My answer would have embarrassed me a few years ago. I used to read a dozen articles before breakfast. And my hypocrisy was on full display, since I tell countless C-suite clients that the geopolitical backdrop matters more than it has in decades. And here I was, sheepish, with nothing to say about an impactful election in a state that matters to me personally and professionally.

The easy answer why is overload. Grieving a loss and keeping up with a six-year-old, a full client load, firm leadership and other personal pursuits have had my cup sufficiently full. (My six-year-old alone consumes more energy than Storm in X-Men). This is all true, but as I examined it, there was a deeper reason…and it surprised me.

I stopped paying attention because I started caring less what was happening to people I'd never meet. Slowly, I put a filter on issues and suffering in other areas of the world: good, neutral or bad for my family, for my clients or for my organization.

Once I had this filter in place, I stopped digging into geopolitical issues with hunger. The intellectual curiosity was still there, but I stopped adding what used to season it.

Leadership Principle: Intellect and curiosity are the foundational ingredients of geopolitical insight. Ambition and compassion both deepen how you read the world. Don’t undervalue compassion.

Surprisingly, most senior leaders I work with, people with plenty of intellect and curiosity, don't have a well developed mental map of the geopolitical landscape. In most cases, they don’t pay enough attention to fully form one. If additional ingredients are needed to focus that attention, the question is which ones they're actually missing.

For me, that ingredient has been compassion. It’s the salt that brings out the flavor of what intellect and curiosity have already pieced together.

There’s an obvious counterargument to compassion as the missing ingredient…and that is ambition.1

I think of a client who runs a globally influential company. He operates as comfortably in Beijing as he does in Washington, as easily in New Delhi as he does in Taipei. Every government he deals with believes he's genuinely on their side, and he actually is. He doesn't fake understanding their position. He does the thinking and has the conversations to actually understand how their perspectives fit into his broader view of the geopolitical map.

But here’s what makes this more than an ambition story: this same leader is genuinely invested in the wellbeing of local workforce in each country. He combines his intellectual savvy with a compassionate understanding of what that government's people actually need. That combination lets him see the whole field and and it’s part of why his company keeps landing win-for-all deals.

So the more accurate answer may be that you need the right balance of ambition and compassion. Ambition fuels your intellect and curiosity toward insights that will make you influential. Compassion fuels them toward another person’s reality, whether or not it helps you at all.

But ambition already gets abundant airtime in how leaders think about global influence. Compassion gets almost none, maybe because it sounds soft. It isn't. It enables you to see clearly.

Compassion is a means of feeling local grievances for what they actually are, of asking how they'd affect you if you were standing in that place, not just reading about it from a distance. It's how you start to understand why a leader you consider “unscrupulous” acts the way he does, not to excuse him, but to actually see him in a way that allows you to engage.

There’s another fair challenge here: isn’t what I am describing as compassion just empathy? Not really. Empathy stops at feeling what someone else feels. In other words, you can feel someone’s suffering completely and still walk away from it unmoved, sometimes even worn down by it, but with nothing that points you toward insight or action.

I’ve done this with rural communities impacted by the AI data center boom. Across multiple states, reports describe wells running dry near new construction, electricity prices skyrocketing and generational farmland selling for prices few can refuse. These realities are part of the same industry explosion that I advise inside every day. I note what they might be feeling, but also have reasons to look away from these impacts.

Compassion takes you one step further: understand the suffering, AND you wish for it not to exist. It's not enough to feel for what these communities are losing. You have to actually desire for their suffering to end.

The next time someone asks if I'm still paying attention to a key geopolitical development, I want a better answer than the one I gave my sister. I hope you do too, and that yours comes from caring enough to look closer.

Put It To Work: Practical and Proven Actions

1. Build a filter that you will actually use…not an endless feed. A simple AI agent works well: have it scour reliable sources for nuanced developments in a region, flag how they connect to your organization’s priorities, and ask you questions to explore each development at a deeper level.

2. Don't let your tool do the caring for you. Your AI agent, or whatever mechanism you create to filter geopolitical developments, can find what's happening. It can't make you feel compassion. Before you move to the next article, ask one question the tool can't: what do I actually wish for the people that are affected? This will further hone your compassion and prevent the news from becoming just another feed.

3. Ask who's paying the cost you're not. Every geopolitical development that impacts an area where your organization operates has costs that never reach your bottom line. Spend time digging into those costs.

Reflect: Some Questions to Consider

1. What region(s) in the world have you stopped paying attention to? What would it take to look again, with both ambition and compassion as key ingredients motivating your exploration?

2. What gets in the way of your own compassion?

3. Who’s a leader you admire who skillfully combines ambition and compassion? What can you learn from them?

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When we exited the freeway, something in how the streets looked felt off. But the GPS was confident, so I kept driving. I followed the directions to the end…and landed more than an hour from my brother’s home. It was the wrong zip code with the same street address, and now I was 60 miles from where I needed to be.

Though it’s comical looking back on this experience, it reveals a leadership danger that is amplified in this current moment of multi-layered turbulence: the riskiest step we can take is to plow ahead blindly when we have a spidey sense that something is off and we aren't sure what.

Leadership Principle: Action is not the same as progress. Allow yourself to persist in the Fertile Void to create the space for sensemaking.

We’ve all experienced that moment when the pressure of not knowing what to do becomes unbearable and everything in you wants to take action, decide, do something to escape that feeling.

Pema Chödrön calls it the “squeeze.” I've come to prefer another name for it from gestalt therapy, the Fertile Void. It's the same idea, but a more hopeful posture toward it.

The Fertile Void is where hard questions emerge and sensemaking2 happens, as opposed to grasping for the first solution that presents itself or following the crowd. Entering the Fertile Void requires two things most leaders resist: the humility to admit you don't have the answer, and the courage to face that anxiety rather than escape into easier problems or settle for an ambiguous plan.

While a few leaders I’ve worked with lack the intellect to navigate the colliding uncertainties of this moment, what I see more commonly is that leaders lack comfort with uncertainty. The fear of not knowing, especially for people whose identity is built around problem solving, can feel like incompetence. So in the name of decisiveness, they take action. Sometimes it’s the right action, but often it’s just driving with the wrong zip code in the GPS.

So if “false decisiveness” is the unskillful impulse, what does it take for the Fertile Void to actually unveil a path forward? Do we just sit all day on our meditation cushion and hope that we see the light? Most likely not.

The Fertile Void demands its own kind of skillful effort, but it can be different than that which most problem solvers are used to.

I’ve seen leaders approach it in different ways, and in every case, their approach required disciplined patience and courage.

A technology executive faced enormous board pressure to do what boards typically demand in a downturn: cut costs, tighten operations, and wait for the cycle to turn. Following this playbook seemed to be the obvious choice, and yet something in him felt off.

Instead of plowing ahead, he stopped the car.

He spent time with customers, not to validate what he already believed, but to understand what they were experiencing. He studied how analogous periods had played out in other industries. He realized that the question he was avoiding was: “Is this still the winning model for our company?” And he wrestled with that question longer than was comfortable.

Sometimes he blocked time to explicitly think through it, but also he gave himself the space and time to process it unconsciously as well. Then he shared his emerging thinking with executives inside the company and experts outside it, using these conversations to force clarity and tease out risks.

By staying in the Fertile Void, he came to conviction that a more efficient version of the existing model was the wrong answer. The company needed to pursue a fundamentally different one, a counterintuitive bet that the old model was structurally broken, not cyclically weak. The board thought the new model was too radical, but he moved ahead with it in spite of their unease. The new model unlocked a period of unprecedented growth and profitability, and ultimately, became the industry standard for years to come.

The wisdom he exhibited was to listen to the voice that says slow down precisely when the pressure says speed up.

From time to time, I think about that late-night drive years ago, especially that uneasy feeling of not knowing that I didn’t trust.

What held me back from just pulling over? The dark of the car, the streets that didn't look right, and the spidey sense I kept overriding, all of that was an invitation to the Fertile Void. I just didn't slow down to accept it.

So I leave you with a similar question for your organization, your career or your life: where are you following a GPS you are no longer quite sure of?

Put It To Work: Practical and Proven Actions

1. Interrogate the fear before you act. When you sense uncertainty about the path forward and at the same time, feel under the gun to take action, pause and ask yourself: “What am I most afraid of right now?” That question will almost always get you closer to the core issue than “What should I do next?” Write it down and marinate on the answer before you share it with anyone.

2. Create distance from your own certainty. This looks different for different leaders. A retreat, a long run, a half day completely off the grid. What matters is creating enough space to see your own mental map clearly, especially where new information doesn’t fit. Seek out one person who is knowledgeable but has no stake in the outcome. Their perspective may surprise you.

3. Spar with the right people. Your inner circle on your team should have at least one person who is this type of challenger. You also should find two or three people adjacent to the problem, inside or outside your industry, who will challenge you without an agenda. The goal of these conversations is to try to figure out where the new reality belongs on your map before you start driving again.

Reflect: Some Questions to Consider

1. Where are you currently plowing ahead despite a feeling telling you something is off? What are you afraid to confront?

2. What would it take for you to create distance from your biggest current uncertainty and what’s stopping you from doing that in the next month?

3. Who are two or three people close enough to your biggest current uncertainty who would challenge your thinking without an agenda and what’s your excuse for not having talked to them already?

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But that’s not what this piece is about.

It’s about blind spots.

I’ve written about the way our identity creates personal blind spots, but there are also cultural blind spots. These exist at the team level, the organizational level, and the system level.

Every car has a blind spot due to how the vehicle is built. The beauty of modern parking cameras is that they give you an angle that the car’s design took away from you.

Organizations work similarly to cars and yet they don’t come with parking cameras.

A highly collaborative culture subtly teaches you that top-down decisions are invalid. A mission-driven organization can make questioning the mission feel disloyal. These cultural messages mold your worldview in such a way that you stop noticing them.

Leadership Principle: Every culture creates blindspots. You need to intentionally seek out “parking cameras” to see them clearly.

I learned this firsthand in my advocacy work for Cuban youth over 20 years ago. We were idealistic, ambitious and scrappy in our efforts. We built a network of thousands of young Cuban-Americans and found creative ways to get resources to young people on the island. We were obsessive in studying Cuba and we believed we were seeing the situation clearly. But in the early days, I’d argue we weren't.1

I wish I could say it was strategy or incisive analysis that allowed us to break some of the distortions we had, but it wasn’t. It was several of us spending more time in Cuba, speaking with our Cuban-born counterparts firsthand and over a longer period of time, so that we had more insight into what was happening and what they needed versus what we had constructed from a distance. These trips led us to update our theory of change, and accordingly what we chose to focus on. They also revealed how thoroughly our organizational context and privileged view from the States had been shaping what we thought we knew.

I’ll never forget how humbling it was to realize that some of our most effort-filled initiatives meant very little to the very people we were trying to lift up.

A similar dynamic played out with a senior product leader that I coached. Her whip-smart team spent months releasing AI-enabled features, working around the clock. But they kept building tools that followed the logic of their legacy products. Her big “a-ha” came when she sat with target customers and watched how those customers were using AI agents to bypass her product entirely and achieve the same if not better output with much more ease. This series of customer encounters changed the product strategy in ways that no product strategy session had come close to producing.

