I first read ’s foundational Getting Things Done 13 years ago. I had already self-discovered the value of to-do lists and on task capture but had never seen or thought about any structure, principles or practices beyond that. This book was a pivotal early moment in my long path towards building my career around productivity.

Getting Things Done is a foundational text for a reason, and, at a ripe old 25 years of age now, I’m pleased to say it holds up as an enlightening and entertaining read. If you haven’t read it, consider this both my endorsement and a homework assignment.

I just finished my first-ever reread of the book and was struck by how much of the philosophy and tactics were ahead of their time. Of course, there are parts that haven’t aged perfectly, but fewer than I’d have expected. The core principles endure, and the ancient references, to e.g. the recently ubiquitous and still-hyphenated technology of “E-Mail”, are charming.

My biggest takeaways

Allen does an enviable job of making his most important points stand out. Here are my favorite quotes from the book where he says it much better than I have and what I’ve learned from my reread:

The number of things to do is only more overwhelming nowadays, and everything else about the time we live in makes it harder to have a positive sense of relaxed control about anything. Designing your productivity processes to be a means of stability and organization, rather than further overwhelm, is a well-stated and keenly oriented primary goal.

When I work with someone who self-identifies as bad at email, organization, or task tracking, or someone who is truly suffering from their current productivity system, they have usually lost hope and lost sight of the very possibility of functioning productively amongst overwhelm. But it is indeed possible.

So, what a perfect foundation for the first sentence of the book. It invites everyone in, promises solutions – and goes on to deliver them.

The word “assured” here is a great synthesis of a throughline of Allen’s approach: you need to have a model that you fully trust, which means you need to design your processes in a way that work for you and everything that makes you unique. You also need to have things that you’re not doing, an important permission for yourself to design around.

Building trust with yourself is similar to how you build trust with your colleagues through how you manage and convey how you spend your time, capture and transfer knowledge, and get coverage from them when out of office. You need to build systems that you can have confidence in as always being up-to-date, reflecting your most important tasks, and dynamically adapting to changing priorities. Your past self should be your best coworker.

Allen also digs deep on how and why to keep a continuous task capture mechanism – when people only make to-do lists after they’re already overwhelmed on a big project, they’re playing catch-up and often adding to their stress and dysfunction. Chapter 2 (and its legendary flowchart) and Chapter 7 lay out a strong roadmap for this.

This sounds like a lot of the best people I’ve worked with. Biasing towards reactive crisis-response work over planning is one of the most common productivity mistakes I’ve seen, especially on high-velocity engineering teams.

So many are more comfortable in the chaos of firefighting, that furious stasis of always pivoting to the latest emergency, than they are actually taking time to plan out and tune the rest of their work. When there are legitimate surprises and pivots, you and your team need to be nimble and ready to sprint, but when that’s not happening, you need to have a healthy set of processes to define and tune your work and not let your planning muscles atrophy.

One way I’ve said it: you can’t always be surging, you have to antisurge, too.

Other chapters of note

The rest of the book builds upon these themes and defines tactical steps for implementing Allen’s foundational GTD system.

Chapter 3 lays out an approachable perspective on project planning that starts by highlighting how the simplest, lightest touch, back-of-napkin-level planning is often the highest return-on-investment (yup). Chapter 12 explores the how and the why of one of the most important pieces of any team’s rhythm of operations: consistently identifying the next action on a project or as the output of a meeting. A few chapters focused on pen-and-paper systems and managing a single, physical space of work suffered from various amounts of outdatedness for me, but still provide food for thought and don’t bog down the read.

Put it into practice

• Read the book if you haven’t, or reread it if you need a tactical GTD tune-up. It’s complementary to what I’m offering you in this newsletter.

• Follow , as I just have, as he’s still at it!

• If you’re looking for some exercises from the book to try, I’d recommend these two, each of which are detailed further in their chapters:

Next week, I’ll examine the few recommendations in the book that I’ve found, over the years, need updates for the modern workplace.

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Productivity means different things to different people. To me, it’s mainly about optimizing operations and making the most of whatever one’s finite time available is, but a seemingly increasing portion of the modern productivity content landscape is focused on the performance aspect that can effectively expand that budget: motivation, energy, intention, goal-setting, diet, sleep, drugs, etc., a mix of things I’ve so far either presupposed or am not qualified to touch.

I think I’m quite atypical when it comes to my own motivation and energy, e.g. fun fact, I don’t drink any caffeine. But maybe my being atypical makes my perspective useful, at least to the other similarly unusual people out there.

There are two main characteristics of a task or project that should inform your approach to your motivation and energy: its direct impactfulness and how exciting the work is to you.

Impactful, exciting tasks

These are the easy ones. You should shape your career intentions and goals towards opportunities that maximize the amount of work fitting into this category, and you should constantly reshape this as your motivations shift.

Early in my career, all I cared about was mathematical optimization for its own sake. Then, for my time in tech, I found a greater motivation: helping drive real-world impact through people-centric software design and deployment. Now that’s shifted towards more broadly teaching people how to optimize. If you’re not steering the ship of your career towards what makes you excited to wake up in the morning, you’ll drift away from it.

Give your impactful, exciting tasks your best energy in terms of how you structure your days and weeks. You’ll naturally avoid procrastinating on these, but you should go further and antiprocrastinate: start them early, monotask on them, and allow them to give you productivity momentum that you can carry into the next category of tasks.

Impactful, unexciting tasks

When the act of performing the work itself isn’t motivating, but the impact of it is, you should turn to your team.

Some tasks are unexciting to you and aren’t something you’re particularly good at. They may be exciting to others. A swap of duties with a teammate that leaves you both more excited may save time and improve the output – I’ve made many mutually profitable trades within engineering teams of their data pipelining work for my data analysis skills.

Sometimes, though, you’re good at tasks that aren’t exciting to you. These are different; you should probably do these. When you’re the best person to get this done right, you can find motivation in your value over replacement; you’re helping your team increase its overall impact by taking this unexciting task off of their plates. In my experience, this gets more motivating the more you like and respect your team, which is why investing in a strong team culture is so important.

Fit these tasks into the best blocks on your calendar for your energy where you can, too. Here, time blocking is a good way to ensure you prioritize them in line with their impact and don’t procrastinate.

Unimpactful, exciting tasks

By “unimpactful”, I mean through the lens of motivation: work that doesn’t give you an immediate, emotional payoff for doing it well. If work is literally unimpactful in terms of the total bottom-line direct and indirect impact on your organization, well, probably just don’t do it.

For this batch of tasks, lean into and wield your passions, but with restraint (i.e. don’t trick yourself into doing low-value work). Find the tasks that matter to your team that are guilty pleasures (or at least unusual tolerances) for you and take it off your colleagues’ plates where you can. For me, that was writing technical documentation and training materials. If you nerd out on something, you likely also appreciate the indirect, longer-term impact of doing it well. That motivation can take the place of the motivation of direct impact.

Limit your time and energy spent on these tasks when appropriate. The directly impactful tasks are often more deserving of your prioritization, and you don’t want to go down the rabbit hole of spending too much time overoptimizing your fun work if its impact is limited. Here, you might use time blocks not to ensure you start the task, but to ensure you stop the task after a certain amount of time.

Unimpactful, unexciting tasks

These are the tough ones.

A few tricks that have worked for me and the people I’ve worked with:

• Gradually build your excitement for the long-term impact of a task. Everyone finds different things inherently exciting, but I’ve honestly never understood how people aren’t motivated by hiring and onboarding new teammates. This is one of the most highly compounding long-term parts of a successful team, and it can be pretty fun when you get good at it! Bottom line, people who talk to me get more excited about interviewing. Find the people in your orbit who are excited about the thing you aren’t, and pick their brain. Learn how to make it motivating for you.

• Gamify and streamline the task. Manufacture a motivation out of your improved efficiency at something you don’t enjoy. For example, when working through closing out or reprioritizing a ticket backlog, you could keep track of how long you take per ticket and see how your “score” improves over time (but hold yourself accountable to doing a good job more efficiently, not rushing). Avoid wasting extra time optimizing or thinking about these tasks with the rest of your time; just get them tuned while you do them, then stop thinking about them. Take notes about what works well.

• Temptation bundling. Life examples are easier than work examples, but just as you save your favorite Netflix show for the treadmill, you could do your monthly-ish full inbox cleanup while on regular business flights (and not allow yourself to check out the movies available until it’s done).

Get this work done in the minimum amount of time it deserves, and slot it into your least productive times of the week, e.g. block your expense reports for 4:30pm on the last Friday of the month. Batch them when possible and multitask on them when you can.

Put it into practice

What are the three work tasks that excite you the most nowadays? What are the three work tasks that excite you the least nowadays?

Review the appropriate section above for each of them to find ideas on how to shift your approach.

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I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

A strong culture of interpersonal feedback is the lifeblood of an effective team. Business outcomes, operational velocity, personal growth, and interpersonal trust are all supercharged when good feedback is given well and received well, and all decay when feedback doesn’t flow.

Across my career leading and facilitating feedback models for different teams, I developed a model of six characteristics of good feedback. We’ll explore them all through a personal example of feedback related to my flirtation on burnout.

An epilogue from the brink of burnout

After recognizing and acknowledging my breaking my personal work boundaries for a last-minute deliverable, I also shared my personal reflections on burnout within the company to show that it could happen to anyone and to normalize talking about it.

I got anonymous feedback via my manager that, despite my best efforts to highlight that everyone’s personal boundaries are and should be different and that plenty of other colleagues have suffered worse impacts than me, my sharing of my experience upset another team who regularly works much harder than I did that night.

Handling unexpected feedback

Feedback is a gift. It takes thought by the giver to give, and it has some amount of value for the recipient. So, the first step is to not dismiss it. It’s very easy when receiving negative feedback to see what’s wrong with it and to become defensive – I knew and acknowledged this! Why didn’t they read my writeup in exactly the tone I intended?!

The skill in receiving unexpected feedback well is to look for what’s right about the feedback, not just what might be wrong with it. In this case, one thing’s very clear from this feedback: Even though I tried to make my writeup welcoming to a wide breadth of work styles and burnout rates in my audience, I didn’t achieve that.

Overall, this feedback was not outright bad, though it certainly could have been better. It meets a few of my six characteristics of good feedback:

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Good feedback is…

⏱️Timely

Really fast feedback is great! Hearing someone else’s perspective as close to the triggering event as possible allows both the giver and receiver to communicate with as accurate a context as possible and for the recipient to put any improvements into place as soon as possible.

An important corollary here: relegating feedback to an annual or semiannual review cycle is losing out on much of its value.

In my example:👍Despite the delays of an intermediary, it came quickly enough to impact my next writeup.

👥Direct

Many people are most comfortable giving negative feedback through an intermediary. I get it. It takes a healthy amount of trust for colleagues to give feedback frankly and directly to each other. But it’s worth fighting for. You build that trust by trying.

The recipient of indirect feedback can never have full confidence in it, as the “game of telephone” adds uncertainty to the context and nuance of the feedback. More importantly, indirect feedback discourages followup questions that can really help clarify and activate the parts of the feedback that are right.

In my example:👎I was grateful for the feedback and don’t at all begrudge the giver. Feedback given anonymously is much better than feedback ungiven. But we each could have learned much more from the followup conversation that couldn’t happen here.

🎯Specific

Euphemisms are the enemy. It’s tempting to generalize when giving constructive feedback, but feedback should focus on what exactly was observed and not extrapolate this to a conclusion – that’s the recipient’s job in synthesizing across all of the feedback they get.

Similarly, feedback must not be vague, as the giver’s details and context will not be obvious to the recipient unless spoken. The feedback giver’s goal shouldn’t be to ease the blow, it’s to speak their hard truths.

In my example:👍The feedback was rightly direct and conveyed their reaction: their team was upset. It didn’t attempt to apply a conclusive label to me (i.e. it wasn’t “Mike doesn’t work hard enough”) or overgeneralize to the experience of other teams.

📈Impact-Oriented

The best feedback is specific about the bottom-line business impact of the observed behavior. If something didn’t meet expectations, did it lead to a worse outcome? A loss of efficiency? A loss of trust? An unforced risk, even if it didn’t come to pass?

