AI for culture audits

We’ve recommended a culture audit here in a piece written many LLM models ago. Our core suggestion there was to survey your people and ask them what the company’s values actually are in practice. That kind of audit is still a useful thing to do.

This is also a strong use case for AI. Models haven’t been trained (yet) to deliver rich, idiosyncratic, creative writing. They have been trained to identify patterns, the bigger the data set the better.

Grabbing a chunk of meeting transcripts, Slack threads, and email exchanges and feeding those to Claude with a prompt like the one below can be a useful part of your culture audit. In a more advanced (and more AI-exposed) approach, you have Claude automatically ingest and analyze this data and give you a report every few months.

Culture audit prompt:

“Our team officially has the core values of [value], [value], and [value]. I’m conducting a culture audit of the organization to determine a few things: 1) how well are we embodying our stated values? 2) what are our “shadow values”, i.e., the values we actually practice and demonstrate a revealed preference for? 3) what if any changes should we consider making to our stated values, based on 1) and 2? Can you review the attached materials and give a robust answer to these questions, citing specific pieces of evidence from the materials?”

-eric

Goals instead of roles in the early going and maybe the later going, too

When your venture or project is just getting started, you might lack the skeleton and exoskeleton a mature organization has. You and your cofounders are holding the equivalent of three or four or nine jobs. There’s no HR department. There’s not even a single HR person.

There’s something useful about this period that you can carry forward into the more mature and exo-skeletoned phase of your team’s life. In the early days, you’re pretty much forced to assign goals instead of roles. Things need to happen. Things need to exist by x date that don’t exist now (products, relationships, org charts, policies, a logo, who knows the list is quite long).

It doesn’t make sense in this protozoan chapter to tell one of the four people on the team “You are the Senior Director of Digital Marketing”. The title says too much and too little at the same time. It does make sense to say, “we only survive if we sell lots of this stuff on the internet. Let’s say ‘lots’ means ‘$1M worth by the end of the year’. Can you own that for us?”

I’d suggest this can be a useful approach after the founding frenzy, too. When you realize you need more people on the team, start with the short list of things the new person will make true by the end of the year. Then back-map a title onto that set of goals.

Starting with the title can confuse you and the candidates you recruit, because titles are little dynamite sticks of cognitive bias. They are three-word behavioral economics poems. It takes a lot of effort to explain and understand what they mean here, now.

-eric

A fun emergency plan

Oh my word the Dowager Countess has croaked and wouldn’t you know, she secretly bequeathed your organization a handsome sum, I mean a 10x-your-annual-budget kind of sum, one fine day while the sun smooched the crocuses and the ill-mannered Pomeranian sat upon her noble lap!

What are you going to do with all dat money???

Run the exercise. Get yourself a robust answer to the question. Adjust the details however you like (I know some people are partial to long-haired Dachshunds, eg, other people prefer their windfalls from Lithuanian gardeners made good, eg).

Two benefits I hope come out of this for you:

1. Object level: you have a plan for what to do in the case of a happy emergency. Ideally this promises a higher return on luck.

2. Meta level: the exercise reveals something that might have been tacit or hidden about your ambitions. You have a clearer sense of what really maxing this thing out would look like. Maybe you also have a sense that you could get there without a wild bequest. The crazy success may be more tractable than you realized.

   1. Also interesting in this thought experiment is what you wouldn’t change at all when you get the fat windfall.

-eric

COMPELLING QUOTATIONS

Critic Henry Oliver on reading Henry James and walking the dog:

Although some of my efforts to read James had been successful … this was an entirely new sensation, and I no longer read in that plodding, linear manner I had become accustomed to with James’s other books. Now I read like an enthusiastic spaniel, who, when let off the lead on a walk keeps running ahead and coming back, making loops, working over a piece of ground, moving on, coming back, making comparisons of obscurely doggy matters, so that in the end, the dog has not only had a walk of three or four times the length of the amused humans, but has experienced everything in a wild, rotating reality, quite different from the pleasant linear walk that takes place beside him.

AI observer Ethan Mollick on the questions he’s now trying to answer:

Two years ago, the question I was trying to answer was how to think alongside a new kind of intelligence. Now the questions are weirder: When should you refuse AI’s help, even when it is offering? When should you hand over the keys entirely? And what do you do when the AI is no longer just your assistant, but your reader, your critic, and the gatekeeper standing between your work and its audience?

Poet David Whyte on witness:

The ultimate touchstone is witness: the privilege of having been seen by someone and the equal privilege of being granted the sight of the essence of another, to have walked with them and to have believed in them, and sometimes just to have accompanied them for however brief a span, on a journey impossible to accomplish alone.

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Sketches of fantasy and maintenance

Fantasy is periodic. When it occurs to you, you enjoy it. For the limited time you’re in the grip of the fantasy, you’re pretending.

Reality is persistent. When you are in it, you might not enjoy it very much. You’re inevitably tending to needs beyond your own pleasure.

Fantasy is envisioning the greener grass.

Reality is mowing it.

This is not an anti-fantasy post. Fantasy is useful. A good look at your fantasies can reveal underlying characteristics that draw your attention. Those characteristics might be available to you in the real world. Maybe you wouldn’t have thought to look for them, or known they were drawing you, without this look at your fantasy. You develop a slightly better map of your own intuition.

Maybe this is just weird lil me, maybe I’m just a creature of infinite scroll, but my fantasies have a fleeting quality. They’re more fragment than feature film. Whether I’m fantasizing about a dream job or a new place to live or a romance, the content of the fantasy is often a moment that plays on loop.

This is one way of saying: I notice that most of my fantasies don’t involve maintenance. They involve acquisition, immersion, creation, surprise – often the fuzzy, bounded beginning of something without the tail of its consequences. The pretending is pre-tending. The action that precedes caretaking, repair, and routine.

Because fantasies recur, it can feel like there is important information in them. Something in the subconscious or in the universe continues to knock at your door. Because fantasies are enjoyable, it’s tempting to think that information is an imperative: bring this about. Make this fantasy real.

Maybe that’s a good idea! Maybe not. One way of sorting this out: imagine, in the greatest detail possible, the maintenance your fantasy would require, once real. Build out the persistent, mundane context surrounding the seductive moment. Water, mow, aerate, fertilize, and weed the greener grass.

What is the tending your pretending will require?

-eric

Using AI to find blind spots

LLMs are trained to be helpful and agreeable to you. They’re trained to be honest, too. But it’s common to sense that the models are more interested in promoting the ideas you show up with, more interested in making you feel good about yourself, than in giving you bracing truths.

They can give you bracing truths! But you gotta ask.

A go-to move for me when I’m deep into a problem-solving conversation with Claude is to ask about my blind spots. What am I not considering? What unspoken tradeoffs am I accepting or what invisible bullets am I biting in the way I’m approaching this? What are my blind spots?

It can also be helpful to ask Claude to run this analysis on itself. “The advice you’re giving seems to come from a point of view or school of thought. It’s not pure, ex nihilo reasoning (if such a thing were even possible). Using what you’ve already said in this conversation, explain to me what the perspective and priors are that you’re relying upon. What are the blind spots or downsides of this perspective?”

As with nearly all of this AI advice, the quality of the response you get increases with the volume of context you’ve provided. Using these blind spot prompts after two exchanges will get you a stock answer. Asking them after two dozen (or two hundred) exchanges can get you something eerily perceptive.

-eric

Thinking of in person work as a retreat

Post-pandemic, many of us are working in some kind of hybrid situation. We’re supposed to be in the office x days per week. Those days might or might not overlap with the days our colleagues are in the office. Lots of meetings are slow and kludgy because half the team is in a conference room and the other half is scattered across time zones.

If you’re in a position to set rules for in-person work for your team, consider using an annual team retreat as your heuristic. That is, think of in person time as expensive, scarce, and shielded from “could have been an email” meetings. The default activity should be a rich, propulsive discussion not reading updates at people or squirreling away into cubicles to do the exact same things everyone does from their home offices.

The in person time doesn’t have to be tightly scripted to the minute. Loose, meandering conversation can be really valuable for building trust. Silliness and laughter build trust, too.

But setting clear expectations for the time and what you want people to get out of it is worthwhile, even/especially if you’re offering folks broad autonomy in how they meet those expectations. Make sure you’re clear on why you have these expectations before you issue them. How do they make the team better, move you closer to your mission? Without this, any policy you set will feel arbitrary to your people and you’ll squander a special opportunity.

-ben and eric

COMPELLING QUOTATIONS

Writer Julia Freeland Fisher on making up machine rules

I’m starting to realize why crossing the street from robots doesn’t teach you to walk toward people. The problem with my own rulemongering is that it’s more focused on what I don’t want my kids to do, and less on what I do want them to do, when it comes to both robots and humans—even strangers.

Self-help writer Mark Manson on the unseen value of goals:

What most people don’t realize is that the value of goals does not come from achieving them—it comes from what the goal teaches us about what is actually valuable (and not valuable) in our lives … Many times, the most valuable thing a goal can give you is the knowledge that you didn’t actually want the goal in the first place. Set goals. But treat them as experiments, not destiny. The point isn’t to achieve your goals. The point is to outgrow them.

Novelist Zadie Smith on art:

Unlike science and technology, art is not subject to the logic of growth or Moore’s law. It won’t definitely get smaller or faster or bigger and more lethal. It is produced in strong and weak economies alike, during war and peace. When it is good, as Forster notes, it will tend to outlast the human disorders that surround it, but it doesn’t get any better or worse at doing that. The odds of making a piece of art that truly matters never really improve.

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Should I make my culture thick or thin? What has to be true either way?

When I’m building a new organization, I’ve often found I’m integrating teammates who come from places across a spectrum of thick-to-thin cultures. Some draw motivation and a sense of safety from a heavily prescriptive culture where clear rules govern nearly all the patterns of our work together. There’s a particular way we open and close meetings, give shoutouts, write email subject lines, etc.

Others find this deeply aversive and constricting. These folks prefer thin cultures where teams are loosely bound together by a sense of shared mission but each teammate can freestyle with relative autonomy.

I’ve seen orgs from each of these schools thrive. When you will have teammates with histories across the spectrum, it’s ineffective to be a dogmatist of the thick or the thin. Fundamentalists of either sect alienate people who would otherwise do excellent work and champion the culture, whatever its breadth.

Ok ok, so what’s the vibrating quantum of culture that must be there, whether you’re thick as a charter school or thin as a consultancy or somewhere in the elastic space between?

This may sound pat. But I think it’s integrity. That is - whatever set of precepts you have, however thick or thin, you honor them. You walk your talk, especially in cases where there are real stakes for the organization or real stakes for you, personally, as the leader. (Those cases are the ones where people can most easily see that you mean it).

Thick and thin leaders both get in trouble here. If you tell your people there’s a long list of detailed ways we do things around here, and then there are obvious, rampant, consequence-less examples of that not happening, your culture is thick as an oak and hollow as a canoe. And the canoe probably has a raggedy hole.

Similarly, if you tout the freewheeling autonomy of your outfit and then swoop in all over the place to dictate local details. Well. That’s also hypocrisy and the unmistakable stink of it will be in everyone’s nose.

Something wise leaders can do well is explain the work ahead, including the cultural refinement and enforcement, as pragmatic experiments. We’re going to do things in this way because we think it will bring out our best. We’ll test that proposition, with diligence and intellectual honesty. If we find that our hypothesis is wrong, we change course. The culture is a means to an end. It’s a tool with a job.

-eric and ben

I’m a new manager. How do I make sense of all this management literature?

This post isn’t a syllabus (although we do like stuff from Lencioni, Jim Collins, Kim Scott, and Stripe Press). A challenge of management literature, especially for truth-seeking folks who know how to sniff out the difference between a sales pitch and a rigorous study, is that so much of the writing is rooted in small case studies rather than big data sets or first principles thinking. (This is reflected in MBA programs, too, where you’re often reading and play-acting through case studies). You’ve got a lot of books that should have stayed put as 1,000-word blog posts. Things can seem under-researched and over-confident at once.

And yet, one of our most consistent recommendations to leaders is to read from this stuff.