I am hoping for a similar breakthrough in how I think about AI transforming my own work. And maybe the answer is that I haven't found my parking cameras yet.

Most organizations are interpreting the AI moment entirely through their existing lens: their assumptions about what customers or beneficiaries want, what work looks like, what their product or service is for. The biggest risk is that your culture makes you the last one to see how AI will disrupt your organization.

My son's curiosity is still unobstructed by the blind spots of culture. My hope for leaders is that the right parking cameras can help them look at their biggest challenge with that same unobstructed view.

Put It To Work: Practical and Proven Actions

1. Name one of your organization's most sacred assumptions. Every culture has them (or at least the 100s of companies I’ve personally advised certainly do). It may even take speaking with a long-time colleague who has left the company to get really clear on what this is. Then ask honestly: when was the last time we wrestled with whether this was a feature or a bug or maybe both?

2. Design your parking camera. Once you've named the assumption, identify at least one experience that would most directly test it. It could be a day with a customer or a longer conversation with someone who understands your context but is not steeped in your organizational Kool-Aid. Whatever you design, it has to take you outside of your organization’s metaphorical four walls.

3. Make it a leadership habit. Build one “parking camera experience” into your calendar each quarter. I’d advise against it being something passive like a conference or a panel. It needs to be a direct experience where you get to actively look at this sacred assumption from a completely different perspective.

Reflect: Respond with Mind and Heart

1. What is the one thing your organization believes so thoroughly that questioning it feels almost disloyal?

2. When did you last engage in a way that allowed you to truly test that belief?

3. What might you be afraid of finding out if you do test that belief?

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I call it the parrot virus: our tendency to speak with conviction on topics we have not truly examined, spouting conclusions without evaluating the assumptions beneath them.

Right now it shows up most in “parroted” hot takes about AI. And these hot takes fall on both ends of the spectrum from dreamer to skeptic:

“AI will never replace human judgment. It hallucinates, so it’s not that useful.”

“AI is replacing knowledge workers…look at all the layoffs.”

“AI is a magic productivity lever. Just deploy it and boom…50% productivity gains.”

“AI destroys creativity and makes everything generic AI slop.”

And the list goes on…2

But this is not really an AI problem. AI is just the latest and loudest place it shows up.

Leaders repeat strategies and insights they only understand at a surface level, and they do it with Tony Stark-style bravado. It can sound polished in a boardroom or persuasive in front of the C-suite, but unearned certainty is like a pair of fake Jordans. They look good on the surface, but after a few days of wearing them they fall apart and hurt like hell.

There are two reasons this matters even more right now.

First, AI accelerates the spread of the parrot virus, especially when people use it uncritically in areas where they lack depth (See this study).

Second, this is precisely the kind of moment when independent assessment matters most. When uncertainty is proliferating, “parroted” insights becomes more costly.

Leadership Principle: When uncertainty is high, don’t parrot someone else’s perspective. Earn your point of view, then hold it loosely enough to keep learning.

So why does this happen so much, even among very bright leaders?

It happens for at least three reasons. Developing an informed point of view takes time, energy, and enough humility to admit when your understanding is still thin. Also, organizations often reward confident repetition, especially when the view belongs to the boss or another authority figure.

And, at its root, parroting is often about self-protection: borrowed ideas are safer than original thinking because they preserve our status while minimizing the risk of looking uninformed or less smart. They may even give us a feeling of safety that we so desperately crave in the unknown.

Since the parrot virus is so commonplace, leaders often underestimate its cost. I’ve seen this pattern in organizations where strategies and targets were built on ideas that sounded inspiring but lacked rigor. The result is sustained underperformance, and worse, employee disengagement and attrition.3

But one of the best CEOs I’ve advised approaches this differently. He scans the external environment like an eagle. He sees the full terrain of his ecosystem and then narrows with precision, triaging uncertainty in areas as diverse as AI, Medicare policy, income inequality, and oil prices. He has a feel for what is noise, what is too far off to matter yet, what requires monitoring, and what is consequential enough to deserve real intellectual investment now.

Most of us will never be quite as skilled as him, but we can borrow his mindset. What separates discernment from parroting is knowing which areas of uncertainty actually matter to your organization (see below for a potentially helpful model).

Importantly, not every topic deserves the same depth of thought. The ones that do tend to be both uncertain and highly relevant to the organization. In these situations, you need more than talking points. You need a robust enough view to make investment and talent tradeoffs.

And once you develop your view, hold it with some humility. Let the facts on the ground update you. Don’t be infinitely flexible like Mr. Fantastic, but don’t be as rigid as the Thing, either.

The goal is not to have a clever opinion quickly, but rather to develop a view that helps you lead your team amidst the seemingly unrelenting fog of uncertainty.

And if the choice is between an eagle and a parrot, be an eagle.

Put It To Work: Practical and Proven Actions

1. Catch yourself using “borrowed” language. When you hear yourself saying a familiar line, ask: Do I actually believe this? What experience or evidence is it based on? Then decide whether it is worth your time or your team’s time to investigate further. The model above can help.

2. State views with WYNTB (what you need to believe). “I don’t know yet” is a perfectly fine starting point, provided that you will do the work to get to an answer. Moreover, once you have arrived at a clear point of view, share your current take AND what you need to believe for that conclusion to hold.

3. Cultivate your strategic network and curate it so you can see the world with eyes of an eagle. Build relationships with people who understand fast-evolving topics deeply. The difference between parroting and leveraging expertise is simple: you can explain the issue in your own words and answer probing questions with logic and data, not bluster.

Reflect: Respond with Mind and Heart

1. What is one important, smart-sounding idea that I repeat, but have not really earned?

2. How can I most effectively gather diverse perspectives to help me develop this point of view?

3. Who can hold you accountable to forming this point of view?

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And boy…can I relate!

As much as I take pride in my ability to focus, over the last year I allowed myself to get seduced by the tyranny of more.1

Part of what makes this so tricky is that in chaotic, rapidly changing environments, focus itself starts to feel risky. When you’re not sure you’ve chosen the right few things, the instinct is to add more.

The lesson I keep having to relearn is that my instinct to do “more” rarely comes from strategy, but from identity.

A part of me wants to be the one who sees the problem first, owns it, and fixes it. The one who gets it right. The “golden boy” who saves the day.

And if I’m real, there’s a related part that worries about what it says about me if I don’t.

Over time I’ve realized these parts of me, which have no doubt served me well, can scatter energy across too many fronts and dry up the well of equanimity that I have intentionally nurtured.2

So this year, my annual intent is: “Grounded Presence, Sufficient Impact”

Each word carries meaning for me, but the underlying principle is: More is a poor substitute for what leaders actually need, which is sufficiency.

Sufficiency doesn’t require lowering ambitions. It does require a refusal to let anxiety or the expectations of others set the agenda.

In practice, this means focusing only on the inputs that actually matter, because those are the ones that ultimately raise the bar.

Leadership Principle: Sufficiency wins. More is often just anxiety disguised as strategy. Instead of more, focus on the few inputs that can actually change the trajectory.

This type of leadership reminds me of Black Panther. T’Challa is ambitious, grounded, and when he acts it is with precision.

But a question that nags at me is “How do leaders create sufficient impact in a world obsessed with doing more?”

To answer that question, I think about one of the best operators I’ve ever worked with: Carlos.3

He walked into a global company where growth had stagnated, but not for lack of trying. There was a list of 15+ global initiatives plus dozens of incremental ones in individual countries.

As Biggie Smalls once put it: mo’ initiatives, mo’ problems.

In his first month, Carlos asked a simple question: Where do we actually win?

What emerged from the data was a clear pattern. The company consistently won when two things intersected: its largest geographic markets and its most differentiated products. Over time those intersections had been diluted as resources spread across too many initiatives and markets.

So he focused the organization on these intersections, putting stronger leadership talent, investing more in the salesforce and technology, and increasing the data quality and his personal attention in these areas. Everything else stopped. Some markets were deliberately starved of resources.

Growth roared back within just 12 months, not because the organization did more, but because it finally did enough of the right things in the right places. And more impressively, the results are repeatable. The company has grown sustainably for nearly three years and the employee engagement scores are the highest they’ve been for a decade.

Whenever I feel myself pressured toward more, I think about Carlos and return to the discipline of sufficiency. In a world that constantly asks for more, it’s worth remembering: sufficiency wins.

Put It To Work: Practical and Proven Actions

1. Notice when the instinct to do “more” is coming from identity rather than strategy. Before evaluating a new initiative or opportunity, pause and ask a simple question: Is this coming from clear strategy or from my instinct to prove value, appease an influential stakeholder, solve the problem, or save the day?

2. Identify the few inputs that actually drive outcomes. Setting ambitious, even stretch, goals is a core part of leadership. But when leaders raise the bar, a common pitfall is stacking lots of activity without enough causal linkage to results. Instead ask “What would Carlos do?” Define the few operating mechanics that make ambitious outcomes achievable and concentrate attention there.

3. Create a shared “pressure-test” before adding something new. Greg McKeown’s4 90% rule is a useful discipline. When evaluating a new initiative, score it from 0–10. If it isn’t a 9 or 10, treat it as a zero. In his words: “In a world exploding with options, we need to see the difference between things that are good and things that are exceptionally good.” The point of this exercise is not mathematical precision. It is creating a shared language for asking: Do we really need more?

This is my 100th Friday Reflection! And it feels fitting that the lesson I keep coming back to is one I need to relearn myself.

Reflect: Respond with Mind and Heart

1. What “part” of your identity can cause you to pursue more rather than sufficiency?

2. Where in your own leadership might you be mistaking activity for impact?

3. Who is your “Carlos” that reminds you to focus on the inputs that actually drive the outcomes you care about most right now?

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And no wonder. Since 2020, we’ve experienced at least one major global dislocation each year.2 Turbulence has become the backdrop for leadership rather than the exception.

This steady drumbeat of chaos has distorted how leaders perceive risk. By risk, I’m not referring to taking bold bets. I mean the threats surrounding every organization: economic shocks, geopolitical instability, technological disruption, competitive pressure and organizational overload.

One of the most innovative leaders I work with has a remarkable instinct for opportunity. It has helped him create new product categories, close ambitious deals and energize teams. But it also creates a blind spot. He rarely slows down to pay attention to risk. Not because he’s careless, but because his instinct is always to spot new avenues of growth.

At the other end of the spectrum, some leaders fixate on threats, slowing decisions and quietly paralyzing their organizations.

Turbulence doesn’t erase these leadership instincts, but rather it amplifies them.

Leadership Principle: In chaotic and uncertain environments, leaders must practice two disciplines at once: vigilance to threats and commitment to opportunity.

Most leaders instinctively lean toward one of these disciplines. They show up as either Opportunity Activators or Risk Guardians. Both instincts are valuable, because one energizes innovation and the other prevents costly mistakes.

If you’ve sat in enough strategy meetings, you’ve certainly seen this dynamic.

