dreams, and skills) to the company (mission alignment and metrics) to the broader impact you’re creating in the world. The workshop is paired with a Notion workbook full of reflection prompts you can use with your team.

It’s part framework, part real talk about the messy realities of managing people, including the team members you hired who turned out to be wrong fits, the high performers who are eyeing your job, and the question every Chief of Staff eventually asks: who fills my cup? ☕

💡 Key Takeaways You’ll Learn:

The Three-Layer Framework

• How to map each team member’s daily work to their long-term vision and the company’s mission

• Why what your company is optimizing for might not match what you want for your team—and how to navigate that

• Connecting individual contributions to bigger-picture impact (without it feeling corporate)

Knowing Your People Beyond the Job Description

• The questions to ask direct reports about their 5-year career and personal dreams

• How to surface skills people want to develop—and create space for them to grow

• Why your hiring lens (passion fit vs. expert fit) should change based on what you actually need

Making Glue Work Visible

• How to track and celebrate the work that holds everything together

• Simple, scrappy metrics tracking that doesn’t eat your whole week

• Creating team-wide capacity (and protected time) for the reflection that drives real progress

Taking Care of the Glue Person (You)

• Why the people holding everything together need someone holding them

• How to articulate the value of glue work when it’s not being recognized

• Filling your own cup so you can keep showing up for your team

⭐ Want to Take Your Membership to the Next Level?

Whether you’re a current or aspiring Chief of Staff, I invite you to check out the Ask a Chief of Staff community. We’re now 4️⃣ 5️⃣ 0️⃣ ➕ members strong, helping Chiefs of Staff navigate their careers through:

💬 Members-only Slack workspace for peer support & real time question answering

🖥 Exclusive workshops & events (virtual & in-person)

🤝 A supportive network of peers facing similar challenges

🧑‍💼 Direct access to experienced Chiefs of Staff and mentors

🌟 Curated job opportunities from leading companies

🙌 Resources and frameworks for immediate impact

Visit our website and click the “Join our community” button to start your journey!

Join Now

Read more

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🚀 Rolling out Claude? Help is here.

Every company I speak to right now seems to be in the middle of a Claude rollout. If this is you, I know some guys you should talk to.

I’ve known the founders from Ambient for a few years, and I’ve been consistently impressed with their depth and thoughtfulness around how companies can go AI Native.

They’ve just launched a new Claude-focused consulting business called, Legible.co. Their belief is that for companies to truly lean in to AI, they need to become “legible” to AI, which often requires changes in policy, operating model, and a general upleveling of skills - all things the Chief of Staff is often in the middle of.

The core offerings of Legible include:

• Claude trainings and enablement

• AI strategy

• Workflow automation and custom agent builds

🔥 Exclusive offer for Ask a Chief of Staff Readers: The Legible founders have kindly offered a free 3️⃣ 0️⃣ minute Claude training session (individual or group). Just include AACoS26 when you fill out the lead form.

Talk to Legible

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

👥 How Can Chiefs of Staff Protect Company Culture in the Race to AI-Native?

This issue is guest authored by Sydney Gorski, Chief of Staff at Collide, a VC-backed startup building AI for energy operators. After nine years planning events and meetings, she found her calling in the magic middle of the Chief of Staff role: where strategy and ops meet people and culture. Turns out running complex events is excellent training for running a company.

Everyone’s racing to become AI-native. Almost no one’s asking what we lose along the way.

That’s our job. Chiefs of Staff are the keepers of company culture, and in the AI race, that job just got harder.

👀 Why We Notice It First

There’s a line I love about this role:

Chiefs of Staff have influence over everyone and authority over no one.

Nowhere does that play out more than on the culture side. We sit at the intersection of every department. We hear what’s said in the leadership meeting and what’s said in the hallway after. We’re usually the first to notice when someone’s mood is off, when someone has one foot out the door, or when someone is stuck and needs encouragement.

Most of us are wired to read people well. That’s not incidental. It’s why this role works.

This matters more than ever right now because everything is moving fast. Companies racing to become AI-native are rolling out new tools and workflows on weekly cadences.

AI is intuitive enough that people assume it’s easy to roll out, and they skip the questions that should come before any major change, like:

❓ How will this affect our culture?

❓ What events, what processes, what rituals make the company what it is?

❓ What are we taking away?

That’s where the Chief of Staff comes in. People look to us to set the temperature for the company.

We’re often the bridge between a leadership team that can feel distant and the rest of the organization. In the age of AI, the bridge job has new weight. We’re the ones who translate between speed and sustainability, between adoption and adjustment, between the excitement of new tools and the discomfort that comes with them.

⚠️ What’s At Risk

When we talk about protecting company culture in the face of AI, there are 3️⃣ risks worth watching closely.

1️⃣ Teams Becoming Efficient, But Disconnected

The biggest risk AI poses to culture is silos.

You can see it forming on almost any team that’s gone AI-forward. Engineers are building tools their teammates don’t know about. Ops folks are spinning up email agents in parallel. Three different people are building three different versions of the same workflow agent. AI is great, but it needs direction and purpose.

Letting everyone run wild gets you people going rogue, building things that aren’t actually valuable just for the sake of building them, and 20 versions of what should have been one tool.

The leadership team is just as exposed. Strategic planning is a perfect example, and AI can absolutely make the process more efficient.

But what gets lost is the camaraderie of being a leadership team together. What’s the point of being on a leadership team if Claude is the one calling all the shots? 🤖

AI is only as good as the information you feed it, and there’s a lot it can’t see. It can’t do the accountability chart work, the right person right seat conversation. It can’t capture the context a teammate picked up at a drink with a client last week, or the read on someone who’s been quieter than usual in standup.

Strategic planning should never live solely in Slack or Microsoft Teams. The work that builds a leadership team can’t happen async.

2️⃣ Collaboration And Peer Learning Quietly Disappearing

When team members can ask AI for advice, the work gets done.

What gets lost is everything that used to happen around the work: mentorship, peer learning, the back-and-forth that turns one person’s question into the team’s shared knowledge.

AI doesn’t have context of how a manager solved this same issue two years ago, or what the team learned the hard way last quarter.

There’s a parallel here to “building in public,” the social media strategy where founders share their work openly to grow an audience. The same idea works internally as an operational strategy. When teammates build with AI in private, in their own Claude window or their own DM with the model, the work stays siloed and the learning stays trapped. When they build in public, in a shared channel where their thinking is visible to the rest of the team, the work compounds and others learn from it.

The problem might be solved when someone goes to AI alone. But did they learn anything? Did anyone else? 🤔

3️⃣ People Losing Their Identity

This one is the hardest. In the US, we say, “I am a Chief of Staff.” In Europe, they say, “I work as a Chief of Staff.” Our jobs are our identities.

So when AI starts automating big chunks of someone’s role, it’s not just a productivity question. It’s: “Who am I without these things I’ve been doing every day for the last couple years?” 😬

This hits hardest for the operations and admin folks, the people whose jobs are made up of small daily tasks. Of course we want to automate those tasks. But the person doing them can’t help but ask: if my entire job is automated, why do I still have a job? AI stops feeling like a thought partner and starts feeling like a replacement.

That fear is real, and it is not being talked about enough.

🎯 What We Can Actually Do About It

This is where the role earns its keep. Here’s what Chiefs of Staff can do to protect company culture in the face of AI, starting now.

🫣 Name The Discomfort Out Loud

Most teams aren’t talking honestly about how AI can make people feel irrelevant.

It’s all so exciting, getting more done, having more ideas. But the discomfort is real, and silence makes it worse 🤐

As Chiefs of Staff, we can be the ones who name it. Help people see the human value in how they show up to the workplace, not just the work product they ship. Make sure they know automating the repetitive parts of their job is a good thing because it frees them up for the things AI can’t do. Then make sure those things actually exist for them to do.

📉 Ask What You Lose, Not Just What You Gain

This is the discipline that needs to become muscle memory for every Chief of Staff. Before any new AI tool or workflow gets rolled out, the team should be answering three questions:

1️⃣ If we automate this, what conversation goes away?

2️⃣ If this is replacing a meeting or workflow, who used to be in the room, and what did they bring beyond the work?

3️⃣ What signal was this process giving us that we’ll lose if we automate it and stop questioning it?

Not everything is worth automating. Manual processes still have a time and a place. When we think about onboarding a new employee, new hires can absolutely work through mundane company policies in a self-guided AI tool on their own time, even before their start date. That kind of low-stakes content is exactly what AI is good for. But someone still needs to sit down with every new employee in person to go over what it actually means to work at your company.

A company is only as good as its values, and core values, beliefs, and mission are the foundation of company culture. Those can’t be writing on the wall or part of an AI onboarding flow.

🐎 Rein In Leadership That Wants To Move Faster Than You

Asking the three questions doesn’t mean you’ll get the answers you want. The CEO might still want to ship the AI tool tomorrow. The leadership team might roll their eyes at the culture concern. Two things help.

✅ First, translate culture into operational language.

“I’m worried about culture” doesn’t move a fast-moving CEO. “I think we’ll pay a rework tax because adoption will stall” does. Frame the cultural cost as an operational one. Speed people care about speed. Show them the friction they’ll create by skipping the human work, the time they’ll lose unwinding sloppy rollouts, and the meetings they’ll spend explaining tools that didn’t land.

✅ Second, always beta test.