The kind of reading we recommend is pragmatic. One way to make it so: when you sit down with a management book, treat each chapter as a candidate for one specific behavior you’ll try. One move. Pick the move and write it down before you put the book down. Even better than writing it down – put in your calendar as a 15-min task (or tell your army of OpenClaw agents to do that for you). Use the move this week and see what happens.

One risk this helps mitigate is reading-as-procrastination. Because these books are often written to be consumed between one airport and the next, they’ve got frictionless prose and a sunny tone. It’s like watching an old sitcom on mute. It’s easy to rip through one, feel proud of yourself for shouldering your professional development, and then change nothing in your practice.

A second move we like is compiling a cheat sheet of all the moves you’re pulling from these books. Keep a running record of them in one place over time. This can be a google doc, notion page, note in Notes app on your phone. Gradually, you’re amassing your own management and leadership curriculum. You’re making it easier to teach future leaders on your team how to lead like you do.

-ben and eric

Micromove: naming contributions and naming contributors

We’re fans of consistent, public acknowledgement around here. It’s one of the cheapest and most powerful levers leaders have and most of them under-use it.

One way to pull the lever: when you’re addressing the team, discussing some effort underway or accomplishment completed, name other people who contributed.

If you’re the leader, especially if you’re the founder, there’s a certain gravity you exert on status and accomplishment. People will attribute success to you by default when they didn’t directly witness the collaboration that led to the success. They assume it’s a you thing. This can have the unintended consequence of lowering others’ expectations of themselves while heightening their sense of the leader’s genius or charisma or special sauce.

If you’re the leader, you don’t want this. You want everyone on the team developing new skills and wiser perspectives and, ideally, making you replaceable. You don’t want them shrinking from leadership challenges and assuming their own incompetence.

So fight against your own gravity. Tell people who contributed and how. Even if the contribution was just an early conversation with you about an idea that has now come to fruition.

This doesn’t have to be fake, inflationary praise. It can be a simple statement of fact. It will likely mean a lot to the person you acknowledge. And it exerts subtle, important pressure on everyone else’s understanding of what people-who-aren’t-the-founder can do around here.

-eric

COMPELLING QUOTATIONS

Polymath Kevin Kelly on you-ness in the age of AI:

The less predictable you are, the less likely you are to be replaced by AIs. Machines are efficient, and they are powered by the predictable. Current LLMs are trained to generate the most predictable solution. So far they are not very good at duplicating what a creative, one-of-a-kind improbable human can produce. To distance yourself from the machines, aim to be as improbable as you can be.

9-time NBA champion Steve Kerr on the challenge of retirement:

The biggest thing that athletes miss when they retire is the structure and routine. A higher purpose and a process to reach that.

Writer C.S. Lewis on types of pain:

Mental pain is less dramatic than physical pain, but it is more common and also more hard to bear. The frequent attempt to conceal mental pain increases the burden: it is easier to say ‘My tooth is aching’ than to say ‘My heart is broken’.

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The kind of writing task “AI writing” is already really good at

When you’re building projects or running organizations, the systems you need to get money or permission or attention from often want you to write something for them. At least, that’s what their website or grant application form or regulations say.

This is misleading. These systems rarely want “you” to “write” “for” them. They need words from your legal person that reassure their legal person (a lawyer, or the system itself qua legal entity). They need a box scratched in a checklist. They need a step completed in a process. For varying reasons, the checkmark has historically been paragraphs of prose rather than an actual checkmark.

But generating that prose barely counts as writing, in my view. I’m thinking of applications, pro forma legal documents, budget narratives. These are pieces that are supposed to bear minimal traces of the author’s personality or weirdness. They’re supposed to be nearly authorless. That way a system can digest them with minimal friction. That system doesn’t really want to “read.”

Doing this “writing” is often a bummer. It can be an especial bummer for a person who likes writing. The fun and curious and intellectually arresting bits of the job get stripped out.

As it turns out, many of the facets of AI writing I otherwise resent are assets for these authorless assignments. A chatbot writes sections of a grant application, an MOU, and an incident summary better and faster than I do in part because it’s a robot doing it.

-eric

Insider fit beats specialist fit

There’s a new kind of work your team or organization needs to deliver. No one currently on the team owns this kind of work or was originally hired to do it for you. No one on the team has a history of doing this kind of work.

In simplest terms, you’ve got two options: you can get someone you already have to develop a new specialty or you can hire an outside specialist who already has that specialty.

Very often, we see leaders assume that the outside specialist is the right default. They think it’s the smart, professional thing to do and think they should do it unless it’s injuriously expensive.

We tend to push leaders to flip the presumption. Your default should be to hire from the team you already have.

Three reasons we like this as the option you need a compelling argument not to do:.

1. Trust and context can outweigh the importance of specialist skill. This new chunk of work likely intersects lots of others. Partnerships needs the program team, fundraising needs the founder, government affairs needs everyone. The insider already has relationships and a lived understanding of your culture. The specialist has to spend time building that understanding. (Sneaky and important bit: building the understanding of a new culture and building new relationships within the culture are both skills unto themselves. There’s a good chance your specialist doesn’t specialize in those skills).

2. Specialists are good at their thing in the contexts where they’ve practiced it. They will inevitably make pattern matching errors. Sometimes they’ll insist on those errors (perhaps because they’ve overlearned lessons from earlier successes). Your org is a new context. Most senior specialists I’ve watched join early-stage orgs spend real time – sometimes as much as a year – unlearning the practices that earned them their title. Sometimes they don’t unlearn at all. Your insider doesn’t carry that baggage. They’re gaining status with their experiments in this new domain rather than risking status they’ve already accumulated elsewhere.

3. Promoting (or laterally challenging) someone with a new function tells the whole team that this is a place where people grow. Hiring someone from outside, especially a senior person, can convey a different message about the limits on advancement around here. In growing orgs, often this retention-and-promotion story has compounding value that outweigh the near-term value of the specialist skill.

The question is whether learning the work is harder for an inside person or learning the org is harder for an outside person. We’ve often seen that the second is harder, takes longer, and the failures hurt worse.

-ben & eric

Do you have to hire true believers?

Very often, it seems like folks on the team with a chunk of career years behind them have rationally adopted a skeptical, ~political take on almost everything leaders say and do. Their default expectation is that leader talk is lip service and that peer action is some version of self-serving or back-stabbing. At the least, they seem to think, one should always be on guard against these as latent risks.

Yet, the best cultures I’ve experienced have a minimal amount of this anti-social behavior and a commensurate lack of hard cynicism. But it feels unwise to make “ be a true believer” a default requirement for someone to join the team. Cynicism can be toxic but skepticism is super useful.

A suggestion: if you’ve hired a skeptic, don’t make it your goal to persuade them using more and more of your words and presence. You’re just helping them pattern-match you to others who have let them down. It looks like you’re optimizing for optics. And you kinda are.

Instead, do something more straightforward: keep your word. When you hire someone, you’ve made plenty of tacit and overt promises already. Fulfill those. You don’t need to add a bunch more.

-eric & ben

COMPELLING QUOTATIONS

AI chronicler Zvi Mowshowitz on getting AIs to write well:

My guess is that you could, with great effort, create an AI that ‘could write,’ but you would have to make that the deliberate focus. It wouldn’t be a model most people would want to call most of the time. Remember, most good writers are not actually great people to talk to in general and definitely not people you’d hire as assistants.

Philosopher Krista Lawlor on being reasonable:

If you are reasonable, you are open to the possibility that what matters to the other person does matter.

US Secretary of Education Linda McMahon on steak sauce:

A school system that’s going to start making sure that first graders, or even pre-Ks, have A1 teaching in every year, that’s a wonderful thing!

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I’ve got some unclaimed time! Oh no, I’ve got some unclaimed time.

Let’s say you’re a leader who has achieved the mighty, rare, and wonderful thing: you’ve gotten most of the day-to-day operations in the hands of other leaders you trust. Now you’ve got some time you didn’t have before. What to do with this unclaimed time?

Before you decide, write the scorecard you’d want to be evaluated against twelve months from now. This is the one-page (maybe even half-page) document that would tell your board chair or your most rigorous critic on the last day of the year whether you were a good executive over the past 365 days. It’s got three or four or five (not nine or ten or twenty) un-gameable measures of your performance on it.

Note that this is not an invitation to lose yourself for weeks in a first-principles strategic planning retreat. You answer a much narrower question with the CEO scorecard and you can probably answer it an hour. What should this one human, in this one body, doing 30 to 50 hours of work per week, have produced or moved by next year?

Two things usually become clear when you do this:

1. First, there are way more outcomes you’re nominally responsible for than you can plausibly own alone. That’s why your team exists.

2. Second, you’ll notice that some of the work you’ve been considering for your “spare capacity” doesn’t correspond to anything on the scorecard. Not because it’s bad work. It’s just not your work. It belongs to a director, or a function lead, or to nobody — it’s a habit you’re holding onto.

The scorecard makes it much easier to know how to use spare capacity. If your capacity idea doesn’t advance something on the scorecard, it’s the wrong idea.

-ben

An alternative view of spare CEO capacity

A sharper version of “where do I invest my spare capacity?” is “what work, if I didn’t do it, would not get done by anyone, ever?”

A few kinds of work tend to land in that slot.

1. Leading stuff that doesn’t exist yet. The fun happy version of this is planning for a new team or business line. The bracing version of this is planning for downturns and disasters that haven’t hit yet (your primary funder pulls out; a major hurricane hits headquarters; I don’t know, a global pandemic quarantines humanity for six months).

2. “We’re good at x. So what?”: Looking at the many local optimizations your team is chasing and pressure testing those. Challenging yourself (and maybe also that team) to explain how excellence at this thing gets the organization closer to achieving its mission. This can help you find things to lead that don’t exist yet (see 1, above).

3. Building and maintaining relationships outside the team: Getting the most out of your board, opening a conversation with a potential funder, learning from vendors, mentors, and competitors.

4. Roving antenna: you’re the one person with an all-access pass to the entire organization, from your own inbox to 1:1s between an entry level teammate and their nearly-as-green manager. Arguably you’re also the person with the best internalized measure of “how excellence looks around here”

A test I give clients: at the end of the week, look at your calendar and ask of every block of time in there: could this have been done by anyone else on the team? When the answer is yes, you have latent capacity on the team and in your calendar. Spend some time training someone else to take the thing from you so you can do more of 1-4 above.

-ben

I need this humble, excellent operator to step up as a leader

When a humble operator isn’t becoming a leader, a diagnosis you often hear is some version of “they need more confidence.” This can be true and also useless, because confidence typically shows up after an underlying identity changes. Confidence is the visible exhaust from the engine under the hood.

Sometimes, the gap between a great operator and a great leader is not a skill gap. The operator knows how to run a project, manage a calendar, clean up a mess, hold a high standard, sweat details. Where they’re on bambi legs is mobilizing other people to take stakes-y bets in service to the mission.

As their manager/coach/leader, you can help them build the leader’s identity with some provocative questions.

1. “What would it cost you, internally, to start asking your peers to take real risks on your behalf?”

2. “What’s the difference between a leader and a project manager? What would have to be true for you to feel like a leader instead of a project manager”

3. You can follow up on 2) with: “What’s the worst thing (or likeliest bad thing) that would happen if you actually showed up that way?”

These questions can help uncover some latent beliefs people cart around and cope around. Stuff like: “I don’t want to ask people to do things I wouldn’t do myself” or “I don’t want to be the person who pushes others into the fire” or “if I’m wrong, I won’t have anyone to blame but me.”

You can’t talk someone out of a hidden commitment.1 But you can name it and ask whether it’s still serving them. You can ask what a version of leadership would look like that doesn’t require betraying the part of themselves they’re protecting.

-ben & eric

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COMPELLING QUOTATIONS

Poet Ocean Vuong on the writer’s job:

We’re out here to write sentences that the species has never encountered.

Songwriter John Darnielle on writers’ errands:

To elucidate is one errand of the writer, and to obscure is another. When I can do both at once, I’m happy.

Poet Pablo Neruda on loving:

I love the handful of earth you are.

Building identity and agreement on day -1

There’s a kind of agreement you can arrange on day one that you can almost never arrange on day one hundred. One of the most important of these agreements is that the person joining your team is hungry for direct, corrective feedback. The way they show that hunger is by acting on the feedback without delay, friction, residue, weirdness, other faff.