In a recent leadership team discussion, I observed this in real time. Before investing in a new technology, one executive kept pushing for more analysis, convinced that another round of data would bring clarity. Another insisted the opportunity was “clear as day” (despite the data only showing modest signal) and that slowing down meant falling behind competitors and disappointing customers.

It was a tug-of-war between opposite ends of the risk perception spectrum.

Interestingly, most leadership teams already contain the balance they need on this spectrum. The Opportunity Activators push the organization forward. The Risk Guardians protect it from costly mistakes. The key is deeply listening to both instincts, and then making the call.

Leaders rarely broadcast that their tendency is toward one extreme, but the signals tend to show up in predictable ways.

For Opportunity Activators, I see two common patterns:

1. Optimism starts to substitute for evidence.

2. The downside gets dismissed too quickly (and often with lots of emotion).

For Risk Guardians, two different patterns tend to appear:

1. Decisions begin to stall, causing paralysis or ambiguity to persist.

2. Possibility starts to disappear from conversations.

All four patterns lead to poor decisions, especially in periods of severe uncertainty.

So what is the middle path? I call it strategic vigilance.

Strategic vigilance is a bit like Professor X with Cerebro on.3 He’s not jumping at every threat signal, and he’s not pretending they don’t exist. He’s calmly scanning for both danger and possibility.

Andy Grove, the former CEO of Intel, famously wrote that “only the paranoid survive.” His point wasn’t that leaders should live in fear. It was that great leaders are clear eyed about emerging threats while still moving with conviction when opportunity appears.

And as we all navigate yet another period of global disruption, it’s worth remembering:

Risk isn’t the enemy. Losing perspective is. And, strategic vigilance is what keeps leaders from losing it.

Put It To Work: Practical and Proven Actions

1. Know yourself and surround yourself with a counterbalance. Opportunity Activators benefit from voices that pressure-test assumptions. Risk Guardians benefit from people who keep opportunity in view. Make sure you have the leaders on your team to balance out your default style and here’s the key…actually listen to them!

2. Build the discipline of strategic vigilance. Create structures that allow you and your team to examine risks quickly and clearly. Set-up a focused cadence to assess emerging risks and monitor mitigation plans. Allocate time at every other meeting to evaluating where opportunity may be emerging during the crisis. Another example is to set decision boundaries amidst uncertainty by asking two questions: What information must we have? What uncertainty are we willing to carry?

3. Continuously reassess and adjust. Conditions change so quickly in these turbulent moments that it often requires recalibration. Build fast reassessment loops like weekly signal scans and monitoring a handful of leading indicators, so your team can update its picture of reality without slowing momentum.

Reflect: Respond with Mind and Heart

1. Where on the risk perception spectrum does your instinct tend to pull you? Opportunity Activator or Risk Guardian?

2. How will you counterbalance this tendency?

3. When was the last time you spotted an opportunity and acted on it amidst uncertainty? How did it go?

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“That’s just how he is.”

“She’s hard wired that way.”

That tone shifts the room from curiosity to conclusion. And sometimes that conclusion is correct. There are real limits in human development and in the organizations we create. Intelligence ceilings exist.1 Deep misalignment of values rarely shifts. Some contexts are ill-suited for certain people.

But I’ve also seen how often we go from “this is difficult to change” to “this cannot change,” as though those two situations are the same. They aren’t.

Every time we say “that’s just how she is,” we should at least ask whether we’re describing her limit or protecting our own limits. Otherwise, we close off potential that may still be there.

Leadership Principle: Change is available more often than we admit. What makes it rare and hard is the conditions required to sustain it.

This principle doesn’t make me naïvely optimistic. It forces me to slow down and disentangle what is going on before I decide someone’s potential to change is capped.

Appetite

The first thing I’ve learned to ask is not whether someone can change, but whether they have the appetite (awareness + motivation) to change.

I’ve been in talent reviews where a leader is described as “stuck” or “limited,” only to discover that the individual in question is painfully aware of the issue and actively trying to improve. I’ve also sat across from leaders who insisted we double down on coaching for someone who had no desire to shift the behavior everyone found problematic. Their optimism in the latter case is as misplaced as wearing a guayabera in Finland in January.

Appetite doesn’t guarantee change, but without it, meaningful change cannot happen.2

Magnitude of the Change

Even when appetite is present, there’s another layer that gets blurred: what, exactly, are we asking someone to change? Not all change is equal.

There is a difference between asking someone to shorten their answers in board meetings and asking them to loosen their attachment to being the smartest person in the room. One is behavioral, and the second runs closer to identity.

Leaders often underestimate this distinction. A pattern repeats and we treat it like a flaw that discipline should fix. But some behaviors aren’t surface habits. They’re identity-level strategies for securing belonging or competence, and discipline alone won’t shift them. It requires reworking how someone sees themselves.

That kind of identity shift takes time, often more than organizations are willing to allow. But, when the appetite is there and runway is sufficient, this type of shift is more possible than we tend to believe.

Context

Even appetite and clarity on the magnitude aren’t enough if the environment demands something fundamentally different and lacks sufficient support.

A few years ago, I worked with an executive who had built a reputation as a deeply analytical individual contributor. He was hired to lead a large function within a Fortune 500 company, and the nature of his work changed overnight. Instead of being the primary thinker supported by small teams, he now had to lead senior leaders who were driving complex agendas of their own.

He wanted to grow into it, and worked his ass off trying to. That wasn’t the issue.

Moving from deep individual analysis to orchestrating leaders at scale is not a behavioral tweak; it is a change in operating identity. He needed to deliver within 12 months, which was like asking a jet to liftoff with too short a runway.

He had the appetite and the ability. What he lacked was change runway.

At some point, continued coaching would have blurred the line between optimism and denial. He wasn’t incapable, and the organization wasn’t unreasonable. The mismatch was between the pace of development and the urgency of the business.

In these cases, the wisest move is not more development, but a different seat or a clean exit. In other cases, with a longer change runway and stronger support, I’ve seen leaders make the identity-level transition.

So Is Meaningful Change Possible?

Recognizing the limits of change doesn’t make it impossible. It makes us clear-eyed about what it will take, for ourselves and for others.

Boyatzis reminds us that people grow when they are anchored in vision, not threat. Yet most senior feedback is delivered under pressure and framed around deficits. This is flawed. We can’t narrow someone’s world and then expect expansion.3

Change becomes possible and more available than we admit when someone can envision a different version of themselves and feel genuinely pulled toward it. That kind of change demands something of you. It often asks you to loosen patterns that once made you successful. It may feel destabilizing before it feels natural.

I’ve watched leaders once described as rigid create rooms where dissent felt safe. I’ve seen executives known for dominance learn restraint without losing their edge, and in doing so earn deeper trust. I’ve also watched people outgrow identities that once defined them and discover a broader range of influence.

In each of those cases, what once felt impossible didn’t become easy, but it did become climbable. And I remind myself even Tony Stark4 had to outgrow an earlier version of himself to become the hero the moment required.

So when I hear “that’s just how they are,” I force myself to pause.

Sometimes it’s true. But just as often, separating appetite, magnitude, and context reveals something more nuanced than hard wiring.

Not everyone will change AND not every system can off the runway to support change. But I’ve seen too many leaders outgrow stories about themselves to accept the premature finality of “He’s just that way” as gospel.

Before you decide someone cannot change, turn the lens on yourself. Does your context allow for sufficient change runway? And have you created the conditions for them to change?

Because once we decide change is off the table, we stop looking for the path. And leaders who stop looking rarely find what’s possible.

Put It To Work: Practical and Proven Actions

Think of someone on your team who needs to “change”:

1. Assess for appetite to change. Appetite shows up in awareness and behavior: seeking feedback, experimenting, and sticking with it after the initial enthusiasm fades. Rate how strong their appetite for change really is.

2. Get clear on the magnitude of the change. Is it a flat mile, a mile slightly uphill or a mile up a steep mountain face? All of these can be conquered, but the time, capability and support required to do so are vastly different. If you are not sure how large the magnitude of the change is, start here for a view on the coachability of particular behaviors and mindsets.

3. Have a nuanced understanding of the “context”. What does this role truly demand? What is required for success in your environment? If you are asking someone to stretch, that’s one thing. Make sure they have the support they need. But reinvention under severe time pressure is another. Change may still be available, just not in your context.

Reflect: Respond with Mind and Heart

1. Where have I decided someone “cannot change” without fully examining the conditions around them?

2. Am I asking for a behavioral tweak or an identity-level shift? and have I aligned my expectations about the change runway accordingly?

3. If I’m honest, is the constraint truly them, or my willingness to redesign the context?

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If more organizations practiced Kim Scott’s philosophy of “care personally, challenge directly,” they would experience a huge jolt to their speed of execution. This is because the clarity that comes from candor speeds decisions.

On the other hand, the issues we refuse to name do not disappear. They resurface later, derailing execution, undermining culture, and compromising impact.

But sometimes getting results requires more than clarity or faster execution. It requires helping a leader outgrow a prior version of themselves.

And in those moments, “care personally, challenge directly” is incomplete.

This is because not every leadership challenge is an avoidance problem. Some are rooted in how a leader sees themselves. And most of us cling to who we think we are far more than we care to admit.

To address these situations, candor must mature or it will fail. What’s needed is Skillful Candor.

The difference is that Radical Candor measures whether the truth was spoken in a caring way, whereas Skillful Candor measures whether the truth was integrated. The first can change behavior in the moment. The second changes who someone becomes.

Leadership principle: Skillful Candor is truth-telling in a way that expands the other person’s capacity to change.

You will recognize the moments that call for Skillful Candor. A leader stepping into a bigger role who must let go of the habits that once made them successful. A high performer whose need to be the smartest person in the room is quietly shutting down ideas. A colleague who feels stuck but cannot see how their own story is the constraint.

The discipline behind Skillful Candor is ancient. Thich Nhat Hanh, reflecting on the Buddha’s teaching of Right Speech, recommends a simple practice: write a letter. Writing forces you to confront your own imprecision before someone else has to.

And his bar is high: “Your letter has to water the seeds of transformation and stir something in their heart.”1

And whether you choose a letter or a conversation, what matters is whether you bring the deliberateness of writing and the patience to wait for a response.

Some guideposts to achieve the high bar of skillful candor:

1. Start with unconditional positive regard. Demonstrate that you understand the external pressures they face and the internal ambition they hold. People are far more open to hard truths when they feel seen in full.

2. Be explicit about the behavior that must change and the leader they want to become. The goal is not to threaten identity, but to expand it.

3. Name the cost of not changing. Objectively describe the ceiling they will hit and the opportunities they will miss if nothing changes.

4. Choose your words with intention. Opt for precision over volume. Use metaphor that makes the shift memorable rather than merely accurate.

5. Calibrate the setting and the dose. Select the medium deliberately: A walk, a written note, or a quiet office can change the emotional temperature. Also, plan for follow-up so they have time to metabolize the message and subsequently integrate its implications over time.

I once worked with a leader who felt deeply slighted by what looked, on paper, like a demotion.