When you can’t stop a rollout, slow it down. “Let’s run this with one team for two weeks before we go company-wide” almost always gets a yes because it sounds like one. The pilot data will tell the story you couldn’t tell with words. If the pilot goes great, you’ve helped the rollout. If it goes badly, the team sees the friction themselves and you didn’t have to be the one to predict it.

✅ And keep coming back to the 3️⃣ questions.

Drop them into the conversation as a shared team exercise, not your personal objection. The conclusions land harder when the leadership team gets there together.

🫂 Protect The Human Rituals

There are touch points AI can’t replace, and we have to actively protect them.

AI can’t make someone feel special on their birthday. AI isn’t going to remember that someone is thinking about proposing or that someone just bought a new house. Those are conversations that happen during drinks after work, on a walk over a lunch break, or in the car driving to a client meeting. Those moments are what make a workplace feel like one.

A few rituals worth protecting and building:

💫 The segue. Start every meeting with everyone sharing a piece of personal good news and a piece of business good news. It’s an EOS practice. It humanizes everyone and reminds the team that we’re not just worker bees prompting AI all day.

🙋 Monthly show-and-tell. Make space for anyone across engineering, product, marketing, ops, or content to share something they’re working on. Depending on the size of your company, this can be company-wide or team-wide. New product, new content, new metrics, a new app. It humanizes the AI everyone is building. It’s one of the easiest ways to break silos and one of the most reliable culture builders I’ve seen.

🏗️ A dedicated AI build channel. Create a Slack or Teams channel where team members can share what they’re building with AI, test ideas with each other, and get feedback before they ship. This is what building in public looks like internally, and it catches duplicative work before three people have all built the same thing.

💼 Monthly AI office hours. Host them with whoever on your team is leading AI enablement. Open the door for anyone to bring questions, blockers, or half-built ideas. This is especially valuable for the less-technical folks on your team who need a low-stakes way to get up to speed.

🎉 Sharing wins in Slack. Small but it adds up.

In-person interaction matters more than ever 🧑‍🤝‍🧑 Not because we want to spend time together, but because we need to make sure we don’t lose the human elements of what makes a company special. This is harder for remote teams, where the casual moments don’t happen on their own. You have to build them in.

🗝️ Chiefs Of Staff Are The Keepers Of The Culture

It is our job to fight for our culture and protect it at all costs.

It’s easy for leadership teams in fast-moving companies to put blinders on and go all in on AI. You can see what happens when AI tools get rolled out company-wide without real onboarding or thought: adoption stalls, the team gets confused, and the promise of efficiency ends up creating more friction instead of less.

This is where the bridge work matters most. We sit between what’s realistic and what’s not, between leadership and the rest of the team, between the technical folks running ahead with AI and the non-technical folks worried about being left behind.

Our job is to translate between them, to flag what’s at risk, and to fight for the rituals, the conversations, and the moments that make the work mean something.

In the age of AI, that’s not a part of the job. It is the job.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

Save Your Seat Now! ☝

💻 Virtual Events

June 11th: AI for the Chief of Staff: Using Claude to Automate Repetitive Tasks

June 11th: Peer Resume Review

June 16th: Where To Start When Your Boss Says: “Figure out AI”

June 23rd: Chief of AI Strategy: The Playbook for Advising on AI Adoption

June 30th: From Slide Decks to Shipping: What Consulting Didn’t Teach Me

👋🏼 In-Person Events

June 10th: Ask a Chief of Staff x Offsite: Atlanta Community Dinner

June 11th: How a Chief of Staff Operates Across Stage & Scale (Atlanta)

June 17th: NYC Co-Working Day at Industrious

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🛍 Custom Merch That Actually Gets Done

This is a company I personally used to make the totes for this year’s Ask a Chief of Staff Summit, and the whole process was exactly what you’d want it to be: seamless, fast, and zero babysitting required.

If you’ve ever been the person tasked with sourcing swag for an offsite, a team gift, or an event, you know it can eat a week of your life. Wayo made it the easiest line item on the list.

Here’s what you get when you sign up through my link:

👉 7% off your first order — a welcome discount just for being part of this community

👉 Custom merch without the chaos — the kind of vendor experience a Chief of Staff dreams about

👉 Quality that looks intentional — merch that doesn’t read like an afterthought

Whether you’re outfitting a team, planning an event, or just want swag worth handing out, this one’s worth a look.

🎁 Use the link to save on your first order!

Get 7% Off Your Wayo Order

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🤖 How Can Chiefs of Staff Help Their Teams Decide What to Automate with AI?

This week’s newsletter is guest authored by Sarah Sheikh, the Chief of Staff at Loop Financial. She is an operational leader with over 15 years experience in fintech, banking and higher education in Canada, the USA, and the UK, working across teams to drive growth, streamline operations, and in scaling businesses.

Loop Financial is a financial technology company built for Canadian companies that need the same financial tools as the largest global enterprises. Loop provides access to world-class FX rates, real multi-currency accounts, and corporate credit solutions – all within one integrated platform.

When most people think about automation, they think about tools such as Zapier, Retool, AI agents, internal dashboards… the list goes on. But in my experience, the real challenge around automation isn’t a tooling problem. It’s a diagnosis problem 🩺

Teams don’t struggle because they can’t automate. They struggle because they don’t know what’s actually worth automating in the first place.

And as Chiefs of Staff, this is where we have disproportionate leverage; not by building everything ourselves, but by helping teams see their own inefficiencies clearly enough to fix them.

🤖 A note on terminology: when I say “LLMs” (Large Language Models), I mean whatever AI tool your organization approves and uses: ChatGPT, Claude, Gemini, Copilot, etc. The point isn’t the specific tool. It’s using AI as a strategic thought partner during the diagnosis phase, then building the actual solution in whatever tool fits the job.

🔎 Step 1: Teach Teams to Spot Friction (Not Just Work Harder)

Most manual work hides in plain sight. It shows up as:

• Copying and pasting the same information every week

• Chasing people for updates before meetings

• Jumping between tools to piece together a simple answer

• Acting as the “go-between” for systems that don’t talk to each other

⚠️ The problem is, teams normalize this and say things such as “we’ve always done it this way.” They don’t flag it as broken and they just keep doing the manual task.

One of the most valuable things I’ve started doing is pushing teams to ask:

• Where are you repeating yourself?

• Where are you relying on memory for something the business depends on?

• Where are you the bottleneck in a process?

✅ If a task is repetitive, time-sensitive, and slightly painful, it’s more than likely a candidate for automation.

Your job as a Chief of Staff isn’t to spot everything yourself. It’s to teach others how to see it 🔎

👥 Step 2: Make Automation a Team Sport (Not an Engineering Request)

One of the biggest shifts we made was moving away from the idea that automation = engineering work. That is no longer the case with the amount of advancement we’ve seen in tooling that is available to everyone.

For example, at Loop, we ran a growth hackathon internally and opened it up to everyone, and especially to non-engineers, which turned out to be a real success. People didn’t just participate, they built things that were immediately useful, such as:

✨ A sequencing flow that scrapes the internet for lead information and sends personalized outreach

✨ An internal tool that reviews customer product usage and flags upsell opportunities

These weren’t side projects. They were solving real business problems.

💡 The takeaway was simple: The barrier is no longer technical skill. It’s whether people feel empowered to try.

LLMs have fundamentally changed the game here. You no longer need to write production-level code to build something valuable. You just need to know how to break down a problem and iterate.

🧠 Step 3: Shift the Focus from “Tools” to “Thinking”

There’s a lot of noise right now around which tools to use or whether to use them at all for fear that you will “AI” yourself out of a job. In reality, the people who get the most out of LLMs aren’t the ones using the “best” tools. They’re the ones asking better questions and iterating faster.

✅ What I’ve found works:

• Start messy and definitely don’t wait for a perfect spec; just getting started is the key

• Break the problem into smaller steps

• Treat the LLM like a collaborator, not a one-shot answer machine

• Keep refining until it’s useful

🗣️ This is a mindset shift. “Prompting” isn’t a technical skill but rather a structured way of thinking.

And once teams understand that, they move much faster.

👉 Step 4: What This Looks Like in Practice

To make this real, here are a few things I’ve built myself and enabled across the team:

🗓 A compliance calendar that automatically reminds teams when key reports are due and removing the need to rely on memory or last-minute scrambling

🗃️ Retrieve historical documents and attachments from multiple inboxes dating back to 2018; something that would have taken hours (if not days) manually

📊 A lead qualification tool for the sales team to quickly assess whether a prospect fits our ICP, reducing time spent on low-quality leads

📃 Trend reports for LinkedIn to showcase our thought leadership positioning specifically targeted to our ICP

🤔 None of these required engineering and I built them on my own in between meetings. They came from identifying a friction point and asking: “What can I do to improve this current way of working?”

🔗 Step 5: Embed the Capability Where the Work Happens

An effective decision I made recently was moving a Business Operations team member to work closely with Operations specifically on automating their manual processes.

🎯 BizOps profiles are uniquely suited for automating processes because:

• They understand the business context

• They’re comfortable across tools and functions

• They can translate problems into workable solutions

Instead of centralizing all automation efforts, we embedded the capability directly within the team.

✅ The result:

• Faster iteration

• More relevant solutions

• Less dependency on a single “owner” of automation

💪 The win wasn’t the tools. It was putting the capability where the work actually happens.