You can ask someone to commit to that during hiring and they’ll mean it. If you ask them to commit to it months and months in, it’s harder to get what you want and need. After several months, you have a relationship that already has its own grammar: what kind of comment means what, what tone signals what, what’s said and what isn’t. You can refine that grammar but replacing it is tough.

So in a fast-growing org, where you’ll run this loop dozens or even hundreds of times in a few years, the hiring process is a durable lever for setting the subtext you’ll rely on for years.

I suggest two moves to get this agreement set:

First, test for it. In a late-stage round, give the candidate a real piece of direct feedback on something they did during the process. Watch what they do with it. Do they act on it before the next exchange? Do they thank you without sounding wounded? Or do they explain themselves at length, dispute the premise, emit anti-social vibes?

Second, model it. Bring the candidate into a real one-on-one where you give an existing teammate — someone you’ve picked because they receive feedback beautifully — a piece of pretty direct feedback. Then debrief with the candidate: that’s what this looks like here. If you can picture yourself in that seat enjoying that exchange, this place will work for you. If that looked grim, this won’t.

With this two-step, you’ve selected for feedback responsiveness and the candidate has chosen the identity of someone with that trait. If you skip this agreement, it’s hard to implant or backfill it. You can end up with a team that’s superficially polite, structurally defensive, and very challenging to coach.

-ben

A thought experiment using younger you

If your thinking feels stale and you’re looking for a fresh approach, run this thought experiment: how would younger you have solved this problem?

Some features of younger me that might also be true of younger you:

• Thinner network

• More physical energy

• Less context (aka knowledge of how things go wrong and which solutions have tended to work)

• Less cash on hand (harder to buy my way out of a problem or outsource it)

These cash out as a self-reliant naivete that can be really useful for prototyping an idea, just making the thing your own damn self, [fooling] around and finding out. If I’ve accumulated lots of reps in a domain over time, I can lose touch with those frisky, improvisational moves, trapping myself in an optimization game where I do the same thing over and over because I’m beholden to some narrow idea of what’s efficient, or smart, or best practice.

This thought experiment can sit in your toolkit alongside a few others we’ve recommended over time, namely:

• Use OOMs to unlock possibilities

• Cosplay to get unstuck

-eric

AI and ClipArt: a millennial tale of taste

Longtime readers here know that we’re avid LLM users. We often recommend prompts and use cases in this very newsletter (for coaching, hiring, career transitions, distinguishing good from excellent, etc).

This short post is more observation and lightly held prediction than advice. LLMs can generate images, prose, and infographics now that sit between serviceable and strikingly good.1 It’s also true that much of this generated stuff carries tells. An AI-generated artifact bears signatures, subtle and obvious, of its origin. (For humorous/snarky roundups of these, check out threads like this one on … Threads).

This moment in AI usage reminds me a little of the mid-90s era of Clip Art and Word Art. Thirty years ago, you could tell when someone had quickly pulled a preset image or template off the first page of the menu in Microsoft Word and dropped it right into their document. Usually this looked better than what the same person could have made in Microsoft Paint (very limited toolkit) or Photoshop (very steep learning curve). To a trained eye or a pro designer, though, these artifacts were amateur, slapdash, even offensive. Eventually, even for the average observer, there was a flat sameness to these artifacts. The style became cliche.

As more and more millions of people start making stuff with frontier models, the default outputs of the models will become familiar and flat and cliche. In some cases, that’s just fine. You don’t need the text of an MOU to wow you with its idiosyncratic artistic flair. But if you are looking to stand out, remember that billions of other people have free access to the same insane mega-computer that you do. Your one-shot prompt will yield something that looks “better” than what you might draw free-hand. But it might also look better in the exact same way everyone else’s does.

-eric

*This entire post a shaky attempt to avoid a rant about the default GPT typeface.

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COMPELLING QUOTATIONS

Poet and lawyer Reginald Dwayne Betts on time in prison:

I have called, in my wasted youth, the concrete slabs

Of prison home. Awakened to guards keeping tabs

On my breath. Bartered with every kind of madness,

The state’s mandatory minimums and my own callus.

I’ve never called a man father; & while sleep, twice

Wrecked cars; drank whisky straight; nothing suffices –

I fell in love with sons I wouldn’t give my name.

95-year-old John McPhee sharing 80-year-old memories of cream:

I was fifteen years old and always hungry. I lifted the heavy mushroom-shaped lid off a milk can and dipped a ladle into the cream. If you have ever tasted heavy cream, this was heavier. Call it viscous. Call it cream that would stand up like mayonnaise, cream that no taste bud would ever forget. It didn’t go into the cereal like milk, it went onto the cereal as a layer.

Mississippian Wright Thompson on New Orleans in 2015:

Rebirth has been the standing field order of the past ten years in New Orleans, a powerful force shaping the city in ways big and small. Everything is governed by this spirit of renewal, and everything is viewed through its lens, from the fervent love of brass bands to the New Orleans Saints, the standard-bearers of a city struggling back to its feet. But within this hopeful word an idea hides in plain sight: For something to be reborn, it must have first died.

1. Power v clarity

Texas Senate candidate James Talarico was a seminary student trying to decide what he should do with his career. His mentor told him:

If you go into the ministry, you’ll have clarity, but you won’t have power. If you go into politics, you’ll have power but won’t have clarity.

I think this is a strong insight that applies within teams as well. As you rise through your organization’s hierarchy, you gain power and lose clarity. This is, in part, because the time horizon you’re responsible for increases as you rise as well. The more senior you are, the more and further you look into the future. The future is famously hard to predict.

That’s one rub for new leaders. A second rub, layered on the first, is that the clarity those folks you manage enjoy - it comes, in part, from you. So, without lying or disingenuously making stuff up, you have to derive and deliver clarity for others. You set goals and chart ways the team will reach them. Meanwhile, you live within cloudiness.

If I was trying to be cuter about this I’d hit you with “clout v cloudiness” instead of “power v clarity” but I’d never actually write that. He said. Disingenuously.

-eric

2. Executive coaching reduced to three questions

Over thousands of hours of coaching sessions, we find we go to three questions more than any others. You can use these on yourself or steal them for work with your own reports.

1. If we time travel 12 months from now and [this thing you’re worried/confused about] has gone exceptionally well, what did you do to make that happen?

2. Have you told them that? (Applies equally to praise/affirmation and feedback/criticism. The answer to this question is almost always “no” or “not exactly” with a face that says “But I know I should”)

3. How can you teach someone else to do this, so you don’t have to?

ben & eric

3. Using small success to build big identity

When someone on the team has earned a win, especially in the early going, there’s big upside for a leader to seize. This is especially true when the winner on the team took on a new challenge or got the win from a new position of power (eg, leading a meeting or managing a project that you’d normally run). You can help this person think of themselves as a strong leader rather than simply as a competent contributor (or, worse, “an occasionally lucky contributor”).

Pretty much any way you can point out to this person that you saw them get this win is worthwhile. You noticing their success is valuable. You can get the biggest return for them and the team if you use this small success to build a bigger identity for them. The ingredients of that powerful species of acknowledgement are:

1. Naming the choice they made (not just the raw input / action - the decision that animated that input)

2. Naming the impact it had

   1. Naming what that unlocks or makes possible for you or for others on the team.

3. Naming what that tells you about this person’s values and character

4. Setting the expectation that you’ll need more of this from them and are confident you’ll see it.

You can do 1-5 in just a couple of sentences privately between the two of you or publicly on a Slack thread. Either way, this small win can help a self-effacing, humble leader-on-the-make embrace a role as a dependable, strong leader within the team (no matter what their title or tenure say).

-eric

COMPELLING QUOTATIONS (back by popular demand!)

Anonymous, in Tehran, on living in a war:

Is it important to write that the aftertaste of my morning coffee seems stronger and more pleasant these days and I don’t feel guilty about it? To write that during this war I have spent most of my time, as I did during the previous war, on the rooftop, because when I am stuck in my room and I hear the sounds of explosions it drives me insane not to be able to see or guess their source?

Novelist Hilary Mantel describing the experience of a beheading:

Beneath him the ground upheaves. The river tugs him; he looks for the quick-moving pattern, for the flitting, liquid scarlet. Between a pulse-beat and the next he shifts, going out on crimson with the tide of his inner sea.

Commentator Chuck Klosterman on movies:

Especially in the early 1970s, everyone was consumed with the auteur concept, which gave directors the to completely (and autonomously) construct a movie’s vision. For roughly a decade, film was a director’s medium. Today [2003], film is a producer’s medium (the only director with complete control of his product is George Lucas and he elects to make kids’ movies).

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1. Product development: a simplified journey

1. Make a thing. Maybe it’s a humble MVP. Maybe it’s the very best version of the thing you can do. Either way, you’re getting some representation of your effort and insight out of your head / hard drive and into someone else’s experience.

2. People like the thing. They ask for more of it. More people ask for it.

3. Figure out how to make more of the thing. Figure that out within the same constraints that originally bound you. Then figure it out with new constraints (more money, more people).

   1. Sometimes in this step, you simplify the thing you made. You strip away features people ignored or didn’t like. Sometimes this hurts because those were features you really liked; they’re ones you thought, and maybe still think, your audience/customers/community should like.

   2. Sometimes in this step, you realize the thing you’re making more of isn’t even the thing you set out to make in the first place. It’s not just a different version; it lives in a different category.

-eric

2. Enrolling those you wish to persuade

There’s a theory of persuasion that assumes at some point you have to remind the one you wish to persuade that you can hurt them. This is the bad cop theory from the movies: “We can do this the easy way or the hard way.” When you’re trying to get reimbursed or renegotiate a deal or get your proposal reviewed on an accelerated schedule, the person you’re talking to might need to pick up on the fact that you’re not afraid of tough talk.

I think this is a theory that applies in a very narrow set of circumstances. But it matches a certain intuition we have about what it takes to get things done. So it carries cultural weight far greater than it deserves. Even agreeable, humble people can enter a conversation with this model whirring in the background, doing unhelpful work.

A counter-intuitive theory that I think applies in a much broader set of circumstances: the person you wish to persuade is not an adversary who needs a reminder you are willing to defeat them. That person is an ally who needs a reminder that you see their virtue, their excellence, their desire to get things done for the greater good.

-eric

3. A suggested replacement

Clarity of purpose, allocation, and boundary can be really propulsive for your team. You, the leader, might be the only person who can provide those.

If you are a people pleaser, it can feel bad, wrong, counter-intuitive to say some of the things you need to say to deliver those clarities. It can feel better, more polite, more palatable to say nothing or to say “maybe”, which is almost the same as saying nothing.

Consider replacing “maybe” with “at the moment, no.” If you’ve thought it through enough to be able to do so, consider adding a one sentence explanation.

-eric

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1. Two questions to return to as you become an executive

   1. Does this need to be me? This question helps you recognize that you’re the bottleneck on many things. At a certain size and reach, the organization is no longer necessarily most benefited by you just strapping down and doing it yourself.

   2. “What are we getting done as a team/organization?” Ask yourself this rather than “What am I getting done as an individual?” When you’re making the transition from IC to manager or manager to executive, your value is increasingly in what you do, not how much you do. It’s challenging but necessary to switch your default from high-ownership, reactive problem solving to high-mobilization proactive problem solving. You’re doing better by the organization over time by building capacity in others than fighting every fire yourself.

-ben

2. Making good use of a rough patch

I’m thinking of a rough patch as a period of time where things don’t go well and most people can tell. You might fail to hit your goal and that failure is clear and measurable and everyone is bummed about this. You might achieve your goal or stay on target but the way it happened was painful and unsustainable.

As a leader, a rough patch, especially the first one, is really useful. That patch carries data about what works and what doesn’t for this team in this context. There’s operational information in it. The rough patch also affords the leader a storytelling and identity-forming opportunity. Think about what made this patch rough - what went wrong and why. Draw a distinction between the right kind of challenge, the right kind of stress, and the wrong kind. Then walk the team through your rough patch analysis and the decisions you’re making based on that analysis.