He had built his reputation as a turnaround operator who thrived in intensity and imposed order on chaos. From his vantage point, this new role in a smaller, growth-oriented business felt like a dilution of his edge. A conventional version of candor might have sounded like, “You need to broaden your skill set if you want to scale.”

I decided that I would not dismiss his disappointment, but wouldn’t I indulge it either. Instead, I reframed the moment for him. What he experienced as a sideways move was, in reality, a change in sport. He had already proven himself as an Ironman operator; this new role required something broader, a decathlon leader capable of competing across disciplines with the same perseverance but greater range. I reinforced that if he tried to compete without changing his approach, he would let down the colleagues he felt so much responsibility for and significantly narrow the breadth of his impact on the healthcare system.

Over time, the role that once felt like atrophy started to feel like an opportunity to grow new muscles. Years later he led the largest business unit in the company, and eventually a company of his own.

The candor worked because it aligned with his ambition rather than arguing with his disappointment.

What this reveals is that Radical Candor ensures the truth is spoken, but Skillful Candor determines whether it becomes part of someone’s future.

Take action: Practical and Proven steps

1. Draft your key messages for clarity. Then write a second draft for tone, one that also articulates how the person’s identity may need to shift. Let the final litmus test be: “Will this sow the seeds of transformation?”

2. Use your preferred AI chatbot (e.g., ChatGPT, Gemini, Claude) to coach you through how you want to communicate with skillful candor. Do not outsource the thinking. Instead, use your draft and then ask the tool to surface blind spots, refine language, and explore alternative framings that might increase receptivity.

3. Plan the follow-up before you deliver the message. Skillful candor assumes the first discussion is the beginning of a conversation, not a “one and done” situation. Consider how much time is needed between conversations and what if anything would be helpful to the person during that “in between” stage.

Reflect: Some Questions to Consider

1. Where in your world right now is skillful candor required not just to improve performance, but to reshape a key leader’s identity?

2. What do you understand about this person’s fears, ambitions, and self-story that might explain why change feels threatening, and why it might also be liberating?

3. When will you create the space to refine your message so that it does more than land clearly, and instead “waters the seeds of transformation and stirs the heart?”

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In these moments, I find there is subtle pressure, especially in leadership culture, to turn loss into insight as quickly as possible, as if unresolved grief were a failure of discipline or mindset.

But my current experience suggests that pursuit is premature. Some holes aren’t meant to be filled quickly. When leaders try, they usually fill them with activity or certainty, but this tends to exacerbate their underlying anguish.

What’s skillful is to accept that these holes will change how you move through work and life - your pace, your patience and even your tolerance for difference. Pretending otherwise often leads to exhaustion or quiet despair (trust me I know).

Leadership principle: Hole-hearted living is staying engaged even when your capacity has been altered by loss, without forcing yourself to meet prior internal or external expectations.

Defining and naming “hole-hearted living” is one thing. Living it is another.

The question I’ve wrestled with is: How do I actually practice hole-hearted living1 when all I want to do is fall apart?

Often the answer is just staying upright until the day is done. And even that can be a challenge.

I am far from having full resolution. But I do have practices that are serving me well:

Practice 1: Return to the sturdy foundation

Rather than try to improvise your way forward, return to the practices that help you remain sturdy. For me, this includes five things:

• Consistent exercise that pushes and rejuvenates my body

• A mindfulness practice that brings me back to equanimity

• Time with loved ones (particularly my son, daughter and close friends) where I don’t need to explain myself

• Re-reading meaningful articles and books rather than chasing new insight; and

• Moments in nature that evoke a sense of awe

Practice 2: Choose clean effort - one thing at a time

These moments of loss can make even a modest to do list feel insurmountable. Mine is occurring during a quite intense period of work (one of the longest Avalanche Moments of my career). Rather than looking at the to-do list in its entirety, I kept coming back to the same mantra - one thing at a time. Focusing on one task per work window forced prioritization. And at the same time, some things dropped and I had to accept the cost of that.

Practice 3: Turn to others for help and support

Many of us struggle to ask for help. And often this is because we don’t know what to ask for. And while I definitely did not put up a billboard announcing my struggle, I did tell a small circle of people in my work and my personal life who I knew I would need help from. Amazingly, there were even a few I didn’t have to ask, they just took on more because they could see I was struggling. People like this make the hard moments survivable, and these people matter more than we realize.

I imagine there are other practices that enable hole-hearted living, but these are the ones that have helped me.

And remember, it’s ok that you are not showing up as an enthusiastic, fully alive person during this time. One of my most treasured CEO clients recently told me “you’ve been incredibly present and impactful for our organization this year, but I can tell a spark is missing.” At first I took this hard, ugh - not exactly the leadership brand I am going for. But after reflecting on it and receiving some advice from a confidante, I realize that I am just being human.

Some seasons simply call for presence more than the spark of enthusiasm, even though organizations are quicker to reward energy than steadiness.

Over time, you’ll figure out what, if anything, belongs in these holes. And most likely, even if you do fill it, there will be a scar or a dent from the hole. Like Mater in Cars, we don’t want every dent smoothed out. Some holes are worth remembering, because they remind us what we’ve overcome.2

And, even if this isn’t your season of hole-hearted living, it may be someone else’s. If that’s the case, take the opportunity to notice, adjust, and lead accordingly.

Take Action: Practical and Proven Steps

1. Develop your sturdy foundation. Choose three of the five practices and commit to them for 14 days without negotiation (or come up with your own). For example

   1. Exercise: Identify an exercise routine you can stick to.

   2. Mindfulness: Sit for 10 minutes daily, experimenting with a meditation app3 or another tool that can support your mindfulness practice.

   3. Reading: Re-read something familiar and meaningful for 10–15 minutes at night. Ideally these are trusted voices, not necessarily new insight. For me, this has been David Whyte, Thich Nhat Hanh, John Wooden, Maya Angelou, Dulce Maria Loynaz, Pablo Neruda and the Psalms of King David.

   4. Loved ones: Schedule one, in-person non-transactional connection each week (coffee, walk, exercise). No agenda beyond being together.

   5. Awe: Once a week, put yourself somewhere that reminds you you’re not the center of the universe. For me that’s Inwood Hill Park…it just needs to have water, trees, sky, or silence.

2. Simplify how you work when your mental and even physical capacity is constrained AND assume something will drop. Release the need to measure success by how many things you juggle at once. Choose one priority per ~60-minute work window and execute it cleanly before moving on. Decide in advance what deserves this attention, while leaving space for the inevitable unexpected ask. Similarly, be clear on what you are willing to leave incomplete even if it does have a cost.

3. Lower the bar for asking for help and acknowledge you may not even know what you need. When you can, make specific asks (e.g., Can you take the lead on this meeting?) And when you can’t, choose a small group of people to share something like: I’m going through a challenging and chaotic personal time and may need support, but I’m not always great at knowing what I need. Notice who steps up without being asked.

Reflect: Some Questions to Consider

1. Where are you pushing yourself to show up with energy or optimism that you don’t currently have and what would “clean effort” look like instead?

2. Which practices keep you grounded when your emotional capacity is compromised?

3. Who already sees that you’re carrying something heavy and how might you let them help without overexplaining?

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“You see obstacles clearly and exude optimism that they can be addressed, but sometimes you give the obstacles too much energy.”

Some feedback stings because it challenges your strengths, or at least what you thought were your strengths.

At first, I bristled because anticipating risk is part of my value to clients. But the comment stuck. I realized that when an obstacle is already well understood1, more airtime doesn’t add value (even when approaching it positively). In fact, it drains momentum and constrains the room’s emotional and cognitive energy. It’s like showing Dracula exactly where to bite.

Leadership Principle: Be aware of obstacles, size them up, but don’t feed them. Shift the center of gravity to the possibilities that obstacles point toward.

Boyatzis’ research2 backs this up: when we fixate on problems, we activate the sympathetic nervous system, the brain’s fight-or-flight engine. Focus on possibilities instead, and you activate the parasympathetic nervous system, the part that makes us creative, open, and collaborative.

I see the same pattern in AI discussions in the C-suite. While competitors run pilots and learn, the companies that are stalling are the ones that keep circling the same obstacles:

• Strategy: How do we adapt our business model before AI reshapes our profit pools?

• Talent: What will we do with junior talent if AI can handle entry-level work?

• Healthcare: What if AI makes the wrong diagnosis?

• Creative: What happens when AI floods the internet with copyright infringing, low-quality content?

These risks are real, but they are also well understood. Once they’re on the table, more airtime doesn’t make them safer; it just keeps people anchored to them. Instead senior executives need to push the conversation toward credible possibilities.

Moving towards solutions only works if the possibilities have substance behind them. It’s not about trading well-understood obstacles for vague optimism. Leaders have to fill in the blueprint, articulating clear actions and a credible roadmap, so the solution space has as much depth as the problem space.

And that’s exactly what my colleague’s feedback made me realize:3 optimism is only part of the equation. In the AI era (and frankly any era), the winners will be those who stop feeding the vampires — the obstacles — and start feeding what’s possible, with speed and substance. Garlic and holy water are of course optional.

Take Action: Practical and Proven Steps

1. Check your vampire (obstacle/possibility) ratio. Be aware of your own tendency to admire problems. When it is feasible, track how much time is spent on obstacles versus possibilities, and aim to flip it.

2. Make the future vivid. Boyatzis’ research shows that vividly describing the desired future activates the part of the brain that fuels creativity and openness. Use language, data, and imagery that make the possibilities more compelling than the obstacle itself.

3. Give it backbone. Be careful not to let vague optimism serve as a replacement for discussion of obstacles. Instead, get practical and push for real solutions. Get clear on a tangible roadmap, credible milestones, and clear proof points, so the solution carries weight.

Reflect: Some Questions To Consider

1. When did you last give more airtime to an obstacle than to a solution?

2. What is an obstacle that you need to address in an upcoming meeting? What actions can you take before and during the meeting to shift the focus to possibilities sooner?

3. How can you ensure your solutions are backed by substance rather than hopeful language?

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A recent survey by Deloitte revealed that ~40% of executives already made a bad call after over-relying on Gen AI. The risk of “intuition dulling” is here now.

The movie Fantastic Four: First Steps1 offers a cautionary echo on a similar theme. Reed Richards, the smartest person on the planet, runs every test on his newborn Franklin and concludes he is “normal.” However, Franklin’s mom, Sue Storm can’t shake the feeling that her child has extraordinary powers. She turns out to be right. Franklin becomes one of the universe’s most powerful beings.

In other words, intuition prevailed where pure analysis failed.

Leadership Principle: Let AI accelerate your thought process, but keep honing your intuition. When the algorithm drives alone, blind spots multiply; when the two work in tandem, new opportunities emerge.

The juxtaposition of the characters Reed Richards and Sue Storm is a helpful metaphor for how to navigate today’s world. Run your “Reed” at full speed (multiple LLMs, other types of machine learning)2, and at the same time continue to grow your “inner Sue”, your intuition.

But how do we hone our intuition?

This is an especially pertinent question, because the very actions that once trained our intuition are now done in the background by tech. Data analysis that took weeks can be done in four minutes. Memo writing that took hours can be completed in forty-seven seconds.