🧑‍💼 Step 6: Your Role as a Chief of Staff

At the end of the day, this isn’t about becoming the most technical person in the room, but rather raising the baseline across the organization. I am a very strong believer in leading by example.

As a Chief of Staff, your role is to:

🩺 Help teams diagnose where they’re wasting time

😌 Create environments where people feel safe to experiment and build

💡 Encourage a mindset of working smarter, not just harder

❌ Reinforce that iteration is part of the process, not a sign of failure

This can feel daunting at first, but the reality is that with LLMs today, most of this is entirely doable.

❓ The most important thing is to start asking the right questions, and keep iterating.

💭 Pulling It All Together

Automation is no longer a technical advantage. It’s an operational one. The companies that move fastest won’t be the ones with the most engineers. They’ll be the ones where everyone knows how to identify inefficiencies and do something about them.

As Chiefs of Staff, we’re in a unique position to drive that shift. Not by building everything ourselves but by turning teams into builders.

And that’s where the real leverage is.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

Save Your Seat Now! ☝

💻 Virtual Events

May 28th: Anatomy of a Great Board Meeting with Edward Norton (free but space is limited!)

June 2nd: Communicating Your Value as a Generalist

June 4th: Strategic Planning: Build and Execute Annual and Quarterly Plans That Actually Work

June 9th: From the C-Suite to Founder — Using the CoS Role as a Launchpad

June 11th: AI for the Chief of Staff: Using Claude to Automate Repetitive Tasks

June 16th: Where To Start When Your Boss Says: “Figure out AI”

June 30th: From Slide Decks to Shipping: What Consulting Didn’t Teach Me

👋🏼 In-Person Events

May 27th: Boston Chief of Staff Happy Hour 🥂

May 27th: DC Happy Hour 🎊

June 3rd: How Chiefs of Staff Build Knowledge Systems That Scale — NY Tech Week Panel 🎤

June 4th: NYC Chief of Staff Happy Hour 🥂

June 10th: Ask a Chief of Staff x Offsite: Atlanta Community Dinner

June 11th: How a Chief of Staff Operates Across Stage & Scale (Atlanta)

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 16,000+ Chiefs of Staff who trust us for actionable insights.

🚨 Don’t Miss Us at Boston & New York Tech Week!

Tech Week is one of my favorite times of year! And this spring, Ask a Chief of Staff is showing up again in a big way. We have two panels and two happy hours across Boston and New York, and I would love to see you there! 💜

📍 Boston Tech Week (May 26-31)

🎤 How Chiefs of Staff Grow & Scale | Tuesday, May 26, 6–8pm

Co-hosted with Industrious. A panel conversation about what it actually looks like to expand your scope, build leverage, and evolve with your organization as it scales. Real talk, real examples. RSVP here.

🥂 Boston Chief of Staff Happy Hour | Wednesday, May 27, 6–8pm

Skip the small talk and come meet people who actually get the role. Good conversation, good company. RSVP here.

📍 New York Tech Week (June 1-7)

🎤 How Chiefs of Staff Build Knowledge Systems That Scale | Tuesday, June 3, 6–8pm

Co-hosted with Notion. A deep dive into how high-performing Chiefs of Staff design systems that keep teams aligned, informed, and moving fast. RSVP here.

🥂 NYC Chief of Staff Happy Hour | Wednesday, June 4, 5–7pm

Co-hosted with The Malin. Same energy as Boston, different skyline. RSVP here.

Full Tech Week Calendar

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

👶 What Does Your Company's Parental Leave Policy Really Say About Its Culture?

This week’s issue is guest authored by Ellise McDonald, Chief of Staff and certified EOS Integrator^TM at a Series C company where she has spent nine years building systems, shaping culture, and integrating all the moving parts. A Brown University graduate with a background in public health, Ellise brings a human-centered lens to operations and strategy. She also serves as an Ask a Chief of Staff Mentor.

Returning from parental leave changes more than your schedule. It changes how you see work, how you prioritize, and how company policies really impact families.

Parental leave is one of the clearest signals of how a company actually supports the people who work there.

Let me explain.

About a year ago, I returned from maternity leave and hosted a small fireside chat called From Strategy to Sippy Cups. What started as a casual conversation about returning to work quickly turned into something deeper. We ended up talking about how parental leave policies shape families, careers, and company culture in ways that are often invisible until you experience them yourself.

Before becoming a parent, I understood parental leave mostly as a benefit. It was a line item in a handbook or part of a recruiting conversation. After living through it, I realized it is much more than that.

📋 Policy vs. Reality

One of the first things that came up during that fireside chat was the imbalance that often exists between maternity and paternity leave.

In many workplaces, mothers receive longer leave while fathers or non-birthing parents receive only a few weeks. Even when policies appear generous, culture sometimes tells a different story.

My husband experienced this firsthand when we lived in Massachusetts. The state offers Paid Family and Medical Leave that allows parents to take up to twelve weeks after the birth of a child. On paper, that meant he could have taken significantly more time. In practice, his company only offered two weeks of paternity leave. The rest technically existed through the state program, but taking it would have felt risky for his role and reputation. Like many fathers in that situation, he took the two weeks and returned to work.

Policies exist, but cultural signals determine whether people feel safe using them.

There is often an unspoken fear that taking the full leave available to you could quietly impact how you are perceived, the opportunities you are given, or how quickly you are trusted with critical work again. Nothing about that experience was unusual.

🌍 A Global Perspective

Another lens that often changes the conversation is looking beyond the United States.

Our team has colleagues in Montreal, and parental leave there looks dramatically different. In Canada, many parents can take close to a year of leave. In the United States, twelve weeks is often considered generous. Even that is not guaranteed for everyone. Some workers rely on saved PTO to cover their leave. Others take unpaid time away from work.

The comparison is not about saying one system is better than another. It simply highlights how much of the responsibility often falls on individual families to figure out how to make it work.

💼 The Return to Work Reality Check

The biggest lesson for me came after returning to work.

Before having children, I remember noticing a group of parents who were often back online later in the evening. After bedtime routines were finished, emails would start moving again and messages would pop up. Sometimes it was catching up on work from earlier in the day. Other times it was simply the reality of leadership roles that do not always fit neatly into a nine-to-five schedule.

After becoming a parent, I understood that rhythm much better. Many people are balancing competing priorities throughout the day and then finding pockets of time to finish what needs to get done.

I came close to falling into that pattern myself. I remember a stretch of a few nights in a row where I logged back on after bedtime to catch up. By the third night, I paused and thought: this cannot become my normal.

There are seasons when late nights are unavoidable, and leadership roles sometimes require it. But one thing I realized during parental leave is that evenings had become something I wanted to protect. After a full day, reading bedtime books and winding down with family became an important way to reset.

For me, that meant focusing more during the day so that logging back on at night became the exception rather than the rule.

Work had always been a huge part of my identity. In many ways it felt like my first baby. Then my actual baby arrived and quietly reordered my priorities.

The shift was both disorienting and clarifying. For the first time, I felt a real need to put guardrails around my time. I became more intentional about how I spent my day, more focused on what actually moved things forward, and less willing to let work expand into every open space.

It also changed how I thought about my role. Instead of being in the middle of everything or constantly firefighting, I started thinking more about how to build systems that could run smoothly even when I was not there.

My job is still important. But it is no longer the center of everything.

💛 If You’re In It Right Now

If you are reading this while preparing to go on leave, or just coming back from it, this part is for you.

One of the hardest things to accept is that the job and the company will move forward with or without you. Decisions will be made. Priorities will shift. New dynamics will form. And when you return, there may be moments where you feel out of sync or like you missed more than just time.

That feeling is real. And it is more common than people talk about ❤

There can also be a quiet pressure to stay close to work while you are out. To check in. To keep context. To not fall behind. But what I wish someone had told me is that this time is finite, and it matters in a different way than anything happening at work.

You will rebuild context. You will find your rhythm again.

The time with your child, the time to recover, and the space to step fully away is harder to get back.

✨ The Quiet Influence of Chiefs of Staff

This is where Chiefs of Staff often play an unexpected role.

We are not always the ones writing formal HR policies. But we are often in the room when leadership teams discuss benefits, productivity, and culture. We see how policies are interpreted in practice.

That proximity gives Chiefs of Staff a quiet kind of influence.

I was reminded of this after the fireside chat, when a soon-to-be dad reached out to me. He asked a simple question on the surface: should he take all of his paternity leave at once, or split it up?

But underneath that question was something else. He was trying to understand what was actually safe to do. What would be supported. How it might be perceived.

It was not really a policy question. It was a culture question.

Moments like that are where Chiefs of Staff can have an outsized impact. Sometimes it is not about rewriting a policy. It is about helping leaders recognize the signals they are sending, and helping individuals navigate the space between what is written and what is practiced.

The most meaningful changes often start by paying attention to those moments and asking what they reveal. Over time, patterns emerge around who takes leave, how long they take, and how supported they feel when they return.

And those patterns say far more about a company’s culture than any policy ever will.

Whether you are the one heading out on leave, just finding your footing on the way back, or the person in the room when these decisions get made, you have more influence than you might think. The culture around parental leave does not change all at once. It changes one conversation, one exception, one moment of paying attention at a time.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

Save Your Seat Now! ☝

💻 Virtual Events

May 14th: AI for the Chief of Staff: Using Claude to Automate Repetitive Tasks

May 19th: How To Scale AI In Your Organization — From Pilot Projects To Embedded Operating Systems

May 21st: Using Claude Code to Build Dashboards

May 28th: Anatomy of a Great Board Meeting with Edward Norton (free but space is limited!)