It’s useful to be able to say, “We’ve seen what happens when we do x. We want to avoid that. So this time, we’re doing y.”

It’s even more useful to be able to say “Around here, we’re the kind of team who does y when x happens. X just happened. I probably don’t have to remind you how painful that was. So here’s how we’re going to do y. That’s what we’re here for / what our values demand / the kind of team we are.”

-eric

3. AI for process insight - what’s happening over there?

One frustration of navigating bureaucracy is a lack of information. You may be told where you sit in a queue relative to others. You may be shown where you sit on an approval pathway. You may have a mere rough estimate of how much time you have to wait before you hear back from someone else in the bureaucracy. In any of these situations, I can feel passive and powerless and quite frustrated.

When bureaucracy gets opaque, I have found Claude to be a useful navigator and clarifier. When I describe the goal I’m trying to achieve, the context I’m in, and the latest message I’ve gotten from someone in the bureaucracy (public permitting office, hospital, etc), I can ask Claude what the the heck is happening over there (in the bureaucracy) and get useful insight that the bureaucracy won’t or can’t give me. I can also get a reasonable indication of how much I can push and where I should apply the pressure. When the bureaucracy is one I don’t have much experience with, there’s a chance there’s a whole category of person in that bureaucracy whose job is to help someone in my situation. But there isn’t someone in the bureaucracy who tells me this. Claude can do that instead.

If you’re stuck in a 2026 Kafka short story, it’s worth a try.

-eric

COMPELLING QUOTATIONS

Writer George Saunders on connection:

These days, it’s easy to feel that we’ve fallen out of connection with one another and with the earth and with reason and with love. I mean: we have. But to read, to write, is to say that we still believe in, at least, the possibility of connection.

Writer Imani Perry on prayer:

Living as prayer. I think that is when I am at my best. Because seeing through prayer provides a remarkable clarity. Not in the doctrinal sense, but because it is, at best, the lens of a love for every tattered inch of this earth.

Butterfly enthusiast Vladimir Nabokov on art and nature:

I discovered in nature the non utilitarian delights that I sought in art. Both were a form of magic, both were a game of intricate enchantment and deception.

1. Getting good feedback to people who are doing quite well already

You have the good problem of a direct report who is difficult to critique because of their strong performance. You presuming people want managers who consistently help them achieve the next level of excellence that is just beyond their reach rather than somebody who’s just supportive.

That’s an assumption you’re wise to make. If you recruit talented, ambitious people, your assumption is probably correct for almost every direct report you have.

What may not be clear is that you both see the value in this kind of manager and in you being this kind of manager for them. And that you both see that you’ve often given little constructive feedback or critique. It can help to acknowledge this, so that it’s the shared story between you, and point to a new approach.

“I have this manager, and they’re the nicest, most supportive person. In fact, they even tell me it’s a struggle for him to come up with things to critique about me. But he always does. And the reason he does is because he knows I want it, and he knows I care about constantly growing and reaching a new bar of excellence.”

If that’s the story your report has about you, then you should feel pretty free to offer criticism and opportunities for new growth or excellence all the time, at whatever level of intensity you can find. The bigger the better, in fact.

The simplest way to establish this shared story is saying something like this the next time you meet,

“Hey, I just wanted to sync up about how I’ve been thinking about this. I’m trying to grow in some ways as a manager. I’m trying to improve this manager-report relationship. I just wanted to share how I’m thinking about that right now. One thing I think it’s important for me to do is offer you direct critique and identify ambitious ways you can grow. So I’m going to make deliberate effort to offer those to you, especially in instances where it would be easy to say ‘Yeah, things are good! Nothing really to change or adjust here.’”

What’s remarkable about this approach is that your report may not have felt you were falling short with your feedback, yet you will get them to agree to this story, and they will be glad for it. This is the same thing a great teacher does when they say to fourth graders, “Do you want the fourth-grade homework tonight or the fifth-grade homework tonight?” Everybody knows the right answer, even if they don’t really want harder homework. And they’re proud of themselves for choosing fifth grade. When they choose it, they get better as a result. At the micro and macro level, the choice feels really good to them to make.

But this doesn’t happen without your intentional framing.

-ben

2. Growth mindset meets pragmatism

You have high expectations for people on your team and for one person, you’re feeling like, “I don’t really believe they can meet these expectations.” What do you do with that?

I simplify that to two questions.

1. What is my belief about human growth in general? My (Ben’s) belief is that anybody with the will can grow to do just about anything, given sufficient time and effort. If somebody who I don’t believe can do something right now puts in the right amount of time and the right amount of effort, they will in fact be able to do it.

2. What amount of time, resources, or effort am I and my company willing to spend to get this person to that point?

Those are two totally separate questions. We typically conflate them. As a result, we end up using our best guess as to whether we can picture this person doing this or not, which is heavily informed by the past and all our cognitive biases. We make a question of training and resource allocation a question of talent and identity, which is inherently harder to answer and act on with confidence.

-ben

3. Unpacking and overcoming a bureaucratic “no”

When you’re a founder or an advocate, you’re often in the business of getting a big, old system that employs lots of people schooled in its rules to do or permit things it doesn’t normally do or permit. You’re trying to change things and you need a system to change, even just a tiny bit, with you.

Often, when you encounter one of the employed students of this system1 they will a) be trying to look out for your interest, as they understand it and b) assume that you don’t know the way the system works. Sometimes this cashes out as a rejection of your request or a delay of the timeline you need for your project/client. “Sorry, ma’am, [x] isn’t available for another 10 business days.”

It helps, more often than not, for you to assume a) and b) as well. In other words, think of this person as a good and helpful person who is trying to have your back. Don’t think of them (and treat them) as a bureaucrat who goes to work every day to make good people’s lives harder.

In addition to the assumption, it can be useful to ask, with genuine curiosity, why you’ve received a rejection, or why the (too long) timeline for fulfilling your request is what it is. Sometimes this reveals further assumptions the system-student has about you: they may be trying to save you money or effort, assuming that you are not extra-motivated or extra-resourced in pursuit of your goal. When you reveal that you are in fact willing to spend extra(ordinary) time, effort, or money, the system-student might suddenly have good, new ideas for you about ways to get your thing done. There’s an alternate pathway, maybe more costly or painful than the standard one, but viable for very-motivated you.

-eric

COMPELLING QUOTATIONS

Artist of noticing Rob Walker on the “unshazamable”:

Everybody complains (understandably!) about the algorithms that shape our entertainment choices and direct our attention. But seeking the unshazmable isn’t just a way of escaping the algorithm. The unshazamable isn’t even in the database that the algorithm is designed to mine!

Tapping into something enjoyable that didn’t come from a database doesn’t have to take the form of consuming a particular cultural object like a rare song; it could be an experience, a moment of presence. Looking at the moon can be unshazamable.

Writer Wright Thompson on land and creation in the Delta:

Farming at its essence is just the practice of getting water onto land and then getting it off again, and the eighteen-county teardrop of the Mississippi Delta does this as well as anywhere on earth. On the eastern boundary between the flatland and hill country a series of reservoirs trapped the runoff and on the western edge levees kept the big river from flooding out crops and people. Humans had stopped the natural order of things, halting the patterns that created their fertile home, working with puritanical resolve to harvest the bounty that had taken a million years to create. Nothing about the physical appearance or ecosystem of the Delta carries any of the Creator's fingerprints. This land is man-made.

Poet WS Merwin on early middle age:

It sounds unconvincing to say When I was young

Though I have long wondered what it would be like

To be me now

No older at all it seems from here

As far from myself as ever

1. An exercise for finding and committing to your true priority (not a list)

I. In your own informal words, write one sentence describing the most important goals for you to reach by the end of the year. Don’t get lost writing detailed bullet points of metrics. What would you say if a friend asked you, “What is it that you would feel most proud of to measure your success by the end of this year?”

II. Now you get to make a really tough choice. Choose only one activity you can perform between now and the end of the year to maximize this goal. An activity might be development meetings. It might be training. It might be data analysis. It might be observation of your reports. It might be hiring. If there is only one activity you can spend your time on for the remainder of the year to maximize this goal, what is it? Write it down.

If you had to make a really tough choice between two things, put the second one down underneath the first. And finally, if you had a third one that was just begging for acknowledgment, you may write that down as well. No more after that.

III. Take two minutes now to answer this one: If between now and the end of the year, you had to spend 30 hours a week and you couldn’t spend time on anything but these three things, how would you set up your week? Assume that others on your team will be extremely gracious about filling in the gaps you’re leaving. This is a blank slate. There’s nothing else on your calendar yet. You need to fill up 30 hours of your week with these three things. You can write bullet points. You can even draw a five-day calendar span. What would that look like? How would you block it?

IV. Now write down one to two things you must do before you could make a wholesale change like this. Maybe it’s prep somebody to handle another major block of your work that this leaves out. Maybe it’s completely sunset one major activity at your organization, team, or school. Maybe it’s hire an additional person.

-ben

2. Servant leadership, trust but verify, and training

In the servant leadership model, a founder starts out a priori with the mission of the organization — you are responsible for the whole of it. All the goals are yours. As you add people to your team, you’re essentially putting those people between you and the mission. They take on some of the goals that you once had yourself.

The trick of servant leadership is that you actually keep all those goals on your plate. You participate in the alchemy that all great teachers practice. They convince their students that the responsibility is 100% the students’ while they (the teachers) in fact retain ultimate responsibility for their students’ success.

What that generally means for a leader is you are a) setting goals for those you lead and b) meeting all legitimate needs they have to reach those goals.

Of course this begs the question: how do I maintain that magical alchemy where they believe these are 100% their goals and that it’s not my job to do their work for them, while remaining vigilant and ensuring that they don’t fail to meet those goals?

The most common way to do this is trust but verify. You give them their goals. You have reason to believe they are competent enough to achieve those goals. You set up, say, a monthly check-in point to verify that they are in fact on track to hit those goals.

Let’s say you start to see very quickly that doing this once a month is actually lowering the chances that they will be on track. In fact, they probably need this weekly, so you switch to weekly. If we continued along this trajectory you end up with checking in once a day with this person.

At that point, the truth is you actually just need to train this person. They weren’t ready for trust-but-verify yet. You need to teach them how to do their job well.

Let’s imagine you’ve gone through that with three people on staff. You’ve tried to do the monthly, you had to switch to weekly, had to switch to daily, and you finally decided, nope, I just need to give this person a boot camp on how to do this job well. When you hire the next person, what might be more prudent to do?

Spend ample time in the beginning making sure they know how to do the job before you go into that trust-but-verify space. And use that moment to gauge to what degree you’re going to need to verify on a regular basis.

-ben

3. Setting people up for direct feedback during hiring

The best way to get people to initially buy in to getting feedback really directly is to expose them to how potent and positive it is in their work. The hiring process is a great time for this. During the hiring process, have somebody in a position to receive feedback from you, give it to them extremely directly, watch them implement and improve from it. Then give them the meta-feedback of how powerful that was to see. Next, inoculate them, by suggesting an interpretation of the that feedback experience.

Look, if that whole cycle was extremely positive for you, that’s a good sign. If it was hard and you don’t want to picture yourself doing that every day, then I think that’s a bad sign.

This way, everybody who self-selects into this feedback pattern is doing so with a chosen identity that they’re going to like this feedback and want it. A softer way to do this is to hold a meeting with somebody you already work with who receives feedback incredibly well. You deliver feedback to this person while the job candidate observes.

When I onboarded people, I would do a model one-on-one for the new hire to observe and usually I’d do this with somebody who was very direct. I give them this experience so that they can picture themselves being in the shoes of my report, getting this direct critique handling it super well, just like their peer is doing.

-ben

COMPELLING QUOTATIONS

Founder-ologist Paul Graham on branding:

Brand age watches look strange because they have no practical function. Their function is to express brand, and while that is certainly a constraint, it’s not the clean kind of constraint that generates good things. The constraints imposed by brand ultimately depend on some of the worst features of human psychology. So when you have a world defined only by brand, it’s going to be a weird, bad world.

Writer Sam Kriss on the difference between Americans and Brits:

The only way an American can really encounter pessimism is by hiring a British person to perform it for them. That’s what I do, basically.