Yet it’s the combination of observing the work, doing the work, getting feedback on it and seeing the results that contribute to our intuition-building over time.

So while we can greatly benefit from AI tools, we cannot outsource our thinking. In fact, a recent study showed that AI consultation alone led executives to make worse predictions and be overconfident in those predictions. Yikes!

I also believe there are even bigger risks that will emerge if intuition erodes. Pattern recognition will become weaker. Moral imagination and empathy will be minimized. And as a result, we will make worse decisions, because our well of “unconscious intelligence” will become much shallower.

So while modern tools will allow us to stretch like Mr. Fantastic, our natural intelligence when combined with the output of these tools is what will enable us to successfully navigate the chaos of our modern age.

Take Action: Proven and Practical Steps

1. Make reflection non-negotiable: Schedule “no input” walks or journaling time and treat it like a board meeting each week. Don’t cancel or multi-task. Use the space to reflect on recent decisions both wins and mistakes. Laura Huang even suggests that you reflect on what you were feeling in these moments as a means to hone intuition. Also, use protected reflection time to sit with a live problem until fresh ideas surface.

2. Deliberately practice flexible thinking: For example, challenge the AI model’s answer by writing down two alternative hypotheses and at least one that directly challenges it. Resist the urge to rely solely on Perplexity or Claude for the answer, particularly when you are grappling with a complicated or complex decision.3

3. Triangulate context: This involves two things: a) thinking critically about what makes the context unique; and b) weighing multiple data sources as you make decisions. On determining what’s unique about context, you can use AI to help.4 To get at multiple data sources, have the AI tool “show it’s work” and try using multiple AI tools as inputs (e.g., Perplexity to gather and synthesize lots of recent data, because it will give links and ChatGPT’s o3 model to be a sounding board to help you perform analyses and structure the rationale for the decision.)

4. Borrow intuition. Keep a “council” of 3-5 people that provide you with unique perspective. Drawing on other people’s hard-won experience is an intuition multiplier, because you draft off their pattern recognition, natural intelligence, and expertise. I put this to the test last month by asking two clients to flip roles and coach me. In twenty-five minutes they surfaced ideas that I hadn’t considered despite weeks of thinking about it.

Reflect: Some Questions to Consider

1. Which upcoming decision deserves both “Reed” (AI tools) and “Sue” (your intuition)?

2. Who is in your personal “Multiverse of Perspective” that can challenge you and ask you better questions? Are you leveraging them enough?

3. What rituals will you adopt to be more deliberate about honing your intuition?

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“No reason, no blame, no argument, just understanding.”
-Thich Nhat Hanh

You’re squirming in your seat, trying to keep a neutral face, while a colleague lays out a proposal that clearly misses the mark.

You can’t believe how much they misunderstand your business and organizational reality. At best, you think “This person doesn’t connect the dots.” At worst…well, let’s not say it out loud.

Your reaction is so strong that the leader and others in the room don’t see it as a critique of the content, but rather a condemnation of the person, protecting your own turf or another attempt to showcase your ‘superior’ intellect.

As I’ve shared before, expressing judgment gives you a dopamine hit (see Antidotes to Sweet-Tipped Poison of Reactive Anger); however, it rarely gets the outcome you want.

Leadership Principle: Judgment is reactive and ego-driven. Assessment is neutral and discerning. And compassion plus curiosity is the buffer to prevent assessment from slipping into judgment.

One seemingly innocuous question from a friend revealed an important truth about the difference between judgment and assessment.

The other day, I was telling a friend about my work, specifically about how I advise leading companies to select CEOs. He paused, tilted his head, and said, “So basically… you’re a kingmaker who just sits around judging people all day.”

At first, I laughed. Then I felt defensive.

“I’m not judgmental,” I said judgmentally.

Then he laughed and eventually, so did I. Because I hate to admit it, but I can be judgmental.1

That said, when I am assessing leaders on behalf of my clients, my judgment filter gets turned off. And it’s not just due to fancy frameworks or following ghSMART’s industry-defining approach to executive assessment.

Because the reality is that judgment and assessment aren’t the same thing…not even close! Judgment comes from a place of ego. Assessment is about neutral discernment.

There are four specific tactics that allow me to stay in “assessment mode:”

1. Grasp the full context: I’m not evaluating someone’s worth as a human. I’m evaluating their fit for a particular role, at a particular moment, in a particular company, in a particular industry and macro-environment. This context is the frame that makes the picture make sense.

2. Peel back the paint. I seek to understand the story behind the canvas. Our experiences and our genetics shape who we are and how we see the world. By getting beyond the sound bites and surface level responses, curiosity guides me to form a deep understanding of how a leader has come to be the way they are today - their patterns of achievement, behavior and motivations.

3. Create a balanced mosaic. I’m just as focused on someone’s strengths as I am on their risks. Not in a gold-star, let’s-all-feel-good kind of way. But in a what’s-your-divine-spark-and-where-does-it-belong way. By clearly seeing both sides of the story, I can discern better insights and make more objective recommendations.

4. Reduce bias: I use a structured process both for data gathering and for analysis that is explicitly designed to reduce bias. Since the ego loves a snap judgment, it’s like putting a governor on my mental engine, preventing me from speeding past data that challenges an initial view I have formed.2

While I’ve honed these tactics in high-stakes C-suite evaluations, the core dilemma of “judging vs. assessing” shows up everywhere. In fact, any time you’re sizing up someone else’s ideas or even their presence, you’re at risk of letting ego steer the wheel. Therefore, judgment isn’t confined to hiring decisions. It shows up in team meetings, strategy sessions, even hallway conversations.

This is why learning to assess rather than judge, is one of the most transferable leadership skills.

Even if the distinction between “judgment” and “assessment” is clear, the application of Thich Nhat Hanh’s words sounds damn near impossible in organizational life: “No reason, no blame, no judgment, just understanding.”

What this doesn’t mean is that you serenely accept every idea. In fact, quite the contrary. Compassion and curiosity enable non-judgment AND at the same time, they unlock the discernment needed to evaluate and take appropriate action.

If you’re ambitious and care deeply about “getting it right,” then there’s a good chance you have some ego (or even an Eifel Tower size ego). That means judgment will sneak in, especially when stakes are high and you are certain you’re right. The test will be whether you can notice when judgment emerges and choose curiosity anyway.

It’s easy to judge. It’s braver to assess with curiosity and compassion. What will you choose?

Take Action: Proven and Practical Steps

1. Create a short ritual before high stakes meetings or interactions where judgment rather assessment could rear its head. One that works for me is repeating the slogan “from self-righteous judgment to curious and compassionate discernment.” And there are even times, where I need to silently repeat this in the discussion. Once you do this enough, you may come to notice patterns about when your judgmental side comes out.

2. Slow down, note your first impression but don’t immediately act on it. Write down your first impression of an idea, particularly when the messenger is someone you’ve disagreed with in the past; however, wait to respond. Then ask yourself two questions: what would need to be true for this proposal to be the right one? and what might I be protecting by opposing this idea? Judgment thrives in speed, so this tactic compels you to engage with curiosity rather than action on your biases. You can even reference the insightful “Curiosity Curve” tool above from Jeff Wetzler to help you remain in the “zone of curiosity.”

3. Lead with curiosity, not conclusions. Explore the assumptions behind a recommendation, the pressures the person is under, and the stakes they saw. Compassion asks: What is it like to be in their shoes? Curiosity adds: What can I learn from how they see the world?

Reflect: Some Questions to Consider

1. When am I more likely to operate from a place of ego-driven judgment? What situations and which people really trigger this?

2. What is an upcoming meeting or discussion where you would benefit from “assessment mode” rather than “judgment mode”?

3. What tactics can help you to shift from ego-driven judgment to more neutral assessment?

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“Hence, anxiety is the dizziness of freedom, which emerges when the spirit wants to posit the synthesis [of our potential and of the limits of real life] and freedom looks down into its own possibility, laying hold of finiteness to support itself. Freedom succumbs to dizziness.”
Søren Kierkegaard

We all say we want freedom…until we face a tough decision where all options are fraught with risk.

Kierkegaard called it “the dizziness of freedom.” This is the moment when three overwhelming realizations converge: 1) that we have too many options, 2) that we alone are responsible for choosing, and 3) that making a choice could result in massive discomfort for us and/or those we care about.1 In other words, it’s a philosophical predecessor to Morpheus, getting at the heart of what makes it so hard for us to “take the red pill.” (Shoutout to 1999 classic the Matrix)2

Leadership Principle: Values must guide your actions when the possibilities and obstacles feel overwhelming.

You’ve felt the dizziness of freedom at home, at work, in the world…What school to send your child to…how to grow your career…what bold investments to make in your business…when to speak up and do something about issues we care about.3

Leaders know this feeling well. It shows up when:

• The data is inconclusive

• The pressure is high

• The timelines are short

• The tradeoffs are hard to juggle

• And the consequences of making the wrong decision feel existential

In those moments, most “decision-making tools” break down. Analysis is insufficient. Emotions and thoughts mislead. Advisors and others we trust disagree.

So what do we do in these moments?

We turn to values.

Values are so powerful, because they are inherently aspirational. They are the themes we want to live by when we are operating as our best self.4

They are also deeply personal. Values can lead different people to make different decisions when faced with the same set of options. That’s a beautiful thing.

Without clear values, the “dizziness of freedom” turns into intense vertigo, especially for the hardest decisions in each domain of our life.

The challenge for many people is that they haven’t taken the time to define their values.

Even when people have defined their values, they often fall into a common trap: their values reflect what sounds good or what others admire rather than conviction about what truly matters to them. The result is very little behavioral clarity. Values only work when they’re yours, when they’re clear, and when they show up in what you do under pressure.

When values are clear, you can then weigh options against those values (see below for an example tool).

One CEO I worked with faced intense pressure to pull her company out of Russia at the outset of the Ukraine war in 2022. Most global peers exited quickly, and even some on her board pushed her to do so. But her company delivers healthcare solutions and she held a deep personal value: responsibility to vulnerable populations.

Staying in Russia would mean reputational risk and financial consequences. Leaving would mean pulling care from people who needed it and had no other way to get access. She made the decision to stay in Russia. It was painful, unpopular, and principled.

Values didn’t make the decision comfortable or easy. They made it clear.

For leaders, values turn freedom into a responsibility worth carrying.

Take Action: Proven and Practical Steps

1. Write down your REAL values. Not what looks good on a website or on your wall. They need to be what you stand for when pressure hits. I have found it helpful to define values with a blank sheet of paper rather than following a formula; however, some people benefit from structure. If you fall in that camp, here’s one tool. The key is to limit them to 4-5 values, avoid vague words and have confidence that these themes accurately reflect who you are and who you want to be. 5

2. Name and pressure test the tradeoff. You get clarity when you name the underlying tug-of-war in a decision: money vs. meaning, coasting vs. all-in energy, security vs. alignment. Name them early. Then test them since sometimes we create artificial tradeoffs by thinking too narrowly or too near-term. For example, money and meaning may come at odds within a short time horizon; however, there are many situations where money and meaning can align over a longer time horizon.