👋🏼 In-Person Events

May 20th: NYC Co-Working Day at Industrious

May 21st: DC Happy Hour 🎊

May 26th: How Chiefs of Staff Grow & Scale — Boston Tech Week Panel 🎤

May 27th: Boston Chief of Staff Happy Hour 🥂

June 3rd: How Chiefs of Staff Build Knowledge Systems That Scale — NY Tech Week Panel 🎤

June 4th: NYC Chief of Staff Happy Hour 🥂

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

THANK YOU for being a premium subscriber to Ask a Chief of Staff 💜

📹 Member Exclusive Recording - This is a previously recorded workshop from our archive, available exclusively to paid members. Free subscribers can preview the content below, then upgrade to watch the full workshop.

Being a Chief of Staff already means running on caffeine, calendar Tetris, and “I’ll figure it out as I go.” Add a kid (or two) into the mix, and suddenly you’re orchestrating cross-functional initiatives between sippy cup refills and trying to remember when you last washed your hair.

This fireside chat with Ellise McDonald isn’t a polished presentation. It’s a real conversation about the messy middle: the meetings with babies wrapped to your chest, the dinner logistics that fall apart, the parental leave guilt, returning to work running on fumes, and how Chiefs of Staff can actually shape leave policies and parent-friendly culture from the inside. If you’re a Chief of Staff and parent, this one’s for you.

Bring your coffee. We see you ☕🤗

🧑‍🏫 About the Speaker

Ellise McDonald is the Chief of Staff and certified EOS Integrator^TM at a Series C company where she has spent nine years building systems, shaping culture, and integrating all the moving parts. A Brown University graduate with a background in public health, Ellise brings a human-centered lens to operations and strategy. She also serves as an Ask a Chief of Staff Mentor.

Recently returned from her second maternity leave, Ellise brings an unfiltered perspective on integrating high-stakes leadership responsibilities with the realities of parenting young kids, including a cross-country move, building support systems, and learning to embrace the chaos of meetings, milk spills, and missed sleep.

📚 About the Workshop

This isn’t a workshop in the traditional sense. It’s an intimate fireside chat that turns into a peer support session. Ellise shares her own story of returning from maternity leave with two under two, then opens the floor for community members to swap real strategies, vent about common challenges, and share what’s actually working.

Topics range from time-blocking and division of labor at home to navigating parental leave policies, advocating for working parent benefits, and modeling boundaries that help shift workplace culture for everyone.

💡 Key Takeaways You’ll Learn:

The Real Talk on Returning from Leave

• Why coming back can actually sharpen your focus (even running on fumes)

• Building support systems that let you do your job and parent

• How small visible choices—like putting “daycare pickup” on your calendar—shift workplace culture

Navigating Parental Leave

• The wide variation in policies and how to advocate for what you need

• Why partners taking their full leave matters (and how to support them in doing it)

• Whether to take that sabbatical when you’ve already taken parental leave

The Division of Labor at Home

• Practical dinner logistics from real families (the part most resources skip)

• Why tag-teaming often beats one person owning the whole process

• Resources like Eve Rodsky’s Fair Play for rebalancing the mental load

Real Questions from Parents

• What books actually help prepare you for parenthood?

• How do you handle stakeholders when you have a sick kid at home?

• What are other Chiefs of Staff parents really doing for childcare, dinner, and bedtime?

⭐ Want to Take Your Membership to the Next Level?

Whether you’re a current or aspiring Chief of Staff, I invite you to check out the Ask a Chief of Staff community. We’re now 4️⃣ 5️⃣ 0️⃣ ➕ members strong, helping Chiefs of Staff navigate their careers through:

💬 Members-only Slack workspace for peer support & real time question answering

🖥 Exclusive workshops & events (virtual & in-person)

🤝 A supportive network of peers facing similar challenges

🧑‍💼 Direct access to experienced Chiefs of Staff and mentors

🌟 Curated job opportunities from leading companies

🙌 Resources and frameworks for immediate impact

Visit our website and click the “Join our community” button to start your journey!

Join Now

Read more

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 15,000+ Chiefs of Staff who trust us for actionable insights.

🎉 Your Cinco de Mayo Party Is Sorted. What About Your Company Retreat?

As a Chief of Staff, retreat planning often lands squarely on your plate. Venue research, vendor coordination, logistics, budget wrangling. All on top of everything else you’re already managing.

Offsite is the go-to resource for any Chief of Staff planning a team retreat. Their Airbnb-style marketplace gives you access to thousands of curated venues and vendors globally, with up to 50% off room blocks and meeting space. Prefer a hands-off approach? Their end-to-end planning services handle everything for groups of 20 to 1,000+ attendees.

Trusted by Perplexity, HubSpot, Remote, Buffer, and hundreds of companies across 25+ countries. Flat per-person pricing. Zero hidden fees.

👉 Ready to get your team together? Book a free discovery call with the Offsite team.

Book a Free Call

Disclosure - I’m an angel investor in Offsite, but only because I wish something like this existed when I was a Chief of Staff planning team retreats at Hugging Face and AngelList!

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🧐 Are You Using Claude to Its Full Potential… or Just as a Search Engine?

Most people I know are using Claude like a smarter Google.

Ask a question, get an answer, close the tab. Maybe paste in a document and ask for a summary. Maybe use it to rewrite an email. That’s it. And for a lot of people, that’s fine.

For a Chief of Staff, it’s not fine. It’s a waste 🗑️

The Chief of Staff role is fundamentally about managing complexity across multiple work streams, people, and priorities at once. That’s not a one-prompt-at-a-time problem. And if you’re still using Claude that way, you’re leaving most of its value on the table (and likely running out of messages before you can finish a project).

⏳ Even power users are hitting Claude’s usage limits right now and concluding they need to use it less or spread across tools. But that’s the wrong fix. The problem isn’t how much you’re using it. It’s how you’re using it.

Most Chiefs of Staff are using about 10% of what Claude can do. Let’s talk about the feature that unlocks the rest: Cowork.

🤝 What Is Claude Cowork?

Cowork is Claude as an autonomous AI assistant. You give it a multi-step task, it works through each step sequentially, checks in before making any changes, and connects to your tools to get things done.

The difference from regular Claude: you stop prompting and start delegating. You describe the outcome, and it figures out how to get there.

💡 One thing worth knowing: Cowork lives in the Claude desktop app, not the browser. It’s a free download at claude.com/download and is included on Pro and up paid plans. Once you’re in, you’ll see Cowork as its own tab alongside Chat. Connect your tools (Mail, Calendar, Granola, Notion, whatever you use) and it can pull live context from the places your work actually lives.

Here are 3️⃣ use cases for what that actually looks like in practice 👇

✅ Use Case: The Deadline I Almost Missed

Last week I nearly blew a deadline for a video submission that I needed to submit for a pitch day. In the past, I would have caught it Friday, panicked, and scrambled to get it done while traveling.

📆 My Monday Morning Digest caught it first.

The Monday Morning Digest is a Cowork skill I built that runs every week without me having to think about it. It pulls from my Google Calendar, Granola meeting notes, and email, and gives me a pre-meeting intelligence briefing for every 1:1 I have that week (context from the last interaction, open threads, suggested talking points, decisions to push toward). It also surfaces anything time-sensitive I might otherwise miss.

That’s what caught the pitch video deadline. Not me scanning my calendar manually. Cowork, connected to my tools, doing the job before I even opened my laptop 👀

I also run a Friday Wrap-Up the same way. It scans the week, flags what’s still open, and means I can actually close my laptop on Friday without that nagging feeling I’ve dropped something.

✨ Both are triggered automatically with a single phrase in Cowork.

Keep reading to get the guide that contains the exact steps for setting your own Monday Morning Digest and Friday Wrap-up 👇

✅ Use Case: Personalized Slack Messages in Minutes

One of our community members, Casey Boyles, shared this in our Slack and I haven’t stopped thinking about it since.

She was running an event and needed to coordinate interview times with nine different people. She gave Cowork the email addresses, it matched them to their Slack handles, drafted nine personalized messages, and let her review and edit each one before hitting send—all inside the Claude desktop app.

No copying and pasting needed. 4️⃣ minutes. 9️⃣ messages out the door 😯

✨ This is what “connecting to your tools” actually means. Not pulling a summary, but executing a workflow.

✅ Use Case: The 9:30am Habit That Keeps Things from Falling Through the Cracks

Another community member, Aisling Douglas, set up a daily task at 9:30am where Cowork crawls her emails, Granola, and Slack and gives her a rundown of all the things she committed to.

Her words: “I LOVE Cowork” 💜

She also has it update a shared to-do list with her executive partner inside Slack. He dislikes adding more tooling or more places to log in, so surfacing it where he already lives means he stays in the loop without any extra friction.

✨ One daily habit. Nothing falls through the cracks. Her executive is always informed.

🙋 Want the Full Setup?

The skill files that power my Monday Morning Digest and Friday Wrap-Up are in my free Notion guide. They’re copy-paste ready, with full setup instructions. You upload them to your Claude Project once, and from then on you trigger them with a single phrase in Cowork.