The feedback recipient has the best visibility into their own costs, not the feedback giver. When the recipient gets that information from the giver, they can make a complete assessment of the tradeoffs.

In my example:👎I was left to speculate on the actual impact of the team being upset. Was it just a fleeting frustration, or did it linger? Did it affect the motivation of any team members?

✅Actionable

What’s the call to action? What should the recipient consider doing differently next time?

It’s useful to be speculative about ideas for change when offered humbly; when I give feedback, I often say something like “This is just from my perspective, and based on a single observation, so take it with a grain of salt, but in case it’s useful, I want to offer you this…”

In my example:👎It’s hard to tell if their intent was more “try getting some more diverse reviewers before publishing, and I’d be happy to do so” or “stop sharing your perspective entirely”. (The former, by the way, is a great example of an idea to offer. It reflects a mutual trust in good faith and interest in improving.)

🤔Curious

You can only offer feedback on what you see. You don’t see what’s in someone else’s head, or even the immediate impact of the actions they take. You only see the downstream implications of the actions, and only from your own perspective.

So, stay open-minded about your assumptions on strategic and tactical goals. Acknowledge the limitations of your perspective. Invite further discussion, from which both parties usually benefit.

In my example:👎It is possible that the giver was empathetic to my perspective and thoughtful to my intent, but one-way feedback with no opportunity for discussion is inherently incurious.

Put it into practice

• Make a practice of saying “Thanks for the feedback” (earnestly, not sarcastically!) when receiving any feedback, just as you thank your relatives for even the most unexciting birthday gifts. They deserve gratitude and it’ll prime you to look for what’s right with it.

• If you want to improve at receiving feedback, Thanks for the Feedback by Douglas Stone & Sheila Heen makes a great book club read for a team.

• Find mechanisms to bake feedback culture into the operations of your team. There’s more to dig in on here, and if your team could use some outside help on how to apply my six principles and on designing processes for regular feedback that fit your particular ways of working, get in touch about my Feedback Tactics workshop:

Workshops

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

We’ve talked a lot about tactics for managing information inflows at work, from email filters to email triage to Slack. Let’s talk about the rest of your life. When it comes to unproductively or regrettably consuming information, many people are wasting more time in their personal life than they are in their work life.

Here’s how I consume information on the broader internet with intention, how I manage a healthy information diet, and where it fits into my productive time.

The cornerstone of my approach is what I’d lovingly describe as an ancient internet technology.

RSS Feeds

What is RSS? RSS is a framework for services to provide a feed of updates in a standardized, structured format. RSS readers are apps, plugins, or software that allow you to subscribe to and manage feeds. These started in the 1990s and ceased active development decades ago, but are still used by some parts of the modern internet.

Why use RSS feeds? Where they work, they’re great. Any RSS reader lets you turn a source that supports it into a “push” rather than a “pull” workflow: you don’t need to actively surf the web (leaning into the 90s of it all) to a page and refresh it to see if there’s anything new, it’ll just tell you in one centralized place for all your sites. RSS and its “inboxification” of updates is a bulwark against an internet that fights for your constant attention.

Where can RSS be used? The parts of the internet that support RSS usually fit one of these categories:

• Newsletters – I’m continually glad (and, cynically, surprised) that Substack supports RSS feeds. Here’s mine! It’s important to me that you can receive this newsletter through the least disruptive method available.

• Articles – Most other news sites, blogs, or other publications that produce discrete articles continue to support RSS.

• Podcasts – Podcast feeds are actually a specific type of RSS feed, and you can follow episodes of a podcast with an RSS reader instead of directly through a podcast app. Similarly, YouTube channels also all have RSS feeds.

• Decentralized social media protocols – Bluesky and Mastodon are the most prominent microblogging services that support RSS. I’m much more inclined to read posts on these platforms than others for this reason.

How to organize your RSS reader? I use a basic, free, lightly ad-supported RSS reader (there are plenty) and group the feeds I follow into ordered categories. Here are the tiers I use in my RSS reader, examples of the types of sources I put into each, and how often I read them:

• Tier 1 (Always read at least once a day)

  • Social media posts from close friends

  • Google news alerts

  • Comments on my publications (Substack doesn’t support this, and the alternative workflow still sucks)

• Tier 2 (Usually read at least once a day)

  • Social media posts from accounts I want to read in full eventually (e.g. dril, the PG-13 poet laureate of the internet)

  • Most Substacks I follow; I read via RSS rather than email, as while there are Substacks I’m excited to read, push notifications are not appropriate for newsletters, which can never be urgent.

  • Most blogs and news sites (e.g. I’ll foreshadow my next link roundup with a plug for a blog you all should check out: Rands in Repose)

• Tier 3 (Sometimes read some of)

  • Social media posts from accounts of medium interest

  • Substacks, blogs and news sites of lesser interest

• Tier 4 (Rarely reach unless I’m bored)

  • Most social media posts

  • Podcasts and YouTube channels of occasional interest, to sporadically pick and choose episodes from. (These are in the bottom tier on purpose.)

I sort these reverse chronologically within each tier, so I’m always seeing the latest posts and articles at any level. When I find an article worth reading, I send it to a read-it-later service that syncs to my devices. My time spent in my RSS reader is triage, much like my approach to email and Slack.

When to read your RSS feeds? I open my RSS reader along with my daily tabs (see below!) and always read at least through Tier 1. Tier 2 if I have a slower day.

When I take my few breaks during the day to catch up on what’s new, I’ll spend most of that time back in my RSS reader rather than on any actual social media platforms, reading longer-form content I’ve chosen myself. RSS feeds are the healthy snack that displaces my interest in overdoing the junk food of ultraprocessed social media.

Bookmark batching

For every website that doesn’t support RSS, I recommend batching bookmarks based on the frequency at which you want to read them, then building morning, weekly, and start-of-month habits to open those folders.

Here’s a look at mine:

• Daily bookmarks, which I open to start each day

  • My RSS reader, as discussed above

  • News front pages

  • Substack and LinkedIn for my daily review of notifications

  • Any collaborative docs for active, ongoing projects, as a reminder to consider my next action for the day and an opportunity to drop in fresh ideas

  • Today’s weather

  • School lunch menu, because my son is going to ask at breakfast

• Weekly bookmarks

  • My week-ahead calendar for review

  • Any collaborative docs or other relevant links for longer-term projects, for my reconsideration and possible reengagement

  • 10-day weather forecast

  • Medium-tier other sites, e.g. lesser news sites

• Monthly bookmarks

  • Monthly bills

  • Event calendars for local venues

  • Lower-tier other sites, e.g. hobby forums

I actually go one step fancier than bookmark folders. I wrote an AutoHotkey script (a Windows scripting technology nearly as old as RSS) that opens all of my Daily bookmarks every day along with lesser bookmarks at frequencies of my choice based on the current date, e.g. don’t open work bookmarks on Saturday & Sunday, open a gaming news site every other Friday, open my credit card statements the first of every month, etc.

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Put it into practice

Look for ways to move pieces of the internet from places you go when you think of them into things you review as a structured batch.

If you’ve never used RSS, it’s a 90s throwback that I wholeheartedly endorse. Take a look at your internet consumption, see how many of those support RSS, find a RSS reader and give it a try to see if it works for you.

Give bookmark batching a try, too. Start small and add things to Daily and Weekly bookmark folders as you become aware of your interest in them. You can also try adding any tab you have open but aren’t getting to right away to one of these folders as a quick read-it-later workflow; just be judicious about unbookmarking things if they become too uninteresting to prioritize soon.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

How do you give your teams the space to discover new ideas, the encouragement to brainstorm, and the autonomy to experiment? Forward Deployed Engineering teams tend to empower their people very well here. What can we learn from them?

This is a sort of an epilogue, and a sort of counterpart, to my Nimble Knowledge Management series, which explores how to avoid rigidity in your knowledge management processes by staying humble, dynamic and focused on the true least common denominators of best practices. Check it out here:

Beyond knowledge management, there are several core pillars of your operations where you can cultivate cultures of open exploration:

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Erode the Hard Boundaries in your Org Chart

You want everyone at your company to feel able to explore any fruitful ideas they have.

That’s easy if you’re working at a small startup, where everyone talks to each other and is responsible for a wide range of creative problem solving on their own. If you’re at a bigger company with a much more complex org chart, look for ways to make the org chart feel more like a startup’s by building connective tissue between people more than one level apart on the org chart.

This looks like:

• People should be able to ask questions of, get information to, and collaborate with whoever the right person across the business is when their ideas are relevant. This helps good ideas get high-level feedback without dying in the game-of-telephone layers of going “up the chain”.

• Direction and accountability should not come only from people’s direct managers. Leadership should seek opportunities to engage with and review the approaches and achievements of people lower in the org chart. This helps reward and recognize individual contributor talent and incentivizes finding good “bets” to make.

• Managers and project leads should be different people. This helps decouple top-down managerial interests on performance (which can bias towards restricting creativity) from solving the novel problems on any given team, and having more than one person helping guide you helps, too.

Invest in Mentorship and Feedback Programs in your Talent Development Processes

A mentor is someone who wants you to succeed but isn’t directly on the hook for your outcomes. In this way, mentorship programs enable creativity and heterogeneous growth, whereas leaning harder on more “management” to guide people ends up discouraging experimentation.

A diversified portfolio of mentors and bosses works best. Mentors should come from related but different teams, or even roles, than the mentees. Mentors need not be more tenured than mentees; in many of the greatest mentorship relationships I’ve seen and been part of, the mentorship flows in both directions with no clear “senior” or “junior”.

The sort of lateral leadership that formal, lightly structured mentorship programs create also sets the right example for what effective collaboration looks like in other relationships, such as between teammates.

Celebrate Discovery in your Communications & Meetings

Calling out successes, especially successful new ideas, at all levels of the org chart is a simple but strong incentive and cultural signal that experimentation is valued by leadership.

When possible, take a show-not-tell approach. Amplifying a writeup of a business win borne from a new approach is good. Having that person talk at an all-hands is better.

Make sure it’s not all just show, either – people who create great ideas should be promoted and rewarded with increased responsibility and compensation. People will quickly develop an intuition for where the real incentives lie, so make sure they align.

Prioritize Autonomy in your Hiring Objectives

Plenty of smart people find reasonably successful careers just by executing on tasks that are given to them. If you value experimentation, don’t hire too many of these people.

Look for motivations, philosophies and past examples of questioning the status quo and finding game-changing innovations. I discussed many of these characteristics here:

In the context of exploration: ownership without authority leads to teams where every potentially good idea is raised and acted on, autonomy is a necessary condition for someone to actually be able to execute on an experimental idea, and grit means working hard to not only solve the problem creatively but to care enough to drive adoption and scaling of their successful experiments.

Want to go deeper on hiring or onboarding design?

Workshops & Coaching

Rotate Responsibilities in your Role Definitions

Keep your roles and titles flexible, too, at both the micro and macro level.

On a day-to-day basis, rotate responsibilities across your team wherever you can do so without substantial efficiency loss:

• Have different people take notes or handle prep for meetings rather than always burdening the most administratively-minded member of your team.

• Have people occasionally share responsibilities and test drive processes of other teammates; out of office periods are a forcing function for this, but do this more often than that.

• Encourage direct feedback across teammates of all roles rather than deferring to leadership to facilitate.

At the big-picture level, look for and allow people to transition across departments or roles based on the strengths they exhibit in their experimentation and the needs of the business. Set up hackathon / 20% time opportunities for people to explore, learn, and work outside their team on any problem they have ideas on. If you don’t give people regular opportunities to try something new, creativity can fall out of the culture entirely.

Put it into practice

The strongest Forward Deployed Engineering teams invest heavily in all of the above, and these ideas translate well to any type of team looking to increase its velocity of reimagining their strategies and tactics.

Whether you’re in charge or brand new to a team, you can help shape the culture towards experimentation:

• If you’re a founder or executive:

  • open up your org chart and spend some time where the people are (e.g. hold office hours, look at Slack)

  • invest your time in sampling everyone’s work and regularly reinvent your strategies and standards based on what you learn

  • elevate frontline wins

• If you’re a team lead, hiring manager or middle manager:

  • prioritize autonomy in your hiring profiles

  • build mentorship programs (multiple, for different phases of career development)

  • give your team opportunities to work on pet projects.