3. Evaluate the options against your values. Ask yourself: which option best reflects my core values, even if it feels scary or uncomfortable? For high-stakes calls, map each option against your values. Green = aligned, Yellow = neutral, Red = conflict. This makes the tradeoffs conscious and can help guide you toward a decision.

Reflect: Some Questions to Consider

1. What are your essential personal values? What are your business/professional values?

2. In what ways do you live your values? Where do your behaviors contradict them?

3. What’s an upcoming decision where you will need to rely on values to navigate the dizziness of freedom?

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You have an idea for an impactful win-for-all initiative.1

It makes sense. You know it could make a real difference. But the people you need to convince resist it like a sick toddler tasting medicine.

It’s not because they don’t care or even because they are overly stubborn. It’s because their brains are wired to perceive change as a threat, even when it’s good for them.

Change isn’t just about logic. It activates deep-seated social triggers in the brain.

Leadership Principle: To get people to commit, logic isn’t enough. Appeal to what really moves them and persevere through resistance.

In Black Panther, King T’Challa had to navigate this. Leading Wakanda out of isolation and into a new global role presented enormous benefits, making it the prudent decision. However, he had to persuade his people and global partners to join him on that path by going beyond logic.2

Real-world leaders face similar challenges even on topics as uncontroversial as seat belts. In 1985, 65% of Americans hated seat belt laws. People didn’t push back on seat belts. They pushed back on feeling forced. The policy was smart. The backlash was emotional.3

What this reveals is that our tendency toward resistance is wired into the brain. But why does it feel so personal?

You already know how this works, even if you’ve never named it.

Maybe you were ignored in a meeting (status). Or micromanaged to the point of frustration (autonomy). That sting wasn’t imaginary. It was your brain sounding an alarm.

Because to your brain, a status drop or a challenge to your autonomy isn’t just uncomfortable, it feels like a survival threat.

Neuroscientist David Rock mapped out why this happens. Five forces, programmed into our brains over millennia, determine whether we resist or commit. He calls the model SCARF: Status, Certainty, Autonomy, Relatedness and Fairness.

And once you see these factors, you can’t unsee them:

I once led a diversity initiative that stalled. I was adamant about a specific design for the program, aspects of which were perceived as unfair to an influential stakeholder. I couldn’t figure out (until it was too late) why they were so opposed to my idea. I had threatened their sense of fairness and the fact that I didn’t seek their input early on threatened their status.

And here’s the problem: threat responses in the brain are stronger AND last longer than reward responses. Once I triggered that threat, no amount of data insights or case studies of success could override it and the initiative was dead on arrival because the leader never came around.

This is why it’s essential to minimize threats across SCARF domains whenever possible.

As you consider how to build commitment, SCARF can be applied at every level: individual, team, organization, and even society. That said, while there’s no 5-step recipe for building commitment, these tactics will help:

Leading change, particularly for win-for-all solutions, means facing resistance. Given that, it can help to reframe resistance FROM a problem TO a test. A test of how well you understand what really drives people and how long you can persevere.

Few leaders get this right. Will you?

Take Action: Proven and Practical Steps

1. Anticipate potential SCARF threats at individual and group level. Identify key influencers whose commitment is essential. Everyone has a primary SCARF domain that matters most to them—find it for the influencers.4 Also, consider how distinct groups might perceive the solution as a threat. You can even use Gen AI tools to help (ChatGPT, Claude, Perplexity). Prompt it to play the role of an organizational psychologist who is an expert in the SCARF model. Try asking it to rewrite an announcement to reduce resistance, role-play difficult conversations to test your messaging, or analyze a new initiative to suggest ways to frame it that maximize reward on each domain of SCARF.

2. Plan specific tactics to minimize threats and maximize rewards in each domain. Some threats can be reframed by appealing to a larger purpose (e.g., showing how a shift enhances status rather than diminishes it like T’Challa did for Wakandans). Others must be offset by rewarding other SCARF domains. For example, if a change creates uncertainty, increasing relatedness (team connection) can stabilize engagement. And in some cases, the win-for-all solution itself must evolve to address real concerns.

3. Commit to the practices that keep you mentally sharp, physically strong and emotionally resilient, so you can stay the course.

Reflect: Some Questions to Consider

1. Which SCARF domain do you personally react to the most? How has it shaped your own decisions or resistance to change?

2. For a current initiative, what SCARF threats might be blocking the commitment of key influencers?

3. When resistance comes, what rituals will keep you standing for the win-for-all path?

Know someone leading tough change? Pass this on to them—it might be exactly what they need today.

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My son enthusiastically and sincerely exclaimed this line as our pawns moved at an accelerated pace towards the victory circle in the classic boardgame of Sorry!.

In his mind, we could be partners in victory.

But with an almost Neanderthalic automaticity, I reinforced the harsh, black-and-white rules of competition: “No son, there’s only one winner in Sorry!.”

And now my son’s reactions reflect this sentiment. When he wins, he skips around our living room mixing gymnastics, hip-hop dance and toddler jubilance, repeating the line: “Champion! Champion!” When he loses, he cries as if he has suffered the final defeat in a battle of life and death. (I have no idea where he gets his competitive streak from 🤣)

It’s easy to laugh at his intensity…but are adults really that different? Many of us carry the same rigid mindset into adulthood, just with higher stakes.

We’re wired to see life as a zero-sum game: “If I win, you lose. And if you win, I lose.” And of course, it’s extension: “If we win, they lose. And if they win, we lose.”

And no doubt, there are scenarios where this is true. When that role you’ve coveted comes open, either you get it or you don’t. When you are in a head-to-head pitch for a customer, either you win the contract or you don’t. When you are competing in the state championships, either you win the trophy or you don’t.

The danger emerges when we apply zero-sum thinking to situations where the optimal outcome requires a different approach. And the reality is we do this ALL THE TIME.

Leadership Principle: Don’t default to zero-sum thinking. Step back, assess the situation, and look for win-for-all possibilities.

There are at least four types of situations where a zero-sum approach leads to weaker outcomes1:

1. Fighting over scraps instead of expanding the pie (Positive Sum): A zero-sum mindset makes you fight over limited resources instead of creating new opportunities. It’s like two kids arguing over the last slice of pizza instead of working together to bake a bigger one when the ingredients are just waiting for them in the refrigerator.

2. Sinking the ship you are both on (Mutual Dependence): A zero-sum mindset makes you compete with others even when facing a shared challenge. Imagine if Boston and New York refused to collaborate on counterterrorism efforts just because of their bitter sports rivalry. The result would be that both cities would be less secure.

3. Burning bridges for quick wins (Reputation Effects): A zero-sum mindset makes you prioritize short-term wins over long-term relationships. Think of a young hot shot employee who hoards knowledge to get ahead, only to find that when he needs support on a big project, no one is eager to help.

4. Trying to Lift a Whale Alone (Collective Scale): A zero-sum mindset leads you to try to tackle a problem alone that’s too big for one person or one organization, missing opportunities to accelerate progress through collaboration. It’s like Captain America trying to defeat Thanos by himself, when he has an entire team of all powerful Avengers sitting on the sidelines.

In the business world, one of the best examples of a shift from zero-sum to win-for-all is Microsoft’s “existential moment” under CEO Satya Nadella. For years, Microsoft treated open-source2 software like a direct threat. Former CEO Steve Ballmer even called it a “cancer.” Under Satya’s leadership, Microsoft flipped its approach. Instead of fighting open-source, it embraced it. They acquired GitHub (home to millions of developers), integrated Linux into Windows, and transformed .NET from a proprietary framework into a free, cross-platform tool for building apps. Instead of losing power, Microsoft gained influence, winning over the very developers it once saw as rivals. This strategy, the partnerships they established and Satya’s leadership unlocked a new chapter of innovation for the company. Now it is third most valuable company in the world and a leading catalyst for the AI revolution.

Consider another example from social policy and advocacy. In the 1960s, most Black workers were excluded from fair wages due to segregation-era labor laws. By joining forces, civil rights organizations and labor unions advocated for expanding the Fair Labor Standards Act to include marginalized workers, and by doing so raised working standards and the minimum wage for all workers. This collaboration not only uplifted millions of workers, but also demonstrated the power of collective action to find solutions to what seemed like intractable problems: civic freedom and economic security for all.3

So, win-for-all solutions aren’t just possible, they are often the wisest way to solve complex problems.

The key is recognizing when a zero-sum mindset is holding you back and taking the time to explore potential win-for-all paths.

The next challenge? Getting others to believe in and commit to win-for-all solutions.

That’s where neuroscience, inner work and relentlessness come together, and it’s what we’ll cover in the next Friday Reflection.

Take Action: Proven and Practical Steps

1. Pick a meaty problem or challenge where competition or some sort of an adversary is present. This could range from a personal challenge to a business challenge to a societal challenge that you care about.

2. Have an informal conversation with someone you trust to help you reframe the situation. They can ask you questions like:

   1. On a scale of 1-10, how urgently do you want to find a solution to this problem? (10 = very urgent)

   2. What’s the bigger opportunity here?

   3. What individuals or organizations seem like obstacles? What shared goals do you have with those individuals / organizations that you perceive as obstacles?

   4. What other individuals / organizations could be potential “partners in victory” that would also benefit from addressing this problem?

   5. For individuals / organizations you identified, what small experiment can you do to prove or disprove that joint action could help you achieve those shared goals?

   6. By when do you want to take this small experiment of joint action?

   7. What could get in the way of taking this small joint action?

   8. How will you measure if this small action was successful or not?

3. Build a reputation for reciprocity. Practice generosity with no expectation of others’ returning the favor. Instead of seeing it as giving up an advantage, share knowledge, connections and resources, because it creates allies and leads to future opportunities. This also is helpful tactic to break paralysis in those moments where you don’t know what to do. Ask yourself: How can I contribute in a way that strengthens my relationships and drives long-term, sustainable success?

Reflect: Some Questions to Consider

1. Where might you be stuck in a zero-sum mindset that’s holding you back?

2. What win-for-all success stories inspire you?

3. How can you apply those lessons to a tough challenge you’re facing today?

If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.

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It’s a hilarious and inspiring moment.1 Tony Stark sees potential in a young Peter Parker and decides to bring him into an arena far beyond anything Peter has experienced before.

And regardless of whether you’re in camp Ironman, camp Captain America or camp IDGAC, this storyline beautifully illustrates a lesson I’ve seen in spheres ranging from sports to politics to arts to corporate America - great leaders unlock the next level of courage in others, beyond their baseline.

Leadership principle: Unlocking courage is about revealing and activating untapped potential. To do so, focus on skillful people, skillful challenges and skillful support.

Skillful People

A surefire way to get maximum return on effort is to invest your leadership capital in someone with the skill and will to succeed at the next level. The skills you need are context dependent (i.e., experience level, the role, the company, the department). When it comes to will, you are looking for a strong drive to succeed in the face of setbacks, impact-oriented motivation and at least a threshold level of balanced risk-taking. What’s surprising is that I repeatedly see even some of the most seasoned leaders misplace their effort in others that lack these attributes. Imagine if instead of selecting Spiderman, Ironman brought “Arm Fall Off Boy” to the Avengers Civil War.2

To ensure you invest in skillful people, ask yourself these three questions:

Q1: How have they responded to setbacks and challenges? What specific evidence do you have that they push through obstacles with determination?