The guide covers 5️⃣ Claude features every Chief of Staff should be using: Personal Preferences, Projects, Cowork, Skills, and the Chrome Extension. It also includes my exact copy-paste Personal Preferences setup and a full Prompt Library organized by Culture, Operations, and Strategy.

Grab it here 👉 The Chief of Staff Guide to Claude

Save it. Come back to it. And if you’re already using Cowork in a way that’s changed how you work, reply and tell me. I read every response!

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

April 30th: The Nonprofit Chief of Staff Exchange: A Peer Roundtable

April 30th: Scaling Teams and Organizations

May 5th: Being A Chief of Staff In 2026: What’s Changed, What Hasn’t, What Matters Now (presented by Offsite)

May 12th: How Chiefs of Staff Move a Room Through Constant Change

May 19th: How To Scale AI In Your Organization — From Pilot Projects To Embedded Operating Systems

👋🏼 In-Person Events

April 29th: Chicago Community Dinner

April 30th: Chicago Happy Hour

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

THANK YOU for being a premium subscriber to Ask a Chief of Staff 💜

📹 Member Exclusive Recording - This is a previously recorded workshop from our archive, available exclusively to paid members. Free subscribers can preview the content below, then upgrade to watch the full workshop.

Here’s an uncomfortable truth: most companies don’t have a crisis plan until they desperately need one. And by then, it’s too late to think clearly, move quickly, or communicate with the nuance the moment demands.

As Chiefs of Staff, we’re often the ones who end up in the war room when things go sideways, whether it’s an internal HR issue, a product problem, or a social media firestorm. This workshop with crisis comms expert Kelly Voelker gives you a complete framework (the S.T.E.P.S. method) to build your organization’s crisis muscle before you need it, so when something inevitably breaks, you’ve got a well-oiled machine ready to activate instead of a panicked committee trying to figure out who’s on first.

🧑‍🏫 About the Speaker

Kelly Voelker is a seasoned communications professional with more than 2️⃣0️⃣ years of experience helping organizations navigate the most complex communications challenges. In 2014, she founded KVA, an agency that specializes in crisis communications, corporate and employer branding, and leading during times of change and transformation.

Since then, KVA has been a trusted thought partner to brands across industries, providing strategic guidance, supporting full-scale execution, and making the process of communicating to every stakeholder easier.

📚 About the Workshop

Kelly shares her practical, tactical playbook built from over two decades of real-world experience, walking you through her S.T.E.P.S. framework with concrete examples, templates, and scripts you can actually use. You’ll leave knowing exactly what to put in place now so that when (not if) a crisis hits, you can act decisively instead of reactively.

The workshop includes real case studies, downloadable checklists, and extended Q&A covering internal crises, managing external experts, and getting alignment from leadership teams who disagree on whether something even is a crisis.

💡 Key Takeaways You’ll Learn:

The S.T.E.P.S. Framework for Crisis Preparation

• Scenario Planning: How to map your biggest risks and focus your prep where it matters most

• Team: Building your bench of experts (and why the CEO shouldn’t be point person)

• Early Warning System: Tools and tactics for catching issues before they become crises

• Process: The checklists, timelines, and protocols that let you move fast under pressure

• Strategic Response: How to build trust when stakes are highest

The First 24, 48, and 72 Hours

• What you need to know immediately when a crisis breaks

• How to assemble your team and gather accurate information fast

• When to respond publicly, and when silence is the right call

• How to manage recovery and watch for second waves

The Anatomy of a Holding Statement

• The key components every statement needs (acknowledgment, empathy, commitment)

• Why making promises you can keep builds more trust than big declarations

• Templates you can draft now and adapt when needed

Internal vs. External Crises

• Why internal crises require even deeper audience mapping

• How rumors flow through organizations and how to get ahead of them

• Managing the political dynamics of sensitive internal communications

Getting Leadership Aligned on What Even Counts as a Crisis

• The red/yellow/green framework for crisis classification

• How to build business-case arguments for crisis prep with skeptical leaders

• Setting protocols for escalation before you need them

Managing External Experts Under Pressure

• How to balance outside counsel with internal knowledge

• Pushing hard conversations ahead of time so you’re not debating in the heat of the moment

• When to trust expert guidance vs. trust your team’s ground truth

⭐ Want to Take Your Membership to the Next Level?

Whether you’re a current or aspiring Chief of Staff, I invite you to check out the Ask a Chief of Staff community. We’re now 4️⃣ 5️⃣ 0️⃣ ➕ members strong, helping Chiefs of Staff navigate their careers through:

💬 Members-only Slack workspace for peer support & real time question answering

🖥 Exclusive workshops & events (virtual & in-person)

🤝 A supportive network of peers facing similar challenges

🧑‍💼 Direct access to experienced Chiefs of Staff and mentors

🌟 Curated job opportunities from leading companies

🙌 Resources and frameworks for immediate impact

Visit our website and click the “Join our community” button to start your journey!

Join Now

Read more

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 15,000+ Chiefs of Staff who trust us for actionable insights.

This week’s newsletter is brought to you by Ambient, a context engineering platform and consultancy for teams looking to go AI-Native. Ambient replaces the manual work teams do to organize their meetings, messages, and documents, so your Claude / ChatGPT / Gemini can work at their best. Schedule a free consultation with the Ambient founders HERE.

Book a Free Consultation

Disclosure - I’m an advisor for Ambient and they also sponsored this newsletter, but I genuinely believe this tool would have been valuable when I was serving as a Chief of Staff.

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

👀 Is Your Operating Model Holding Your AI Back?

This issue is guest authored by Lawrence Coburn, CEO / Co-Founder at Ambient, an AI-powered consultancy for leadership teams looking to go AI-Native. A four-time founder, Lawrence has spent the last two years speaking with hundreds of leadership teams about AI adoption, and what actually separates the companies getting real results from the ones still tinkering.

Recently, Jack Dorsey and Sequoia’s Roelof Botha published a piece arguing that companies don’t just need to change their tech and behaviors for the age of AI, but they actually need to reinvent the org chart.

🗣 Their argument: Today’s org charts are mostly a relic of humanity’s limitations, designed to pass information and context up and down the hierarchy.

Block, Dorsey’s company, is reorganizing itself as an “intelligence,” where AI replaces what the management hierarchy was built to do: route information, maintain context, and coordinate across teams. Middle management, a layer that was invented as a conduit to push updates up and strategy down, becomes obsolete. Human roles get morphed into one of three archetypes: builders, owners, and player/coaches, all working in the “places the model can’t go.” The keeper of the company’s knowledge becomes the AI.

🤔 It’s a provocative vision. And directionally, I think they’re right.

But here’s what I know from spending the last two years in the trenches with leadership teams, conducting over 400 interviews with C-suites about their AI posture: almost no company is set up to get there overnight.

There is simply too much change management in the air: new tech, new skills, new behaviors. The gap between what AI can do and how companies actually operate is enormous.

But the bottleneck isn’t your tools. It’s your operating model and behaviors.

And there’s one person in your org already equipped to help fix that: the Chief of Staff.

🧠 AI Effectiveness Is a Context Problem

There is a fundamental law of the AI era that most companies have not internalized: AI impact is directly proportional to the context it receives.

For single-player tasks, context engineering is easy. Your Claude or ChatGPT can see what you can see: your calendar, your email, your docs. But it gets trickier for teams.

Context is the raw material that powers AI’s ability to reason, synthesize, and act on behalf of your team. And right now, most companies make it nearly impossible for AI to access the context it needs to deliver team-based gains.

Where is context leaking in most organizations?

• Strategic thinking is locked in the CEO’s head, shared through private texts and one-on-ones that no system can access

• Decisions get made verbally in meetings and never documented

• Updates travel through hierarchies like a game of telephone

• Communication is fragmented across Slack DMs, email threads, text messages, and four or five different note-taking apps

• Critical institutional knowledge walks out the door every time someone leaves

This isn’t a tech problem. You can deploy the most advanced AI tools on the planet and they will underperform if your organization is not set up to feed them the context they need.

💭 I recently spoke with a Chief of Staff whose company is anti-recording (at the advice of counsel) and where critical project updates are often communicated over text. Unless behaviors and norms change at that company, AI simply cannot help, and they will continue operating like it’s 2023.

🥱 The Unsexy Work Is the Real Work

The companies getting genuine results from AI are not the ones with the fanciest tools. They’re the companies doing the boring operational groundwork that makes AI effective.

💭 One of my investors recently told me about the founder of a $400M company who was walking around asking his AI lead, “What should I name this document?” That is not a trivial question anymore. Every piece of metadata, every channel name, every meeting subject line is a signpost for an AI system trying to navigate your company’s knowledge. Naming conventions are now mission-critical.

💭 Another team I work with demonstrated that a task requiring four hours of manual context-gathering was completed in twelve minutes. The AI did nothing magical. The operating model made the magic possible because all the necessary inputs already existed in organized channels and recorded meetings.

🙄 And don’t even get me started on token consumption. If you lazily ask Claude to ask across the History of Everything to give you an update on a project, you are going to burn through your tokens lickety-split. Somebody needs to do the work to point your AI to the right neighborhood.

Here’s what separates companies that get real AI value from those still tinkering:

🎙️ They record everything by default. The AI assistant stays in the room unless there’s a specific, justified reason to remove it. Meetings are a chance to memorialize your smartest team members’ experience, perspectives, and thinking. (Do you ever find yourself waiting to start a meeting until the AI assistant has been admitted? Yeah, me too.)