Novelist Fyodor Dostoevsky

The worst sin is that you destroyed and betrayed yourself for nothing.

1. Before you fire someone

In my experience, people’s uncertainty about whether they need to fire somebody profoundly limits their ability to help that person grow, if they are not in fact firing them. A useful question to ask yourself is “how valuable is this person’s contribution relative to what we think we could get from someone else out there?” In baseball, an increasingly popular stat in recent years has been VORP: “Value Over Replacement Player”. This stat is an attempt to quantify this “before your fire someone” question. How valuable is this teammate over a median replacement?

The time horizons to think about with a value-over-replacement-player approach are three, six, and twelve months. If you were to terminate this person within the month, how likely is it that you would have a better substitute in place three months from now? Same question at six months. Same question at a year.

What you do with your answer to the VORP scenarios depends on your context. In some industries, if you can get more value out of this person’s replacement within six months, finding that replacement is exactly what you should do. There are a number of fields where there’s no way they would do this. The quality of talent available to them and the complexity of the job mean it would be too risky and costly to put in a replacement, even for someone who is currently underperforming.

If you realize after looking at VORP that the person in question is going to be here for at least another six months, then you ask: can they keep performing at their current level for another six months? The answer is probably no. Here’s what you do next:

You need to find a way to express to this person the gap between performance that would let you say “I could have this person working here for another six months at this level” and their actual, current performance. Essentially say to them: here are the clarified stakes of the job. You want to get them to opt in to closing the gap as a condition of them remaining on the team.

How much do you invest under these circumstances? That’s completely dependent on the degree to which you are unwilling to terminate this person within a period of time. Ask yourself: what is the earliest I’m going to terminate this person if they don’t improve? That will right-size your interventions fairly quickly.

A sequence I find very effective, if somebody’s relatively safe for another six months, is to imagine what you would put on their performance improvement plan. What would make their contribution valuable compared to what they’re currently offering?

Before you present this as a performance improvement plan, if you have three to six months, present it as a sort of “re-hiring” condition first. Say: “I want you to know you’re not at the right performance level. If that were to continue, we couldn’t work together anymore. Here are the major behaviors, habits, and skills we would need to see for me to stop saying this. I want you to think about the fact that probably if these don’t improve in, say, a month, I’ll put you on a performance improvement plan that spells it out. And if improvement doesn’t follow from that, then we’ll let you go.”

“So I want to know that this change is actually something that you’re invested in. And I’d be perfectly understanding if you weren’t. So I’m going to ask you to take the weekend. Ball’s in your court—come back to me and say, ‘I plan to change this.’ Or not.”

If they say no: they are opting out. They’re making it easy on you.

-ben

2. After you fire someone

When a colleague is fired, almost no matter who you are, if you didn’t know about it until it happened, you’re thinking: could I be fired like that?

I think it’s critical that you have conversations with people almost immediately after you’ve had the appropriate conversation with the person you’re terminating. The purpose of that conversation is to let them know where they stand in the organization, what degree of security they have, and to name both of those explicitly. I don’t think it should be a subtle thing at all.

Come and say: “Today was [x]’s last day. I want to be really clear. If I were in your shoes, I might be wondering what happened. I might be worried that something similar will happen to me. I want to tell you the reasons why this is not happening to you right now, and what would happen in the future if this sort of thing were to happen to you.”

Explain that clearly, almost in bulleted, numbered form. Here’s where you stand in the organization. I’m incredibly happy with your work. I have had zero thoughts as to whether you need to be replaced or terminated. If I started to, here’s the first thing I would do. Then here’s the second thing I would do. And here’s the third thing I would do, all the way up to telling you that it’s your last day. That is to say, I don’t feel close to those things at all. And if you were ever wondering whether that is no longer true, this is how quickly you would know it.

If you’re having this follow up conversation after terminating somebody without a multi-step warning process, it’s worthwhile to name that specifically, too. “I made a decision that it was much more productive for the person involved to have clarity from me right away. I did that with the best interest of that person in mind. This is not what I generically or generally do. What I plan to do with everybody else is [bulleted list from above].”

-ben

3. Refreshing feedback when it gets perfunctory

A good 1:1 agenda for a manager and report often has a feedback exchange set piece. You both give and get feedback as a standard part of the meeting. Sometimes this exchange is split out as its own meeting on a monthly cadence: you give and get 2 appreciations and 2 critiques.

If you find yourself staring at that criticism box and coming up with small-bore things like, “You said you would give me an update on Thursday but it got delayed by a day” that might speak to doing the exchange a little less frequently than you are currently. Perfunctory feedback isn’t great.

In addition to extra time to observe, you can shift the prompt for the feedback. Instead of asking yourself “what is the thing I want to improve about this person?” target a more concrete question. For example: if this person were significantly leveled up six months from now, it would be because they finally started doing what?

If you already have a plan for a big level up over the next six months, you can make that weekly question: what this week was in line with that level up, and what were examples of not having leveled up yet?

There’s an affirmative, agreeable subtext for this question that can open up productive conversation. You, of course, want to level up. If we look ahead six months, a year, we’re both excited by the idea of you leveling up. So now we’re unafraid to ask the question: what did you have to work on and show evidence of in order to do that?

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COMPELLING QUOTATIONS

Former NFL coach Bill Parcells on deceptive routines:

Don’t confuse routine and commitment.

Former CEO of Hallmark Don Hall on brutality:

In a business environment, you need to be brutally honest, and to be brutally honest you can’t have a culture that’s brutal.

Earth cataloguer Stewart Brand on realism about repair:

Repair is nearly always a disruptive intervention in an intricate system.

1. Managing people who have more technical skill than you do

Critiquing people who far exceed your technical skill set in the thing you’re critiquing is a very common part of management. It may become even more a part of your management work the higher you go in the org chart. A CEO usually has emerged from a specialty, like operations or sales or product, rather than having been a generalist who has done all of those. Despite how common this responsibility is, people are often terrible at it for the reasons we’d guess.

I was very lucky that I had a management mentor early on in my life, when I was a 28-year-old principal managing teachers who had double the experience I had. I was very nervous about that all the time. And that mentor just gave me this phrase: your job is not to be better than them, it is to make them better. I held that in my head and repeated it, over and over.

If you share that story with those you manage, they will likely agree with you and they’ll be glad they agreed. It can help to do this explicitly: our story, by the way, is not that I’m better at this than you, and that’s why I get to tell you what you need to do to improve. The story we share is that I am the person we have both agreed can make you better at this. And that is what allows me to push you the way I’m about to.

The next step can be talking with them about the ways in which they can envision that happening. You can identify some things where I don’t need to be inside the technical skill set to tell you whether it’s improving or not. I don’t even need to know what hacks, tips, and procedures make somebody better at that thing. We can brainstorm those things together. It’s my job to make sure we have the brainstorm. It’s my job to hold you accountable to what we produce in that brainstorm. Who else is going to do it if not me?

What I’m sketching here is manager as coach. I’m holding us both accountable to you identifying, with me sort of stamping and agreeing and perhaps even critiquing and vetoing occasionally, the next level you want to get to. I can hold that. If you say, “Today I would correctly assess myself as a six,” I can say to you, “Okay, by next quarter you should be an eight.” You might know way more about what that six-to-eight leap is going to require than I do, so I’m going to ask you to identify what those things are. Whether it’s additional guides who aren’t me, or resources I can give you, or focus and accountability I can give you, or the opportunity to thought-partner — I’m going to provide every single one of those things.

That is my role as manager: to marshal the resources and the clarity to make you better.

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2. Building a culture of candid feedback (a real one)

Establishing a culture that promotes constructive feedback—specifically voluntarily, not just when prompted—starts with a shared theory of why that’s important that’s explicitly nameable among all teammates.

It’s usually something like: one, we don’t want to miss any opportunities to get better, and the thought that we’d leave a bunch of those on the table all the time is worth avoiding. And the other—which I actually think is more compelling to people in the long run—is just better trust throughout the team. The knowledge that you walk around this place knowing no information is being withheld from you. Therefore there’s no politics. Nobody’s ever reading between someone’s lines. No one’s ever worried somebody’s not going to be humble enough. Nobody’s ever worried that somebody’s going to have a personal agenda driving their moves underneath the surface.

Whatever it is, it’s something you should decide together. If a third party were to ask, “Why do you guys seem to give each other corrections so often?”—everybody would have the same answer independently. That helps immeasurably.

Care Personally, Challenge Directly

I endorse the Kim Scott radical candor principle: care personally, challenge directly. The more evidence there is of real caring across relationships, the more valuable, warranted, and motivated constructive feedback becomes. Retreats, recognizing when people are doing the right thing, the moments you have where you’re asking people about their lives and how they’re making it all work at work—these moments produce not just more opportunities for tough feedback, but actually more desire for it from people, because they feel safer and they want to know what you think.

A distinction generally to make: our feedback should not make anybody feel comfortable, but it shouldn’t make people feel unsafe.

Three Things That Build the Culture

I tend to think there are three things that help create a culture of strong, candid feedback if you don’t have one.

1. Open the gate by creating moments of risk and vulnerability on a regular cadence. How often are you having that retreat where you ask the question: could any of you have given this feedback earlier? How often are you having people actually tell their stories of their experiences? Having step-backs to do that is really useful.

2. Raise the ceiling on the level of candor. This is usually done by spotlighting really intense candor for others to see—most often by people at the top receiving it. Nobody will ever think it’s okay to give feedback that is stronger than what they’ve seen you receive. So if you simply raise that ceiling—somebody sends you really tough feedback that is really helpful on Slack, share it with the rest of the team. Intentionally create a moment where somebody could give you feedback live. The more people who enter into that space doing that, the more safe they feel, and the more safe others feel in those interactions with them.

3. Make it regular and unavoidable. Set an expectation that everyone will do feedback exchanges in regularly occurring structures like the 2x2 and the 360 review, that occur outside of formal performance reviews. This makes feedback delivery and receipt a high-value but lower-stakes practice, rather than a dramatic, only-in-extremes performance.

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3. Structures for a steady stream of feedback

A good goal to chase is a steady stream of feedback, such that people on your team never get feedback too late and people never feel like they’re sitting on feedback that others could be using to improve. Here are some structures that can get you there:

• The 2x2. At the individual managerial level, do something called a 2x2 in your one-on-one meetings. You have a spot in the agenda where, let’s say you’re the manager: you give a piece of feedback to yourself, positive; a piece of feedback to yourself, constructive; a piece of feedback to the report, positive; a piece of feedback to the report, constructive. And the report does the same. You both come in with that.

• 360 reviews. When people get performance reviews, are they getting reviewed by their peers, their leaders, and those who report to them as well? This can creating a motivating, holistic picture and also bring some very clear themes to the surface. Generating this can be as simple as a Google form asking for a piece of positive and a piece of constructive for each person.

• A #feedback Slack channel. Structure and reify feedback via channels like Slack. If you create a Slack channel for productive feedback for the team, that automatically signals that it’s more welcome and creates a vibe around it.

• Retreats. Have a somehow more foundational moment where you say: what do we really need to productively change about the team to improve? Usually vis-à-vis some big goals you just set for yourselves—what’s going to keep us back from this?

• Feedback speed dating. I used to do this at those same events. Everybody looks around the room, finds a piece of positive and a piece of constructive for everybody there. You run a two-minute total speed dating round. Each person talks with each person, and they have to go really quickly. It’s gamified and fun, but you’re still getting a lot of content out there really fast.

And: the question that builds culture

A worthwhile measure of your culture of feedback: is productive feedback exchange happening even outside of the regular structures? In other words, is your culture wholly reliant on those structures or have people embraced it in a more robust way?

After a speed dating round or a big group feedback session at a retreat, I like to ask: is there anything that you shared today that could have been shared earlier … before this retreat, in other words? If so, what kept you from sharing it earlier?

It’s good to get some answers that are not shared out loud in the group. Have people write them down and submit them. What people tend to say out loud is “it just didn’t occur to me” or “I didn’t have time.” What you want to discover is people saying: I didn’t know whether this person would receive it well. I didn’t know if in my role I had a right to feedback on this thing. I could have had it, but I just wasn’t prompted to have it, so I never formulated the thought.