• Even if you’re just an individual contributor, your actions can help change cultural norms:

  • reach out to leaders outside of your direct area of the org chart when prudent

  • seek mentors, and offer to mentor others

  • make sure your teammates rotate their responsibilities and check out each others’ work before the need for out-of-office coverage

In other words, be a lateral leader, no matter where you sit in whatever type of org chart you face.

In the spirit of sharing the good ideas you find:

Share Processes for People

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

I’ve always been a podcast guy, back since they were actually on iPods. In college, I was a glutton for learning, so I’d constantly listen to podcasts alongside all of my work and study. As life went on and work got more complicated and demanding of my focus, and as I learned more about my brain, I eventually tapered these off. There are only a few activities I’ll do alongside a podcast today.

Multitasking, in work or in life, is fraught with inefficiencies when done naively or gratuitously. Wikipedia’s summary of the research is illuminating. Every type of “multitasking” is actually a constant switching between tasks, which has costs. You’re not retaining as much as you think from half-listening to a podcast or, for that matter, a meeting while working remotely.

So when to multitask comes down to making nuanced assessments of the task-switching costs weighed against the time savings on an activity-by-activity basis. Sometimes it’s worth it, though not nearly as much as young me thought.

There’s a model of learning and skill execution from psychology that’s instructive here.

The four stages of competence

The four stages of competence models how humans develop their skills at different activities.

• For any new task, you’re likely starting at the bottom, unconscious incompetence: you suck at this, and you probably don’t yet realize how much you suck. A common task where people start at the very bottom is interviewing, on either side of the desk.

• As you learn the basics, you’ll get a sense for what matters and the nature of the learning curve. Before long, you reach conscious incompetence – now at least you know you suck. You can start to seek resources and opportunities to practice to improve at what you see you’re bad at for e.g. interview tactics.

• If you’re capable of learning and improving at this task, you’ll eventually reach conscious competence after enough reps. You can do the task well, but it requires your active attention. Most interviewers will reach this stage after leading several interviews with deliberate practice and training in between.

• Only for some tasks will you ever attain unconscious competence, a level of expertise and intuition where the task becomes second nature and something you can perform well at even without giving it your full attention. Interviewing notably is never one of them; only shallow, common, low-stakes activities are.

Self-promo tangent: I offer workshops and coaching to raise your interview game.

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Each stage of this model corresponds to a different approach for whether or not you should multitask.

Unconscious Incompetence: 🚫Monotasking as Default

Unconscious incompetence is a multitasking trap for the reckless. You start here even if you’re smart (talking to you, college Mike). This might be a new type of software tool, communication method, or meeting series. Even a simple household chore benefits from active initial attention so that you can optimize it.

So do not be reckless. Make monotasking your strong default for any new type of task. Assume you’re unconsciously incompetent at first and keep an eye out for aspects of the task at which you could improve.

Conscious Incompetence: 🗑️Find the Garbage

This is less of a trap, and you still mostly shouldn’t multitask, but now you’re in a position to make value judgments to find the exceptions.

You’ve either got a clear path towards the next stage of conscious competence on this task or you know where to look to build your skills; perhaps you’re exploring and tuning your configurations for a new piece of software, researching optimizations for a chore, or finding a mentor to help you grow.

The exceptions are tasks where it might be okay that you’re incompetent: those that are both low-value and low-frequency in your life, such as:

• Annual administrative burdens in the office – not your annual review, but possibly some training refresher videos

• Mandatory meetings outside of your area of interest

• Routine winter maintenance on your hot water heater

Find these garbage tasks and be willing to multitask with them at the cost of staying mediocre. You don’t have to be great at everything (talking to you again, college Mike).

Conscious Competence: ⚠️Danger Zone

Conscious competence is a multitasking trap for everyone. Even when you’re good at something, when it still requires your conscious attention, you’ll quietly pay serious switching costs if you’re multitasking. Wikipedia says it well: “demonstrating the skill or knowledge requires concentration, and if it is broken, they lapse into incompetence.”

Don’t get complacent from your competence. Resist the temptation to multitask until and unless you achieve unconscious competence. Look for opportunities to test and measure how much you’ve optimized a task, how strong your B-game is, and keep putting in the reps until it becomes second nature.

Many tasks should never move past here. For the most complex, mentally strenuous, heterogeneous and high-stakes activities, your intuition will constantly continue developing, such as interviewing.

Unconscious Competence: 🟢Green Light

Here’s where you can usually multitask, especially on lower-stakes matters, such as:

• Triaging and handling simple replies to email or Slack messages – only after you’ve adjusted to a new team’s rhythms

• Routine administrative tasks such as expense reports or timecards

• Task capture and prioritization, once you’re practiced enough at it

• Half-listening to low-importance meetings, knowing you won’t retain much but that it’ll be okay

  • A great candidate task to pair up with the above; I recommend doing so openly by overlapping your comms block with the meeting

• At home, it’s chores like washing dishes, mowing the lawn, folding laundry, walking a dog (but not this one quite yet, still developing my intuition!), exercising, or driving where podcasts fit into my life nowadays

For high-importance work, you still need to assess the tradeoffs – giving a task that you’re an expert in your full attention will usually still yield better results.

Put it into practice

• Think about the most important skills you exercise in work and life. Sort them into the four stages of competence. Reflect on your current approach to multitasking with them, adjust as necessary, and hold yourself to it.

• Find your best monotasking activities and your most conducive monotasking conditions.

  • For me, writing up post-interview reports needs my full attention while my memory is fresh, so I block my calendar for these, relocate to a different room than my usual desk, and listen to music on noise-cancelling headphones. Multitasking becomes impossible.

  • Find the right music for each activity. For me, interview notes? Always jazz. Other stuff? Sometimes classical, sometimes classic rock or pop garbage, can’t really explain it. Experiment with what works for you. It might be epic film scores or background noise that sounds like a coffee shop.

• Leave room for generating new ideas in your day, too, by getting away from all screens and having space to think. I rarely get good ideas when listening to podcasts, but get them constantly while swimming.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

My new puppy asks: How do you optimize periods of distracted work, when you’re not actually out of office but need to work differently and less efficiently?

(She asks it in her own way while trying to chew the wires under my desk. My mailbag is open to paid subscribers of all species.)

Thanks for the question. Good girl.

We’ve explored how to optimize and protect your time during normal times:

During abnormal times, this can all fall apart pretty quickly if you’re not ready.

Whether it’s a new tiny animal, a new tiny human, something tiny getting sick, you getting a bit sick, a working week with extra travel, or even just a really rough night of sleep, when forces in life disrupt your usual routine and rhythms of getting things done, you need to plan for how you’ll work differently.

Some of these disruptions come with ample advance notice, and those that don’t are inevitable. Here’s how I approach these unusual work periods and what I’m learning on my latest round from my pup.

Measure

While it helps if you have a solid baseline understanding of your time portfolio for a typical week, it’s more important, and easier, to understand the supply side: how much time you’re losing relative to your default, and for how long.

Perhaps you’re at somewhere in the vicinity of 50% capacity for a few weeks or days where you and a spouse are splitting attention to a new pet or sick kid. Figure out that exact % and coordinate: you’ll probably be able to doing some amount of work, albeit at lower efficiency, during some of your time spent caring (naps), and it might make sense for one of you to take a larger share of the time (that’s me this time).

Maybe you’re the one feeling not great, but feeling well enough to be working normal hours on paper. In practice, you’ll probably work slower, perform worse, and output less. Model some amount of drag on your efficiency and figure out which types of tasks get weighed down the most by this.

If it’s a working week with lots of travel, you may even be working more total hours, but be realistic: if you treat your in-flight time as work hours but always fall asleep on a plane or can’t resist a movie, don’t count on all of that time being productive.

Consider, too, cutting down on non-work activity to free up some time. It’s somewhere between prudent and necessary to cut down on your exercise time for a bit in any of these examples, as 'I’m doing.

Prepare

The closer you’ll be to fully offline, the more your preparation should resemble going out of office; check out my series on optimal OOO prep here. (And do take off as much time as you can for parental leave. I’ve never met anyone who regrets taking too much.)

When you’re back to mostly working but not at 100%, you’ll want to plan out where the lost time you calculated above will be coming from:

• First, rule out entire categories of work where you can. Some are easy: if you’re traveling, you can and should skip many typical meetings. I’ve taken all of my lower-importance work off my plate until the puppy is settled.

• Then reassess and tighten the time budget for each remaining category. It’s OK and necessary to temporarily pare things down below their long-term sustainable rates. I decided to limit my meetings and stop travel but to not miss a week of writing this newsletter.

• Some work will be slower. I anticipated writing to take more time than usual, and indeed this one ended up taking 1.5x as long as usual (I’m writing this very sentence at a time the puppy should be napping but super isn’t).

• Get ahead of important long-term tasks where you can. Which big projects are going to matter the most a ~month from now? I made sure to get a bit ahead of my next few newsletter drafts before adoption day. Move those up in your priority order now as you…

• Start deferring tasks that can be done during the period, such as handling emails and administrative work that can be reasonably done while away from a desk. I’m catching up on reading alongside couch cuddles.

Adapt and Iterate

No modified work plan survives first contact with the enemy. (No, pup, you’re not really my enemy. It’s just a saying.)

Your estimates won’t all have been perfect. You may not be able to muster as much energy for work as you hoped. If you’re anything like me and also older than you’ve ever been, you might find that you need your own naps. Give yourself grace and take what you need to be healthy.

Be mindful of the types of mistakes you might be more likely to make during distracted work, e.g. you might want to double-check for typos more diligently than usaul.

You may need to plan out the timing of routine tasks around the logistics of your situation. For now, dishwashing and cleaning cat litter are scheduled strategically around the minutes of mealtime and when we’ll be near the right rooms. Tasks like this that usually live in your head will take up too much space there when you can’t follow your normal habits to get them out, so get them onto your calendar or to-do list instead.

Put it into practice

If you’ve got advance notice on an upcoming change to your typical work rhythms, measure how much time you’ll have and start preparing accordingly. If you don’t, start thinking about what would happen if you suddenly had about half as much time in a week, a decent approximation for many common disruptive situations.

As you get different things done in your normal routine, start clocking what’s at risk, what you’ll temporarily stop doing, what you’ll batch in a different way, and what you can do from your phone at a reasonable rate of efficiency.

And don’t forget to enjoy the fun parts of life (not applicable to the sickness examples, wash your lettuce thoroughly, y’all).

Now, if you’ll excuse me, it’s playtime.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

You’ve gathered and refined the raw knowledge. Now it’s time to turn it into valuable fuel.

Knowledge transfer is where you transform your work from Parts 1 & 2 from a liquid set of notes into a solid artifact: a checklist, SOP, or documented best practice. Your goal is to ensure that the hardened shape your artifact takes is the most useful one, a tool that your colleagues will want to embrace.

Knowledge Transfer in my training program example

As I finished synthesizing data from my first several runs of the underdocumented software training program, I invested in cleaning it up so that it could reach as many people as possible.

I redesigned the format of my checklist so that the most important steps were visible on page 1, and I took yet another pruning pass to deemphasize the less valuable steps.

I moved my template into the simplest functional Asana view, knowing that this was the most popular knowledge management tool at my company, but also knowing that plenty of people didn’t regularly use it and would not want to figure out the complexities of its advanced features.

It helped that I was widely respected across the company as an expert in both training design and optimizing operations. People wanted to hear from me. But I was also sure to keep the checklist unpretentious, my approach curious, and the content open to continuous updates from myself and others.

My checklist saw immediate adoption and quickly began to spread across the business. Future runs of this training were executed more efficiently and produced more consistent high-quality delivery outcomes, saving the business hundreds of person-hours and capturing millions of dollars per year of extra client revenue.

All for a job I gave myself because I saw that nobody else was doing it.

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Transfer Strategy

Knowledge capture is mostly technical, knowledge synthesis is a mix of art and science, and knowledge transfer is mostly human, its own sort of user adoption challenge.

The same single accountable person for synthesizing knowledge should also own the knowledge transfer, though others can join in on the responsibility of reaching different audiences. Knowledge transfer is fundamentally a matter of influence, which can happen top-down from the leadership of an organization or bottom-up via word of mouth among the actual users of the knowledge.