📁 They organize context around projects and relationships. One Slack channel per initiative. One channel per key client. Recurring meetings mapped to their corresponding channels. No orphaned communication floating in general channels or DMs.

🚫 They kill the status meeting, and double down on brainstorms. AI can do your status updates, async, better than you can. But brainstorms become more important than ever as a way to memorialize knowledge and thinking.

🛠️ They standardize tools at the team level. The “everyone picks their own tools” era is mostly over. When a company runs five different note-taking apps, you lose shared memory. Each tool becomes a silo. A unified context layer is now a strategic asset.

✏️ They communicate with machine-readable clarity. Instead of “let’s circle back on that deck sometime soon,” they say “I will complete the draft by Friday, February 14th.” What’s good for AI turns out to be good for humans. More clarity means better alignment and better accountability.

🔇 They eliminate the backchannel. Work updates don’t belong in side conversations or informal texts. Companies with transparent, documented cultures will be the winners in this next chapter.

None of this is glamorous. None of it requires technical sophistication. But it’s really hard. It requires top-down leadership, discipline, and the willingness to change behaviors that feel comfortable but are now holding your company back. The hardest part? The execs themselves are often the ones most in need of changing.

❓ Who is equipped to change behavior and operating models at the organizational level? It’s a very short list: CEO. Chief of Staff. Maybe COO or President. And the stakes are getting higher by the day.

🗂️ The Org Chart Can Wait (A Little)

Dorsey and Botha are making a claim that goes well beyond “change your behaviors to unlock AI gains.”

They are arguing that the org chart itself, the hierarchical structure that every company on earth partially inherited from the Roman army, was designed around human strengths and human limitations at the time, and is no longer relevant.

🧮 The old math: Humans can only manage so many people. Humans can only hold so much context. So we built layers. Managers to route information. Middle management to coordinate across teams. Staff functions to synthesize and report.

🤖 AI changes the math on all of that: When a system can maintain a continuously updated model of an entire business, the rationale for many of those layers weakens. Companies will get flatter. Roles will be redesigned for an AI-centric workplace. The traditional org chart, optimized for a world where humans were the only coordination mechanism, will evolve into something we’d barely recognize today.

🧭 I believe this is where we’re headed. But we’re not going to get there overnight.

The good news: there’s no shortage of places to start. The behavioral changes above, like recording by default, organizing context, standardizing tools, and communicating with precision, make AI effective today and lay the groundwork for the deeper structural transformation that’s coming.

Org charts can morph gradually over time to reflect the work. Too much change at once is difficult for any company to digest.

🎯 The Chief of Staff as the Bridge

Someone has to get your company from here to there. And the Chief of Staff is uniquely positioned to be that person.

Think about it. The Chief of Staff is already the human version of what AI wants to be 🤯

They’re in every room. They connect the dots across functions and keep tabs on key initiatives. Through a combination of access and judgment, they fill in the blanks that nobody else sees. They hold context across the entire organization. They already understand the information flows, the political dynamics, and the gap between how a company thinks it operates and how it actually does.

The Chief of Staff becomes the context engineer, and the final boss Human in the Loop. The person who:

✅ Audits where context is leaking

✅ Drives behavioral changes around recording and communication norms

✅ Configures AI systems to reflect how the team actually operates

✅ Serves as the human in the loop where judgment still matters

Over time, as AI takes on more of the coordination work, the Chief of Staff is the one guiding the organization through the structural changes that follow. Which roles evolve. Which layers compress. Where humans still need to be in the loop, and where they don’t.

This is a specialized form of change management, not software deployment. And it is the hardest part.

💭 Every operator I’ve talked to who has tried to install a new operating model says the same thing: the volume of questions from teams about where to put updates, what to name channels, which doc goes where, who owns the setup… there’s a whole layer of coordination and operational rigor that most companies under a thousand employees have never built.

🔮 I go back and forth between thinking of the Chief of Staff of the future as “Chief Human in the Loop” or “Chief Context Engineer.” The answer is probably both.

Dorsey and Botha wrote about the destination. It’s clear to me that the Chief of Staff is going to be a critical player in building the road to get there.

Most of the world is still debating whether to record their staff meetings. The window is open, and the person best positioned to drive this transformation is already in the room.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

April 16th: AI Tactics That Work

April 21st: Spring Job Search Reset (A Two-Part Workshop Series)

April 30th: The Nonprofit Chief of Staff Exchange: A Peer Roundtable

April 30th: Scaling Teams and Organizations

May 5th: Being A Chief of Staff In 2026: What’s Changed, What Hasn’t, What Matters Now (presented by Offsite)

👋🏼 In-Person Events

April 16th: DC Happy Hour 🎊

April 20th: RESCHEDULED FROM FEBRUARY: Ask a Chief of Staff Summit: NYC 2026 🗽🍎

April 22nd: Ask a Chief of Staff x Generalist World NYC Happy Hour

April 30th: Chicago Happy Hour

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 14,000+ Chiefs of Staff who trust us for actionable insights.

🦁 Tame Your LinkedIn DM Chaos with Kondo

If your LinkedIn inbox has turned into a second job, you’re not alone. As a Chief of Staff, every DM could be a client, a partnership, or a warm intro you really don’t want to miss.

That’s why I started using Kondo. It’s like Superhuman, but for your LinkedIn DMs. It makes your inbox actually operational instead of just overwhelming.

A few features I’ve found especially useful:

📥 Split inboxes: Triage by priority so you’re always focused on what matters most

🔔 Reminders & snooze: Resurface conversations exactly when it’s time to follow up

⚡ Snippets & keyboard shortcuts: Move through your inbox without touching your mouse

🏷️ Tags, labels & notes: Keep context organized across candidates, partnerships, and community convos

🔗 Cross-workflow sync: Connect your LinkedIn DMs to your larger operating system

🎁 Ask a Chief of Staff readers can try Kondo free for one month.

Try Kondo Free

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

💼 So, What Does a Series C Chief of Staff Actually Do?

In earlier newsletters, I interviewed 4️⃣ Series A Chiefs of Staff and then 4️⃣ Series B Chiefs of Staff to map how the role evolves as companies grow. The most consistent follow-up question from both issues: “What happens at Series C?”

Series C is a fascinating inflection point. The scrappy startup energy hasn’t fully disappeared, but the pressure to scale sustainably, build repeatable systems, and prepare for what comes next (an IPO, an acquisition, continued growth, etc.) is very real. The Chief of Staff role at this stage reflects all of that complexity.

For this issue, I interviewed 4️⃣ Series C Chiefs of Staff to highlight the common threads and meaningful differences in the role at this stage.* Our panelists:

• Nicole Schultz (NS) — Chief of Staff at Medcrypt

• Alex Mangum (AM) — Former Chief of Staff at Atlas Obscura

• Amy Healey (AH) — Chief of Staff to the President at Pelago

• Eve Lechowicz (EL) — Chief of Staff for Business Operations at Loft Orbital

*Answers have been edited for length and clarity.

1️⃣ Tell me about yourself and where you are a Chief of Staff

NS: We had just closed Series B and were starting our growth trajectory when I joined as employee number 20. Over the following eight months, I hired employees 21 through 50. Medcrypt helps healthcare technology companies ensure medical devices are secure by design, providing cybersecurity products and strategic consulting to help medical device manufacturers bring life-saving connected technologies to market.

AM: Atlas Obscura started its Series C fundraise about six months after I joined as approximately employee number 60. Atlas Obscura is a travel media company dedicated to exploring the world’s hidden wonders.

AH: When I joined Pelago, we had just raised our Series A. I came on board as employee number 31, originally as one of the regional Vice Presidents of Sales. Pelago is the world’s leading virtual clinic for affordable and accessible substance use management, delivering evidence-based, virtual care through partnerships with employers, health plans, and pharmacy benefit managers.

EL: I joined Loft Orbital right as the company closed its Series C. The round was announced about six weeks after I started, which gave me the chance to help lead the announcement. I came in at around the mid-200s in employee count. Loft Orbital makes space simple: we provide a fast, reliable path for customers to deploy their missions by integrating, launching, and operating spacecraft end-to-end.

2️⃣ Tell me about your background and how you moved into a Chief of Staff role

NS: I started as an EA at small startups where the role was often undefined, which gave me room to take on larger projects over time. I eventually worked into CoS roles and did fractional CoS work, which helped me become fairly industry-agnostic. This is not my first Chief of Staff role, but it has been my longest tenure to date.

AM: I worked in content licensing at the New York Times in Paris, then produced branded content at a boutique agency before becoming Executive Producer of a commercial production company in New York. I then pursued a dual MBA and Master’s of International Affairs at Columbia, and took on the Chief of Staff role at Atlas Obscura immediately after graduating. It was my first time in the position, and I was drawn to the variety of the role and excited to be at a mission-driven company.

AH: Before stepping into the Chief of Staff role about a year ago, my career spanned sales, enablement, and strategic roles across health and benefits. The mission at Pelago is deeply personal to me. I’ve seen friends and family struggle with substance use and the barriers that prevent people from getting help. As Chief of Staff to the President, I get to translate that mission into execution. This is my first Chief of Staff role.

EL: I’m a three-time startup Chief of Staff. I began as a classroom teacher, spent time working with government agencies in D.C., and eventually found my way into the space industry. I was drawn to Loft Orbital primarily because of the people; I’d met the COO/Founder through my network years prior, and when the timing was right, I jumped at the chance. Life as a Chief of Staff moves fast and changes daily, and that’s what I love most.