That actually can give you a recipe for how to make the culture much stronger on a regular basis.

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COMPELLING QUOTATIONS

One-time aspiring math professor Ulysses S. Grant on punishment after the US war with Mexico for Texas:

Nations, like individuals, are punished for their transgressions. We got our punishment in the most sanguinary and expensive war in modern times.

Painter Francisco Goya on cause and effect:

The sleep of reason produces monsters.

Supreme Court Justice Anthony Kennedy on learning:

The nature of injustice is that we may not always see it in our own times. The generations that wrote and ratified the Bill of Rights and the Fourteenth Amendment did not presume to know the extent of freedom in all of its dimensions, and so they entrusted to future generations a charter protecting the right of all persons to enjoy liberty as we learn its meaning.

1. I do - you do - we do for the workplace

There’s a common approach in K-12 teaching called “I do, we do, you do.” You can imagine how this approach works just from reading the handle. The part that can easily get lost when you apply this in the workplace is that all three steps require full attention from both parties. Too often, a leader delegating something skips straight to “you do” and only looks at the output of the delegate’s work.

When handing off a skill and practicing it, the “I do” part doesn’t mean the teacher is just doing it in a vacuum. “I do” means the teacher is doing it and the student is paying attention to how they do it. It’s still a two-way street. “We do” can take a few different forms: we’re either sharing the task by taking different parts of it or we’re literally holding hands on the same pencil and doing it together in lockstep. Obviously, this step requires full participation of teacher and student. In the “you do” phase, the student does it and the teacher is paying careful attention, giving feedback.

When you’re transitioning a skill set or a set of structures, you’re roughly using that framework. It’s worth noting that all three steps of this can be done in a pretty short amount of time, depending on what the skill or task is that you’re delegating. You may not need a detailed work plan or calendar gymnastics to get it done. Watch me open this meeting, then we’ll open the next one together, then the one after that, you open on your own (with me observing).

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2. How to pre-load your confidence in your direct feedback

My confidence in giving somebody corrective feedback very directly is based on two things.

One: a fairly robust history of my noticing just as many positive things about them, or even more, that I’ve communicated to them. I’ve removed the worry that this person might reasonably think I don’t ever approve of them, or that this person is going to be concerned that they’re in some binary state with me at all times (fine or maybe-about-to-get-fired).

Two: I’ve usually constructed a fairly clear agreement with this person on the front end of their employment that they are hungry for corrective feedback and so am I. That agreement is the subtext of my feedback. If there is a thing I leave unsaid, because it’s mutually understood, it’s a prelude like: “Hey, I know when you came on board you said one of the most important things you could get from your boss is really direct, clarifying feedback that you could act on right away and it would change things in a big way. So I’m going to give you something.”

I usually have literally asked a member of my team to commit to that when they join the team and even practiced it with them as part of their hiring process. Again in their onboarding, I’ve usually gone out of my way to make this a pretty densely experienced phenomenon for them.

Hiring and onboarding are your only real opportunities to set durable, helpful subtext for difficult feedback. Otherwise, you should hire people who just don’t need much feedback.

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3. Methods for enrolling people in the exchange of difficult feedback

• Make them an exemplar. You give them some tough feedback, they take it pretty well, and you immediately tell them how powerful it was for you that they just took it so well. Bring this up again later. Use them as an exemplar to other people — shout somebody out on the Slack for being not just ready to hear some pretty tough feedback, but acting on it right away and going out of their way to make me feel good about having given it to them. This builds their identity on the team as somebody who is an exemplar of this. They want to be proud of and protect that identity.

• The second-grade homework approach. A teacher says to second graders: “Okay kids, tonight for math, do you want second-grade homework or third-grade homework?” The kids of course all actively choose third grade because it makes them feel cooler to take on the bigger challenge. The feedback delivery version of this could sound like: “I could say all this to you in a variety of really couched ways, or I could give it to you really directly—which do you prefer?” Invariably people will say directly. But that act—even if that’s not what they feel in their bones—the act of choosing it really does help galvanize them in a way that not having that choice does not.

• Re-inoculate aka re-hire This is a bracing and useful approach. You say something like: “Look, feedback here—it’s got to be fast and direct. You’ve got to be ready to receive it. You’ve got to even be ready to receive it well and with gratitude, or it’s not going to work. I need you to get to that place, or we have to have talks about changing this whole thing up. Take some time, get back to me.” Changing things up could mean any of the following: they have a different job, they have a different manager, they leave the team altogether.

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COMPELLING QUOTATIONS

Maintenance maven Stewart Brand with a science lesson in four words:

Rust is slow fire.

Careful observer of patterns Kathryn Schulz on extinction:

To European observers [of the 1820s], the scariest thing about … dinosaurs was, ironically, the same thing small children find reassuring about them today: they no longer exist. For people accustomed to the idea that nature was eternal and unchanging … the idea of extinction was profoundly troubling. The Flood was one thing, but what kind of God would destroy his own handiwork again and again? And what did that mean about the fate of human beings?

Writer Sam Kriss on 21st century maxxers:

The twenty-first century is going to be a century of the maxxer. It won’t take many maxxers to make a century; when you drag yourself to the absolute furthest point in a distribution tail you leave a lot of turbulence in your wake. The twentieth century was a century of the masses, class and ethnic conflicts, nationalism and the great contests of history. The realist novel, the personal essay, the strip-mining of ordinary life for patterns and insights. Our century will not make nearly as much sense.

Onboard and upskill through example and exposure

For a new leader, most of what they will learn to do effectively they will learn by example and exposure. The overall headline I bring to the onboarding / upskilling challenge is: how do I immerse them as quickly but as comfortably as possible in the experiences he’s going to eventually be responsible for?

Onboarding a new teammate using positive peer pressure and exposing them in as many ways as possible to excellence around the team is good but not sufficient. It’s important to add and accept that they’re going to have to take on responsibilities for which they’re probably under-equipped and they’re going to have to do this before they feel ready. Articulate that reality, that future state; make it clear and expected. If your new leader expects those responsibilities and is spending time with the people who shoulder them now, watching them do what they do, that will maximize the speed at which they will take on and succeed with those responsibilities.

This shakes out into roughly two stages. One stage where they shadow you in every meeting that you’re in, followed by maybe a five-minute debrief about what they took from that each time. At a meta level, they’re stamping what they learned and what they’ve taken away from the shadowing.

Then there’s the second stage where they’re doing more themselves, which will bring up new questions for them. They’ll think they’ve directly, fully modeled you, but then they go into a meeting and they’re stumped a few times, and now have more questions for you, and maybe need to observe you a little bit more. Then they’ll do that observation and go back into trying out your moves on their own.

If you want this process to be fairly robust, you could plan for the first stage to unfold over the course of two weeks. In the first week, they observe and name takeaways. In the second, you let them dive into the independent practice of stage two, with you observing a little bit at the outset to make sure they’re handling it well.

I don’t think there’s any chance they spend an entire week shadowing you at meetings where they don’t come out quite evolved in their ability to handle the things you’re handling there.

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Moving on from disgust

It’s unfortunate that most bosses’ immediate response to underperformance — mine included — is disgust. That’s obviously not the state of mind from which we should operate to solve underperformance.

I also think there’s an adjacent problem: when we do feel aversion, personal grumpiness towards somebody, to what degree is that a sign or anti-sign of them actually being a bad fit or not performing?

In my best moments, when I’m checking that for myself, what I’m doing is looking ahead to the future and saying: in six months, if this is a high-performing employee, what am I seeing that is different from what I’m seeing now? And is my answer to that question something idiosyncratic and particular to me only, or something I genuinely want to develop people to have in the organization?

So if my answer would be, like, Eric is just less annoying — and by that I mean he’s more considerate of people’s time, he’s more thoughtful in how he frames his negative commentary — okay, now I’m thinking, yeah, that is something he should improve. And if he’s not improving on that in six months, I know the stakes of that and I might not keep him around.

But if I can’t really identify an actual trait that is worth developing, then I have to pause and say: am I just in a mood about this? Do I need to balance my aversive reaction with some more data about his actual performance?

The bigger question is: am I going to invest in developing this capacity in this person? Is that doable for me? Can that happen here?

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Three prompts for good skip-level conversations

When I was using skip levels most effectively, making my way through the full cohort every quarter, there were three purposes.

One was to establish relationships with people I wouldn’t see as frequently. It wasn’t like talking to them for a half hour every couple of months was enough for a robust relationship all on its own, but it often opened the door to more conversations, and that was helpful.

Two was gathering feedback for their manager. I always said to the person in the skip level meeting: I’m not bound to confidentiality on any of what we’re talking about today, but I do want to learn what you think would help me help your manager succeed.

And finally, the third was to ask: What are you thinking — and what are others maybe thinking — about the organization that I might not know, that would help me to know? Usually, having gotten warmed up on the first two prompts, they are fairly candid about that.

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COMPELLING QUOTATIONS

Whole earth cataloguer Stewart Brand on maintenance and precision:

Although precision in manufacturing was initially driven by the quest for conveniently interchangeable parts, it soon proved to be about something far deeper than maintenance and repair. The progress from efficient steam engines to an efficient assembly line to the extreme density of nanoscale microchip fabrication is a saga of multiplying capabilities for humanity. Simply by becoming masterly at doing ever more with ever less, again and again, we live in a time of such potency that we have to be careful about what we wish for. Maybe considerations of long-term maintenance of the whole process can help us frame our desires judiciously.

Butterfly enthusiast Vladimir Nabokov on place and memory:

As if feeling that in a few years the tangible part of her world would perish, she cultivated an extraordinary consciousness of the various time marks distributed throughout out country place. She cherished her own past with the same retrospective fervor that I now do her image and my past. Thus, in a way, I inherited an exquisite simulacrum — the beauty of intangible property, unreal estate — and this proved a splendid training for the endurance of later losses.

Observer of places Tony Hiss on simultaneous perception:

Normal waking consciousness adn our sense of separateness from the world protect us from harm by allowing us to focus instantly on any source of danger… So for simultaneous perception to emerge, we need a place that seems safe, where the information presented to each sense is complex but not overpowering. If louder signals appear, they will tend to drive simultaneous perception underground. That is why we lose touch with it when we leave Grand Central and walk over to Fifth Avenue.

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1. Matrix management: using solid and dotted lines so everyone has a manager

In a traditional reporting line, if I report to you, you’re the person I go to to meet my needs. The manager is a one stop shop. In a growing organization, you’ll often have a project that doesn’t align tightly with the shape of your org chart. You need people to work on something that isn’t in the purview of their official manager. That manager can’t be a one stop shop for this person, while they’re working on this project.

In effective matrix management, you maintain clarity about whom to go to for what. The “whom” will be more than one person, not solely the “official” manager.

You’re going to have a dividing fork in assessing who meets needs of each sort. If I have needs related to this project, I go to Person A. If I have needs related to that project, I go to Person B. And if I can’t decide, I know exactly who I go to when I can’t figure it out (could be Person A, Person B, or a whole other Person C, depending on your context).

Organizations that adapt well in these situations define what a solid line looks like in a reporting relationship and they define equally well what a dotted line looks like in that relationship. When they can’t have a one stop shop manager, they ensure there is a backstop manager.

The particulars depend altogether on the context. No matter how those particulars are arranged, the individual is fully managed. There’s never a situation where they feel like they don’t have a manager they can go to for needs or guidance.

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standing out vs standing in with AI

You can rapidly use an LLM to create a useful, credible “stand in” for an otherwise expensive thing you need. You can often do this in one shot: you write a prompt, within minutes you get a working draft of the thing. If, however, you need to “stand out,” you shouldn’t count on one shot. You should plan to engage in a thoroughgoing exchange, make a ton of edits, and, if you’re new to the domain where you’re making this thing, building skills and judgment of your own.

Succeeding in an exchange like this, where you operate at the edge of your own skills in tandem with an LLM, is a skill in itself.

Two illustrations of “standing in”:

TASK 1: Last summer, I ran a hiring process where we explicitly encouraged candidates to use LLMs in their late-stage performance tasks. Candidates who had made it through screeners and a couple 1:1 interviews had to respond to several complex prompts in less than a couple hours.