Q2: What fuels them to succeed at their core: personal ambition, recognition, a need to please others, a drive for impact3 or something else? What are specific examples of how they channeled that motivation into action?

Q3: When have they taken a meaningful risk despite uncertainty? What was at stake, how did they handle it, and what does that reveal about their baseline level of courage?

Remember it’s essential to invest selectively. If any of these three questions cause you to feel some hesitancy, then this person is not a candidate for your primary investment and there is no need to ask the next four questions.

Skillful Challenges

To unlock courage, the opportunities you provide need to align with each person’s confidence and capabilities. Too much too soon can lead to flaming out, while too little can stunt growth. At the same time, aside from helping them grow in their courage, a skillful challenge should also help them deliberately grow a new skill or mindset that is needed for the future. This reflects my belief that tapping into and expanding one’s potential is an essential component of unlocking courage.

To ensure you place them in a skillful challenge, ask yourself these two questions:

Q4: What new, specific skill or mindset will help to accelerate their growth?

Q5: What new role or experience will enable them to demonstrate mastery of that specific skill or mindset?

Skillful Support

“Sink or swim” mentality is mostly an overplayed cliche in organizational life. Many of those who have “made it” to the top often re-write history saying things like “well I did it on my own, why can’t the next generation.” This is garbage. As a leader, you’re responsible for ensuring those you invest in have the support to succeed. Tony Stark knew this and so he got Spiderman an upgraded suit, equipping him for the battle.

Child development research shows that children build skills beyond their current abilities by tackling more complex challenges with the support of adults and guidance from peers. Adults learn in much the same way. To grow, they need opportunities that stretch them (“skillful challenges”), along with the reassurance that they have support if they stumble. When they know you have their back, they see mistakes not as failures, but as stepping stones to growth, reinforcing your investment in their long-term success.

To ensure you provide skillful support, ask yourself these two questions:

Q6: What support will they need to be successful in this new experience?

Q7: What commitments will show them you have their back if they fail? What might get in the way of you actually living up to these commitments?

Take Action: Proven and Practical Steps

1. Identify the “Skillful People” whose courage you want to unlock. Use the three “Skillful People” questions to figure out who these people are. Make sure you also take the time to identify what context-specific skills are needed for your organization. Lastly, avoid sentimentality in answering these three questions…it will only hurt you later.

2. Match them to a “Skillful Challenge.” Select a project, role, or experience that fosters a critical skill or mindset they need to grow into future leadership roles. Be explicit with them that this new opportunity will stretch them in this area (e.g., long-term thinking, negotiation, leading change).

3. Make your “Skillful Support” visible and tangible. Provide structured feedback, mentorship, and access to resources (training, coaching, connections to others).4 Clearly communicate that failure is a learning opportunity, not a career setback. More importantly, show them that you mean this. Have their back in front of other colleagues and take ownership of their setbacks (don’t blame them or critique them). Also, consistently remind others that the purpose of their new role or experience is to help them develop in a new dimension - it won’t be smooth sailing from the get-go.

Reflect: Some Questions to Consider

1. Are you investing in skillful people?

2. What are specific roles or new experiences that you can create to unlock courage in others?

3. Do the people you are investing in know that you have their back? If so, how do they know? If not, what do you need to do differently?

If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.

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I may constantly cry that I need more time, but actually time needs more of me. More of our spacious, uninterrupted, timeless time to live out and understand both its extraordinary depths and its incalculable far-off horizons.
-David Whyte

Finishing the year can feel like stuffing a suitcase that is already filled to the brim. We often have more we want to fit in than space allows, which can intensify our tendency to “constantly cry out” for more time. And yet, the end of the year also offers us a unique window to embrace a more expansive view of time, as David Whyte so beautifully articulates in this line from his poetic essay simply entitled “Time.”1

Leadership Principle: Embrace a more expansive view of time, particularly at year end, so you can finish strong, re-charge intentionally, and enter the new year boldly.

For today’s Friday Reflection, I share a holistic view on how to use this arbitrary yet nearly universal inflection point (calendar year end) to finish strong, re-charge intentionally and begin boldly.2

And because it has been on repeat for the last couple weeks, I incorporated a lyric from Kendrick Lamar’s new album, GNX,3 to bring to life each concept.

Finish Strong:

“Got my foot up on the gas, but somebody gotta do it, huh…hurry up and get your muscle up.” (from the track ‘tv off’)

With time as your ally, give one last push on the ONE THING you feel stirred to get done before the year ends. You’ll know it’s the right “one thing” because it solidifies achieving one of this year’s important goals AND it sets the stage for the upcoming year. Aim to be fully present as you take action, feeling time’s supportive presence rather than its pressure.4 Pick the one thing, put your foot on the gas and make it happen.

Re-charge Intentionally:

“Emotional stability…a sound body and tranquility…I deserve it all.” (from the track ‘man in the garden’)

The burdens of leadership can take a toll, and so you need to find ways to re-charge…to gear up for next year’s marathon. Use the CARE model (see below) to help you figure out what you need to re-charge. In addition to nurturing our body and mind, these re-charge moments offer a glimpse into “spacious, uninterrupted, timeless time.”

Begin Boldly:

“Use your heart and not your eyes…if you got time, then I got time…free your thoughts and watch them fly…use your heart and not your eyes.” (from the track ‘heart pt.6’)

Finishing strong and re-charging intentionally give you the energy and confidence to begin the next year boldly. This is also where it can help to consider what Whyte calls time’s “incalculable far off horizons.” Let the wisdom of our cosmic insignificance inspire you to take some bigger swings. From this vantage point, the fears that hold us back from bold action feel smaller, like microbes on a pale blue dot.

Ask yourself: what’s one transformative change you’d pursue if you had full freedom and could subdue fears of failure, something that feels just out of reach, but would redefine how you serve and support the people who depend on you (customers, colleagues, beneficiaries, friends, or family)?

My prescription to begin boldly is to set “goals with soul” and a compelling “annual intent.” Goals with soul are not new year’s resolutions. They are goals that connect to our core motivations (heart not eyes), rely on community support, and aim to create lasting impact. An annual intent involves using a resonant metaphor (e.g., the year of wings) to bring your intention for the year to life. When you veer off course or hit the “Avalanche Moments,” this annual intent can ground you in presence and keep you focused on where “time needs more of you.”

Take Action: Practical and Proven Steps

1. Finish strong: Review your current goals and commitments, then ask: “Which single action would have the greatest impact if completed before year’s end?” Consider what is both doable and beneficial.

2. Re-charge intentionally: Schedule specific activities in specific windows of time. This post (Re-charge) and this post (Re-charge 2.0) have more specific ideas and tips on how to do so. Many of us have responsibilities (kids, elderly loved ones, other life commitments) and history that can make the holidays actually more stressful than a “run-of-the mill” week. It is imperative that you ask others to help you carve out this space. You deserve it all, but no one will make this space for you.

3. Set goals with soul and an annual intent to begin the year boldly. These three posts provide a roadmap for how to do this: Goals with Soul Part 1, Goals with Soul Part 2, and Annual Intent. There are other effective ways to prepare your mind to begin the year boldly. This is just what works for many leaders that I advise and what works for me.

Reflect: Some Questions to Consider

1. What is the ONE THING that you want to do before the end of the year?

2. Over the next couple weeks, what do you need to re-charge intentionally? How can you get creative and ask others for help in getting time for what you need?

3. What is your bold annual intent for next year? What actions in the first month of the year will give you confidence that you are beginning boldly?

If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.

“Look around, look around
at how lucky we are to be alive right now…
Look at where we are, look at where we started…
the fact that you’re alive is a miracle.”
-That Would Be Enough from Hamilton the Musical

There are times when I need to hear this song more than others, because even in the darkest moments, these lines are true - we are lucky to be alive right now.

The challenge is that our brains and our culture are wired to fixate on the negative. Moreover, we allow the inevitable suffering of life to create layers of mental and emotional scar tissue that can exacerbate this tendency towards disillusion.

And yet in this current period of hyper polarization, the world needs leaders that inspire us to hold on tight to optimism (while still acknowledging the seemingly intractable challenges of this moment).

Leadership Principle: Disillusion, cynicism and inaction are the easy path. Optimism is hard. Choose optimism. Choose action.

In my life, one event, perhaps more than any other, had a profound disillusioning effect on me. What’s surprising is that it is also tied to the person who taught me the most about optimism.

For over a decade, I was actively involved in the Cuban-American community. My passion for youth empowerment and a shared vision with like-minded Cuban Americans led me to support Cuban youth in shaping their own future.1 After a year or two of working on efforts from the U.S., I felt a pull to travel to Cuba. I wanted to see the reality of my heritage with my own eyes. Not just as portrayed by the media or by family who had left, but to understand the multiple “true” narratives that could only be uncovered by spending time with relatives who still lived there and others ranging from artists to barbers to basketball players.

On my second trip, I met Harold, a Jesuit priest and pro-democracy advocate just a few years older than me. Our first meeting in the city of Camaguey stretched into late-night hours - conversation ranged from his dreams for Cuba, his life’s hardships under a communist regime, and his faith. Surprisingly, we also bonded over a shared love for U2, which led to Harold singing “I Still Haven’t Found What I’m Looking For” as we sat in a plaza near a public fountain.2 His quiet conviction and unshakable belief in the potential of our people gave him a magnetic presence that I will never forget.

Over the years, I returned to Cuba a few more times to learn from Harold. Despite the hardships he faced, he spent every day trying to improve the lives of others.

Then, one day, I received a call that still haunts me: Harold had been killed in a car crash, which was seemingly engineered by state operatives targeting him and another pro-democracy leader. The loss was devastating, and the disillusionment that followed was acute.

For years, I told myself that increased work and family demands were why I withdrew from more formal activism. And while that certainly contributed, when I hold up a mirror, the reason was far more personal: Harold’s death left me questioning whether purity of purpose and courage could make a big enough difference in a world that often rewards cynicism, greed and oppression.

Yet, Harold’s example continues to inspire thousands of activists on the island and abroad. In a different way, it also inspires me daily. Though I’ve yet to fully regain the fervor I once had, his courage and unwavering belief in the power of hope shape how I approach my work with leaders from all walks of life. Whether supporting them to navigate challenges or to inspire their teams, I carry the lessons I learned from Harold with me.

And when I catch myself in moments of pessimism, I return to a book of poems he gifted me during what would be my last visit with him. One line from Dulce Maria Loynaz, a favorite of ours, embodies Harold’s resilient optimism:

I share Harold’s story because, like many, I’ve recently felt the seductive pull of pessimism. Optimism feels scarce, and there is inertia toward cynicism and self-protection. But Harold’s legacy reminds me—and perhaps can remind you—that even in the bleakest of circumstances, we have a choice: Optimism or pessimism; action or inaction.