3️⃣ How would you bucket your main responsibilities as a Chief of Staff during this stage?

NS: My primary areas are operational efficiency and change management, sales enablement and customer lifecycle management, and people operations. When I joined, the role leaned more toward support than strategy, but over three years I’ve found my voice with the C-Suite and now sit more squarely on the strategic side while still owning core business-operational accountability.

AM: My focus was on three areas: fundraising, leading cross-functional initiatives and special projects, and providing operational support to our largest revenue-driving division, brand partnerships. As the fundraise wrapped up, I leaned more into board management, investor relations, and hiring and onboarding. I worked closely with finance, editorial, product, and brand partnerships.

AH: My work falls into four buckets: strategic partner to the President; driving execution of initiatives that lack a clear owner or need noise reduction; ensuring cross-functional alignment so we operate as one commercial organization; and optimizing operational effectiveness through tighter rhythms and decision-making. In my first few months, I focused on building context. Over time, that shifted to shaping decisions and identifying what drives growth and helping the team move faster with greater clarity.

EL: My work centers on turning strategy into executable process. That includes supporting People and Finance as an internal consultant, board coordination, culture-building programs, improving how our executive team operates, translating strategy into annual plans and goals, and stepping into interim leadership when needed. I served as interim head of marketing for a period.

4️⃣ What is your favorite thing about being in the role at this stage?

NS: It’s still a new challenge every day, and I love feeling like I have a direct impact. Being able to work cross-functionally and unblock people at so many levels is incredibly rewarding. We’re also at a stage of maturing our processes, which lets me look back, tweak what still works, and completely revamp what we’ve moved past.

AM: I enjoyed being at the center of large, cross-departmental initiatives and bridging communication gaps between teams and department heads. As Chief of Staff, your influence is directly tied to the quality of relationships you build with other leaders, and I genuinely loved cultivating that trust.

AH: Seeing strategy turn into motion–when the organization shifts from reactive to intentional and you can feel it. I also love the moment when team members connect their day-to-day work up to company strategy. When people see how what they do impacts where the company is going, there’s this clarity and pride that fuels real motivation.

EL: Seeing people grow and stretch as we move from development to scale. We’re constantly pushing to build better, faster, more efficient products and processes, and it’s pretty awesome to watch it take shape.

5️⃣ What was the hardest thing about being in the role at this stage?

NS: The easy tendency to fall into “doing X is what got us here, so let’s just keep doing X.” Great products and processes helped get a company to Series C, but they aren’t always the ones that will take it to the next level. From my experience, companies that stall past Series C often get stuck in legacy thinking. Being willing to articulate a new vision and burn some old ways of doing things is critical.

AM: There are growing pains to growth and scale–systems that used to work break, and you have to move quickly to fix them. Team members may be attached to doing things a certain way, and rallying support for necessary change while preserving what matters about the culture is a real balancing act.

AH: At Series C, you’re straddling two worlds: the speed of early stage and the discipline needed to scale sustainably. The biggest challenge is pacing change–building systems fast enough to support growth, but not so fast that they stifle innovation. And you can’t forget to bring your people along. If they’re not bought in, the best strategy in the world won’t move forward.

EL: Change is hard, and leading people through it without creating drag or eroding culture is a daily balancing act. Some days are easier than others.

6️⃣ How have you seen yourself change or grow during your time as a Chief of Staff?

NS: Finding my voice has been the biggest shift. Coming up from EA into the Chief of Staff world, I was used to operating behind the curtain. I’ve learned to present my perspective on a larger stage, and I’ve gotten more comfortable being wrong. Most Chief of Staff types are perfectionists, and it can be hard to put yourself out there and admit when your premise missed. But failure is part of the process, and realizing your team respects you even when you need to pivot is very freeing.

AM: I developed a deeper knowledge of the fundraising landscape and how to move different teams with different working styles toward the same goal. I’ve always valued relationship building, but I’ve learned that doing it authentically–lending a compassionate ear to each department’s pain points, then speaking with radical candor when decisions require compromise–is what makes it stick.

AH: I’ve built stronger muscles around systems thinking and executive communication–learning to anticipate interdependencies earlier, translate complex ideas into simple frameworks, and bring clarity to ambiguity. I’ve also learned to lead more through influence than authority. What surprised me most: how powerful shared clarity really is. Driving that shared understanding of what “good” looks like has become one of the most rewarding parts of the job.

EL: My discernment has grown the most–learning when to push and when to pull back has been a years-long work in progress. Having been in this role at two prior companies also gives me perspective on what’s reasonable chaos versus actual red flags. The most surprising thing has been how addicting startups are. I wasn’t sure I’d love it coming from big companies. Now the next item on my career bucket list is to join as early as possible.

7️⃣ What advice would you give to someone considering a Series C Chief of Staff role?

NS: Ask yourself: does the company’s vision (who they were, who they are now, and where they’re going) match your own passions? Did they maintain their mission as they scaled? Does their trajectory align with your career goals? And if you’d be the first Chief of Staff, make sure there’s a clear understanding of your KPIs, otherwise you’ll spend your energy fighting for your voice instead of using it.

Questions to ask: “What decisions did you make to get to Series C that you’d do differently with hindsight?” and “If you could IPO or be acquired tomorrow, what three things would be critical to maintain about the current business?”

AM: Vet the executive leadership team extensively and get a thorough understanding of the company’s funding situation–are they focused on raising more or on profitability? Do they have a Plan A, B, and C? The mindsets that matter most: flexibility, persistence, and patience.

Questions to ask: “What are the biggest challenges the company faces when it comes to scale? Is the company profitable and are the unit economics sustainable? What are the top three strategic priorities over the next 12–18 months?”

AH: Look for a company that knows what phase it’s in, with leadership that’s ready to evolve. The Chief of Staff role at Series C only works if the executive team sees it as a force multiplier, not just a fixer. You need systems thinking, adaptability, and business fluency. And the emotional intelligence piece can’t be overstated. Trust is what gives a Chief of Staff real influence.

Questions to ask: “How does leadership define success for the Chief of Staff role? Where does the company need the most leverage right now? What does the next 12–18 months of growth look like, and where might the Chief of Staff add the most value?”

EL: Get comfortable being uncomfortable. You have to be energized by chaos, ambiguity, and change. The more you can discern which hills to die on and which to leave, the more effective you’ll be. The people are the most important part of any startup: you’re going to be working long hours on hard things, so alignment with the people around you is everything.

Questions to ask: “If you knew what you know now, would you still have taken this role?” And: “Do you feel like you have someone you could call at midnight if there was a crisis?” That second one tells you everything about the culture.

💜 Huge thank you to Nicole, Alex, Amy, and Eve for sharing their experiences as Series C Chiefs of Staff! We hope this issue helps you understand what the role looks like at this stage, whether you’re considering it, currently in it, or just curious about what comes after Series B.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

April 2nd: Communication Intelligence for Chiefs of Staff: Practical Tools for Navigating Team Dynamics

April 9th: Peer Resume Review

April 14th: Big Tech Chief of Staff: Secrets to Success

April 16th: AI Tactics That Work

👋🏼 In-Person Events

April 14th: NYC Co-Working Day at Industrious

April 20th: RESCHEDULED FROM FEBRUARY: Ask a Chief of Staff Summit: NYC 2026 🗽🍎

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now

Welcome back, aspiring and current Chiefs of Staff! 👋

If you're reading this as a forward or from LinkedIn, subscribe to Ask a Chief of Staff to get these insights directly in your inbox. Join 14,000+ Chiefs of Staff who trust us for actionable insights.

🧠 The only email inbox system I trust

When email is your command center, you don’t need more organization hacks: you need a system.

As part of the Superhuman suite, Superhuman Mail is the one inbox setup I’ve stuck with because it actually keeps me ahead without constant tinkering.

Work effortlessly. Stay ahead all year.

What makes it work for me:

• Split Inbox keeps me focused, even when my inbox is overflowing.

• Auto Drafts automatically drafts replies so staying on top of follow-ups becomes second nature.

• Ask AI instantly surfaces key details from long threads, eliminating manual search, keeping your workflow fast and focused.

🎁 Set it up once and stay in control all year. Sign up for Superhuman Mail with our link and get one month free!

Try Superhuman Mail Today

*If you’re interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!

🏗️ Are YOU Holding Your Organisation Together — Or Is Your System?

This week’s issue is guest authored by Tyla Cleator, a Chief of Staff operating at the intersection of executive judgment, power dynamics, and organisational design. With global experience across scaling and complex environments, she focuses on building systems that enable durable ambition at scale. She is an award-winning Women in Digital Skills Development leader and writes on sustainable ambition and structural leadership through The Shadow Strategist.

📌 TL;DR

• Relational trust is necessary, but it doesn’t scale without structure.

• At scale, trust lives in decision rights, escalation design, governance consistency, and incentive alignment.

• As organisations grow, misalignment becomes a systems problem, not an interpersonal one.

• If you’re constantly re-translating intent, you’re patching a system that was never designed to hold without you.

• Trust holds when how decisions get made and what the organisation says it values actually match—especially under pressure.

🛡️ Trust is often treated as a soft skill—something built through rapport and reinforced through communication.