The exact tactics will depend on the shape of your culture, but there are four common elements of successful knowledge transfer:

Knowledge Transfer must be Valuable

Why should your colleagues even click your link, or open your email? Why does the knowledge you’re transferring matter?

It won’t be nearly as obvious to others as it is to you, and the people who need it most might be the most ignorant of the value.

So make the bottom-line value into the top line of how you transfer the knowledge. Call out what you’ve learned and how it’s impacted the business. Speak to the outcomes you’ve achieved through these best practices and how your transferred knowledge will help them improve theirs.

Design your artifact to surface the most impactful elements on whatever its first view is: the headings of your document, the bold sections of your checklist. Tuck the more granular tactical details away a bit so that users who want to go deep can find them but that users who just want to skim it will still hit the most important parts.

Knowledge Transfer must be Accessible

Why should your colleagues overhaul their ways of working to adapt to your best practices?

If there’s too much friction, they might just not use your artifact, even if they see the value in the content.

So reach everyone where they are. When choosing your medium, bias towards the popular and simple collaborative applications.

If knowledge transfer falls in an email and nobody reads it, it doesn’t make a sound.

Knowledge Transfer must be Credible

Why should your colleagues trust your knowledge on a topic?

Maybe you’re their boss, or maybe you’ve got a big title at the organization. That helps, but don’t take it for granted. You might be able to make people read something, but they still might not trust it.

Maybe you’ve shown yourself to be an impactful individual contributor on your team, a high-trust colleague, someone who goes out of their way to help others and leaves every process better than they found it. That’s more work, but it’s a path available to anyone.

So don’t be shy about sharing some information about why you know what you’re talking about here. Craft your communications strategy so that your credibility shines through and reaches new people.

This itself is a great reason to have the accountable party be a subject matter expert in the topic they’re capturing knowledge for, too.

Knowledge Transfer must be Humble

Why should you make all the rules, anyway?

You want to be seen as a credible expert, but you should avoid coming off as infallible. (Trust me, you’re fallible.) Even perfect knowledge today becomes imperfect before too long.

So make your knowledge transfer robust to your imperfections and to shifting goals by:

• Inviting, explicitly, further collaboration and iterative improvement to your artifact; open up edit rights, include a way to leave feedback, call it a “living document”

• Caveating which of your conclusions are lower-conviction or based on smaller sample sizes, to facilitate the flow of the above feedback

• Acknowledging the inevitability of future imperfections by noting the last updated date

The knowledge management cycle is continuous; transferred knowledge will lead to more knowledge to capture, which in turn will require periodic resynthesizing into the new best practice.

Put it into practice

You might not have a worthy example of a process for which to capture, synthesize and transfer knowledge on your plate right now. Decide to be the type of colleague who keeps an eye out for gaps in knowledge. This’ll often start from something you first document for yourself, or for colleagues as you step out of office, or as a fleeting discussion in a postmortem. Those are natural starting points for the knowledge management process. Don’t miss the opportunities they present.

The maximally optimal implementation of a people-forward knowledge management lifecycle is specific to you and your team, and if you’d like to work together to get to 100%, check out my offerings here and contact me for a free consultation.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

OK, so, you’ve captured a lot of knowledge. What do you do next with all of that data?

You investigate that knowledge to interrogate what’s true, to determine what matters and to find the common threads through the data points that yields transfer-worthy pieces of knowledge or a best practices. I call this the knowledge synthesis phase.

Synthesizing in my training program example

As I captured notes, hypotheses, and data points from my first few runs of my software training program, as soon as I hit the N = 2 of my second run, I started marking elements that mattered in both, often just with a simple “+” at the end of a bullet point in my knowledge capture. I continued this for my third run, at which point I also started crossing off ideas that had turned out to only matter in one.

I kickstarted the synthesis process this way simultaneously with my delivery of each training, but I also set time aside after each run to fully review and further synthesize my capture. I augmented my small sample sizes by leveraging the intuition of my training design subject matter expertise to find the best hypotheses; others would have needed to run more trainings before developing conviction in what mattered.

Now that I had a handful of theories, I was able to validate them by investigating previous data through researching old Slack rooms, emails, and github tickets to understand the frequency of different technical stumbling blocks and by interviewing (informally, often just a quick question or two) others who had run these trainings in the past. While I did this, I started transitioning my notes from a raw document into a unified, structured checklist template, which got it ready to be used by others running these trainings.

The last step of synthesis before moving on to transfer was pruning; I removed from that checklist all ideas and hypotheses that I either didn’t have enough conviction in or that were likely to have only a small impact on the outcome. I kept these in a backlog in the original document so that I could revive them later in case more data was gathered, but for these ideas to be adopted by a broader audience, I would need to be sure the list was not overwhelming and that each element pulled its weight.

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Synthesis Strategy

Unlike knowledge capture, which should be open and crowdsourced to everyone, knowledge synthesis needs an accountable and responsible party. It’s usually easiest for a single member of your team to be in charge of synthesizing everyone’s ideas around any given deliverable or focus area at any given time.

This person should wear a few different hats while they synthesize. They should be:

• An analyst, able to find trends in qualitative data, not necessarily in any explicitly statistical way, but in a practical way built on their also being:

• A subject matter expert, ideally the member of your team with the most experience in in the topic at hand so that they can augment the data with their own well-honed intuition

• An archaeologist, searching through team records to test hypotheses against older data; in a frictionless world where all knowledge was captured, this would be unnecessary, but in practice, you’re going to be searching Slack

• An interviewer, validating findings from the above or theories from the captured knowledge with other real humans who imperfectly captured their own knowledge

The synthesizer must be opinionated, but not judgmental to approaches others have taken. When someone made a decision or took an action different from what they’d have done, that’s a chance for them to learn and for the quality of the synthesized output to improve via incorporating others’ perspectives.

Overall, this sort of synthesis is a mix of art and science and a deeply people-driven process. Anyone can learn it with practice; different members of your team should be given opportunities in line with their subject matter expertise.

Synthesis Tactics

• Prune aggressively when you find captured knowledge that doesn’t replicate across experiences. It’s easy to fall into making a high volume of weak conclusions, particularly when faced with having to cross off ideas from respected colleagues. That doesn’t set you up for maximal success, though, when your end goal is knowledge transfer concise enough for others to be willing to consume. Let what matters most speak loudly by not being crowded out by speculation.

• Hold and measure against outcomes of the process being synthesized. The synthesizer should be the one focused on the outcomes, while others contributing to knowledge capture should be encouraged to be wide-ranging in their ideas. Hear everyone out, and follow up with questions where necessary to get their whole perspective, but the synthesis has to aim for what matters most to the team in aggregate. Get in sync with leadership’s priorities first if you’re not sure.

• Start gradually moving synthesized data to its eventual final platform, such as going from the sprawling Google Doc to a Wiki-type resource or other dedicated technology solution for knowledge management. Note the checklist as a work in progress and add ample caveats on any elements that are still being investigated, but if a teammate can make careful use of even partially-synthesized knowledge today, you should invite them to do so. This will often even lead them to find their own new knowledge to capture that they can feed back into your checklist.

• AI tools have a place here, and any agents available to you could be helpful with the qualitative analysis and the archaeology elements of the synthesis, particularly as the scale of captured data increases. Think of a Large Language Model that can read through 100 debrief reports from prior runs of a training, for example. AI agents, if tailored enough to be reliable and useful knowledge transfer references for your team, are also another sort of “customers” of your captured knowledge, and there’s much to explore there, but expert human judgment and curation will still play an important role in identifying what matters most.

In Part 3, we explore the final phase, transfer of synthesized knowledge into actionable, useful material for people:

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

Knowledge management, to most teams I’ve worked with, evokes thoughts of onerous, slow, ten-step processes, fruitless friction to actually getting things done.

I keep my model lean, nimble, and approachable. Effective knowledge management needs only three phases, and over the next three weeks, I’ll share my strategies and tactics for each of these:

1. Knowledge capture: Getting learnings and notes out of your head and into somewhere

2. Knowledge synthesis: Finding the common elements and best practices from that data

3. Knowledge transfer: Operationalizing those principles for the actual people who need it

Why capture knowledge - My best example

When I first started leading a portfolio of software trainings (yep, the ones that almost burned me out), this particular training program had been run over 100 times for other clients already, but shockingly had almost no notes on best practices.

There’s a fine line between best practices and constraints, especially early in designing a dynamic new process. It’s good that the first of these trainings had given complete freedom and autonomy to the delivery teams to customize and creatively solve for the best approaches for their clients. But there’s no way that was correct for the first 100+ runs. That’s way more than enough time to have discovered and shared those best approaches, compounding that value for the next teams to run them. It’s just that nobody had done it because it didn’t feel like their job.

The lost upside from the foregone knowledge management was palpable in my own first runs. We didn’t have strong examples of curriculum design and didn’t know how much time we should devote to testing and validating the software. These led directly to needless losses.

So, from day 1 of my involvement, I took constant notes on every step of logistics, every technical hurdle we hit, and every design hypothesis we had, both for my own next runs and to eventually grow it into guidance that could transform the business. I did this by jotting down checklists in a collaborative document, including every speculative idea. It was messy. It almost immediately became unwieldy to anyone other than me. But it worked for me short-term, and it ensured I captured a complete foundation of what I’d be able to grow into extremely valuable knowledge transfer later.

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What knowledge to capture

Anything you learn around any aspect of your or your team’s actions that is likely to be done again in the future is worth considering for knowledge management. This could be:

• Decisions you’ll make again

• Decisions someone else on your team will make in the future

• Actions a teammate may cover for you on while out of office (knowledge management now saves coverage prep later!)

• Tasks similar enough to tasks that will recur in the future such that lessons can be learned and applied

• Notes to yourself on something that may someday become one of the above

There’s no hope of memorializing these in the knowledge management process if you don’t first capture them by getting them out of your head. Just as it’s valuable to capture tasks you’re going to do in the future, it’s valuable to capture knowledge from your present from the things you have done and will be done again.

When to capture knowledge

You should continuously move ideas from your head to a permanent repository. Just like when you learn of a task you have to do, you capture it in your notepad, in an email, in a digital document, or an app, you should do the same when you learn of a piece of knowledge that may be worth preserving.

The most important time to actively dedicate time to knowledge capture is as soon as possible after any significant milestone, delivery, or outcome, especially for deliverables that you’re most likely to repeat. Do this during your post-mortems, reflections, and definitely your antisurges:

You could also add periodic backstops for regular opportunities to take a few minutes to see if any recent knowledge is worth capturing, perhaps as often as every week (a short calendar hold in your Friday afternoon) but at least every few months (a worthy exercise during quarterly planning).

Where to capture knowledge

For the knowledge capture step, you should use whatever is quick and convenient for you. You could use the exact same mechanism as whatever you’ve chosen for your task capture. It need not be pretty or easy to read; that’s for later.

Other good systems for easy knowledge capture include:

• directly into dedicated technology solutions for knowledge management, e.g. Notion, Wiki

• Google Docs

• Slack Canvases (their version of simple, collaborative docs)

• pinned Slack threads

• or even just an email to the team

Any system that permanently retains text will do at this stage.

Who should capture knowledge: Everyone!

It’s important that this be not only the job of the team leads, or the job of a team admin. Every member of your team, regardless of role or tenure, should play a part at this stage of capturing ideas that may be worth memorializing.

Make this clear in your communications and in the way you share the knowledge you capture. Invite collaboration into your documents, and ask for others’ thoughts or changes.

Avoiding pitfalls and preempting complains

Knowledge management slows us down! It can, so the way we do knowledge capture must be quick, a simple note taken alongside regular work or a few-minutes reflection in a monthly team meeting. We don’t worry about polish.

Knowledge management wastes time when people’s captured knowledge never gets used! It’s a risk, so the way we do knowledge capture must be transparent and collaborative, always sharing and inviting comments. Future phases of the knowledge management process will be a particular member of the team’s accountability and responsibility to ensure that good raw knowledge doesn’t die on the vine.

Knowledge management falls out of date quickly for high-velocity, ever-changing work! It sometimes does, so the way we do knowledge capture must be dynamic, with everything a living document, always open to edits now or in the future, and understood as being an imperfect, incomplete model of our world.