For most of us, choosing optimism does not need to mean pursuing social justice in every waking moment. In fact, that doesn’t feel like what we need right now.

I’d love to see more leaders that embody Harold’s spirit of temperance and hope, and then take action in big and small ways to ignite optimism in others.

Take Action: Practical and Proven Steps

1. Fortify yourself with optimism and empathy. Put together a list of quotes, stories, poems, songs and other works of art that can pull you out of pessimistic thinking. Spend more time with pragmatic optimists. Moreover, ensure you also spend time seeing the world through lenses of people that you disagree with, so that your optimism does not feel detached from their reality. An old short story by Frank Harris called Magic Glasses is a beautiful allegory for the power of seeing the world through different lenses. (I’ve also written another reflection The Superpower of Skeptical Optimism.)

2. Role model optimistic temperance. As you tackle the next inciting incident in the world or respond to employee activism, focus on the needs of those you lead - demonstrating a service mindset and actively listening to concerns. Once you’ve decided on a course of action, accept that there will be subsections of your employee population that will be disappointed with what you’ve communicated and/or the path you’ve chosen. Don’t let this disappointment cause you to fall into self-righteous defensiveness or worse, to be wishy washy about the optimistic tone you are aiming to set.

3. Prepare for optimistic responses in the face of outrage. A recent interview of Karthik Ramanna outlines principles, mindsets and practical actions to help us lead in the “Age of Outrage.” One such practical action is to designate small committees during the “calm,” so that when an outrage event erupts, they are ready to help outline a path forward for your organization.

Reflect: Some Questions to Consider

1. In moments of disillusionment, what practices or sources of inspiration help you choose optimism and action over pessimism and inaction?

2. Who in your life has shown you the power of optimism, and how might their story inspire your own path forward?

3. What small actions could you take this week to role model optimism?

If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.

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Leadership Principle: Avalanche moments are inevitable when you aim to have great impact. You have a choice to experience them as soul-sucking sacrifice or as laboratories for equanimity.

In Avalanche Moments, it can feel like the only way out is through an obsessive focus that sacrifices every other aspect of life. The anxiety that usually helps high achievers anticipate risks and plan ahead can escalate into overdrive, overwhelming your mind and leaving little mental capacity for anything else. This often leads to unskillful reactions, causing suffering for yourself and others through reactive anger, anxiety, or fear, or simply a lack of being present.

There is also a more sneaky unskillful reaction that masquerades as a skillful one - disassociation or plainly put, an all-consuming seriousness. In this state, you wear a mask of calm on the surface, but are numb on the inside - far from the fully alive state that we want at our core.

On a personal level, the cost of this serious, “nose-to-the-grindstone” mentality can vary. For some they are modest. And for others they are debilitating. But, when present in a leader, its effects are more unequivocally negative, eroding engagement in teams and organizations.

That said, it is possible to experience these Avalanche Moments without reactive energy completely consuming you: Reframe Avalanche Moments from soul-sucking sacrifice to laboratories of equanimity.1

Equanimity, a mental state and practice that is lauded in nearly all flavors of ancient wisdom, offers a path through these intense periods. As Joseph Goldstein describes in The Path to Insight, equanimity is “neutrality of mind,” a state where your mind remains unaffected by external events. The Christian tradition similarly speaks of “inner peace that passes all understanding…that guards our hearts and minds.”

Equanimity is often seen as something reserved for those who spend most of their days in deep thought. Because of this, you may resist the idea. After all, to to live a life of impact, you can’t just sit around contemplating consciousness, the cosmos and impermanence all day.

So how can we avoid unskillful reactions in Avalanche Moments AND operate in GSD mode required to dig out of the avalanche?

Convert your mind into a lab of equanimity.

Labs are where we perform experiments. Also, by definition, we make mistakes in the lab. If you are more like me and less like the Dalai Lama, then you’ll still have many times during Avalanche Moments where equanimity does not prevail. This is a normal part of the cultivation process. In fact, mindfully observing the self when you are in reactive mode is a form of equanimity practice.2

What I want to emphasize is that Avalanche Moments don’t have to feel like a martyr’s walk. With the right mindset and practices, they can become a powerful laboratory for building equanimity—helping you grow more balanced and effective in everything you do.

So what specifically can you do? (This is just a start…curious to hear more ideas)

Take Action: Practical and Proven Steps

1. Communicate and prepare. Let those around you, at work and at home, know that you’re entering one of these intense periods. Like a giant redwood tree whose deep roots allow it to easily withstand the avalanche, remind yourself what keeps you rooted - this is often our values, our confidence that we’ve made it through these moments in the past and our closest relationships. Set “appointments” for things like physical activity or time with those we love as they actually play an important protective role. Be intentional about asking for help to ensure you can honor these commitments.

2. Anchor yourself. Embrace the spirit of Gandhi’s famous line about meditation: on the hardest and busiest days, he meditated twice as long. Why? Because the more intense life becomes, the more you need to anchor yourself. Decide which grounding rituals you will keep in place and practice them daily (e.g., spending time in nature, movement, listening to music, journaling, or meditating). Unless you are already more centered than Gandhi, you need more energy devoted towards these rituals (not less) during the Avalanche Moments.

3. Listen for the “mindfulness alarms” going off. Notice when you get stuck in a reactive mindset. This is akin to having mindfulness alarms in your laboratory. You don’t need to do anything more than observe yourself: “I’m reacting anxiously.” or “I’m in overly serious mode.” Sometimes it can be helpful to find someone to share with when these alarms go off, but other times you’ll simply note it for yourself. Also, try relying on “in the moment” actions like mental noting or even breathing and pausing so that you can use these small moments contain multiple equanimity-inducing experiments.

4. Lighten up and physically shift. Inevitably, the lab of equanimity will shut down at points during Avalanche Moments. When this happens, pay attention to when you are disassociating or become overly serious as it’s a reaction that can surface more subtly. Then, follow Pema Chödrön’s advice: do something to break the pattern.3 Look out the window at nature, sing in the shower, read a short story that makes you laugh, splash cold water on your face, or even practice a physical motion like a wall angel —anything to reset your mind. Moreover, create space for laughter as this also has the potential to unlock another benefit - you’ll come up with better, more creative ideas to dig out of the Avalanche.

Reflect: Some Questions to Consider

1. How can you better prepare for your next Avalanche Moment?

2. What grounding rituals can you rely on during the Avalanche Moments? If none, what are one or two that you can experiment with?

3. What are one or two ways to get you to “lighten up” while still keeping your eyes on the prize during Avalanche Moments?

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Medical advances in drug development over the last 100 years have transformed our lives.1 From penicillin to polio vaccines, chemotherapy to statins, birth control to insulin, the promise is clear—take the medicine, and it leads to longer, healthier lives.

What baffles me is that over 50% of patients prescribed life-saving therapies abandon their treatment. They find a seemingly rational excuse to quit, only to watch their condition deteriorate, a problem the medical community calls non-adherence.

As perplexing as non-adherence may be, a similar phenomenon happens in leading large organizations. Upgrading talent can relieve organizational pain AND accelerate performance, but too often, senior executives ignore the prescription.

Leadership Principle: Putting A-player talent in critical roles is like a miracle drug. It relieves chronic pain and accelerates performance if you have the resolve to consistently keep the regimen.

Replacing underperformers demands significant time and emotional investment, both before and after the decision. Developing B-players into A-players requires frequent feedback, thoughtful crafting of roles, focused coaching and advocating for them to get new experiences. Furthermore, talent that works well today may not be suited for future goals, often forcing heart-wrenching decisions to replace leaders who once delivered great results. No wonder adherence to this miracle cure is so low.

Similar to non-adherent patients, it's easy to rationalize inaction. "External hires often fail here” as the saying goes (the data backs this up, 50%+ of senior executives hired from the outside flame out within 18 months). And the list of “who dilemmas” goes on and on (read more on this here).

Yet when you skip a dose of upgrading talent, you leave your organization exposed to the very issues that have caused you pain in the past. Moreover, strong, high potential talent gets poached by your competitors, weaker talent “survives”, and over time, the entire organization atrophies and struggles to deliver the desired impact.

On the flip side, the relief and lift in performance that comes from sticking to this regimen of upgrading talent is undeniable.

A senior executive I coach made two key changes to their leadership team in the first six months, yet performance and her own bandwidth were still being weighed down by another leader on her team, who we’ll call Carla. Carla was valued by the CEO for her strengths, but the role required decisive execution, and she was more of a consensus-driven strategist. Knowing her boss’s (CEO) fondness for Carla, the senior leader I coach began hesitating to make the tough decision she knew was necessary.

During a few early morning discussions with me and others that she trusted, she came up with a script for the conversations with Carla, a list of potential A-player replacements and a plan to get others, including the CEO, on board with her decision. This gave her the confidence to act.

Ultimately, she followed the prescription and replaced this leader with an A-Player. Within weeks, the team felt renewed, and within six months the company was set on a stronger path for growth. In this moment, her sentiment echoed a line from Eminem’s Hallie’s Song: “It’s like the greatest gift you can give, the weight has been lifted.”

Relief…followed by improved performance…I think we all could use more of that.

Take Action: Practical and Proven Steps

1. Identify the blockers: Take a hard look to understand who is underperforming in critical roles. These individuals are “blockers,” because they are holding back performance AND they are in a leadership role that other high potential talent within and outside your organization could have. Make sure to look beyond your direct reports; sometimes, the blockers can be skip-level leaders in high value roles. Be sure to differentiate between who needs to be replaced and who has coachable development areas where they can improve.

2. Challenge your “story” for why you can’t upgrade these “blockers” now. Just as patients rationalize their decision to stop taking a medicine that helps them, it’s easy to come up with a story to delay action on talent decisions. Speak with a confidant you trust to help you see all the angles and come up with a plan and timeline to take action. If you don’t have that confidant, consider leaning on the multi-verse of perspective to really test whether your story is a good enough reason not to act. (It usually isn’t).

3. Follow a disciplined process. Whether the solution is an internal promotion or an external hire, match capabilities and skills to the specific scorecard for the role. In some cases, external hires are necessary to inject new capabilities. To get the hiring decision right, especially with external talent, you need to follow a science-backed process.2

4. Overinvest in onboarding: A lack of a rigorous onboarding process is one of the top three reasons why external hires fail (and can even affect internal hires). Don’t leave their “integration” to chance or delegate it solely to HR. Be clear about the key relationships your new hire needs to foster and guide them through the unwritten rules of your company culture. For some ideas on best practice onboarding, you can check out this article I co-authored with my amazing colleagues Karen Welt Steeves and Dina Wang.3

Reflect: Some Questions to Consider

1. Who are the blockers in your organization that you’ve been hesitant to address because of how hard it will be? What are all the costs of inaction?

2. When was the last time you reassessed the talent in your critical roles? How aligned is each individual’s capability and skills for the next chapter of growth?

3. How can you improve the onboarding experience for new leaders you hire to ensure they don’t trip over any unstated cultural norms in their early days?

If this week’s Friday Reflection was practical or enjoyable (or maybe even both!), please share it with your colleagues and friends.

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