But at scale, especially in the age of AI where visibility increases and execution accelerates, the cracks in how you’ve built trust don’t stay hidden. They get exposed.

In this piece, I explore how trust evolves as organisations mature, and what it takes to design systems that hold under pressure.

🤝 It Starts With Relational Trust

Most Chiefs of Staff begin their role focused on trust.

You build it quietly, by following through, exercising discretion, and doing what you say you will. Relational trust is consistency under pressure. It accumulates slowly and can disappear quickly.

But if you’ve been in the role long enough, you’ve likely felt a different tension. You can be fully aligned in the room and still watch execution drift outside it.

You re-translate decisions. You clarify intent. You correct sequencing.

Over time, you start to notice that alignment holds only when you’re there to reinforce it. That realisation isn’t philosophical. It’s operational.

A strategic priority may be clearly agreed at the executive level—resources aligned, messaging consistent. Yet months later, different parts of the organisation are still working toward different definitions of success. No one is acting in bad faith. The system simply hasn’t ensured that words and outcomes stay connected.

✨ That’s the inflection point. Relational trust is necessary. But without structure, it doesn’t scale.

💡 A Systems Thinking Approach

Systems thinking shifts the question.

Instead of asking whether people trust each other, it asks what the organisation reinforces when pressure rises?

At scale, trust lives in the practical machinery of how organisations operate:

🙋🏻‍♂️ Who has the authority to make decisions

⚠️ How problems get escalated

🏆 Whether incentives match stated priorities, and

🎯 Whether accountability is real and visible

When those elements bend under stress, trust erodes—even if individual relationships remain strong.

✨ Trust becomes architectural because it determines whether leadership intent survives complexity.

🧬 How Trust Evolves as Organisations Mature

Trust changes as organisations grow. What works early rarely survives scale unchanged.

I’ve seen three patterns consistently emerge across environments:

Stage 1️⃣: Proximity-Based Trust

In tightly held environments, proximity substitutes for structure. Clarity flows through conversation. Alignment is reinforced in real time. Decisions are social before they are formal.

Speed hides the lack of formal structure because decision-makers are close enough to catch misunderstandings quickly. Relational trust carries execution.

✨ The Chief of Staff translates and amplifies but doesn’t yet need to design. This works until complexity outpaces proximity.

Stage 2️⃣: Scaling Complexity

As organisations grow, informal alignment becomes insufficient. Stakeholders multiply. Incentives diverge. Constraints tighten. Velocity increases. Leaders may agree in principle while execution fractures in practice.

Formal frameworks often exist, such as capital allocation models, sequencing guardrails, and cross-functional sign-offs. The intent is clear. But under pressure, those guardrails get skipped. Informal pathways replace formal structure. The strategy may remain intact, but the mechanics shift.

When performance slips, the question becomes: “Why didn’t we see this earlier?” That burden frequently lands with the Chief of Staff.

At this stage, trust begins to erode. Without structural reinforcement, someone absorbs the gap.

✨ As the Chief of Staff, if you are repeatedly re-translating intent or manually correcting sequencing, you are patching holes in a system that was never designed to hold without you. That pattern is structural, not personal.

Stage 3️⃣: Governance Maturity

In more mature organisations, governance mechanisms exist. Decision forums are defined. Approval thresholds are documented. Accountability structures are visible.

Yet fragility persists when those mechanisms are inconsistently applied. And inconsistency is subtle; it rarely announces itself. It shows up as a one-time exception that quietly becomes precedent. A process that gets bypassed under pressure and never reinstated. A standard that bends for a senior stakeholder and stays bent.

Having the structures in place isn’t enough. Consistency under pressure is what creates trust, not the existence of the framework itself.

✨ At this stage, the Chief of Staff often becomes the institutional memory of what the rules actually are (and were). Which sounds like influence. But it’s closer to exposure.

The question becomes: Will this design hold when conditions change?

⚠️ When Trust Erodes

Trust breaks down when how decisions actually get made stops matching what leadership says matters.

Strategic objectives may be communicated clearly. Leadership may signal what matters. But under pressure:

↘️ Decision rights compress

↘️ Escalation pathways are bypassed

↘️ Capital allocation shifts without explicit trade-offs

↘️ Incentives reward outcomes that contradict stated priorities

The issue isn’t messaging. It’s the gap between declared standards and what actually gets enforced.

Organisations learn from decision patterns, not stated intent. If the rules flex unpredictably under stress, teams recalibrate. They optimise for what actually gets approved, funded, and rewarded.

✨ For the Chief of Staff, this is where things get visible. You find yourself explaining why a framework was adjusted. Clarifying why an exception was made. Reinforcing a priority the system just contradicted.

That work may smooth friction in the short term. But every unacknowledged exception makes the system a little weaker.

Trust doesn’t weaken because people disagree. It weakens when what the system says and what it does pull apart.

🛠️ What Good Trust Design Requires

Building trust into how an organisation operates comes down to a few practical foundations.

✅ Clear decision rights. Who contributes input, who makes the call, and who is accountable—especially under pressure.

✅ Designed escalation. Escalation follows structure rather than whoever has the closest relationship to the decision-maker.

✅ Decision memory. Trade-offs are recorded. What wasn’t decided is named. Conditions for revisiting a decision are explicit. Without this, reinterpretation becomes political.

✅ Stable standards. If declared priorities shift under stress, teams optimise for self-preservation. Good design means standards hold, even when inconvenient.

Trust isn’t just what is said in meetings. It’s what the system reinforces when you’re not in the room.

🤖 AI, Visibility, and What Gets Exposed

One of the most strategic parts of the Chief of Staff role is making sure work actually moves—not just administratively, but structurally.

That means decisions convert into action cleanly, trade-offs are understood, dependencies surface early, and escalation follows predictable pathways.

AI tools accelerate all of this through visibility and real-time alignment. But speed is a stress test. The faster things move, the harder it is to paper over gaps in how the organisation is designed to operate.

In complex organisations, leaders can be fully aligned at the top while execution drifts at the operational level—where priorities get sequenced differently, attention gets allocated inconsistently, and stated direction doesn’t always match what’s actually getting resourced.

👀 AI doesn’t create that misalignment. It reveals it.

If work only moves when someone is manually pushing it forward, that’s a signal worth paying attention to. The issue isn’t speed. It’s the underlying structure.

✨ As the Chief of Staff, the goal isn’t to remove yourself from the equation. It’s to build a system that doesn’t depend on you to function—so your energy goes toward decisions that actually require judgment, not patching gaps that shouldn’t exist.

Relational 🆚 Structural Trust

Relational trust asks: “Do I trust this person?”

Structural trust asks: “Does this system protect clarity under pressure?”

When the system isn’t well-designed, you end up re-translating decisions, absorbing drift, and becoming “indispensable”—not because of your strategic value, but because things fall apart without your constant intervention.

🚨 That isn’t leverage. It’s exposure.

💭 Building Something That Lasts

Ambition without good systems creates intensity. Ambition with good systems creates durability.

Organisations that hold up over time are ones where incentives actually reinforce the stated strategy, governance doesn’t collapse under urgency, and decision rights stay stable even when things get hard.

Trust isn’t built in alignment meetings. It’s built in what holds when you’re absent. If alignment depends on constant intervention, the organisation isn’t robust. It’s reliant. And reliance doesn’t scale.

Early in the role, you ask: “How do I build trust?”

Later, the question becomes: “How do I design trust so it holds?”

Trust isn’t a soft skill. It’s architecture. And whether strategy survives scale usually has less to do with alignment in the room—and more to do with what holds when no one is watching.

👩🏻‍💻 Level Up Your Chief of Staff Skills

Ready to accelerate your growth in 2️⃣ 0️⃣ 2️⃣ 6️⃣ ? Paid Substack members get exclusive access to a growing library of 2️⃣ 0️⃣ ➕ workshops from industry experts—covering everything from strategic planning, to navigating your next career move, to keeping cool under pressure 🧘‍♂️

New workshops added monthly! Recent additions include:

$1️⃣ 0️⃣/month or $1️⃣ 0️⃣ 0️⃣/year. Cancel anytime.

Join 300+ Members

🎥 Upcoming Events and Workshops:

💻 Virtual Events

March 24th: The Hidden Operational Cost of Mail (This is a webinar hosted by one of our partners, Stable, and I highly recommend attending if you’re struggling with the very real problem of snail mail! 🐌)

March 24th: From Full-Time to Fractional: Making the Leap as a Chief of Staff

March 26th: Shifting from Reactive Problem-Solving to Strategic Thinking

March 31st: Chief of Staff & The Skill of Emotional Fortitude

April 2nd: Communication Intelligence for Chiefs of Staff: Practical Tools for Navigating Team Dynamics

April 9th: Peer Resume Review

👋🏼 In-Person Events

March 26th: NYC Co-Working Day at The Malin

March 26th: Ask a Chief of Staff Los Angeles Happy Hour 🎊

April 14th: NYC Co-Working Day at Industrious

April 20th: RESCHEDULED FROM FEBRUARY: Ask a Chief of Staff Summit: NYC 2026 🗽🍎 (Early bird tickets still available!)

🔑 Members-Only Events

March 18th: Strategy in Practice: Drop-In Office Hours with Aarti Bhatnagar

As a reminder, events and workshops are free or heavily discounted for all Ask a Chief of Staff community members.

Visit our website and click the “Join our community” button to start your journey!

Join Now