In Part 2, we move to the second phase: synthesis of captured knowledge into the least-common-denominator best practices it identifies:

🌟BONUS - Announcing a new way to reference my archives

Table of Contents

In many ways, this Substack is like a book on productivity that I’m writing out of order. Most posts are intended to be timeless, foundational ideas rather than fleeting newsletters.

Now that I’m half a year into writing every week – and thank you to all of my subscribers for your support so far – and have accumulated a solid base of content, I’d like to start helping you treat it like a book.

No, I’m not trying to sell you an actual book. I’m just looking to make my archive more booklike and more useful as a reference for you, a way that you can more easily use my portfolio of newsletters as onboarding or continuing education material for your teams.

So if you’d like to read through my archive in a less random way, here’s a “table of contents” that puts my prior newsletters into a recommended reading order, grouping related topics together and building on the content across each “chapter” in the most linear way. I expect that this will be useful both as a full front-to-back “book” or with each part being its own “mini-book”.

Previous chapter:

Next chapter:

Here are the ideas that stuck with me the most over the past three months:

📫 April: Triage

raises the bar for what a practical, human newsletter from a company can be, and their April edition explores an interesting frame of your inboxes:

Todoist Newsletter

📫 April: Triage

After last month’s newsletter, the comments were full of one request: go deeper on inbox triage and prioritization. So here we are…

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5 months ago · 178 likes · 33 comments · Naomi from Todoist

Our inboxes aren’t storage. They’re a queue for our attention. [...] cognitively not much different from a slot machine.

From there, it takes a brief tour of the psychology of variable reward systems, leading to as close to a universal recommendation as one can get: Check your inboxes less often than you currently do. I agree.

I’d expand on this further: when you’re trying to be productive and operate optimally, you should design processes in your life to avoid or degamify anything even slightly resembling a slot machine. This includes most shapes of modern inboxes and message queues. They certainly are not worthy of your near-constant attention via prominent banners or badges whenever you look at your phone, just as you wouldn’t have a slot machine widget take up half of your home screen. The audible triggers of new notifications, like other variable reward systems, exacerbate the hold they have on your focus.

Instead:

• delay and batch as many inbound emails as you can

• set up smart, intentional notification schemes that minimize real-time pulls on your focus

• develop habits to review each of your inboxes at the appropriate frequencies

Honorable Mention: In their March newsletter, Todoist discusses a “Start work” task to bundle up your minimum viable administrative beginning-of-day tasks, a worthy experiment for anyone who hasn’t built the habit. Also, respect for this April newsletter’s better definition of the “Delegate” quadrant (one of my personal soapboxes) than most: Delegate something “if it’s not actually yours to handle”, not simply if it’s urgent but unimportant.

Really fast feedback is great

Nate Meyvis strikes again with another short and simple idea that offers much to marinate on:

Feedback is great, fast feedback is better, and really fast feedback is disproportionately effective. Really fast feedback is so effective that it’s often worth sacrificing on other dimensions (including, but not limited to, p50 response time) to give more feedback quickly. [... and often we can do this] pretty cheaply--e.g., by tackling some tasks LIFO instead of FIFO when they include an element of giving feedback.

Feedback is one of the more overlooked-but-critical cultural processes of any effective team (and while I haven’t written about effective feedback habits much here yet, I run a workshop on it). Giving feedback quickly and generously has always been a key part of building trust among and increasing growth of my teams, and it’s one of the most important ways that you can make yourself a more impactful and respected colleague in any organization.

Nate correctly observes that giving feedback is often different from most other tasks in your to-do list, because feedback is most valuable when given very promptly. Really, giving feedback isn’t something you should model as a task at all – it transcends your capture system. It deservedly should jump over the rest of your task queue. It needs to be something you just do as close to immediately as possible, like tying your shoelace.

When it’s not practical to give the feedback truly in the moment, e.g. amidst a fully-scheduled day in a large group, I steal a minute to draft a quick, 1-2 sentence email to the other party with the feedback, and I schedule it to send later that day. Ideally you find an opportunity to give the feedback verbally (and then cancel the scheduled email), but in case you don’t, a short email is a much better fallback than feedback deferred.

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Hidden Tax Your Startup Pays Every Friday Night

Fellow productivity Substacker has been digging deep on the mental drag of open loops: the unresolved actions and undecided decisions that kick around our brains if not handled by a process.

Calm Productivity

Hidden Tax Your Startup Pays Every Friday Night

It’s 10:00 pm on a Friday. You closed the laptop two hours ago. You’re standing in the kitchen, the kettle is on, your kid is yelling about Lego, and your brain pulls up a file you didn’t ask for…

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3 months ago · 3 likes · Anshul Kumar

He distills it down to a key tactic here:

The cognitive cost of an open loop drops sharply when you write down a specific next step. Not “follow up with Priya.” A time, a place, a concrete action.

It’s an alternate angle on many of the philosophies I’ve written about. In the teams I’ve worked with, I’ve seen high-output professionals get increasingly overwhelmed by the scale of open loops they face. Having a – any – system other than keeping it in your head really does go a long way, and the psychological relief of closing a loop is a real incentive worth building your processes around.

Anshul’s three practical changes are, like Todoist’s recommendations, worthy experiments for anyone who hasn’t found the right version of this habit for them.

From my own perspective, other approaches you can take alongside these:

• capture tasks and ideas out of your head and into some system truly continuously

• have times in your days and in your years where you allow your brain to not worry about open loops (antisurges, optimal OOO)

Honorable Mention: Shout-out to the May 10, 2026 New York Times Crossword and its “close the loop” theme, a good definition of the term and a good crossword design.

Burnout is breaking a sacred pact

I found myself revisiting another great piece recently as I wrote about my own perspective on burnout. Cate’s is a different perspective that I find to be a fitting complement to my own:

Useful Fictions

Burnout is breaking a sacred pact

I am a connoisseur of burnout. In my four decades on this earth, I’ve tasted many of its varieties — some subtle, some gross. There are Emmett Shear’s core three — permanent on-call, broken steering, and mission doubt — but many others too: burnout from constantly shifting goals, burnout from ruinous empathy that pulls you in a dozen directions at once…

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8 months ago · 918 likes · 98 comments · Cate Hall

It’s easy to extend this framework to explain burnout. You can think of the rider and the elephant as having agreed to a sacred pact: In exchange for doing what the rider asks, the elephant is promised certain rewards. When things are going well, the needs of both rider and elephant are satisfied, even if the balance isn’t exactly even day-to-day.

It’s hard to capture the depth of the elephant and rider metaphor in a single quote, but Cate’s perspective focuses on the instinctive and emotional “elephant” that, when it comes to long-term burnout, will overpower the rational desires of your brain if not “fed”. I do think that my own elephant is tamer than most, but even for my elephant, the early signs of burnout are “an emergency. It will always get worse if not addressed, and the cost compounds; the level of intervention required to address it grows steeply over time.”

If you found my take on burnout to be too tactical to resonate with the burnout challenges you face, then give this a read and get to know your wild elephant.

Need a partner to find the best approaches to your inbox, team culture, and task management? I offer interactive workshops and coaching on these topics to help leaders and future leaders operate optimally.

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Next “chapter”:

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

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Everyone works differently. That’s good, that’s why I’m here, and that’s why this newsletter is a portfolio of ideas and modifications instead of an impossible search for universal solutions.

When you work with others on teams, you need to meet each other in the middle on your preferred productivity and communication methods. How do you find the overlaps of the comfortable boundaries of everyone’s individual ways of working? Where can setting expectations, rather than strict guardrails about how your team pulls on each others’ time preserve freedom while optimizing collaboration?

These questions can seem daunting, but, across the many teams I’ve worked with, I’ve found a lightweight calibration exercise that solves most of the friction between preferred work styles.

Here’s the survey I use when I work with teams:

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The Questions

The primary goal of asking these questions is to establish that these are individual preferences which can and should exist and that they are worth knowing and sharing so that colleagues can accommodate each other as best as possible. Many positive operational changes and discussions will flow downstream of this goal.

What are your preferred working hours?

Start simple: when does each member of your team prefer to work? Especially if there’s any amount of variation in time zones across your team, or in when people at your company are allowed to start and end their day, it’s worth asking.

Invite and accommodate common modifications to a rigid start time and end time in this question, such as if someone needs to end work early one day a week or usually resumes work after a long break in the evening.

When are your preferred meeting times?

People get their best focused work done in blocks of all sorts of shapes and sizes, and even for a colleague you work with closely, you’d often guess wrong about their most productive times. Not only is it useful to know this about each other, but it’s useful to prompt people to know this about themselves.

The answers to this question will be immediately actionable – you’ll probably reschedule at least one recurring team meeting right away and reap both productivity and happiness gains from doing so.

What’s a painful amount of meetings for you?

There are more intense interventions, e.g. time audits, that you could undertake to figure out exactly how many meetings you can fit in your schedule, but that’s rarely a worthwhile exercise to force upon an entire team. After all, time is finite, and that’s kind of the point here. So go with the quick version that this question gets at, as people’s gut intuitions on this can be surprisingly accurate, especially when framed as a threshold of pain.

There will often be barriers to implementing change based on the responses to this question. Variation across team members may yield no clear solution, and you’ll probably find people who find any amount of meetings painful.

Much of the value of this question is in the team conversations it starts. Sometimes, it ends up leading to rescoping or descoping a recurring meeting (a win). At other times, it leads to conscious tradeoffs. Even if you have to exceed some pain thresholds for your team sometimes, at least you’ll know you’re doing so and can do so more empathetically.

How responsive should we be to different types of communication?

Now that the stage is set for thinking about preferences and limits, the most valuable calibration exercise of this survey is figuring out how quickly you and your teammates should feel they have to respond to each email, Slack message, document edit, or other ping.

Pose the question as asking each member of your team how often they expect others to respond to them. Afterwards, when discussing this as a group, ask them how quickly they try to respond to each type of communication. You’ll usually find a huge gap in the bidirectionality of communications expectations.

The most common example: a teammate who knows that their Slack messages rarely have to be seen within the hour may nonetheless try to respond in real time to everyone else’s Slack messages. Often, most on the team are this way. Once it’s known and agreed upon that nothing breaks if Slack messages are seen within 2 hours, rather than within 2 minutes, you’ve just given your entire team permission to massively overhaul their focus. (A huge win.)

You should also ask which types of communication should warrant someone’s focus during a typical meeting. Phone call? Probably. Just a Slack message in the team room? Probably not. Similarly, decide which types of communications require attention outside of preferred working hours and which can wait until the next day.

There aren’t right or wrong answers to how quickly to respond to each type of message, and it’s not a simple majority vote on what the teamwide standard should be for each. The discussion is the point, and you’ll settle on at least a range of acceptable expectations.

Put it into practice

• Create your own survey for these questions or use the template below, then have every member of your team answer these questions somewhere publicly within the team, such as in a collaborative document.

• Next, take a few minutes to compile the results and find the surprising findings and areas warranting a deeper dive.

• Then, put a live team discussion of the results onto the agenda for 15 minutes in your next team meeting. Take notes in that meeting and make group decisions on new operating rules for the team, e.g. “avoid Monday meetings when possible”, “no Slack during meetings”, or “no email or Slack after dinner (anything urgent would be a text message)”.

• Put that finished product – especially the final decisions, but consider also memorializing everyone’s individual responses – somewhere permanent and transparent within the team. Make it part of your team onboarding materials; different teams within your same company culture will find different conclusions from this exercise, so make it easy for new team members to adjust to your ways of working…

• … but acknowledge that it’s a living document. Repeat this exercise at least once per year, both to adapt to new team members’ preferences but also to existing team members’ evolving preferences. It’s a great short activity to break up a team offsite or quarterly planning day.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

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Most meeting invites have little to no information in them, sometimes just a title and a Zoom link.

It’s easier in the moment, sure, but how much time are you and your attendees collectively losing to unclear objectives, ineffective preparation, or scrambling around to find related materials?

It’s worth taking a few minutes to build your calendar invites in a way that enables everyone to decide on their participation and stay oriented towards the outcomes and goals of the meeting – especially for recurring and/or large-group meetings.