When we got back the responses, it was striking how … almost all of them sounded exactly the same. It was clear that most candidates pasted our prompts into GPT 4o (the default free model with biggest brand recognition at the time) and then pasted the output from GPT into a google doc and hit send.

This made our job as reviewers a lot easier. None of these copy-paste candidates stood out. They all blended together. To be clear: their pasted responses weren’t “slop.” The responses were thorough, smart, and clear. The writing had no obvious mistakes. But the responses were all basically the same.

TASK 2: I’ve recently gotten ~obsessed with native trees and their benefits for my beloved, precarious New Orleans landscape. I’m doing a pro bono project in conjunction with GW Carver High School – we want to plant an “Alumni Forest” where each graduating class since 1958 has its own tree and each forthcoming senior class will plant a tree of their own.

Long story short, I used Claude Opus 4.5 to generate a 3-D visualization of my draft design for the forest and the small park that it will sit within. It’s a little buggy, but you can “walk” through a virtual version of the alumni forest, toggle between stages of tree maturity, look at the design from birds-eye view, ground level, and any angle between. Having a landscape architect build this would likely cost hundreds, even thousands, of dollars. I got it for (close to) free in three minutes.

This visualization is a stand in. It’s a rough draft that accelerates progress toward a real thing in the world, that will be built with community and idiosyncrasy, that will ultimately stand out.

-eric

immodest proposal: don’t do meta-work

In this piece, former Rockefeller Foundation exec Zia Khan talks about all the “meta-work” he did at one of the world’s largest philanthropies. Meta-work is the planning to have a plan. It’s the strategic, theoretical, back-to-first-principles writing and deck-building. Sometimes it takes the form of “stakeholder engagement”.

My immodest proposal to you - don’t do this kind of work. If it must be done, assign it to an LLM. You, human, agentic, idiosyncratic you - you build a draft of the actual thing. Run a pilot. Bring a rough version of your plan into the ring, let it take one on the chin, then decide what’s next.

This is my advice for most sectors but I think I offer it with most enthusiasm if you work in some kind of social service sector. The thing you want to do or offer is probably going to be useful to the community your organization exists to help. Instead of meta-work, do some tiny amount of that! See if it’s as helpful as you think. At the worst, it’ll have no effect. You pay the opportunity cost of the modest time and cash you put into the experiment.

Worth noting: you woulda paid that opportunity cost anyway, sitting at your desk editing the footnote on the white paper about the experiment.

This advice is coming from a personal perspective. The kind of perspective you have when your eyes are squinty because you are also gnashing your teeth and gripping a tabletop with both hands.

Here’s what I mean: A handful of years working in philanthropy made me a little bit of a crazy person. Zia Khan’s experience there is common. There’s so much (high-salary) talk about social change and deep inhibition about the walk of social change. As far as I can tell, the teams that make the biggest demonstrable difference absorb the bruises and reputational nicks from their fearful peers and actually give the money away. They actually build stuff. They don’t coast on “convening power” or “building the ecosystem” or whatever other jargon-y camouflage is available for “spending the money on talking with other people who aren’t spending the money about how we might someday risk-lessly spend the money, meanwhile spending the money on ourselves.”

One reason I have deep respect for the folks at Coefficient Giving - they look at the proposed use of almost every dollar and ask: “Is this going to do more good than just giving it, straight up, as cash to someone in need?”

-eric

COMPELLING QUOTATIONS

Writer Sasha Chapin on misguided reaches for happiness:

The most interesting finding in human psychology, ever, is that basically all of us are born with the wrong intuition about how to be happy. We think that doing enough tanha, enough grabbing, will please us. But actually, grabbing is the source of something like 90% of our unhappiness. It’s a basically dissociative reaction to reality which creates a sense of temporary dissatisfaction, like putting on tight shoes so that later your feet will feel good again. Skip it altogether, as much as possible, if you want to be at peace.

Journalist Jerusalem Demsas on the price of expertise:

Delegation to an independent authority is a commitment device not to allow short term political pressures to influence macroeconomic policy. But the commitment device is straightforwardly anti-majoritarian. The risk is that policymakers will take steps that the public doesn’t like.

Observer Chuck Klosterman on old selves:

When you start thinking about what your life was like 10 years ago--and not in general terms, but in highly specific detail--it’s disturbing to realize how certain elements of your being are completely dead. They die long before you do. It’s astonishing to consider all the things from your past that used to happen all the time but (a) never happen anymore, and (b) never even cross your mind. It’s almost like those things didn’t happen. Or maybe it seems like they just happened to someone else. To someone you don’t really know. To someone you just hung out with for one night, and now you can’t even remember her name.

A useful oversimplification of strategic planning

I have heard so much grief from clients trying to both perfect and enact a strategic plan. There are seemingly endless obstacles to each. And I’ve sort of fallen down on a keep-it-simple-stupid method for this.

Consider the strategy to be that which will get you to the goals you most want to have achieved either three or five or ten years from now. Take your pick of timeline. For some organizations, ten years might be the right window; for some, it’s three. Let’s imagine for your team it’s five.

If the organization has fully maximized its mission five years from now—say, January of 2031—that means we will have achieved what? Write those achievements at the bottom of one page. Then at the top of that same page, write today’s date. Divide the paper between those two points into sections for each of the intervening years. Then work backwards: if we achieve xyz by by 2029, what must we have achieved by 2028, 2027, and so on.

Now you have a one-page draft of a strategic plan that is the one ring to rule them all. You break out each of those years as they come upon you, usually three to nine months in advance of the year’s start. And say, okay, we have these goals for 2026 if we were to hit this place by 2029. What does that mean each of our departments is responsible for? You break out goals for the departments based on what those annual goals are. This is your annual planning process.

I have a client who just did this—philanthropic advisors who work with ultra-high net worth individuals to steer their giving towards a particular type of social value. The most senior leaders straight up did it this way, in an hour, in front of me. They did that as a brain trust together. Then they brought the cabinet together and presented it at a two-day retreat, socializing the cabinet to it. Then they gave the cabinet time to set their departmental goals against it, set their people’s individual scorecards against it, and backwards map the OKRs on a quarterly basis that led up to it. Each group presented to the other, they celebrated and agreed on ways they’d check on it and troubleshoot it, re-evaluate it, and made a calendar. That was it.

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In strategic planning, focus on goals, not tactics

Strategic planning should be far more about the what than the how.

What actually matters is the benchmarks you’re setting for yourselves. The optimal moves that get you to those goals along the way will reveal themselves. Those ground-level tactics do not need to be contained within a strategic plan. In fact, putting them there can overcommit you to measures of success and uses of cash, time, and talent that will prove irrelevant. In other words, you set yourself up for wastefulness instead of learning.

You can add some tactical precision to your plan as you learn what works best, year by year. But usually that tactical precision, when you reach for it ahead of time, is arbitrary or aspirational and not based in ground-level learning. You do yourself a disservice by pretending to certainty at that level in a five-to-ten-year planning process.

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One way to handle library fatigue

Last month, Seth Godin offered a pithy label for a modern problem. When you face abundant options, you feel blind and overwhelmed, rather than spoiled and free. Godin calls this “library fatigue.” (He also calls it “vegetable blindness” – you lose sight of what you might want to cook once you hit the fifth rainbow of produce arrayed before you at the farmer’s market).

Library fatigue can flummox you every time you open your phone. You’ve got the Claude or GPT app there. You can summon and send forth the most powerful computer ever assembled. And with the recent vogue for Claude Code, you may now have the sense that you should be using that most powerful computer not just to answer questions and learn things but to build Literally Whatever You Can Imagine!

Choosing three wishes from a genie is hard. Surprisingly, choosing any one wish when you have infinite wishes may be even harder.

My happy fool’s advice is to let the blindness be your friend for a short, defined period. Let randomness be your friend as well. In the library, beset with fatigue: cover your eyes and pull a book off the shelf. At the farmer’s market, hungry and lost: pick the first three vegetables of different colors that you see. With Claude Code, make a crude single page website or an infographic of a spreadsheet.

When you’re overwhelmed, you can’t optimize. Your blind, random choice serves as a starting point. Maybe you like the track it puts you on, and now you can run down that track, refining and optimizing. Maybe you think what you made is utterly useless — now you can try something that has the ~opposite set of characteristics.

The good news is you’re now making your second attempt with some greater knowledge of the tool and of your preferences. The n-1 set of possibilities seems less like a sublime ocean and more like an old phone book – you’re not going to get swallowed up and there’s a ton of stuff in there you can safely, happily ignore.

-eric

COMPELLING QUOTATIONS

Philosopher Agnes Callard on blind spots:

“Error does not tend to survive introspective awareness of itself: when you catch your mind in going astray, at that very moment your mind cleans up its act. As soon as you realize it’s a mistake to think something, you become unable to make the mistake of thinking that. You can still think about it, as, for example, something you used to think, or something someone else might think. You can look at the erroneous thought, but you can no longer look at the world through it. Our errors are blind spots, which is why real open-mindedness is so difficult.”

Philosopher Socrates on Athenians feeling some type of way about his refutations:

“I realized, to my sorrow and alarm, that I was getting unpopular.”

Therapist Esther Perel on intimacy:

As a psychotherapist focused on relationships, I am interested in intimacy in all of its expansive definitions. It is becoming ever more clear that intimacy is not only romantic; it is civic. It is the willingness to be implicated in another person’s safety and dignity. It is the communication, silent or screaming, that your life touches my life and my life touches yours. It is the village reemerging, not due to nostalgia but due to necessity. Crisis, sometimes, makes us kin.

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A test for choosing retreat activities

There’s one big pressure test to make sure you’re planning the retreat as effectively as possible: you’re taking time out, you’re taking space out, you’re changing people’s work routine and workspace. We are all together with no interruptions, no outside world for this period of time. What is it that we’re able to do communication-wise with those different parameters that we could not do in our regular day-to-day work lives?

For a lot of people, this answer comes with exploring vulnerability and trust development. A huge advantage of people being in a shared mutual space with no social distractions is they learn to trust each other more. That usually comes from being more willing to express vulnerability—what they’re worried about, what they feel like they’re not strong in, giving each other feedback more easily.

That’s why there are often bonding and social components to the event. The best versions of that are not just “for fun,” but actually scaffold a level of trust and candor among people that you’d want to see extend to the work. The test for selecting retreat activities should be: is this building a behavior that would accelerate our work when we’re back in our regular context?

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Retreat planning hack: Using the behavior test

A way I prefer to hack all these questions: if we pick a couple of people in the organization at different levels, how will they be behaving differently after the retreat than they did before in their day-to-day experience? What impact on daily behavior will this retreat have?

So for a senior researcher, the hope might be that their awareness and greater clarity on the priorities would guide their strategic choices—they could plausibly choose substantially different research projects over the coming months. For a junior researcher, the hope would be they’d be more able to dive into projects they’ve been given or taken on and feel more comfortable doing so. Or, if they think the projects are mistaken, push back and say so—rather than existing in a river of confusion or feeling like they must have missed something.

In other words, the clarity that people arrive at from this process of understanding and improving on the priorities turns them into priority-accelerating machines on a daily basis, as individual cells in a whole organism.

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Retreat planning hack: using a phantom future retreat

The second hack I like to use in planning retreats is to think about retreat cadence as the driver. Start with a kind of phantom next retreat as your goalpost. Ask the question both of yourself in planning and of everybody else transparently while you’re there: when we return to a similar space like this six months from now and are celebrating what we have done, what are we literally celebrating?

The retreat unfolds in two parts: the objective you have for their learning, followed by the objective you have for their behavior, laying that all out, teaching that to them. And then planning at a high level: what is it that we did to bring that to fruition that we will celebrate at our next retreat? Really getting people to envision what that would look like makes more concrete the planning between now and then.

Now, what happens if you get on a kind of retreat high, make a whole bunch of plans that don’t necessarily make sense a few weeks from now? Or it’s clear you don’t really know—it could be this thing, it could be this thing, and none of these ideas feel big enough to commit to a plan?

The phrase that helps with this: instead of “at our next retreat, we’re going to be celebrating outcome A,” try “we’re going to be celebrating clarity on the question of X.” We will have made the choice among A, B, and C, or we will have gotten clarity as to which direction we’re going. We no longer have confusion about that.