Here’s my model of what most good meeting invites should have:

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1) Title

Keep it concise but clear around the purpose and objectives of the meeting. Frontload the purpose of the meeting to the beginning of the title, as most of it will be cut off on some views. Words like “weekly” and “Monday” don’t pull their weight, as these characteristics are obvious.

2) Duration

The length of a meeting should always be intentional. Resist the 30-minute default; the pace of meetings will usually increase to fill up any space you’ve given it on the calendar.

I book lots of 15-minute meetings. Challenge yourself to pick the minimum duration that makes the goals of a meeting viable; while it’s nice to “get 10 minutes back” when a 30-minute meeting is finished in 20, it’s even nicer for everyone to be able to plan for productive use of those 10 minutes by simply booking the meeting for 20 minutes.

Build in at least a short buffer between meetings whenever possible. Here’s a great experiment to try if you haven’t before: book 25-minute meetings instead of 30-minute meetings, 55-minute meetings instead of 60-minute meetings, etc. It’ll get you operating incrementally more tightly while allowing people to take proper breaks when booked back-to-back.

3) Location/Medium

Don’t choose a video call unless visuals are necessary. Audio-only calls have their advantages, such as avoiding the “Zoom fatigue” of expending mental energy on the appearance of oneself or others. I’ve found many people are more able to absorb an audio-only meeting while taking a walk or doing household chores than they are to focus on a Zoom call taken at their computer with its accompanying stimuli and distractions.

And perhaps the medium isn’t a meeting at all, but rather asynchronous collaboration in a document. Most decisions that feel like they can be made this way will be faster that way.

4) Guests

Your team’s time is expensive. There are plugins that can calculate and show this within the meeting invite, but just remembering that time is expensive will help you ensure you keep the audience tightly tailored to the goals of the meeting.

If you’re not sure if certain people might need to be there, call that out in the description; more on this in “Skip Conditions” below. You can also set certain attendees as optional, which helps you make clear that you’re not demanding someone’s attendance, you’re simply inviting it.

5) Busy, Tentative & Free

You can usually preemptively mark your meeting as something other than a solid “Busy” on attendees’ calendars. Gmail allows for “Free” and Outlook allows for “Free” or “Tentative”. Setting lower-priority, eminently skippable or rescheduleable recurring meetings as open or partially open on everyone’s calendar helps people prioritize other meetings or work over them when necessary.

Description

The description of a meeting invite is your chance to communicate to your attendees and to your future self. The following elements often prove useful as references:

• 6) Goal(s)

  • Why it’s worth a meeting belongs at the very top. Don’t make people guess.

  • If you can’t easily articulate the goal of the meeting in a few sentences, that’s a red flag that this topic may not be ready for or worthy of a meeting.

  • Most meetings should result in decisions being made, immediate action being enabled or collaborative work happening during them.

    • Good recurring standup meetings, for example, are structured to routinely enable efficient transfer of actionable information.

  • It’s sometimes useful to call out boundaries on what a recurring meeting is not for, as in the example pictured above.

  • If, as the meeting draws nearer, the goal is no longer a priority for your team, this will help someone realize to cancel the meeting.

• 7) Agenda

  • Most meetings will have more than one decision, action, or topic. If they do, lay out your best estimate of how much time will be spent on each.

  • You needn’t be precise here or use a stopwatch during the meeting, but setting rough benchmarks will help attendees participate more effectively and not crowd out the final topic. Everyone wants to avoid the dreaded second meeting for overflow.

• 8) Skip Conditions

  • Think about when certain people should potentially skip part or whole of the meeting, or when the meeting should be canceled altogether, and give your team permission to do this by writing it in the description.

  • Especially for recurring meetings, think about the quorum needed for the meeting to be effective – maybe you want to empower anyone to cancel an instance of the meeting whenever more than 2 teammates are unavailable.

  • Think about when the “time quorum” of any given week might not be enough for the meeting, too. For example, during a week with a holiday, you should almost certainly either cancel or shorten some of your regular meetings, otherwise you’ll displace too much time away from other work.

• 9) Reference Links

  • Add links to any collaborative documents that relate to the impetus of or brainstorming for the topic of the meeting. If an ad hoc meeting was borne from a Slack discussion, link that thread to capture its context.

  • Set up a collaborative document for the meeting or recurring meeting series in advance and put the link here. This avoids people losing track of where the stuff related to each meeting goes and enables those who skip the meeting (a design goal!) to catch up later at their own discretion.

Put it into practice

To take another perspective on this model: by writing down and sharing the purpose and context for a meeting, you’re proving why the meeting couldn’t have been an email.

Pick a few of the new tactics and try them out. Hold yourself accountable to calibrating goals and durations that fit the cost of the meeting, even if others don’t. You’ll run better meetings and, even more importantly, reimagine and cancel your meetings more often.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

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I’ve long espoused a simple ethos when it comes to hard and important work:

Give it everything you can, but be sure to not give it any more than that.

But even conscientious productivity-minded people can fall victim to the siren song of overwork. Here’s the story of the last time I veered towards the cliff of burnout, how I stopped myself before reaching it, and what we can learn from my mistake.

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When I gave more than I could

A few years ago, I was leading a large portfolio of software training programs and found myself suddenly surging on a priority client. It wasn’t a particularly novel challenge, just a particularly narrow deadline. It took all of my skills at both training design and process efficiency to wrangle and motivate all the players, define the viable logistics, write the right content and get the nascent tech working to support it.

There was almost enough time to get everything fully polished prior to the training. But the day before the event, a few things went wrong at once. I had to find several more hours to rebuild what I wanted to deliver.

This manifested through me having my laptop open and my focus absorbed for the entire time I was parenting my toddler that evening, and he ended up watching much more TV than we were comfortable with.

Yes, that’s it. That’s the biggest negative impact of my overwork in this story. Yes, I know many people who wouldn’t have worried about this, and many with much more serious burnout stories. And yes, my kid was, of course, fine.

But I crossed a personal red line here. I had always set firm boundaries around my top life priority of being an engaged parent, and even a singular incursion was a wake-up call for me; not burnout, but a glimpse at its precipice.

What happened next

The aftermath came in a medley of acts, each with its own lesson and, because this is how my brain works sometimes, each with its own 90's song soundtrack:

• Farce: I got food poisoning as soon as I woke up to fly to the training the next day.

  • Lesson: Hard work may be wasted due to circumstances outside of your control.

  • Soundtrack: Alanis Morissette - “Ironic”

• Epic: Despite my entire day’s subsistence being solely two PB&Js, I somehow mustered the energy to perform at the top of my game, executing excellently and leading directly to a multimillion dollar contract.

  • Lesson: Some would use this outcome to justify the overwork, but it didn’t make me feel any better about mine. Instead, this showed me that I could have kept my boundaries and likely still delivered a good-enough result.

  • Soundtrack: New Radicals - “You Get What You Give”

• Tragedy: This success was not reflected in my performance evaluation, the outcome retroactively seen as no longer the critical priority it was in the moment.

  • Lesson: Maybe sufficiently important business outcomes could exist to bend your burnout boundaries, but be wary not to overestimate the importance of your current project. Hard work may be wasted due to circumstances outside of your control.

  • Soundtrack: TLC - “Waterfalls”

What I did next

I acknowledged that my overwork was my fault. You are the responsible and accountable party for your burnout. Few colleagues would ever ask you to give less than you’ve chosen to give. Even a perfect culture with generous, compassionate teammates won’t see most types of burnout indicators. You have to look out for yourself, and that has to stay near the top of your internal alert systems.

I decided it would be the last time I bent a boundary around my parenting time. And it was. When it comes to setting red lines between work and the most important parts of your life, you can just do things. It’s not always simple, but the alternative – on-the-fly compromises in the heat of the moment – is unlikely to work out for you or your employer in the long term.

I found a new project. While traveling for this training, I happened to get outreach from a different team who needed my skills for a different shape of work. So I said yes, and I prioritized working on projects and for teams with more respect for the finiteness of time.

These tough, but clearly correct, choices quickly got me off the burnout path and back to a healthy relationship with my work.

Most others would have not seen the burnout trajectory this early, when its impact on others was minimal. Most others would not, even at that point, have had the foresight to make the resolutions above. And most others would not, even after making those resolutions, have held to them.

I’m here to tell you to get caught trying.

(And yes, I did antisurge afterwards.)

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Put it into practice

So, what if you can’t do what I did?

• Well, everyone can certainly do the first step: acknowledging your role and responsibility for your own burnout. You can’t help yourself until you know yourself and see yourself.

  • Think about your own red lines and the triggers that may indicate you’re getting close to them. Become ready to be your own early warning system.

  • Think about how long your life needs can afford being bent without becoming broken. Maybe you can afford this level of personal life incursion for a few days, but not for a few months. Everyone’s different.

• You can’t always say no to work or find a new team, and there are plenty of reasons to be in a job that at least occasionally demands too much of you, I get it.

  • But you can sometimes say no, and it might be more than you think. Start conversations about how the shape or size of your work is spilling over into negative life impact and starting to burn you out. There might be a way to change it.

  • Or, say a “yes, for now” instead of a “no” to the work and accelerate your search for your next career opportunity somewhere more aligned with your needs. There are tradeoffs to be made here, but you’re best served by facing those tradeoffs rather than pretending they don’t exist.

• Fight the siren song in the classical sense: tie yourself to some masts. I wouldn’t have thought that I needed this sort of thing, but I wish I had set an audible alarm that night for the 20 minutes I thought the work would take, or not unpacked my laptop charger. Find methods to hold yourself accountable.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

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Aligning on these expectations allows everyone to shape how often they check Slack appropriately. This, in turn, establishes the framework for and helps build trust that teammates are respecting each others’ time and striking the right balance between signal and noise. So let’s dig in to why each step matters.

Direct Messages for the discreet

There are types of genuinely private communications that do belong in either 1:1 or small-group Direct Messages (DMs), such as sensitive project planning, personnel discussion, good ol’ socializing and constructive feedback. (Bias towards putting positive feedback where more people can see it!) But unless something is truly sensitive or private, if it relates to a project or team, it probably belongs in a Slack room.

You are doing your team no favors by gatekeeping information that may someday be useful to them. Slack is most useful when it’s a live, ever-evolving knowledge base, and if you put information into DMs, your current and future colleagues won’t be able to find it through search or through Slackbot, such as if they’re covering for you on your OOO or if others on your team take over some of your responsibilities in the future.

Put it in the project or team room, tag the primary person or people you’d otherwise be DMing, and use threads to contain the rest of the conversation. This will cause minimal bother to your team while maximizing situational awareness.

Worried about asking a stupid question in front of a larger group? Everyone feels that way sometimes, and if you can’t find it through search or Slackbot, then nobody’s ever asked, and if you ask, nobody else will ever have to ask again. So, do it.

Bonus tip: If you’re using small talk to tee up asking for something, put it all in the same message. Don’t add the double latency cost of waiting for them to send, and for you to see, their “Hi!” back.

Threads for the discrete

Every individual topic or discussion in a Slack room should have its own thread. At their core, Slack threads allow your teammates to opt in and opt out of participation in conversations based on the topics that matter to them. A Slack room becomes a digestible index of topics rather than an unwieldy wall of text.

They’re quick to spin up:

And threads are quick to opt out of via unfollowing – or by my unfollow + save workflow that converts noisy ongoing discussions into simple future catch-up reading. That’s one of the biggest upsides of setting a culture of threading and enables useful knowledge capture that would be too messy without threads, such as taking live notes on a meeting or capturing a long list of related followup actions.

If there’s a major update on a topic, or an aspect of the discussion so important that you need your full team to see, avoid the temptation to put it in the main room instead of its related thread. Instead, put it into the right thread and use the check box to “Also send to” the main room. When this leads new teammates to enter the ongoing conversation, they’ll be easily able to scroll up the thread to gather its previous context.

And if a teammate unknowingly starts a second thread on a topic, you can helpfully (and only slightly passive-aggressively) add a link to the original thread into that new thread to help others navigate.

Threads also for the long

Overly long posts in a Slack room make it harder to keep up and opt in to what matters. Instead of posting something more than a few lines long, post a quick summary, throw a 🧵in it, and paste all your details into the thread. This has the added benefit of letting you break out each detail into its own message in the thread so that it can be reacted to or upvoted individually.