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COMPELLING QUOTATIONS

Economist and America’s most voracious reader Tyler Cowen on a skill worth developing:

If by any chance you are wondering how to make yourself smarter, learn how to appreciate almost everybody, and keep on cultivating that skill.

Novelist Ernest Hemingway on cutting material from drafts:

Nothing is ever lost no matter how it seems at the time and what is left out will always show and make the strength of what is left in.

Writer and Calvinist Marilynne Robinson on the vagaries of selfhood:

There are times when selfhood feels like exasperating captivity, times when it feels alone with its ghosts, times when it feels confident in its particular resources, times when it is deeply disappointed with itself, distrustful of itself. Yet it is a constant in experience. And, within it, a history of life, a coherency of thought, a system of persisting loyalties, language, culture, habit, learnedness, even wisdom, accumulate and enrich themselves for all the world as if the self were a shelter from the storms of change. It isn’t, and it is. Vulnerable to influence of every kind, recidivist, intractable, through all its variations it is an indubitable presence. The wealth we can make of our capacities and perceptions we have entirely by grace of our selfhood. It is our part in the drama we all live out in this theater—of God’s glory, Calvin would say.

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ONE: High-leverage retreat structure

Retreat activities that I think of as high leverage, in order of appearance:

1. A kind of “state of the union” address at the beginning from the leader that essentially allows people to feel momentum by pointing out wins. Find some authentic way, either in that moment or immediately after, to recognize people for their contributions to those wins without making anybody feel left out. Search for everybody’s contribution.

2. Getting on the same page with a group on strategy and priorities. To do this, you really do think like a good teacher. When you’ve been taught a set of concepts that you didn’t know before, how did people do that for you?

   1. Often this involves some constructivism. Rather than giving them a memo with your ideas, you’re presenting them with perhaps a higher level version of what you’re accomplishing and asking them how they would make sense of that at a more concrete level, or giving them options. I think the best way to do this is to somehow lead them on the journey that you took in arriving at this.

   2. If I were doing this with, say, a group of math teachers who I was going to give a new curriculum, I would probably lead them through the following: here’s some instruction I saw in your classrooms that was working and here’s some that wasn’t working. What conclusion would you draw from that? They’d be like, “Oh, we need different material.” Then I’d continue to walk them through that so that there is a narrative supporting what you arrived at, not just a statement. Narrative is more memorable. A narrative makes sense. If one of your goals is to give them the confidence to make decisions, knowing the back story—literal story—is going to make them a lot more able to do that.

3. Clarifying and improving the work this strategy will require. I would backwards map from the next retreat: How do we bring these things to life? How do we bring them to the next level? For this, you’re probably mixing the modes of the work. The format goes from lecture Q&A style to maybe breakout groups or partners, people coming back and presenting to each other, and so on.

4. Brass tacks planning. This is especially useful when you can separate it from the more story- and strategy-driven first day, ideally with a night between the two. When we wake up tomorrow, we’re actually going to talk about what it means to put all this into actual practice and what we’re going to plan. To get to the brass tacks, I would give them very simple questions with a lot of autonomy:

   1. When we celebrate our success in this at the next retreat, we are celebrating what? What did we literally put in our calendars between now and then to make that happen? What did we change about how we work as a group to make that happen?

   2. Use breakout teams. Have people go off on their own for a while or with groups to work on this and feel the weight of it personally, rather than just letting it hover above the group.

5. Final presentations. I do think the best retreats end in changed calendars and actual real thoughts from the team that we’re going to really implement this. Like, I can tell that we’re going to implement this because we made it concrete somehow. Having your breakout groups share even rough, informal drafts with the rest of the team is a way to make it concrete.

6. Finish with some sort of gratitude for specific contributions people made to the plan for what’s next and maybe give folks a chance to articulate what they’re excited about.

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TWO: Adding a new leader (and layer) to your organization

I think it’s really useful to treat adding a new leader to your organization like any fairly significant change management challenge. If you were going to radically change your strategy or move the offices to the UK, for example — what would be all the things you would anticipate and proactively deal with?

In this case, as in all change management cases, usually the biggest gap that bites people is that the team is not informed and not aligned with the leader’s reasoning for why the change is happening. In this case that would be: we are adding a leader in this role for the following reasons, and we chose Eric for this role for these reasons. To whatever degree somebody does not know what’s in your head about that, that’s an opportunity for them to resist, push back, or fall into a negative space about it.

So the big picture thing is: does everybody know why he’s here? Not just at a high headline level, but why this person in particular was chosen for this. For example, if you do expect him to hold more people accountable, you can say: one of the reasons I chose this person specifically is that I had every expectation that they would raise the accountability level that you’ve been experiencing, having only reported to me so far. So now your team is actually predicting that as one of the consequences of this change and is not being surprised when it happens. I think it’s worthwhile to have a good think about that and make sure the team is aware. It’s probably good to put some of this in writing for them to refer back to: We’re bringing Eric onto the leadership team and here’s my reasoning.

I think the biggest move you can make long term is freeing up your time such that the number one thing on your schedule, whenever a new leader joins, is you making sure that person is successful. Your attention and time on this are going to be more valuable than everything else.

It’s also useful to establish a skip level type of structure, if you don’t have one already, where you’re in conversation with folks who report to the new leader, specifically asking: how’s it going with Lars? As these skip level meetings unfold, you remain pretty close with Eric. You hold fairly frank conversations about how everything is going on at least a weekly basis. So you’re getting insight both from his internal point of view and from others’ point of view. If you are noticing in between those meetings that this is impacting your workload in ways you don’t like, then that becomes an agenda item for your next meeting with Eric.

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THREE: Hiring and managing an expert

There’s a personality dynamic that I see a lot when somebody is hiring somebody who’s had high performance in a general role or competency before. That new hire clearly identifies as an expert in the domain you hired them to run / operate within. Perhaps you explicitly hired them with that understanding: that they’re an expert. You and the new hire share a belief in the new hire’s expertise.

The danger in hiring somebody as an expert is that if you’re not actually ready to give them full autonomy to exert their expertise, they might have resistance when you assert yours, or guidance of any kind.

The expert faces a dilemma when you tell him, “I don’t know that I agree with your instincts here.” They can say, “Thank you, I appreciate that, I will take your direction,” which seems like a decent compliance move to make with your boss. But – doesn’t that prove that they were the wrong hire? Didn’t the leader want somebody who could come up with this themselves? So maybe I need to push back. Maybe I need to disagree. Or I lose the only value they thought I brought to the organization.

Whether or not this is true for your expert, I think it is helpful for you, as the leader, to get out of this situation.

Generically what I’d say is: the way to help the expert succeed if he’s in that dilemma is to help him rely less on the identity that he was hired as an expert, and help him rely more on the identity that he’s joined the team to collaborate and learn together how to do this most effectively. “Actually, the person we wanted to hire here was definitely somebody with your background and your passions, but we didn’t presume that you would already be an expert on how we do this. In fact, we presumed we would build that together. And that’s what I’m trying to do with you now.”

When you say this, you release them from one part of the dilemma — that he needs to protect his expertise or your vision of him as being expert.

Ideally, you would have found out in the assessment process, before you hired them, whether their intuitions about what the most important things were aligned with what was most important for your organization. So the best upstream move here: run a hiring process that helps you identify whether somebody truly is an expert. If they are, they’re going to get massive amounts of autonomy, such that when you disagree, you’re ready to trust them instead of you. If somebody is not in that position, you’re not hiring them as an expert. You’re hiring them as something else that’s good, but not an expert.

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COMPELLING QUOTATIONS

Blogger extraordinaire Seth Godin on creativity:

We don’t make stuff as much as we make decisions.

Journalist (and mother) Kelsey Piper on hard things:

An important generalization for parenting and for life: You don’t get extra virtue points for doing things that are hard, and in fact, the most virtuous thing is usually to make an up-front investment in making things easier, so that going forward, you are not making high day-to-day expenditures of your patience, energy or happiness. A lot of people get this wrong when it comes to parenting, and it makes them miserable.

Songwriter John Darnielle on proximity to disaster:

The details of everything around something big are, for me, the places wherein the poignancy of a given scene can be most deeply sensed. Not the cars crashing but the person a block away who hears the crash. Not the fire but the way the room looked before the fire. Not the moment of the overdose, but the dozen things the man who overdoses, beloved by so many and with so much more to do in the world, will do, without thinking about them, for the last time on that day.

1. Resolve anxiety over quality when delegating

Imagine you’ve delegated something, and you’re worried about its quality. You’re watching the delegated work unfold at a lower quality level and wondering: is this worth it?

Here’s one answer to the dilemma.

I tend to feel okay watching something unfold at a lower quality level if I have the structural – or mental – equivalent of a clipboard.

I literally used a clipboard when I would watch someone lead a meeting in my organization. The clipboard meant: I’m paying attention, and I’m recording what needs to improve. The person I was observing knew ahead of time that this is what I was doing.

This matters because it norms the situation as a developmental experience. While I’m holding the clipboard and writing on it, everyone else in the room understands there’s an acceptable “lower quality” level in the moment — because this is part of someone getting better.

It becomes a constant signal: this person’s lower-than-mine performance is okay for now because we’re actively raising the bar. Around here, people take on new challenges and level up.

And you don’t have to have a physical tool. The “clipboard” can be any process you lean on—any shared frame that makes it clear what’s happening. Your “clipboard” could be, eg, a manager sitting on a Zoom call off camera. The point is to create a visible container for work that’s in progress: the stakes might be real, and the quality might be uneven, but you’re present, and you’ll jump in if needed. With this container in place, you communicate to everyone that improvement is part of the job here.

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2. Transitioning from founder to CEO

There’s a transition you have to make: from being primarily a founder—incidentally the CEO—to being primarily the CEO, and only symbolically the founder.

That transition is a must.

Your meaning as a founder never goes away, of course. But everyone’s day-to-day interaction with you is primarily as the chief executive. And whether they say it out loud or not, they’re comparing you to someone who is extremely technically proficient at that job—someone who isn’t you—someone who could come in and run the thing exceptionally well.

Many founders (myself included) operate with an unspoken belief that we don’t need to be that person, because we have so much “juice” from the founding story: the vision, the origin, the purpose, the credibility.

And people will love that when you’re making speeches. They’ll love it when they see you on podcasts. It will be a major reason they say they love working there.

But their day-to-day experience — like, if you could poll every hour and 23 minutes to ask “how’s it going?” and get the average of those responses — will be about their experience of you as an executive, not as a founder.

Behaviors that are appropriate for founders — like forcing something through when it needs to be done — carry different meaning in the CEO role. And often, that meaning is reliably more negative.

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3. How to move forward when no one can agree on the plan

The silver bullet with any sort of loggerhead disagreement with a report where you suspect that you’re correct, but you’re not fully clear on how to assert that, or you don’t feel like you have the data to back it up yet, is just to say:

I’d love to ask you if we could try it for X amount of time.

And at the end of X amount of time, I’m going to put a reminder for us in our one-to-one to hit the refresh button and check if this is still good, or if you think this is still worth doing.

I’ve seen this work in so many different situations where otherwise we’d hem and haw in trying to make a decision.

-ben

COMPELLING QUOTES

Avid blogger Zvi Mowshowitz on feedback:

A rule for game designers is that:

1. When a player tells you something is wrong, they’re right. Believe them.

2. When a player tells you what exactly is wrong and how to fix it? Ignore them.

3. Still register that as ‘something is wrong here.’ Fix it.

People are very good at noticing when things suck. Not as good at figuring out why.

Deeply human polymath Cate Hall on your elephant and rider:

Ultimately, you can’t go anywhere without your elephant. Sure, the rider can imagine it controls everything — that it’s capable of endless achievement, that it will never rest again, that it doesn’t possess humiliatingly normal needs. The rider, gifted with imagination, can pretend it is an infinite being, right up until the moment the elephant stops playing along.

Writer John Brinckerhoff Jackson on the use of “landscape” as metaphor

We should not use the word landscape to describe our private world, our private microcosm, and for a simple reason: a landscape is a concrete, three-dimensional, shared reality.

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