Main room for everything else

Everything else starts in the main Slack room as a new topic, where, if it sparks discussion, it grows into a new thread.

If your team uses different rooms for different projects or subprojects, take a moment to think about which room fits your message best – and if it isn’t clear, or if the purposes of different rooms aren’t clearly defined, propose those definitions yourself and get them into the descriptions of each room.

Put it into practice - Exceptions

If you’re already doing something similar to my flowchart, find the gaps and try out filling them. This will often look like threading even more discussions and building the rhythm of searching for and renewing old threads.

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While my approach in the flowchart above is the right fit for most teams I’ve worked with, it becomes more OK to thread less and put more information into the main room the smaller, more rapid-paced and more temporary your team is, as the upsides of tidiness are diminished, e.g. in an emergency response room where the engineers who can fix it are joining in to diagnose and fix a major outage. (But even here, I’d tuck some longer analysis and sidebars into threads.)

If your team is established in their non-threading ways, you might not be able to make immediate changes. Same if there’s an implicit culture of nontransparency and a lot of discussions happening in DMs. You’ll need to work on building a culture that values transparency and forges trust – my Feedback Tactics workshop is a great way to kickstart teams at building this muscle group – but you can still try and reshape the team’s habits by threading your own messages and suggesting to move nonsensitive conversations out of DMs and into rooms. As always, productive collaboration is driven by the individual choices of teammates like you.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

You built your out of office document and used it to maximally and meaningfully unplug from work.

Now your leave is over. It’s Day 1 of reentry. You power on your laptop and are met with a deluge of unread communications. Where to begin?

By leveraging the decisions you made before leave and following these steps, you can cut through the noise to find the signal that matters, bring your refreshed perspective to the new landscape of tasks you’ve returned to, and reprioritize your own duties based on what you’ve learned.

Step 1: Don’t dive right back into the deep end

You’re going to invest some amount of time into digging out from emails, Slack notifications, and other inbound communications. Depending on your circumstances, it might take several hours. In my experience, reorienting goes best when you do this digging out up front so that you can understand the questions you need to ask as well as the topics that are newly at the top of your prioritization.

This means not joining in on every meeting on your calendar. My default is to skip most meetings and routine tasks until I’ve completed digging out from email (Step 2), and to skip lower-importance meetings and tasks until I’ve completed identifying my new priorities (Step 3).

Make exceptions for work that is both urgent and important (and, ideally, quick, to not derail your reorientation) and the highest-priority meetings.

Think of your out of office time as having been similar to the time displacement on your calendar discussed here, except on a larger scale. You are way underwater on comms. You’re going to bail out as efficiently as you can, and it should tend to take priority over pouring more water in.

Step 2: Dig out

Catching up on all of the messages you’ve received can seem daunting, but with a methodical approach to skimming, you can swiftly triage your massive inboxes into a tight list of notes and questions to follow up on:

• First, delete what you planned to delete, e.g. if you declared Slack bankruptcy. (SHIFT-ESC. It’s deeply satisfying.)

• Decide how far back in time you’re going to review. I recommend at most a week or two. I experimented with looking further back after my parental leave. None of it contained unique material which still really mattered.

• Next, skim emails sent to:, rather than cc:, you. (to:me -cc:me), starting from the most recent.

  • Read only a few lines into each email. Then give up on almost all of them. Continue only when they seem both important and likely to still be relevant.

  • As you do, take short notes in your out of office doc with what you learn (e.g. “Looks like Q3 presentation went well overall but with some new due-outs”) and possible questions for teammates (“What’s still outstanding from the Q3 due-outs?”)

• Then, repeat this for emails sent cc: you, and maybe for the most important tranches of other types of emails that you’ve filtered away from your inbox.

• Finally, review all of the notes you made during this process and group them by topic.

  • You’ll likely find that some of your potential questions were answered by other things you went on to read. Remove them from your list.

  • You’ll likely also find that some of your other potential questions are not among the top priorities anymore. Move them down on your list and consider worrying about them only after processing the top questions on your list.

After you’ve gained the context of your entire digout, it’s finally worthwhile to start asking questions and rejoining more meetings.

Step 3: Discern what actually matters

In this step, you’ll seek out the answers to your top questions from the prior step. This can be done in group meetings, team Slack channels or through 1-on-1 outreach.

As you find answers, translate your questions and notes from your digout list into your task capture mechanism as the actual actions that will make up your new work priorities. Only at this point have you gathered enough context on, clarified any questions you have about, and confirmed the ongoing relevance of your potential work for this to be useful.

Step 4: Descope what didn’t actually matter

You’ve dug out, but don’t turn your full focus to your new work quite yet. It’s worth spending a few extra minutes to learn about which of your routine duties you can do better and which you can stop doing.

• Circle back to your out of office doc and look over the tasks you identified for coverage.

• Check in with the people who covered for you and spend a few minutes asking them questions.

  • How did the work go?

  • Did your notes make sense?

  • Most importantly, what was their perspective on covering for that piece of your work? Your teammate may have found a better way to do it, or they may have found it’s not worth doing. Listen.

• Then look at the optional coverage tasks you identified at the bottom of your coverage section, the borderline ones you didn’t necessarily seek active coverage on. Ask around a bit.

  • Did anyone do these?

    • (Probably not, but if they did, ask why – it might be more important than you thought.)

  • Most importantly, did anyone miss any of these tasks not happening in your absence? If it turns out that you’re the only person who cared about it, it’s probably not worth doing.

• To cap this off, take a look through your entire to-do list and deprioritize (or outright delete) anything that you’ve learned is less important than you thought.

Put it into practice

The post-out-of-office moment is a rare opportunity to overhaul your priorities, occurring at the convergence of the new approach you bring to your work after your out of office, your teammates’ fresh perspective on covering the work you usually do, and the necessity of having to take some email digout time regardless. Make the most of it.

If you found it particularly energizing to bulk-clear your Slack messages or to skim your emails more quickly, now’s also a great time to try tightening your approach to your everyday comms. Experiment with it. Your teammates will afford you some extra leeway as they know you’re reorienting. If a more lenient approach to your messages feels good and still works, make it your new normal.

That’s it. Bookmark this three-part guide here, set a reminder to check back in with them a few weeks before your next leave, and enjoy your time off.

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter:

Last week, I introduced the foundation of your out of office document in the lead-up to going on leave.

In preparing that doc, you’ve bought yourself the confidence in your coverage and the mental space you need to turn off your work brain and focus on your fishing, your family, or your freedom of whatever sort you need.

Now, use these tactics to help you maximize your time away.

Deciding your out of office policy

Take inventory of both the policies and the cultural practices that your organization has around leave.

What do you want or need your leave to be? Figure that out, and make sure you take it – because nobody’s going to give it to you.

The wrong way to do this is to assume that you should behave the way your current teammates seem to while they’re out of office. Laptops on the beach? Sending the more-than-occasional email? Peeking in on Slack? Those can be right for some people, but make an active decision on if it’s right for you and aligned with the goals of your leave. Don’t just follow the crowd, and don’t assume that others expect that of you.

Let your company’s policies be your starting point, not peer pressure. The cultural practices of teams tend to be inflationary around expectations of attention to work while out of office – maybe they started in line with the written rules, but then some people started staying more plugged in during their vacations, so then more people started following them, and so forth. Reject that.

Some out of office policies clearly have implicit cultural limits (unlimited vacation, I’m looking at you), so you’ll have to do some amount of investigation on what’s expected and allowed. You don’t, however, have to pick the average of what you find. You can pick something on either extreme, or you can be the trailblazer to stretch expectations to meet your goals.

Preparing your phone and other devices

Your phone controls where your attention is drawn, and you almost certainly have some changes you should make to your phone setup during your leave.

For each app you use for work, you should do whichever combination of the following fit you best:

• Delete the app – The most extreme, the most simple, and my most recommended approach for workplace communication apps like Slack. If you’ve already committed to not only ignoring Slack while out of office, follow through, “burn” the boat, because in an emergency, people can reach you in other ways, or you could reinstall it.

• Turn off notifications for the app – You’ve set up notification schemes for specific apps and specific categories of emails that match your normal work rhythms, but they probably don’t match your out-of-office rhythm. Try turning them all off for your leave. If you’ve committed to paying attention to any sort of email, try bounding your time to checking once a day.

• Remove the app from your home screen – Even with notification badges off, seeing a workplace app among your leisure apps may be an unwanted mental intrusion during your leave. Taking the icons off of your home screen is quick and easy to reverse. I do this for everything even slightly work-related, e.g. LinkedIn.

Do the same for other devices, if applicable. Don’t bring a work laptop on a vacation unless you’re certain it’s needed for a specific piece of your coverage plan.

Finding your out of office mindset

Much of this is easier said than done sometimes, I know. I get it. These are big short-term habit changes. Shifting your mindset can help them take hold quickly.

Your job affords you the opportunity to take leave. Often, it is incentivizing you to do it. It’s part of your job to be out of office sometimes. When you’re on leave, you’re realizing part of your compensation for your job. You don’t feel bad spending your salary, nor should you feel bad taking leave.

Because it’s part of your job to be out of office sometimes, it’s part of your teammates’ jobs to cover for you sometimes. You’ve already done more than most by creating your out of office doc. Trust in the guidance you’ve built for your team. Trust in your teammates’ ability to execute on it. And trust that they would scold you if they knew you were worrying about this during your leave.

Trust, too, in the processes you’ve built to defer and manage your work: your email filters; your task management; your prioritization of important, urgent and quick tasks. These systems will be there when you get back, and they will continue working for you.

Therefore, hold your ground on the boundaries you established for your leave. You may have impulses to break them. Identify these urges, disarm them and dismiss them.

Focus on what matters to you

The above will help you successfully detach your brain from the micro of work and achieve a goal that is restorative, rewarding, or rehabilitative in whatever way you need.

Perhaps counterintuitively, your leave can be a good time to think about the macro of your career, especially if you find you usually don’t have much brain space to think about it.

Your current job is just a single job in your career, which in turn is just a single component of your life.

• Is your current role helping you grow at the skills at which you want to grow? Do you even still want to be growing at the skills you thought you wanted to grow at a year ago? It might be time to start figuring out a new role.

• Alternatively, if what you valued in your current role is that it lets you leverage your already-strong skills, from the temporary new vantage point of your leave, are you sure you still value that?

• How are your finances doing? Perhaps you’ve missed that it’s long overdue for you to ask for a raise or to start searching for an employer more aligned with your impact. Or perhaps you’ve been saving a lot and should soon start either spending more or working less.

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Put it into practice

Don’t overthink it, but don’t fall into your typical rhythms, either. Now is not the time to be too productive. At the end, you’ll be ready to return to work with renewed energy and a newfound perspective.

Next, in Part 3, we’ll talk about how to spend your first few hours or days back to maximize your reorientation:

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

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As you plan your vacation for the summer, you should also plan to step away from work the right way.

Over the next three weeks of this newsletter, I’ll lay out my personal processes and methods I’ve honed over many out of offices for optimizing the before, during and after, whether it’s five days of vacation or five months of parental leave.

Setting your team – and yourself – up in advance of your unplugging is the most important part, and it’s built around one simple artifact.

Your out of office document

Before you go out of office, start up a fresh collaborative document in whatever system your team uses to write and share text. You’re building your out of office doc, a high-value investment in reassessing your priorities in advance of your leave, a reference for your colleagues while you’re gone, and a roadmap for your own recalibration afterwards.

There are five critical components of an effective out of office doc (and yes we still like alliteration here):

Chronology

Start with the most important information at the top: when will you be gone, and when will you be back? Simple, but it’s what your colleagues most want to know.

Communications Plan

Next, address two types of communications:

Communication during your leave: Is there anything that might come up during your leave that will need you? If so, how do you want people to let you know about it (hint: phone, not email or apps), and how soon should they expect a response?

Hold a very high bar here, and strongly bias towards unplugging fully, even in a “small” vacation or an “easier” personal leave. You’re fighting against constantly-inflating expectations of availability, so interrogate your instincts here. The fact that you’re creating this document will give your team the context and confidence to handle things without you. It’ll also give them an opportunity to raise concerns about what they think they might need you for – let them come to you with these discussions.

Communication you’ll catch up on after your leave: Of all the myriad comms detritus that you’ll come back to, which ones will you bother catching up on? How long do you expect to spend doing so? How can people get the most critical information to the top of your digout pile?

Here are my favorite defaults:

• Preemptively declare full Slack bankruptcy, even for DMs. Most Slack environments, as compared to email, are too low signal-to-noise and have a shorter half-life of usefulness of information.

• Instead, commit to eventually reading every email sent to: or cc: you. When something important happens in Slack, invite your colleagues to simply email you a link to the Slack thread, and then you’ll read those.

• Plan to dig out your email from newest to oldest, and encourage colleagues to email you on the day of your return with what needs your most immediate attention.

Context

What information might live only in your head but could be important when you’re gone? For all of the projects that you touch, even if you’re not the outright owner, what are the most important goals and next steps?

This is the toughest piece of the out of office doc to fill if you try to do it all last-minute. It’s easy to overlook the context you take for granted when you aren’t looking for it, so in the lead-up to your leave, keep an eye out for every time you use knowledge that others might need and immediately take a note on it in your out of office doc as you go.

Start a few weeks before you leave and look for these in all of your regular meetings and duties.

Coverage

Then, shift from the macro to the micro: What specific subset of your usual duties do you need a teammate to do while you’re gone?

Lightly document each item with two audiences in mind: the person who will be covering for you, and other people who would otherwise seek you out about this duty.

Remember, your team’s time is finite, so if you’re out, your team either has lower total output or other people are working longer hours. Lower the output wherever you can; for any meeting or task where nothing major will break if it’s missed, bias towards not asking for coverage for it at all – but put it in a lower-priority list of optional coverage tasks at the bottom of this section. (You’ll use this later.)

You’ll usually seek coverage for those of your tasks which are both the most timely and the most important, but you’re not handing off your entire to-do list, and for running the most important meetings you’d usually run, but not blindly holding every usual meeting (especially those that are less useful with a lower attendance; cancelling these is a great place to reclaim some team time).

Checklist

Finally, you can use your out of office doc to manage a checklist of the small logistical mechanics of starting your leave, either in addition or instead of your usual task capture mechanism. This will typically include sequential steps such as getting necessary approvals, finalizing the out of office doc, sharing it, and setting OOO in different systems.

You’ll use this finished checklist as the starting point for your next out of office checklist and improve it each time.

Put it into practice

• Set a reminder for two weeks before your next planned long out of office. As you go through your work during those two weeks, start your out of office doc by taking notes on the meetings, tasks, and projects that matter the most, along with any important context on them that others might not know.

• Two days before you step out of office, look over those notes and pare them down to only what matters most. Benchmark: if the person you asked to cover for you on something ended up not doing it for whatever reason, would it be a potentially serious problem? If no, then cut it.

• Share the out of office doc with your team at least a day before you leave. Don’t expect your entire team to care or to read it in full, but put a link to it where people can find it if they need it.

Then unplug and trust that things will be fine with you gone.

More tactics for that in Part 2:

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

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I’m not an executive assistant (EA). I’m not trained as one. I don’t consult as one. EAs have many skills that I don’t.

But when a founder friend of mine had a gap in their EA coverage and a willingness for an unusual experiment, I agreed to plug in on owning and managing their inbox and calendar for a few months. Forward Deployed Productivity Coaching, in a strange sort of way.

The vast majority of us will never be EAs nor have EAs, but through embedding into managing someone else’s email and calendar, I discovered lessons that all of us can learn from.

I won’t actually run your inbox for you, but I *do* offer hands-on productivity coaching and group workshops to help you find your best way to take control of your email and calendar.

Coaching & Workshops

Defining implicit assumptions

When it comes to personal components of productivity such as our email and calendar methods, most of us have never defined or articulated our processes. With an EA, the principal can’t operate on the fly as they must provide guidance and instructions to at least one new person. And once there’s a starting point of context, any new set of eyes can find new answers, and new questions worth asking.

During my experiment, I found a few implicit assumptions that were overdue for reevaluation:

• The principal and their old EA had an intuitive sense of which people and types of projects were most and least important. I was starting from a blank slate and had to ask a lot of questions. In doing so, I prompted the reevaluation of stale assumptions. The forced refresh of defining who and what matters helped the principal reorient their prioritization away from what mattered last year and towards what mattered most today. Lower-priority requests were then batched by the EA for intermittent review.

• The principal didn’t really know how many hours of meetings they could accommodate in a typical day or week. That’s an important number to calculate for any busy person, and since I needed to know this as the EA in order to effectively control their meeting inflow, I helped them measure this, refine their expectations, and define boundaries accordingly.

• As the EA, I’d use email as my way to ask the principal about non-urgent matters. In theory, they agreed this was right, but in practice, we found that they weren’t consistently seeing or responding to all of their email, even from their EA. This insight led us to build an email tagging system and weekly check-in meeting rhythm – the EA is in a perfect position to lead these meetings – that let the EA set up backstops for non-urgent, medium-importance matters and fit the way they operated.

How sure are you that you meet your own soft expectations for your inbox? Defining them is the first step towards retooling your processes.

Accounting for the abnormal

Once we settled into a productive operating model for the normal periods, my next focus was finding changes in approach to use during the busiest periods:

• I found that some types of meetings at some times of day would often end up needing to be cancelled last-minute or would be kept but were disruptive to the flow of their core work. These are hard patterns for anyone to see on their own when they’re in the thick of it but are easy to see as an outside set of eyes. I helped them adjust the hours they offered for and to raise their standards on lower-value meetings, finding certain types of discussions that became up-front polite “no”s rather than eventually regrettable “yes”es.

• The principal had frequent business travel where they were able to keep up with most of their core work duties, and even their inbox, but had to put off most meetings until after their return. Without adjustment measures in place, this led to an overwhelming amount of meetings the next week that both impeded their productive time and drained their energy. I set up tighter meeting availability for post-travel weeks to mitigate this – and documented it and handed it off to the next EA.

• During these busier times, when it was hard to frequently sync up with the principal, in my managing of their inbox, I switched from using email drafts as a pure to-do list to using drafts on threads to capture ongoing context and different types of followups, e.g. “check in if they haven’t replied in 1 month”, “principal has already connected with them off-thread”, “offer up meeting times only after [most important meeting of the week] is locked in”. I’d review my Drafts folder daily and as part of our weekly review meeting. Particularly for a part-time EA switching between other contexts, I found this process to be a low-friction way to keep track of notes on next steps – and I started doing this more in my own inbox, too.

Put it into practice

All of these insights were easiest to see from an outside perspective but can also be bootstrapped by some dedicated, compartmentalized time that you afford yourself. You can act as your own partial EA if you set up some regular time to take a breath, stop the rhythm of your usual work, and force yourself to objectively review your email and calendar processes.

Try setting aside somewhere between 15 minutes per month and 15 minutes per week to:

• Review your meeting flow. What felt overwhelming? Which meetings did you regret saying yes to?

• How much time did you spend on meetings or work for projects other than the project that matters most to you? Why did you spend time on other things? Was it worth it?

• Or team up with a trusted colleague to trade perspectives with each other. You don’t need full access to each other’s email as long as you can see each others’ calendars. Ask these questions and see what you can each discover for each other.

And be grateful for (real) EAs and appreciate the work they do.

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I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

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From the mailbag:

I’m looking to grow a company that highly values operational efficiency, collaboration and knowledge transfer. How much of this happens by finding the right people at the hiring level versus building the right skills at the onboarding & cultural level? – Anonymous

Thanks for the exciting question! Hiring and onboarding are passions of mine (workshops & coaching available) and, along with productivity, are among the most highly compounding investments that a team can make into its culture, and this question gets deep into the juicy overlap of all three.

I wouldn’t be here if I didn’t believe that almost anyone could grow to be good at productive operations. These are eminently learnable skills that don’t depend on specialized talent. So my first-order answer is that onboarding and culture will always be the dominant factor for forging productive teams.

That being said, just because almost anyone could grow to be good at this doesn’t mean every type of person will be equally eager to do so. If you want teams full of people who are great at productive operations, there are characteristics you should hire for.

How to hire incrementally more productive people

The top characteristics to enable productive and collaborative teams likely overlap with what you’re already looking for in your hires:

• Ownership without authority helps new hires find their own optimal ways of working amongst the expectations and needs of your team, and it also empowers them to identify and speak up when they find processes that could be improved – valuable signal to get from each new set of eyes.

• Self-reflection skills enable people to see, understand and reevaluate the performance of their processes. Ask how a candidate approaches productivity and managing their own work. You’re not looking for a specific “right answer”, you’re looking for people who have an answer because they’ve thought deeply about their own operations.

• Autonomy is a prerequisite for collaborative productivity. You don’t need everyone you hire to be at the level of a project manager or an executive assistant, but you do need people who don’t always rely on a project manager or an executive assistant to tell them what to do.

• Customer service mindset is indirectly relevant to effective collaboration in even internally-facing roles. Your teammates are customers of your ways of working and communicating, and vice versa. “Internal customer support” activities like investing in writing great knowledge transfer material and SOPs help ensure that best practices are retained and built upon.

• Grit, the resilience and willingness to work hard on hard problems, helps motivate even process-averse people to engage with systems of productivity once you’ve actively proven to them that these systems have value. Try to couple this with strong showings on the above, as a high-grit person may also be willing to work hard while myopic to an inefficiency.

Increasing the value of facets like these in your hiring process will help you build a high-output collaborative culture, but hiring alone is neither necessary nor sufficient for this. Onboarding and culture are necessary.

How to grow any of your people to be more productive

Even with perfect hires, you won’t achieve consistent operational efficiency across your teams without a prominent investment at the cultural level.

First and foremost is the need for leadership to model and execute on the company’s expectations around operations and collaboration without imposing overly rigid systems universally. Founders and team leaders need to be responsible for seeking out and distilling the least-common-denominator across their teams of productive ways of working and then showing, not telling them as often as possible, e.g.:

• If it’s important for everyone to record and share learnings from important meetings and milestones, then leadership should be writing theirs themselves and sending them often.

• If clear and transparent expectations around teammates’ time and priorities are important, then leadership should make their calendars public and frequently share reflections on how their own personal priorities are evolving.

• If it’s important for teams to have time each day where they aren’t plugged in to work communications, leadership should not be sending emails at all hours.

Failure to do this will quickly lead to cynical abandonment of productivity values as employees pivot towards whichever values leadership is perceived as pushing; visibly demonstrating strong operational culture should be a prerequisite to promotions.

Secondary to that is onboarding. New hires take strong initial cues on the relative importance of different topics based on their proportional representation on their onboarding schedule, so you should have at least one dedicated session and/or scheduled reading activity that conveys both the why and the what of your most important operational principles – and you should weave these themes into as many other sessions as possible.

• Make your most important operational principles explicit. Write them down in a big font somewhere. Explain why they matter. Show a few different effective examples of implementation of each across roles, e.g. different real calendars across different roles.

• Leave room for each individual team to bend these principles and make them their own. You don’t want to be overly prescriptive on the exact implementation of ideas; for example, different teams will likely have different ways they define their meeting cadences, and that’s good as long as they’re within the bounds of companywide expectations.

• Build a reading list with books and articles that focus on productivity in line with your company’s values and provide tactics that new hires can put into practice quickly. These can even be given before a new hire’s first day. Bonus points if you incorporate a discussion group on that reading into their onboarding schedule – this can be a good soft topic for lunch one day.

Finally, your most important operational principles should be reinvigorated periodically so that your more experienced hires, far removed from their initial onboarding, have opportunities to be reminded of and to reevaluate these against their shifting work. Show successful outcomes from your productivity tactics in your all-hands meetings. Celebrate gains in operational efficiency. Actively revise or delete principles as soon as they’re no longer the right fit for the shape of problems you’re facing today.

Productivity is a lifelong journey, not a destination.

Invite your team to join you in a quick weekly productivity level-up:

Share Processes for People

I’ve organized my archives into a recommended reading order. You can learn more about this “book” here or hop to the next or previous “chapter” via the links below.

Previous chapter:

Next chapter: