GCR problem #8: Leaders weaken themselves with misapplied epistemic humility

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Most leaders in this cohort under-rate their own authority. They trust their self-criticism more than their confidence. They convert authority they demonstrably already hold into hesitation, asking whether they’re allowed to decide a thing that is plainly theirs to decide.1

This shows up so often among GCR leaders because epistemic humility is the field’s core virtue. Rightly so. Humility about whether you’re right soaks through the question of whether you’re allowed to lead. These are different questions. Collapsing them stalls a capable leader who waits for permission a) they already have or b) they simply can’t get (because they are the founder/boss – they are the ones who have to make the low-information, high-stakes decisions, the decisions you can’t get timely, epistemically pure, and authoritative answers for).

Fixing this requires separating the two questions.

1. Humility about the truth: keep it, it’s a strength.

2. Uncertainty about your authority to decide and to direct: this is miscalibrated and it costs your team in ways that aren’t in your line of sight. Your right to make a call is not a claim that you’re the smartest person in the room. That right rests on your accountability for the performance and well-being of the whole endeavor. If you’re the founder/executive, you’re the only one who carries that responsibility.

Once you’ve set these questions apart from each other, take outside data at face value. You get a 360 review because you have unfixable blind spots. Your ability to self-assess is limited. The epistemically humble leader will often tilt their self-assessment downward. So when the feedback says you’re more capable, more respected, or more authoritative than you feel, you should take that as signal rather than flattery. Treat the gap between how you see yourself and how a dozen colleagues see you as information to act on, not a discrepancy to explain away.

And for the reverse error: if you find yourself sorting reviewers into the ones who “get you” and the ones who don’t, immediately after a 360 landed uncomfortably: stop. The reviewers who surprise you are usually the ones with something to teach you.

-ben

Related: acting on blind-spot feedback and one sign your feedback culture is strong.

Teach them to think like you do > teach them to do like you do

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A leader I work with wrote out a beautiful set of frameworks that were adopted across the organization. Across a few hundred people, the team applied her tools confidently. Alas, they were doing this in the wrong situations and for the wrong reasons.

Ex: Somebody wrote a one-page script for a tough conversation with a direct report that included the phrase, “I want to reassure you that you’re not in trouble” five separate times. If you have to tell someone five times they’re not in trouble, they know they’re in enormous trouble.

Leaders will sometimes fault a framework for low performance and then offer more frameworks to the person floundering. If the diagnosis is that people are being too literal about frameworks, telling them to use more frameworks reproduces the bug at higher volume.

To fix all this, it helps to imagine yourself as a ninth-grade English teacher. Imagine you teach your students that a good thesis statement addresses a core theme of the book, takes an argumentative stance on it, and makes clear that’s the focus of the essay. Everybody nods and gets it and tries it. Then every thesis statement you read looks like this: In this paper, I will show that a core theme of this book is [ ].

The students in this hypothetical learn the formal convention but not the point of that convention, the reason it should be deployed. An argumentative essay exists because a reader wants a controversial take from you, backed up with good evidence or reasoning. The real skill at the hear of it is generating a clear argument you can support. But the students learn to mimic the shape of a particular kind of sentence instead.

The failure mode in coaching adults is quite similar. When people apply your expertise clumsily or in the wrong context, they aren’t thinking like you think. They’re pattern-matching to things they’ve watched you do. They grab whatever you told them most recently and apply it to whatever’s in front of them.

A way past this is to change the question you tell them to ask themselves. Instead of “What have I seen my (trusted, expert) leader do in situations like this?” they should try “What advice would the (trusted, expert) leader give me about the situation I’m in?”. Better still: “What questions would she ask before giving any advice at all?”

-ben

transcribe your way through the darkness

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When you are managing a big project, like putting on an event, and you are dutifully exercising productive paranoia, I suggest keeping your hands off the keyboard, at least to start. Instead, turn on the transcriber (Otter, Granola, Zoom, iphone voice memo, whatever suits your fancy) and say everything that comes to mind. All the details, the rabbit holes, the worries - get it all out there and don’t worry about keeping it linear, hierarchical, crisp. This is a messy first draft on purpose.

Then copy that transcript into your LLM of choice (Claude Opus 5.5 around here, for now) and ask that LLM to impose order upon it. Turn the transcript into an action plan or a set of communications to all the relevant people, stack ranked in order of priority, that you can review and send.

In this mode, you’re hiring Claude as a Chief of Staff. You’re sparing your actual staff the crazy-making burden of translating your anxious stream of consciousness, inferring what’s important from your tone of voice and the weird things your eyebrows do when you’re stressed.

In this mode, you’re likely also saving yourself significant low-output low-value time rejiggering the cells of a table or spreadsheet. Don’t fool around with paint swatches when you’re still mixing the concrete for the foundation.

Transcribe your way through the darkness.

-eric

COMPELLING QUOTATIONS

Critic Henry Oliver takes a road trip:

And who knows what else is coming? Drive the suburbs and see the great variety of houses, the bizarre Halloween decorations, the endless businesses; drive the highways and see the blaring and sublime advertisements that line all the roads—NOW HIRING, WE BUY GOLD, CHEAPEST CIGARETTES FOR MILES, SHE WANTS THE DECK, WORLD’S LARGEST FIREWORK SUPERMARKET, WE SELL FLAMETHROWERS—go to the supermarkets and see the great variety of life, go to the Piggly Wiggly, which was the first self-service market, and is now a living museum, with the old beige shelves, brands from the 1960s, and the typography your grandmother would have known. Nothing is boring in America.

Journalist Bob Woodward on the connection between paper and power:

So much of the U.S. government ran on paper. What Darman understood better than most was the flow of paper, what it said and what it left out. Darman introduced me to one of my most important channels of information: the staff secretary. “A key to understanding what goes on in any White House,” he told me, “is the staff secretary.”

The position sounded to me like a paper pusher, a mindless cog in the bureaucracy. In fact, as Darman tutored me, the staff secretary sees and controls all information that goes to the President.

Poet Ocean Vuong on poet Anne Carson:

For decades, Carson’s unapologetically erudite work has centered strangeness and mystery as methods of human revelation. And its myriad and restless formal enactments have granted endless permissions to multiple generations of writers. Like the best work out there, it fosters others as it forges new ways to be and think for itself.

GCR Problem #9: Keeping (and cultivating) senior talent

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In many organizations in the sector, one or two senior people hold the place together. Those same essential leaders are flight risks. I intermittently track departure risk in coaching sessions, asking coachees to estimate their likelihood of leaving the team, and I regularly hear numbers like 40, 75, 80 percent.

The same folks offering these estimates often have no designated successor or defined opportunity above the one they currently hold. If they quit, there’s no one to replace them; if they stay, they’re stuck in place indefinitely. Understandably, mission-driven people in this situation feel unhappy, unappreciated, and despite themselves will start looking for a job elsewhere.

To their credit, the executives I coach recognize the importance of these senior folks and the risk of losing them. In my experience of the last few years, retention of one or two people consumes more coaching session time than any other operational topic in this cohort.

Let’s assume you’re also in a sector with small organizations, breakneck growth, for-profit orgs pulling talent up and out, and a labor pool of mission-aligned people that all your peer orgs are also fishing within. In these conditions, how do you keep your best folks?

More likely than not, you cannot out-pay frontier labs, eg, so it’s better to compete along two axes you do control: ceiling and belonging.

1. Ceiling: The reason a strong number two feels unappreciated is usually structural, not emotional. There is literally no bigger job for them to grow into and they are savvy enough to have seen and felt this. So one option is to fix the structure: define a role above/beyond their current role and build the path to it with them explicitly. A known path up can matter much more to a high-performer than a raise thrown at them to stay put.

2. Belonging: Retention in mission-driven work hinges on whether someone feels seen and ~irreplaceable. One cheap lever managers have to achieve this is regular, direct, career-focused conversations. The convos that build that sense of belonging are not flat “are you happy?” prompts (or spicier “how likely is it that you leave in x months?” prompts) but conversations that include takes like “here’s where I think you could go, here’s what I’d invest to get you there, here’s why it’s important for the org that it’s you that does this.” Most leaders have this conversation far too rarely with the people they can least afford to lose. Your all-stars burn bright but they’re not fires to put out, so they get ignored.

In addition to building a tractable future for your current senior folks, you need to build a bench with those same senior people. Many in this cohort resist investing in the next layer before it’s obviously necessary. That investment usually looks like giving real, stakes-y responsibility to less-proven people and coaching them through it. You bite the bullet of some shaky work from them in the near term so you can have a robust pipeline of leaders over time.

-ben

Relevant:

• Adding a new leader (and layer)

• skip-levels and developing the people under you.

Teach 12 people, train 100

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For seventeen years, while I led a school and then a network of schools, I taught a leadership class at 8am on the first Saturday of the month. The class was open to anyone, from assistant principals to custodians. You just had to put in the time. Over the life of that organization we never once hired a school leader externally; every one of them started in an entry-level role. Those same leaders stayed in their roles longer and performed better than their counterparts nearly everywhere in the country.

The best outcomes of leadership class came from the structure and requirements more than any particular set of insights I imparted. In other words – leadership class transformed the organization due to what the leaders were asked to do after class more than what I said in class.

Here’s the structure and the requirements:

1. Structure: You take 12-18 of the most influential leaders in the organization (this was ~1-5% of our total headcount; you can adjust numbers accordingly for your team). You choose participants based on their influence, not their title. For us, the meant cohorts that included C-suite, principals, assistant principals, and many people several rungs down whom everybody listened to. This group did one session a month, one objective per session, for six sessions.

2. Requirement: Between each session, every participant has to reteach the objective they just learned to four or five people who weren’t in the room. To be clear - summarizing it doesn’t count. Forwarding notes with an email that says “check this out” doesn’t count. Teaching it, observing implementation and giving feedback on that implementation - that counts.

With the numbers above, by the end of six months, the organization trained close to a hundred people in the material and — more importantly — had 12-18 trained trainers who could run cohorts of their own without me.

An obvious win here is getting a leadership pipeline that includes folks who aren’t yet in senior roles. A less obvious win is that you’ve assembled a cross-hierarchy group that shares a common language for leading people. Change management happens dramatically faster. There’s a built-in bat signal that lasts for years. People feel like leaders, feel seen and appreciated and upwardly mobile, because they are.

-ben

Quick wins as permission slips

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For coaches, for product designers, for new managers: identify and deliver a quick win for your new/prospective client. If you’re good at what you do, you probably have a robust mental model of a high performer. You have a catalog of best practices and a catalog of interventions that can achieve those practices. You may even have a curriculum, where those interventions are sequenced and stacked.

Very likely, the full sequence, the whole stack, is hard. Doing it hurts. If it were quick and easy, your client would have done it already. Everyone else would have, too.

Your client may never take on the hard, painful parts of the curriculum that can transform their performance without evidence that you know what you’re talking about. Your glittering record of success may not be enough. Your client will think, with some justification, that their situation is unique and that any template you have in mind is Not For Them.

Win the trust you will need for the challenging curriculum by solving something observable now. Consider doing this for the low low price of free. The quick win isn’t fake or cheap, in the broad pejorative sense. It’s immediate and it shows that you know what you’re talking about and you get what they’re struggling with. You get it, so you give it.

-eric

COMPELLING QUOTATIONS

Poet Andre Bagoo on experience machines:

All art forms are experience machines. But unlike films, plays, and paintings, poems are mainly constituted by language. And language is everything. “There is what we say there is,” said W.V. Quine. Because I also think poems can be made of things, I sometimes feel poems can control me, and that we are all living inside a poem. A poem contains what contains it. Perhaps this is why we need to believe in higher things like gods, biscuits or spirits – to close Pandora’s Box.

Writer Jeanie Riess on horses in New Orleans:

One summer night, when I was twenty-five, I was sitting on my porch and a horse galloped by without a rider, headed for the river. I’m not sure what happened next. Horses gallop by sometimes in New Orleans, and no one writes an article about it for the newspaper.

Poet Jack Gilbert on love and Pittsburgh:

By insisting on love we spoil it, get beyond
affection and wade mouth-deep into love.
We must unlearn the constellations to see the stars.
But going back toward childhood will not help.
The village is not better than Pittsburgh.
Only Pittsburgh is more than Pittsburgh.

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Introducing a new series: The Top 10 Most Common Leadership Problems in the Global Catastrophic Risks (GCR) sector:

Over the past year I spent about 250 coaching sessions with leaders from some 40 organizations working on global catastrophic risk. That cohort includes AI safety labs and evaluators, teams working on AI policy and governance, biosecurity, and the funders finding and supporting them. Relative to other sectors, this cohort is unusually thoughtful, humble, and well-funded. Yet, each of those assets casts a shadow where some common failure modes lurk - failure modes that crop up in other sectors that may not have these assets in abundance.

Each week ahead, we’ll share one of the top 10 most common problems these leaders encounter, with a proposed solution to address it.

-ben

GCR Problem 10: Improvised governance and unwritten rules

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Many of these organizations are about five years old, have grown tenfold, and inherited their governance from a founding group of friends. In the early days, trust and proximity did the job of governance. But now the org is bigger than its founding friendships and it hasn’t adapted its governance accordingly.

This failure mode can manifest a few different ways:

1. The board loses confidence in the CEO but gives multiple, vibes-y, conflicting reasons for the loss of confidence. This leaves the CEO, absurdly, with the job of teaching the board how to fire them properly.

2. Senior staff have reporting lines below them but lack a clear line above. Their work gets less focused and useful and they are, in practice, unmanaged.

3. Great-on-paper hires from outside the movement fail unspoken cultural tests and fall prey to insider-outsider dynamics. These talented folks underperform or quit or get fired. The team burns time and cash and trust on multiple hiring rounds.

The fix here is not glamorous and mostly consists of three moves:

1. Write the CEO’s scorecard. Have the board ratify it. Have the board use it for a calendared performance evaluation (likely an annual one). The worst version of the board problem is a board that only forms a view of the CEO when it’s unhappy and then can’t articulate why. If you and the board have agreed, in writing, what a good year looks like for you, you and the board can approach the year and make your respective decisions with greater confidence.

2. Convert tacit operating approaches into transparent, documented rules. Ambiguity that is harmless among a group of five friends who basically work in one continuous group meeting becomes toxic with thirty people arrayed in verticals. Reporting relationships, decision rights, and information flows are three places to bring your attention in particular. (If you’re in a phase of speedy growth, it’s good to name these rules as subject to revision. Things that work well with 30 people can collapse when you get to 100).

3. Codify unwritten cultural norms. A good place to find these is in the negative space: what’s the concrete, observable thing that unsuccessful outside hires fail to do? That thing is probably (adjacent to) a core value of your team. If there’s a real “us-ness” test that outsiders keep failing, it’s either a value worth stating explicitly (so candidates can self-select and you can hire for it) or a bias worth killing. Nb: What you write here can explicitly be a living document - you don’t have to freeze your team’s culture in place.

-ben

Related:

• Adding a new leader (and layer) to your organization

• Before you fire, after you fire.

Fix the acknowledgement asymmetry

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Most managers I’ve encountered embrace an unhelpful asymmetry: when something goes wrong, they tell people immediately. When something goes right, they almost never say so. Yet, people are doing worthy things constantly.

I borrowed an idea from The Carrot Principle and made a crude spreadsheet called a recognition frequency chart. For years, using this sheet was the highest-return fifteen minutes of my week.

Here’s what it looks like:

• Leftmost column: a list of of my direct reports, plus their direct reports. Those two layers constitute my orbit.

• Each column to the right: “week of _____” and the question: “has this teammate done anything worthy of praise that I haven’t yet praised?”

• Every Thursday at 9am a calendar event popped up with a link to the sheet. My rule was that I could spend no more than ninety seconds per name. Once I got in the habit, I tended to finish early.

Because the sheet asks what they’ve done that I haven’t yet acknowledged, I’m never making anything up. The sheet isn’t manufacturing fake positivity.

Rows I left blank were a useful signal. If I went more than about three weeks with nothing next to a name, it either meant a) I had low visibility into that person’s work or b) they were underperforming. Both are those were worth knowing and acting to change.

Blanks for my reports’ reports could also prompt a next step. I’d write their manager and ask, “How’s Erica doing?” The manager would then come back with something concrete. Then I’d write Erica directly and say, “I asked your manager how you were doing and he told me you’d gone above and beyond on this.”

The manager economics of this were excellent.

• Cost to me: ninety seconds.

• Value to the person receiving a specific, sourced piece of praise from their boss’s boss inside a three-week window: enormous.

People treat recognition as temperament (either you’re warm or you aren’t) but a generally warm person can go months without naming a single specific thing someone did well. Default friendliness won’t get you to the right baseline volume of recognition. A recurring calendar event and a simple sheet can.

-ben

the race within the race

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I ran my first marathon last Sunday. Before the race, during my training, I read many a Reddit thread and running book that warned of the infamous “bonk” at mile 20, where many first-timers (and veterans, too) find they just can’t go anymore. They might hobble or walk to the finish, but race pace and race goals slip away.

Thankfully, I didn’t bonk Sunday but the splits don’t lie: mile 20 onward was a different animal than all that had preceded it. I ran significantly slower for a few miles, fell meaningfully behind my pace group, and began collecting evidence that I was not going to hit my goal for the day. Half miles melted away in the first couple hours of the marathon; after 20 miles, each of those half-miles felt more like its own challenging movie, with a complete dramatic arc and minute-to-minute intensity.

I learned in a direct way that there’s a race within the race. Or, put differently, that the first 20 or so miles are the prelude to the actual race.

I realized that the four months of training were designed to make the first 20 a prelude. Those months wrote me a license to operate, a permission slip to join the actual race that started after 20 miles were gone.

A thought exercise I’m getting something out of: how do the race within the race and the 4 months of training map onto other endeavors? When I’ve built a team to chase a big mission, what was the hard, time-consuming work that just got us into the Actual Race? What was that Actual Race? How well did I prepare my team for this strange (and for some, infuriating) pattern?

-eric

Related: the second 90 percent

COMPELLING QUOTATIONS

Journalist Lizzy Goodman on Andre Agassi as philosopher:

… regularly present in our time together was Philosopher Andre — a sage, fluent in self-help speak, who talks younger players through crises, analyzes the game with astonishing emotional clarity and cries easily. Philosopher Andre deals in seemingly self-generated aphorisms like “The human condition is undefeated” and “Epiphanies don’t change your life, but what you do with them can.”

Investor Auren Hoffman on “pronoia”:

The best way to live life is being pronoid (the opposite of paranoid). Instead of believing everyone is out to get you, you believe everyone is out to help you.

Economist Raj Chetty scrutinizes test scores and privilege:

Children from families in the top 1% are more than twice as likely to attend an Ivy-Plus college as those from middle-class families with comparable SAT/ACT scores. Two-thirds of this gap is due to higher admissions rates for students with comparable test scores from high-income families; the remaining third is due to differences in rates of application and matriculation. In contrast, children from high-income families have no admissions advantage at flagship public colleges. The high-income admissions advantage at Ivy-Plus colleges is driven by three factors: (1) preferences for children of alumni, (2) weight placed on non-academic credentials, and (3) athletic recruitment.

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Delegation as three default moves

My take is that delegation is not complicated. In concept, it’s simple: you give others things to do that you used to do. Yet, people find this hard to execute or they make the threshold criteria for trying it super exacting. They’ll only delegate when they’ve got ample evidence that the other person has succeeded at doing this exact thing in the past. They delegate sparingly because they assume delegation is a clean and complete giving away of responsibility.

In my experience, good delegators delegate a lot. When they delegate, they rely on three defaults:

1. They delegate by default. They flip the presumption that they should do most things and sparingly hand things to others. They need to justify when and why they are not delegating.

2. Then they trust but verify by default.

3. When verification fails, they micromanage (or “teach, model, and supervise”, if you prefer) by default.

Almost every delegation failure I see is someone stuck in one of these modes and refusing to use the others. The person who only delegates has abdicated responsibility. The person who only verifies has built a bottleneck. The person who only micromanages hasn’t really delegated at all.

Fluency with these defaults lets you delegate with confidence. You don’t have to answer a big painful question about how much you trust people or even how skilled your team is. You’re constantly handing responsibility to your people, checking that they’ve exercised that responsibility well, and teaching them how when they don’t.

-ben

The sudden sabbatical test

When an executive tells me they have no time for strategic work, they often also tell me they need more staff. Specifically, that they need a chief of staff.

A variable of at least equal weight rarely comes up in these conversations. That variable is the strength of their leadership team.

An executive is truly operating at an executive level when they’ve handed what they used to do to the leadership team as a collective. The bar for this is high. You should ask yourself: would my leadership team do a fantastic job if I were suddenly on sabbatical and they had no time to prepare?

Here’s a two-part test that can help you figure out what to

1. Give yourself five minutes to write your succession plan. If you need to step down, who holds what? Five minutes is an intentionally short amount of time, so that you write the instinctive version of this plan rather than a galaxy-brained one.

2. Now imagine you and the team have no opportunity to plan, not even in this instinctive five-minute way. You take emergency leave, you’re unreachable, team’s gotta figure it out on their own. How would they arrange themselves?

Once you’ve done 1 and 2: ask how closely that arrangement from 2 matches the plan you spent five minutes writing in 1. Are the two plans 90% aligned? 40%?

Most leaders I run this with say something north of 80%. When that’s so, the thing they think they’re missing already exists. They have a strong brain trust in place and they may not be leaning on it enough to free up their strategic time and headspace.

If the percentage of alignment between the two plans is low, instead, you’ve got a different project on your hands. You likely have a capacity problem and the gaps between the two plans show you

The objection that comes next is always the same: my reports are already stretched, so I can’t hand them more. Which is fair, and mostly beside the point. What you’d be handing over isn’t more hours. It’s a higher tier of thinking about work they already touch.

-ben

One cool trick for scaling your culture

When your team is no longer a small ragtag group of founders, when you can see that you’ll soon be managing people who are managing people, you can have some very reasonable fear that your culture is going to fall apart. The special rhythm and vibe you and your co-founder friends have cultivated will get lost as your team becomes populated with newbies and strangers. You don’t want this to happen.

You also recognize that you’re just you. You can’t be everywhere, all the time, holding a cultural standard that others will intuitively understand and meet.

One of the cheapest, most useful things you can do is define your go-to moves. Make a list of the specific, observable behaviors that you and/or the most effective imaginable teammates do. These are behaviors you want to see scaled as the organization scales. If, at future date x, you can walk into any room and confidently expect to see these behaviors, you also expect that your team will be on track to achieve its mission.

We often call these behaviors, these default moves, these go-to’s “values” but that label can be distracting. It says too much and too little at the same time. These behaviors aren’t just “wholesome attitudes we’d prefer to see”; they’re also less grandiose and more concrete than “the most noble aspirations we hold for ourselves.”

You’re doing a good job identifying these behaviors if you can readily build a hiring process that screens for them and you can write a clear, data-informed performance review based on them and you can provide newcomers with clear illustrations of them from your team’s current work.

This list of ~5 behaviors, the most critical 5, is the path and the guardrails for scaling your culture.

-eric

COMPELLING QUOTATIONS

Writer Matt Yglesias on threats to liberalism:

Liberalism is under threat, not just implicitly but increasingly overtly, as prominent politicians seek reputations as thought leaders explicitly by disavowing liberalism’s main elements.

Vice President JD Vance and Sen. Chris Murphy, D-Conn., come from opposite ends of the political spectrum and have little overlap on specific public policy questions. But they both have new books out arguing that America has badly erred by overemphasizing individual freedom at the expense of some vision of “the common good.”

Songwriter John Darnielle on beliefs that sustained him:

This is me at nineteen: unable to tell anybody “no,” incapable of showing my naked face to the world, unhappy in my own skin, resentful of the real me still living under all the layers of hurt and anger — layers that stand in for me to the world, layers that then constitute my knowable self. I am alive today by grace, and because the wounded being at my core — the person I really was and am, the one I could not kill — believed in the magic of fragile things, in the holiness of thin ice, and because he held those beliefs strongly enough to fight back.

MIT professor John Maeda on motivating students:

My ten years of data as a professor show that giving students a seemingly insurmountable challenge is the best motivator to learn.

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A sentence good teachers and coaches don’t allow themselves

Good teachers and good coaches and good managers tend to be high agency folks. They don’t disempower themselves in the face of poor results.

When I managed outstanding teachers or visited schools loaded with them, there was a sentence I never heard from them that always seemed to be on the tip of the tongue of crummy teachers. The good ones never say, “I taught it but they didn’t learn it.”

The good teachers were not necessarily harder on themselves. The sentence was simply unavailable to them; it didn’t compute; it wasn’t of interest. They took full responsibility for the development of the people they worked with. They focused their energy on the thing they could most directly control: their own behavior.

Of course, there’s a bit of a paradox here, or maybe a trick. Great teachers have great agency and take that full measure of responsibility for student outcomes. But the students only get those outcomes when they develop great agency and apply it successfully.

-ben

A coaching requirement that can make clients squirm

I need to see a fair amount of your work in real time. This can be recorded meetings you send me asynchronously or a draft document you’re currently putting together. It needs to be something live. I’m pretty insistent about this, to the point that it becomes a dealbreaker for some.

The reason I insist comes straight from my time in schools. When I was a school principal, I would never have had a teacher come to my office, describe aloud how things in their classroom were going, take my advice, and then expect good results. A teacher’s account of their classroom is not the classroom. Rather, it’s a reconstruction, assembled by the person whose blind spots I’m responsible for addressing.

A core premise of having a coach (or a manager) is that at least some of the things that will improve your performance are things you will not notice on your own. You’ve got blind spots; your coach/manager can see things you can’t.

One obvious objection to turning over live examples of work is confidentiality, but in practice this hasn’t been much of a barrier, even with clients in extremely buttoned-up parts of government. There’s almost always something shareable whether it’s interviews with prospective hires, external communications, a redacted document, or live role play.

I not only insist on this, I think it’s total hackery when a coach doesn’t do it. Without this, we’re play-acting a coach-coachee relationship. With it, we have the essential material needed to actually build new skills.

-ben

Prompt your reports to distinguish wants and needs and bring you the needs

A leader I work with was being pulled in five directions at once and told me what she wanted was some kind of edict from on high confirming she was prioritizing correctly.

A first thing I told her is helping with this is her boss’s bread and butter. Making sure highly effective leaders are working on the right things is his single most important responsibility and his best lever for moving team performance. To reduce it further: helping his people prioritize is pretty much his job. If you manage people, that’s probably true for you, too.

To make this go best for managers and reports, I recommend that managers tell their reports something like this: “Before you walk into our 1:1, distinguish for yourself between what you want and what you need. Then lead with the need.”

In the prioritization example I’m using above, the difference between want and need often looks like this:

1. WANT: I want to be able to do all of this and not have it overwhelm me, and not have any part of it suffer because of the rest. I want somebody to make these problems go away.

2. NEED: What I need from you is help prioritizing, because there’s a real chance that if I don’t get it, the work is going to suffer and so am I. That version names the consequence, and it names it for both the work and the person, which is what makes it a need rather than a complaint.

It has been remarkable to me how well smart people make this distinction, essentially every time, once they’re asked. They’re just not taking the time to do so without you prompting it.

-ben

COMPELLING QUOTATIONS

Investor Auren Hoffman on moats:

Castles did not slowly decline. they got obsoleted in about fifty years.

once gunpowder artillery got good, a wall that took a generation to build could be knocked down in a week. constantinople had the best walls in the world for a thousand years. the ottomans brought cannons in 1453 and walls stopped mattering.

by 1550 nobody was building tall stone castles anymore. every one of them was still standing. every one of them was worthless.

the cannon for software is AI.

Blogger Zvi Mowshowitz on a law of human stupidity:

Sixth Law of Human Stupidity (that if you say that no one would be so stupid as to, you are always wrong) remains undefeated.

You’ll be so stupid as to because Think of the Potential, and because otherwise someone else will be so stupid as to first. Same as always.

Critic Henry Oliver on Jane Austen:

The more I read Jane Austen, the more I come to appreciate her quietness. Throughout Sense and Sensibility, comments are made about the consideration—or inconsideration—characters give to each other when they are upset. When Elinor is trying to retain her equanimity, when Marianne is hysterical, Austen is alert to who gives them peace, who intrudes, who closes doors with the consideration of silence. She is not just a novelist of what is seen, but of what is unseen. She brings to our attention the various aspects of life that many people never think about, and she shows us how they work upon our inner lives. This is a very English way of living. Her heroines are so often introverts or learn to love the retreat of their mind. Marianne’s resolution at the end is to read for six hours a day and thus to acquire the “instruction” that will tame her “self-provocation.” Solitude is a virtue from the opening page when we hear that the Dashwoods live in the center of their property. That is the spell the opening line casts like a fairy tale. The family of Dashwood had long been settled in Sussex. It sounds like this is all happening once upon a time. Jane Austen’s magic is to make it happen now, with the sort of people who are always intruding upon our solitude, imposing upon our feelings, and with the sort of situations that make us realise we must be the ones to become worthy of being praised.

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360 reviews have few facts, strictly speaking, and are still useful

A provocative view of a 360 review from your team is that it contains no facts. Or if you prefer: the only facts it contains are that this group of people, whom you chose, said these things in response to these prompts on this day. You have facts about people’s perception of you; this is different than having facts about your performance.

It’s worth spelling out this potentially obvious thing because most good natured leaders can’t help but take feedback from the team as the most pressing thing they must act on. A pile of feedback like this can displace your metrics, your objective performance, your sustainability. You read the “areas for growth” section as an urgent to-do list and start running at as many items on it as you can.

The attentive, responsive spirit behind that is right but the blind, scattered execution is wrong.

Consider an example: suppose in your 360 there’s a preponderance of “I wish he were more in the weeds, I want to see him handle more on the ground.” It may be perfectly clear from everything else you know that you should, in fact, be doing less of that weeds-y stuff and delegating it deliberately. In a case like this, the feedback doesn’t tell you what you should do. It tells you that people’s expectations of how you’ll use your role need to change.

-ben

What to do with a 360 review once you get it back

1. First, break down the responses into units. A unit is a repeatable behavior or a discrete mental move. Then cluster the units by what’s upstream of them. When you have put together a good cluster, fixing one upstream thing, one upstream unit, addresses all of the items in the cluster.

2. Second, if you’re reviewing this with a coach or manager of yours, write out the patterns you see before getting the take from your coach or manager. You’ll see things in the raw data that your leader might not because you have more context. You lived the experiences that are being evaluated and categorized in the feedback.

3. Before you read the growth section, where everyone tells you how to get better and/or stop screwing up, keep this in mind: In every 360 I’ve delivered over fifteen years, there is more raw text in growth areas than in strengths. This is not because everyone I work with has more growth areas than strengths. Rather, people giving feedback in these reviews work harder to justify criticism than praise. They want to get it right, so they write more. At first glance, you’re likely to see the higher word count and conclude that the team, on net, thinks poorly of you. Don’t fool yourself this way.

4. A final move that can be especially helpful: describe the person on this page, the one getting all this 360 feedback, as if they aren’t you. Maybe this is a leader you’re considering hiring, and the feedback in this review is all you’ve heard about that person so far. In your summary of the 360, you’re telling someone else you trust about this candidate.

-ben

What if it’s not the journey or the destination

After a couple decades off, I got back into running a couple years ago. Gradually, I’ve been building up my weekly and monthly mileage and shaving down the time it takes to complete that mileage. I run 2 or 3 races a year.

A thing I’ve come to appreciate about this sport is the competition is the exact same activity as the training. That can make me less anxious about the competition and it can enrich the experience of the training. There’s usually a day or two (sometimes many) in a training cycle where I tumble into a well of gratitude. “Hey, whatever happens in the race is cool. But I have what happened today.”

I’m healthy enough and safe enough and this hurricane season is quiet enough that I get to do this. I get to move under oak limbs, look at an ibis, and sweat ~5 lbs of liquid weight into my shoes. The point of this isn’t the race or the training cycle, the destination or the journey. It is point-less; it is this point in time.

When I’ve been at my best at work, work feels like this and I feel this way about it. Maybe this is obvious, maybe it’s a coincidence, maybe it’s a paradox: somehow this has also been the mode and mood when I achieve the most.

-eric

COMPELLING QUOTATIONS

Writer Annie Dillard (RIP) on encountering a weasel:

The weasel was stunned into stillness as he was emerging from beneath an enormous shaggy wild rose bush four feet away. I was stunned into stillness twisted backward on the tree trunk. Our eyes locked, and someone threw away the key.

Our look was as if two lovers, or deadly enemies, met unexpectedly on an overgrown path when each had been thinking of something else: a clearing blow to the gut. It was also a bright blow to the brain, or a sudden beating of brains, with all the charge and intimate grate of rubbed balloons. It emptied our lungs. It felled the forest, moved the fields, and drained the pond; the world dismantled and tumbled into that black hole of eyes. If you and I looked at each other that way, our skulls would split and drop to our shoulders. But we don’t. We keep our skulls. So.

Blogger and project-doer and home cooking enthusiast Seth Godin on history and leadership:

Significant work involves tension, change, and the transitions of starting and finishing. What we’ve done will change what we do. What we do will change who we are. And the cycle continues. The challenge of leadership is helping people put that history to work in a positive way.

Writer Teju Cole on American sentimentality and moral reasoning:

That is what made me compare American sentimentality to a “wounded hippo.” His good heart does not always allow him to think constellationally. He does not connect the dots or see the patterns of power behind the isolated “disasters.” All he sees is hungry mouths, and he, in his own advocacy-by-journalism way, is putting food in those mouths as fast as he can. All he sees is need, and he sees no need to reason out the need for the need.

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Don’t be cagey in interviews

Inoculation hiring can present a tension between a) giving the candidate the most robust info about your culture, expectations, and challenges that you can and b) getting trustworthy signal from them about how they’d do on the job.

This is likely to come up in work tests, where it can feel like you should hide the ball a little. You want to avoid getting back a response that has been tailored to match your expectations but doesn’t truly reflect how that person works.

If a premise of inoculation hiring is that candidates will tell you what you want to hear, shouldn’t you withhold some info about what you want to hear?

If you feel like you have to conceal your expectations, that likely means your work test is currently measuring who’s good at echoing your answer key. Unfortunately, concealment doesn’t fix that. Instead, it makes the test measure who’s good at guessing your preferences. But chances are that guessing ability is not a skill you’re hiring for.

The fix is to design a test where knowing exactly what you value doesn’t help them fake the answer.

A test is fakeable when the candidate can reverse-engineer an exemplary response from your stated preferences. A test is more robust to this kind of fakery when it reveals judgment and reasoning. You can get at those skills by presenting a genuinely messy situation that doesn’t have a clean answer, a tradeoff where you track how they weigh the options rather than which option they pick, or a scenario-based prompt that has a structure like: “here’s what happened, what would you do and why.”

If you notice that you’re wanting to be cagey, revisit the design of your test. Rebuild it so that you can evaluate their reasoning. That lets you offer full transparency about your expectations. The best candidates will distinguish themselves and you won’t have to worry (as much) that they’ve just sung you a song in your preferred key.

-ben

In praise of principles

This is not legal advice but it’s advice that might sound legal or lawyerly.

Your organization has its bylaws; it operates in a sector that’s regulated in some way by local, state, and federal codes. That’s the law law.

Beyond the law law, you might have an employee handbook that maps out board-approved policies on things like PTO, salary increases, and filing grievances.

Beyond written policies, you may also have a layer of cultural norms and guidelines that dictate things like default email response time. Around here, we reply within a business day, unless there are extenuating circumstances.

All of those layers of law, policy, and norm might not touch challenging, non-obvious decisions you have to confront on the regular. For those kinds of decisions, it can be useful to articulate a principle you want to shape the decision. Those principles can be broad and conceptual, especially in the early drafting phase. They can also become specific and quantitative when the situation calls for it.

Here are some signals that you might benefit from a principle:

1. You’re having a debate over and over about the same topic

2. You are the bottleneck on lots of decisions because you don’t trust the judgment of your peers or reports.

3. You notice a dilemma, especially a recurring dilemma, where values or policies you hold sit in tension with each other. It’s not obvious how you (or others) should adjudicate that tension.

-eric

Getting at the existential question

If you’re finding yourself frustrated over and over again with your own situation or with someone who reports to you, it can be useful to dig down to the existential question.

The existential question is something like “what would make me quit [this] altogether?”

[this] = this job, this working relationship, this company. Quitting it, if you’re the employer, could mean firing a report. It could mean enacting a succession plan. It could mean a hard pivot into a different line of business.

A less dramatic but still useful pair of follow up questions:

1. “How close am I to that (to quitting) right now?”

2. “Whatever my answer to the prior question, can I afford to quit?”

Repeated frustration can feel like a muddle or a game of painful increments. You start keeping score, possibly on metrics that don’t really matter.

The existential question can give you the clarity of a fork in the road. You’re not blistering your hands on 100 little dials, trying to wring satisfaction out of low-stakes moves. You’re choosing between (def)ending and building. You’re either gonna fire yourself (or that person) or you’re going to take the steps to make this go as well as it possibly can.

-eric

COMPELLING QUOTATIONS

Linguist John McWhorter on writing as a drug:

… the preference to see Marvel films captioned shows that our brains are still “on writing,” just as one can be on a drug. Literacy transforms how we process language. Once technology allows us to watch speech joined by its written equivalent, we embrace the writing — speech is completed if we see it simultaneously spelled out.

Critic Henry Oliver in the debate about the “death of reading”

What that old TV culture did do was to make it easier to be a passive high-brow. The internet still provides all of that content in podcasts, on YouTube, and frequently on Twitter feeds. It may stick in the craw of some people to admit this, but a lot of what they want is widely available and widely consumed. Whether it is less consumed than it used to be is harder to say. When most people turned off Clark and Bragg they went straight into The Generation Game rather than picking up Don Quixote. That they now flick over to Facebook or watch TikTok videos doesn’t, to me, seem to be a very significant difference.

Poet Mary Oliver on love and attention

If you love something, you give it a lot of attention. And if you give something a lot of attention, you very often learn to love it.

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Leader as ambient threat

Something happens to people who step into a position of real structural power for the first time. It often goes unnamed. The feedback they get gets worse and they conclude that they got worse.

The moment you can materially alter someone’s life, by, eg, altering their pay, their standing, whether they even have a job, their nervous system reclassifies you. They now have to watch you more closely than anyone who isn’t their boss. Their safety depends on reading you correctly. This is negativity bias doing its job. Once you’re a leader, you’re an ambient threat by default.

A couple things that can follow from this:

1. Your neutral behavior can read as hostile. Something otherwise innocuous, like a short reply to an email, can trigger defensiveness, blame, a whole story of palace intrigue with you at the center.

2. You may start hearing things nobody used to say to you (or about you). If I find you threatening and also think you’re too powerful to be hurt, I have little reason to take your feelings into account. You’ll be fine. You’re the boss.

This shows up in teacher-student dynamics all the time. A teacher can make a good-natured joke that a twelve-year-old may interpret as mockery. They might not tell you and may not even admit it to themselves. And you, a perfectly decent first-year teacher, can’t conceive that you could hurt this confident kid at all. But you hold the power and that power can inflict harm even absent your intent.

These dynamics scale, too. When my team grew from one office of fifty staff to five of four hundred, complaints spiked. Our management had not gotten worse. We were hiring people whose previous jobs sat within threat-laden hierarchies. Since we now had a hierarchy, they pattern-matched their old job to their new one. An implication here is that you should expect the sharpest feedback from whoever feels least empowered relative to you.

One way to address this is to overcompensate. Say what you appreciate more often than feels necessary; appreciation is the cheapest way to lower ambient threat. Notice who gets the least exposure to your vulnerability. The people who never see you struggle or admit that you’re wrong are the folks who are likely to have the least generous interpretation of you and your motives.

-ben

A taxonomy of leadership team problem types

When I x-ray a leadership team conversation that hasn’t gone well or didn’t go much of anywhere, sometimes I see a category error. The team approached a problem with the logic and heuristics of a different kind of problem.

So here’s a rough and ready taxonomy of problem types (with other categories likely to be added in future posts):

1. Cruxes are open, pivotal, often wicked questions, or a single key considerations everything hinges on. A really sharp leader who is facilitating a discussion that is going badly will sometimes stop the discussion and assign someone the job of identifying the cruxes. That might take a round of research and writing before a next meeting. But the conversation likely has a much better shape and flow once the cruxes are id’d.

2. Tradeoffs are choices with priced goods on each side. The team’s has to weigh the relative merits and demerits of the goods and pick one. A tradeoff requires sizing up, even quantifying. There’s a discipline in that that can be very useful; it can also lead to a false sense of precision or an unnecessary desire for precision. Sometimes, you can make the right call about a tradeoff by just being directionally right.

3. Bets. A bet is a choice whose outcome is genuinely uncertain. Unlike the tradeoff, you’re you’re wagering on a payoff that’s hard to see. Should we make this hire, enter this market, back this risky project? The defining feature is irreducible uncertainty. Making a bet well means sizing the wager (how much are we risking; can we survive the downside?) and separating the assessment of decision quality from the outcome. Often it’s useful to timebox the bet. Pick ahead of time the near-medium term point where you assess the outcome.

4. Dilemmas. A dilemma is a values conflict. Do we protect this beloved underperformer or protect the team’s high standard of performance? Do we keep the promise to the funder or the promise to the staff? One mistake here is pretending a dilemma is a tradeoff and addressing it as such. Dilemmas often lack clear quantitative solutions and teams will (reasonably) want the choice explained in terms that aren’t game theoretic or mathematical. That often means calling the dilemma a dilemma and naming the conflicting values at play. Another mistake is leaving decision rights unclear, which leads to circular debates. Someone should be empowered to call it a dilemma and decided which horn of it you’re taking.

-ben and eric

More on tradeoffs

When I’m writing for folks who outrank me, I try to find my way to a tradeoff that I can name for them and my recommendation of what to choose in the face of that tradeoff. Often I can delete a lot of the windup and reasoning that precedes the bit about the tradeoff.

I like doing this and often recommend it to others for a few reasons:

1. Sizing up a tradeoff is the way a senior leader has to think about problems so much of the time. This shows that person you can think (and worry) like they do. You’re not myopic in your local context or wishing on distant stars without a sense of the cost and engineering space travel requires.

2. A good leader will give you feedback on your framing and resolution of the tradeoff. They’ll calibrate you. They’ll help you develop better judgment.

3. Sometimes, when you think you’ve found the tradeoff, you’re wrong in a fortuitous way. The blocker or bottleneck that you think is forcing a hard choice is something the leader can take care of for you. They can call an influential friend, unlock a discretionary fund, tell someone on the team “hey, do this thing for [you].” They might not have thought to do this or known it was needed without you framing up the tradeoff for them.

-eric

COMPELLING QUOTATIONS

Theorist Roland Barthes on the pleasures of etymology:

His discourse is full of words he cuts off, so to speak, at the root. Yet in etymology it is not the truth of the origin of the word that pleases him but rather the effect of overdetermination which it authorizes.

Critic Brian Dillon on looking closely:

Stared at as closely and keenly as possible, even the most elegant, precise or selfsame forms are revealed as monsters.

Blogger Scott Alexander asks an impertinent series of questions:

Do thousands of airplanes involved in the same wind tunnel test form a secret society to subvert its judgments? Do airplanes with unflattering entries in their flight recorders take steps to falsify their records? Do airplanes give themselves names and choose leaders? Do they hack flight simulator companies? Do they egg on other airplanes to crash themselves, kamikaze-style, for the good of the swarm?

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Your dream list

A question we find ourselves bringing to clients more than most questions is some version of: “what would this look like if, ~6 months from now, it had all gone really well?”

This can untie someone who is in knots or affirm someone unsure about what to do next or settle someone who is struggling to weigh the relative importance of different time-consuming decisions. We’ve found it useful for clients who have heard it from us before. The anchoring pull, the gravity, of what has just happened and what is happening now is very strong. It can dominate the attention of even the most galaxy-brained.

This makes “what would success look like from a future vantage point” good for levering out of a quagmire. It’s also useful when you’re pre-quagmire, in an early and open design phase. In that mode, the question could take a variety of other forms:

• 6-12 months from now, you’re working for your dream list of clients. Who is on that list?

• 6-12 months from now, you call your partner to say you had the best day ever at work - what happened?

• 6-12 months from now, the employee who you’re considering firing has completed a remarkable turnaround. What are they doing and what are they no longer doing?

-ben and eric

Beware the board-based bonus, part 1

If you run a non-profit, you likely need help fundraising to keep that non-profit going. Maybe one way you’ve addressed this is recruiting financially-minded board members with well-heeled networks. If those board members worked in finance, they’ll be drawn to offer solutions from the world of finance.

One such solution I often encounter and just as often dislike is the performance-based bonus. In some fields, that bonus is nearly a sacred institution. People stake their futures on it. They buy houses and enroll their kids in schools in expectation of it. Folks in these fields take it as a given that bonuses are a) what good, mature organizations do and b) strongly motivating for good, mature professionals.

For most non-profits I’ve coached, led, or worked for, I haven’t found a) and b) to hold true. Good, mature pros and their good, mature organizations benefited more from bonus dollars getting allocated in other ways.

-eric

Beware the board-based bonus, part 2

I generally dislike bonuses in the non-profit context, despite generally favoring above-median compensation wherever possible. Some reasons for this and some alternatives I like better:

Reasons (a few; not an exhaustive list)

1. In industries where a bonus works well, performance of the firm and the individual are often measured in dollars. There’s a logic here that’s conceptually obvious and concretely observable. You did a good job, so the firm got more money, so you get some of that money. This doesn’t apply for most non-profits. By definition, their performance may not be indexed to their revenue at all. The weak logic model makes for weak motivation.

2. In many non-profits, the size of the bonus has to be small in relative and absolute terms. It’s a low percentage of annual compensation and the total number of dollars may be (well) under four figures. No one could make a real estate decision in expectation of the bonus. It feels weird to me to (potentially) withhold this amount of money from someone on the assumption that it is an effective stick or carrot for an entire year of work. (Note: I am not claiming that anyone, given the choice, would leave $500 on the table.)

3. Lots of variation here but: if you’re working at most non-profits, you’re foregoing higher pay you could be getting elsewhere. The mission, the culture, the location matter more to you than sheer dollars. My personal take is the organization owes you the most affirming, healthy working conditions it can deliver within its financial constraints. It’s a way to soften and humanize a tough tradeoff and it’s the right thing to do. A bonus is an inefficient, oblique stab at this. Wrong tool for the job. There are better ways (see alternatives below).

4. (maybe actually 1b): Because performance can be hard to measure in dollars, boards have to invent other criteria. They are often bad at this. Even when they are good at it, they have to decide, usually near the end of the year, whether the ED or the team met the criteria. They are often bad at this, too. By bad, I mean - slippery, intellectual shifty, epistemically suspect. One version: If an ED has done a fine but not fantastic job, the board doesn’t want to withhold the bonus because that feels punitive. So they give the bonus. Or, if there’s a proportional option, they give the same proportion they gave last year, even if performance was meaningfully different year-over-year. The so-called performance bonus effectively becomes delayed salary (you’re going to get it every year but you have to wait until the end of the year). Why make people wait?

Alternatives

1. Use the modest bonus pool to elevate base salary instead.

   1. And, if possible, set up a scheduled cost of living adjustment.

2. Narrow the scope and specify the source of the financial incentive. Instead of “hustle all year in hopes that budget magic occurs and you get a bonus from the board-managed heavens,” see if there’s something available that’s more like, “as a team, we’re chasing x award, due in 90 days. If we get the award, we all share it equally.”

3. Increase PTO. In the US, give the team the whole week of Thanksgiving. If possible with the seasonality of your work, give them back the week between Christmas and New Year’s. This one I like in particular because it’s the rare place where the organization can afford true generosity. The marginal day (even week) of PTO might not cost the organization anything at all.

4. Look at tweaking or upgrading other benefits. Can the org cover dental premiums? What about matching 401k/403b contributions by another percentage point or two?

-eric

COMPELLING QUOTATIONS

Writer Oliver Burkeman on attention

To describe attention as a “resource” is to subtly misconstrue its centrality in our lives. Most other resources on which we rely as individuals – such as food, money, and electricity – are things that facilitate life, and in some cases it’s possible to live without them, at least for a while. Attention, on the other hand, just is life: your experience of being alive consists of nothing other than the sum of everything to which you pay attention. At the end of your life, looking back, whatever compelled your attention from moment to moment is simply what your life will have been.

Writer Tressie McMillan Cottom on listening to Dolly Parton

One day, I turned on college radio to drown out the silence. Dolly’s 1968 song “The Bridge” was playing. It wasn’t the first time I heard it. It was the first time I understood the young girl in it, pregnant, abandoned, contemplating suicide to end the pain. The juxtaposition of that pain and Dolly’s high, lonesome voice broke me wide open. I cried for the first time for everything I would not have. When I was done crying, I was the person I would be after loss.

Composer Matthew Aucoin on Dylan Mattingly’s music

I think that his commitment to impractical and borderline impossible projects has proved more than worthwhile. He has summoned into being a region of musical experience that’s all his own, a welcoming, abundant, sun-drenched landscape that teems with tinkling, deliriously retuned pianos and raucous grooves that last long enough to offer a taste of infinity.

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Questions worth exploring with a prospective senior hire

In senior hiring over the years, I keep seeing that leaders tend to reprise the locally shaped roles they’ve held before. Somewhat counterintuitively, they even do this in cases where they struggled or failed in those prior roles. I’ve done this, too. Despite ourselves, we try to do again what we have already done.

So one useful goal for an interview with a senior candidate is something like “identify the weird geometry of this person’s recent leadership work” because chances are they’re going to force that geometry on your organization / their role at your organization, even if it’s subtly and over time rather than all at once. It’s hard to recreate oneself for a new context, especially once you’ve logged 10-15+ years in a career.

Similarly, accomplished, senior folks will have schema for how a professional, well-run effort operates. They will expect that your organization will have/offer xyz conditions or supports by default. Part of your team’s core strategic bet or cultural weirdness/beauty might be a deliberate choice NOT to have/offer xyz.

So it’s good for you to flag these potentially aversive, dealbreaking conditions and then ask about their past experience working within similar conditions. A risk for both sides is a faulty pattern match fueled by shared desire to achieve a match. A scrappy entrepreneurial person takes a job built for a steady technician (or vice versa) and everyone is dissatisfied.

-ben and eric

One way to use AI and talk about it with your team

AI polls remarkably poorly. Data centers in particular have become the rare contemporary issue that earns bipartisan scorn. So you may manage a team of folks who sit somewhere between wary of- and outright hostile to- use of AI at your workplace.

An approach that might cut through the angry politics and shaky reporting on this:

Well-deployed, AI tools can protect human judgement. That protection comes from taking on the tedium that normally gobbles up human time and attention. The tedium isn’t usually what your wonderful people have gotten into the game to do. Smart hustlers find ways to get relatively good at that tedium; they build workarounds, they hack together google sheets, they make a template where there was a mess. But smart hustlers usually have a whole intuitive, hard to replace, head-and-heart-and-hands set of skills that they’ve refined during their careers and maybe their whole lives. Those skills are the ones you need maxed out and the ones those hustlers really enjoy flexing. In tough cases, they get to do that less than half the time because of the mountain trail of tedium they have to hike every day.

So, if you want to unlock better work from your people and a better work experience for your people, consider using AI as judgement-protector instead of person-replacer.

Who’s to say why, really, but I’ve found “I want to protect your judgement and offload the most annoying parts of your job” is more palatable than “Me and GPT gonna drink your milkshake.”

-eric

Small task: map the universe

When you are in an early design phase, sorting out what your team or project is even going to do, the perceived vastness of your options can daunt you. You could be so many things. How to choose?

One worthwhile approach to shrinking this problem sounds like it might do the opposite: map the universe. More specifically, map your universe.

Your current constraints, including any design choices you’ve already made, set the bounds of the universe you’re mapping. Solo operator vs co-founding team of 5; making money vs giving away resources; a skillset you already have vs one you’re interested in relying on or developing. Any of these can be constraints that delimit the options you map next.

Once you’ve established those boundaries, make a list of all the alternatives available within those boundaries. Aim to keep the alternatives at a common level of altitude and detail. When in doubt, keep the altitude high and the detail light.

This list of alternatives is your map. It’s the hazy romantic expanse of The Universe distilled to the judge-able, tractable shape of Your Universe.

From here, you can weigh the alternatives against one another with any heuristic you like. Sometimes intuition alone is just fine. Sometimes you’ll find value in a more sophisticated rubric.

You can also repeat the exercise, this time within the bounds of the alternative you like best from your first map. Map the universe of options that exist within that first option.

-eric

COMPELLING QUOTATIONS

Writer Ava on safety and aliveness

If you want to know if something is alive, ask yourself: does it thrill me?

If you want to know if something is safe, ask yourself: do I intuitively feel I can depend on it in every realm that matters?

If you care too much about safety, you’ll be terrified of risks that lead to more aliveness because you’re so indexed on what you might lose: This is good enough.

If you care too much about aliveness, you’ll struggle to create a solid foundation from which to experiment and grow, or the intuitive sense that you are fully held.

Writer Adam Mastroianni on speaking vs reading:

Without any formal instruction, approximately 100% of humans will learn to speak, and approximately 0% of humans will learn to read. Talking comes easy and early, enabled by ancient mental structures that hoover up words and extract the meaning behind them. These are the original LLMs, and still the best in the known universe. Reading, on the other hand, comes late and laboriously, piggybacking on bits of brain that were never meant to decode squiggles on paper, let alone comprehend Finnegans Wake.

So when thinking about any human ability, it’s useful to ask: is this more like speaking, or is it more like reading? Is this an ancient capability that we get for free just by living long enough, or is this a modern skill that you can’t get without working for it?

Writer Sam Kriss on the reverse panopticon:

We’ve built this reverse panopticon where the gaze of a hundred million people converges on a single point, and it turns out all those concentrated eyeballs have the force of a ten-kilowatt laser, they start stripping off the skin, they peel a man like an orange. Put anyone you like in the machine and turn it on—vicar, imam, sweet old widower tearing up bread for the ducks with his trembling hands—and before long you will discover something that retroactively justifies putting them in the machine. But it will never be you. You get to watch as today’s subject is slowly ground down to a nub, a thin film of dust covering the bright clean mirrored room, and didn’t we see some crazy stuff inside that guy when we opened him up? Wasn’t that cool?

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Who to hire first in start-up mode

If you’re in start-up mode, the radical advice is to throw away the reassuring and symmetrical org chart for your first few hires. Determine what the bottleneck is and hire the person who opens that up for you. Repeat that move.

The bottleneck is more serious than a pain point or a gnarly process. At the earliest stage, it’s work that, if it went undone or badly done, would sink you fastest. Sometimes it’s the product not existing. Sometimes it’s, “um, there is no money is coming in.” Sometimes it’s that you personally are the constraint on every decision.

This sounds obvious but it requires some real discipline and sometimes, a stomach for low-status moves. Maybe in good faith you want to do what a “real organization” or a “grown up organization” does. But that can lead you to hire a senior operator before there’s enough of an operation to run, eg, instead of getting someone less shiny who will chase clients for you like there’s no tomorrow.

At the start you don’t really have an organization. That’s painful in a lot of ways and freeing in many as well. Instead of an organization, you’re closer to the nakedness of a mission and a set of barriers to reaching that mission. Ideally each early hire loosens or softens the worst of the constraints, the most existentially threatening of them.

Eventually, a structure will emerge or the existential risk for your organization will be the lack of that structure. Then you address that problem, rather than pretending you can solve it before it’s there.

-ben

How a leader can make a graceful exit

A leader with a high sense of ownership and responsibility usually wants to make a deliberate and graceful exit from their organization. They’re not trying to cut and run. Yet, so often, the exit feels painful and protracted for everyone involved.

Making a transition like this go well starts way before anyone (including the exiting leader) knows it’s going to happen. Developing a strong default of building capacity in other leaders helps immeasurably. If the pattern of your own leadership has been prepping others around you to be on stage, make stakes-y decisions, and think about the medium- and long-term, your exit asks others to do something they’ve already practiced. That means your exit can likely occur quicker and sparks less anxiety on your board, among your junior folks, and on your leadership team. Chances are higher everyone has already seen what this looks like, at least in miniature.

In addition to building leadership muscle around you all the time, whether you’re planning to leave or not, consider these moves as well:

1. If you have an immediate successor already on the team, move as quickly as you reasonably can to having that person field questions, make decisions, and otherwise assume the responsibilities of the leader. If you’re a high-ownership person, this likely will feel like you’re shirking responsibility but it’s actually a gift to your successor and the team. Ambiguity sucks, for everyone. You getting off stage fast prevents one painful species of this ambiguity from taking hold.

2. When you have a rising star working for you and you’re not sure what feedback to give them or what to assign them, ask yourself, “What would worry me about having them step into my role next week/month?” Then have them get good at that thing.

-ben and eric

Two ways to address AI usage in work tests

A challenging, true-to-life work test can be a powerful part of inoculating your job candidates. Ideally, you’re giving them work to do that is very close if not identical to the work they’ll do on the job irl, including the abrasive unresolved parts.

We’re fans of making the rubric for these tests explicit. “Here’s what we’re looking for and why. Here’s what we’re not worried about / interested in.” A really good work test gives you evidence of the skills and values that really matter to you and doesn’t hide those skills and values from the candidate.

If “using AI tools well” is one of those skills, don’t just give candidates permission to use them. Say more and ask for more so you can learn more about your candidate. Two moves to try:

1. Include something like this in the instructions for the work test:

“Using AI tools well is a key part of the job. So you are welcome and encouraged to use AI tools to help you complete this test/task/assessment. If you do use these tools, we ask that you write a concise summary of

• Which tools you used

• How you used them and

• Why you used these tools in this way”

2. Then, before you grade any candidate work, feed your assessment to a frontier model (as of this writing, Fable 5 or GPT 5.6) and have that model complete the assessment in one shot. You can use this one-shotted sample to cross-check the work you’re getting from candidates and get a sense of how much of their own taste and judgement shaped the output they got from the bots.

-eric

COMPELLING QUOTATIONS

Economist John Maynard Keynes on purpose and cats:

The “purposive man” is always trying to secure a spurious and delusive immortality for his actions by pushing interests in them forward into time. He does not love his cat, but his cat’s kittens; nor in truth the kittens, but only the kittens’ kittens, and so on forward forever to the end of cat-dom."

Critic Henry Oliver on ideas in literature:

Every novel is a novel of ideas, not in the sense of being a novel that explicates and sermonises but in the deeper, broader sense that nothing can be written that is not founded on some belief, some worldview, some ideology, or some instinctive understanding.

Advocate of clinical trial reform Saloni Dattani on medical progress:

Medical innovation has transformed our lives, but hardly anyone realizes it. You can tell people that global life expectancy has doubled in a century and watch it fail to register – it just sounds like an abstract number, and numbers don’t convey how different life used to be. So let me describe it another way.

If you collapsed with a heart attack in 1950, hardly anyone around you would know how to help. CPR wouldn’t be invented for another decade. If you reached a hospital, a doctor would likely give you morphine, tell you to lie still and hope for the best: the prevailing view was that once the heart stopped pumping, nothing could be done.

That changed in the 1970s. Cardiologists began to understand that with each passing minute, more heart muscle would be starved of oxygen, and once dead, it wouldn’t be able to recover. But doctors could limit that damage by swiftly restoring oxygen supply with a clot-busting drug or a balloon catheter, opening blocked blood vessels and rescuing heart muscle.

In other words, the idea that a heart attack is something you could actively treat is only about fifty years old. Since then, the share of patients who have died within a month of having the most severe type of heart attack has fallen by two thirds.

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You’ll see on the homepage that we now have a lineup of our most popular recent stuff and links at the top for collections on frequent topics: feedback, hiring, AI/Claude, mvps, etc. We’re tagging and organizing the 136 other issues in our full archive in Kermit-at-the-keyboard fashion; for now those links will give you a first sampling.

As always, we love hearing what you find useful and what challenges you want help with. If you have a moment, reply here and let us know or forward this one on to a colleague who could make good use of it.

Enjoy!

ben & eric

1. Managing people who have more technical skill than you do (from Leaflet #116)

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.

-ben

2. I do - you do - we do for the workplace (from Leaflet #115)

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).

-ben

3. essence and maintenance (from January 23, 2025)

In one bewildering season of my time as CEO, Ben made a typically perfect book recommendation. He suggested I skim The Four Disciplines of Execution. I did and then carried chunks of it to my team and said - we are doing this. Let’s try it.

I liked the realism of the recommendations in the book. Specifically, the authors recognize that there is inevitably a “whirlwind” of responsibilities blowing around and through any brilliant central stratagem you and your team have come up with. Total, exclusive focus on the most important thing isn’t really possible or advisable. Someone has to file all the state taxes, answer customer calls, make sure that the right number of rooms are booked for the conference (anyone who works in operations knows this list could stretch to another 50-100 items before you have to think hard).

For his part, Greg McKeown recommends making a daily list of essential items and maintenance items: 2 essential and 3 maintenance. Richard Rumelt’s writing about the cost of having a strategy at all presumes that you’ve got beaucoup maintenance on your hands and may have to tradeoff on some of that maintenance to execute your strategy (so think twice, dear reader, before you commit to having a strategy at all).

The through line here is essence and maintenance. Classifying the two in your own work, giving them both their due. Especially in fast-paced early days, where you’re scrambling for survival or, happily, scrambling to keep up with rampant demand, you can lose sight of one of these two halves.

Often, essence feels sexy and maintenance feels safe. Different people on the team will be drawn to one of the two, so much so that they’ll see it as the sole guarantor of success. A challenging truth is pretty much every day of an organization’s life (and of your own) requires attention on both.

-eric

COMPELLING QUOTATIONS

Buddhist scholar Geshe Shawopa with an admonition:

Do not rule over imaginary kingdoms of endlessly proliferating possibilities.

Austrian poet Elfriede Jelinek flipping the script:

They remain at the edges of things, not because they’re afraid of the light but because the light, understandably, is afraid of them.

Poet Rosanna Warren on source and destination:

The stars are a wheel of fire
broken off from earth fire, surrounded by air.
We came from the unlimited, to it we return. So taught

Anaximander of Miletus, who thought we would be destroyed.

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“Federal rules” for your flat organization

Schools in a network; franchises of a restaurant; research teams at a think tank or alignment non-profit - there are good arguments for decentralizing and distributing decision-making power in these organizations. A couple such arguments:

1. When sub-teams have freedom to develop their own cultures and ways of doing things, they can achieve some real local pride that rigorous standardization doesn’t enable as readily. These teams work harder for and with each other because of that pride.

2. You can run tests or experiments of a variety of approaches to the work that’s common across the teams. Not just an A/B test: an A/B/C/D/E/F/G… test.

If you’re a leader at the hub of a distributed organization like this, it can be useful to scaffold the decentralization with a shared understanding of the powers you, at the hub / nerve center / central office, do retain. Law students’ brains melt during the study of the near-infinite nuances this takes among federal, state, and local governments. In your organization, you can keep it simple.

I think a good short starting list of “federal powers” has these two:

1. Setting standards of performance. You spec the floor if not the ceiling. “Every team must at least deliver _____.”

2. Scaling best practices (as they’re discovered). If a team isn’t performing at least at floor level, you get to swap out a current practice of theirs for one that has been proven out elsewhere in the organization.

-eric

You are not at the mercy of your software, part 2

I’ve written here before about Claude Code as a rescue from the (oppressive) dominance of enterprise software that isn’t meeting your needs.

Maybe you’ve already gotten locked into a contract with Salesforce or your parent organization uses the Office suite so you have to use Office the suite, too, whether you like it or not.

The good news is that you don’t have to build a whole new CRM or email client from scratch. You don’t have to rebuild Salesforce. You can use Claude Code to build a lightweight layer on top of that big, existing system to get it to work for you and with you in ways you like better. You can say pretty much that exact thing to Claude Code in a prompt:

“I hate that I have to export this data from Salesforce, reformat the spreadsheet, then pdf it for this board report - this takes me an hour and I often make a mistake I have to go back and correct later. Can you build a lightweight layer that works with Salesforce to do this for me?”

So much of the computer-based work that happens in the knowledge economy, especially at resource-strapped orgs, is translation. You, wonderful human – hired for your deep experience, sound judgment, mighty head and heart – are converting one kind of bit into another kind of bit. You’re stuck doing the robotic part so you can hopefully get to the human part.

This is yet another vote for assigning the robotic part to the robots. When this goes well, you have more time for relationships, judgement calls, nuanced interpretive work, clever writing.

Worth a try.

-eric

Team roles as naked objects

The wonderful Rob Walker drew my attention this week to an essay by Roohola Ramezani about writing poems. Ramezani guided his students to write “phenomenological” poems about objects in their lives. The core rule was that the poems couldn’t ruminate on the meanings and contexts of the objects. The poets stripped the objects of all that cultural clothing to attempt poems about “naked objects,” described as directly as possible through the ways they struck the five senses.

Leaders of small, growing organizations often struggle to know whom to hire next. The stalwart band of co-founders has probably done a handful of jobs each. There’s a lot of work that isn’t getting done at all, yet. Some of these leaders reasonably look at what big, mature organizations have at the top of their org charts and try to mimic those lineups. This can lead to wasted energy in hiring and, sometimes, to hiring expensive, seasoned executives you don’t need.

One useful exercise could be writing up the next role you hire for as a “naked object”. Don’t write what your’re going to call the role or who is going to manage it or what it looks like at your highest-performing peer organizations. What, specifically, does this person need to do / change / achieve in the next year? Start with that and figure out what to call that bundle of assignments later. The title, org chart bubble, salary band, reporting line – that’s all clothing on the naked essential contribution you’re looking for.

-eric

COMPELLING QUOTATIONS

Newly published author Cate Hall on serving as your own crisis manager:

Imagine you’ve been parachuted in your life as a stranger. Whoever was here before you certainly made a mess of things, but now someone more capable is here to take over. Using the resources available, how can you, the crisis manager, get to work on improving the situation?

When you’re messing your life up, the crisis manager is superior to your normal brain. It’s not worrying about sunk costs or wedded to your old processes. The crisis manager throws away the old to-do list and simply asks, “What is the most important priority, and what is the next thing required to achieve it?”

This is a key attribute of the crisis manager’s utility. The crisis manager doesn’t know or care about the standards of the person who created the crisis. She has one standard: better. She is simply taking whatever action would make the situation a little better, right now, over and over again.”

Former Marine Corps general Jim Mattis on technology and confusion:

Digital technologies do not dissipate confusion; the fog of war can actually thicken when misinformation is instantly amplified.

Student of habits James Clear on numbers and attention:

Whatever can be measured grabs our attention. How much money we make. How much weight we can lift. How many bedrooms are in the house.

And once we notice a number, it is natural to want to improve it. We find ourselves wondering how to make more money, lift more weight, add another bedroom. What is measurable becomes what is important. Not because it matters more, but because it is easier to see.

Sometimes a new perspective is helpful. Rather than asking, “How can I get more?” Try asking, “What is an inspiring way to live?”

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When is shipping an MVP the wrong move?

Many a Leaflet has extolled the virtues of shipping fast and acting timely on feedback. (See, eg, demos over memos). This approach assumes failure is cheap. If your rough version flops, it’s no big deal. You didn’t spend a ton of time or cash to make it. You learn and you try again with a whole new version or a variation on the original flop.

But there are cases when failure isn’t cheap. It’s worth knowing those cases so you can avoid them and also reassure risk-averse teammates (or board members) that you’re not a total MVP-at-all-costs dogmatist.

Cases where you shouldn’t ship first and ask questions later:

1. Safety-critical work, where a failure hurts someone relying on you. You don’t ship a minimum viable version of the thing keeping a patient alive, or the structural element of a K-12 school, or the protocol that protects a vulnerable person.

2. Trust-critical work. Some kinds of trust can’t be recovered if a first experience isn’t excellent. MVP-based iteration assumes you’ll have multiple rounds of feedback, an ongoing conversation, give and take. Sometimes you don’t have the history or status with a partner that enable those.

3. Legally-bound work, where missing features or blurry edges mean you’re breaking a rule, mishandling someone’s data, or violating their rights.

In these cases, the cost of an early failure dwarfs the cost of building carefully the first time, so an “expensive” polished version is actually cheaper. Put another way: the standard of viability of products in these domains is too high for you to offer the minimum.

-ben and eric

How should you manage work in a domain that’s hard to quantify?

Comms, relationship-building, the political and policy parts of the work: these domains can seem “scorecard-proof” because they’re hard to quantify. Whether you’re a subject matter expert in these domains or not, you’ve probably been assigned a metric or goal that feels fake because it pastes a numerical target on something.

You, good leader, want to avoid that fakery. You, good leader, also want to avoid getting hoodwinked by supposed experts who hand-wave at goals.

Here’s one way to achieve both of those. The outcomes in these domains are often noisy, hard to pin to deadlines, and driven by handfuls of exogenous factors. It is hard to quantify whether a relationship “worked” or whether the policy environment improved.

One way to deal with this is to track and score the observable behaviors that reliably produce the good outcomes you want.

Every domain has practitioners who are obviously good at it. Watch what they actually do. Look for the repeatable, observable actions. The great relationship-builder, eg, follows up within a day, remembers the personal detail, never lets a thank you note languish in drafts. The great comms operator publishes regularly, tailors the message to the audience’s values, avoids jargon.

So instead of a fake outcome goal, you hold the person accountable to a real input goal. The inputs are behaviors that, in your best judgment (or industry best practice, if you have to have a proxy), cause the outcome.

If you’ve chosen the behaviors well, you can avoid a Goodharting pickle, where people nail a metric without actually delivering what you need. Behavioral standards are a description of doing the work well, instead of a stat that can be juked while doing it badly.

-ben

A central contradiction of strong leadership

You are responsible for the whole mission, and your job is to get it done by making the people around you better, not by being better than them.

New leaders often get this backwards. They rise because they were excellent at the work, so as leaders they keep doing the work, or they hover around and hand the answers to the people who replaced them. Both of those moves can feel generous while making the team less capable. Over time, solving your reports’ problems for them makes you the bottleneck for ~everything in the organization.

Instead of this, think of yourself as a teacher. We’ve written here before that a great teacher pulls off a particular alchemy: they convince the student the responsibility is 100% the student’s, while the teacher in fact retains 100% of the responsibility for the student’s success. You don’t let any goals drop. You place people between you and the mission and spend your energy making them capable of handling their piece of it. You do this by setting clear goals for them and meeting every legitimate need they have to hit those goals.

A small set of habits bring this to life.

1. When a report brings you a problem, ask how they’d solve it without you first.

2. When they nail something on their own, even something incremental and small, name it, so they know to do more of it.

3. Picture yourself as a helium balloon whose natural place is the ceiling, where you can see the whole room. You come down on a string when you must, but whatever you do down there has to build capacity in others, so you can return to the panoramic view only you can hold.

When you’re doing this reasonably well, your best people need you less every month, your one-on-ones get shorter and more strategic, and you get closer to achieving your mission through other people’s efforts. By contrast, when you’re screwing this up, you’re indispensable, somewhere between quite tired and exhausted, and bear both of those status as badges of honor.

Own the outcome completely. Give the work away completely. Living into that apparent contradiction can carry you a long way.

-ben

COMPELLING QUOTATIONS

Marketing maven Seth Godin on selling:

Selling is simply a dance with possibility and empathy. It requires you to see the audience you’ve chosen to serve, then to bring them what they need. They might not realize it yet, but once you engage with them, either you’ll learn what’s not working in your craft or they’ll learn that you’ve created something that they’ve been waiting for, something that is filled with magic.

Novelist John Steinbeck on biblical translations (in East of Eden):

The American Standard translation orders men to triumph over sin, and you can call sin ignorance. The King James translation makes a promise in ‘Thou shalt,’ meaning that men will surely triumph over sin. But the Hebrew word, the word timshel—‘Thou mayest’—that gives a choice. It might be the most important word in the world. That says the way is open. That throws it right back on a man. For if ‘Thou mayest’—it is also true that ‘Thou mayest not.’ Don’t you see?

Memoirist Helen MacDonald on wildness:

Elusive, spectacular, utterly at home, the fact of these British goshawks makes me happy. Their existence gives the lie to the thought that the wild is always something untouched by human hearts and hands. The wild can be human work.

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Pro bono advice, part 1

Build something for a team you believe in or care about. Build it to spec for them. Make it really good. Design with sensitivity. Ride along with the folks who will be using what you build. Perhaps the most radical part of this suggestion, at least to anyone not in the legal field: consider doing this for free.

A few lovely things can emerge from this kind of effort:

• The organization you care about now has something well-designed and useful

• You learn, potentially quite a lot, about how to build this kind of thing

• You have a portfolio now. At the very least, the beginning of one.

In the US, we tend to think of this kind of model as only-for-interns. Something one does very early on with little expertise. It might be more useful to everyone involved mid- or late-career, when you have lots of schema and (hopefully) seasoned empathy for the clients you’re designing for, even if your expertise in the precise domain where you’re building is nascent. You know how teams and individuals work now in a way you didn’t then. That could make what you build that much better.

-eric

Pro bono advice, part 2

The morning pages from Julia Cameron’s The Artist’s Way have become famous, beloved, dreaded. But for me, the most provocative and useful exercise in the book is one where Cameron asks you to write down a list of jobs/professions you have dreamed about but never attempted. Then she tell you to do some activity in the following week that gives you a taste of that profession.

Sometimes, this small step into that imagined world can sate you, all by itself. Sometimes, it reveals the line between fantasy and maintenance and further reveals that you may not have interest in crossing that line.

A third possibility: a pro bono design project like the one described above in part 1. It serves as a robust Cameron test. You live the fantasy, do the maintenance, and learn how the work looks and feels beyond self-helpful indulgence.

-eric

Bringing big team moves into small collaborations

We’ve found in context after context that planning backward from a bold definition of success, acknowledging incremental progress, tying productive choices to your team’s stated values, and hiring with thorough inoculation serve teams well and get significantly underestimated. These are cheap to practice and yield outsized results.

The moves work well when you’re running a big team. It can feel strange or awkward to pull them in much smaller collaborations. But they work there, too.

Don’t let go of your best practices because you’re in a more relaxed leadership team setting or a 1:1 partnership. Adapt them to that context.

-ben and eric

COMPELLING QUOTATIONS

AI observer Zvi Mowshowitz on changing the world:

If you have a good plan to change the world, it is going to involve causing a bunch of otherwise low-probability events to happen, either intentionally or via good luck.

Veterinary behaviorist Ashley Elzerman on cats:

I am always excited to see empirical work that increases our understanding of the social dynamics of cats, especially in multicat households where subtle, chronic tension can be hard for owners to identify.

Man of many tools Kevin Kelly on how LLMs work:

Catness is a direction, and so is fluffiness.

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Anxious? Connect or create. (or recreate)

When I’m not in the throes of anxiety and I can try to unpack what was happening in body and mind during those throes, I’m struck by how confident my anxiety is. Or maybe it’s how confident I am in my anxiety. Instead of open, curious, contemplative me, I’m hyper-focused, certain … distraught me. When I’m anxious, I have a pre- and post-verbal belief in what the future holds. Maybe not the events or circumstances, but at least the threats and feelings. I’m at the mercy of some version of, “1) I don’t know how, but 2) this is going to hurt and 3) I won’t bear it.”

Really? Is it? Will it hurt that bad?

Anxiety offers an unwinnable game. It makes bold assertions and gives everyone else the burden of proof. It’s often invincible to probabilities, common sense, even the other selves of you who cluck their tongues at anxious you.

To get out of it, or even pause it for a bit, I’ve gotten good advice to play a different game than the one anxiety offers. Get out of the actuarial business. Don’t predict. Connect or create. Talk to a real person you care about. Make a first draft of something and send it to someone else to look at and critique. If you can swing it, walk or jog for 20 minutes.

In each of these escapes from anxiety’s clutches, there’s a moving forward, an escape-to. Instead of mapping the future in an overconfident panic, you participate in a tiny piece of that future, ideally with someone else.

-eric

Proactive communication is like hydration

Here are a few ways this is so:

1. The signal you get that you need more of it is a lagging signal. When you’re thirsty, you’re already dehydrated. Of course you should drink that glass of water but that probably won’t even get you back to baseline.

2. Doing this well doesn’t necessarily make you feel better than you remember feeling before. This makes it tempting to let it slide.

3. Yes, you can overdo it. But overdoing doesn’t happen casually or even with serious effort. It happens in truly extreme circumstances.

4. Yes, you can accomplish this with muddled, alternative inputs. There’s water in coffee and lots of food. This can fool you into thinking you’re doing enough of it without effort or dedicated systems or rituals. There’s a good chance the defaults don’t cut it.

5. People invent, then sell, tools of varying cost and complexity to smooth or assist your practice of this. Like all other practices, this one is susceptible to fixation-on-tools and displacement-by-tools. Your Stanley cup might be the thing that gets you to drink all the water you’re supposed to drink. Or, it might be the thing that makes you think only certain water in certain vessels of certain style works for you, when the Elkay water fountain at the local airport, eg, does the job just fine. All to say, don’t wait for a sophisticated tool to begin your practice. Get it in.

6. Doing this poorly has symptoms and knock-on effects you don’t intuitively associate with doing this poorly. You feel bad, things feel bad, and perhaps you have a theory why. Before chasing that theory, double check this. Do some of this.

-eric

Reality can be persuasive (or, ditch memos for demos)

So much of the work within a team, especially a leadership team, is translation and persuasion. You have to make your idea intelligible to others across your differences of dialect and identity; you want to convince them it’s useful and good.

This feels stupidly obvious to me as I type it, because I’m thinking back on all the stupidly painful times I failed to practice it: reality can be far more persuasive than theory.

Let’s say there’s a continuum from Description to Depiction to Demonstration. As you move across that continuum, things get more real and you get more persuasive. A verbal definition of a shovel < a picture of a shovel < an actual shovel moving actual dirt.

If you’re feeling unheard or stymied in your attempts to translate and persuade, consider ditching your memo for a demo. In your context, how can you stop talking about a shovel and actually move some dirt?

-eric

COMPELLING QUOTATIONS

Songwriter John Darnielle on risk:

The canary in the mine saves you from what killed the canary when you released it into the mine, but you also don’t get to see the inside of the mine. That’s the trade-off.

Journalist Gary Sernovitz on units of currency:

For [Citadel CEO Ken Griffin], half a billion dollars is a basic unit of currency. He spent that much for twenty-seven acres in Palm Beach; for the joint purchase of a Jackson Pollock and a Willem de Kooning; in gifts to Harvard; and in political contributions, mostly to conservative candidates. He dropped a mere forty-five million on a stegosaurus skeleton, called Apex, which is now on loan to the American Museum of Natural History (though “the dream,” Griffin told me, “is one day she’ll be in Miami”).

Birder Stan Tekiela on the Brown Thrasher:

A prodigious songster. The male Brown Thrasher has the largest documented repertoire of all North American songbirds, with more than 1,100 types of songs.

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Leader vacation as leadership opportunity

You’re taking real-for-real time off, right? You better. It’s good for you. It’s good for your people, too. Ideally, you’re modeling for them what healthy management of a life and calendar look like.

There can be a second benefit of your real-for-real time away that pays dividends long after you get back. Your vacation can be a leadership opportunity for others on the team.

To make that so, name it that way and set your expectations. Prep the interim leader(s), set a goal with/for them, and tell the team whom they’re supposed to go to with questions. This will be the most real-for-real leadership development if these interim folks get to make actual decisions without consulting you while you’re away.

The defaults the team might rely on otherwise could be more cautious or humble than you want. Folks who could excel and grow might play it small for fear of overstepping. Others might resort to calling / Slacking / emailing you and/or waiting around for your return.

-ben and eric

Consider swapping out a standard 1:1 for an hour-long observation

Whether you are a manager or a consultant, you may be much more helpful to your report/client as an observer than you are as an interlocutor. In other words, watching what someone actually does can get you both a lot further than just talking to them about it post-hoc.

You don’t have to toggle all the way to observation and totally scrap discussion. But if the current proportion of your management time is something like 95% discussion - 5% observation, consider recalibrating.

You can target this observation, too. Sit down with your person and ask them to walk you through the most painful, energy-sucking part of their work. Sometimes you’ll be able to tell them right there that they don’t even have to do this part of it at all anymore. Sometimes you’ll be able to code or outsource it away. Sometimes you’re an expert at this noxious task and you can upskill them relatively fast. They might not like the task but with greater skill to dispatch it, they may not need to dread it anymore.

You can also ask them to walk you through the part of their work they love and draw energy from. Your vantage point, a little removed from the direct doing, can allow you to see places they might be able to do more of this thing they love, to their satisfaction and the good of the team.

-eric

Using Claude to unearth your revealed preferences

Wouldn’t you know, we’re now in the back half of 2026. Earlier this week, I had Claude put together a review of the first half of my year. I shared my calendar, the transcript of my other Claude conversations (which amount to a sort of daily journal), and a long list of financial transactions from credit card and bank statements. I had Claude connect to my Strava account and gave it access to this very blog.

I told Claude in a few sentences what my intentions and goals were coming into the year. Then I asked for a review of all that data to get at what my revealed preferences are. I wanted to know: Where is there a gap between intent and execution? What does the actual allocation of my time, attention, and cash show about my true passions? What’s inaccurate in the story I tell myself? What near-term moves could I make that would make that story truer?

Here’s a lightly edited version of the prompt I used, in case you want to try:

Today is June 30, so the halfway point of 2026. I want to do a searching review and assessment of the first half of the year, in part as a reflection and self-awareness exercise, in part to set up a maximally satisfying and effective second half of the year. I’d like this to encompass all of my projects and workstreams: my running, my work, my pro bono projects, my personal life (family, therapy, dating, friendships, etc). I think it’s probably most effective if it draws from Claude conversations, my calendar, my email, Strava, my writing at thisistheleaflet.com and any other data basins you might be able to draw from. I’m looking in part for revealed preferences that might surprise or sober me - where am I actually spending my time, attention, and energy, despite what I say or believe? What am I committed to or interested in but gets comparatively little time and investment? This is the first time I’m prompting the creation of an artifact like this but I could see myself wanting to set it up as something like a quarterly review-and-look-ahead in the future. I’m also conscious that the second half of the year will have some special events: [event, event, event, event.] Rather than one-shotting this, I’d like to think with you about approaches to design and delivery, marshaling any new connectors or plug-ins we need to, then running it. Based on this, what do you advise?

-eric

COMPELLING QUOTATIONS

Practitioner of surrender Sasha Chapin on introspection:

The proper end of introspection is not being filled with facts about oneself. Your introspection is successful if it is finite, if it leads you towards direct contact with experience. Get out of the way of your becoming.

Author Ian Bogost (via Rob Walker) on gratification:

The more I worked on understanding gratification, the more I tried to deemphasize the idea that feeling gratified requires work. We’re so used to thinking that feeling good must require effort! But the good feeling of your senses connecting to the world is weirdly effortless. It happens all the time. I’m touching the keys of my keyboard as I type these sentences. My forearms sense the smoothness of my desktop. In another room, I hear the tink-toss of a garment careening around in the clothes dryer. So I’ve found it helpful is to think of gratification as something the world gives and that you accept. The keyboard is offering me smoothness and clickiness; the dryer is tendering tink-toss sounds. To enjoy the momentary delights of the physical world, all I have to do is accept the sensory gifts it offers.

Sculptor and scholar of charts Edward Tufte on information

Information consists of differences that make a difference.

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Replacing opaque power moves with transparent teaching

Leaders often tell me that talented (young) folks they manage don’t yet have good judgment. They often seem skeptical that these folks will develop that judgment. So these youngsters get passed over for leadership opportunities. Leaders choose costlier or more complicated paths than assigning a young person on the team a new responsibility that will require the exercise of good judgment.

To borrow a phrase from my mentor Nancy Euske: one way that you can develop judgement in your people is to “teach them to worry like you do.” When you make a decision about something, especially if that decision involved a judgement call of some kind, walk your people through the process that brought you there instead of just handing down the conclusion.

Here’s the info and context I had, here’s what I noticed, here’s the pattern it rhymed with, here’s the thing that tipped me, here’s the tradeoff I saw and the bullet I was willing to bite.

This decision, even if it’s a relatively low stakes one, can become a parable of your team’s values and your own mental models. It’s a story people can learn from.

The school leaders and coaches who train elite teachers do this all the time. Teaching one period of one class is rife with judgment calls (which kid do you call on first, which kid do you correct silently vs out loud, when do you let uncomfortable (thinking) silence persist, when do you scaffold in some support, etc etc x 100). These great leaders and coaches model and narrate their thinking, then have the teachers they’re training do it live.

Like almost any other skill, good judgement can be taught. Organizations that believe this and then get good at it outperform the ones that don’t.

-ben and eric

Beware the trappings of 1990s television

Hey, in this economy, you might have heard, each of us has many demands on our attention. If we’re on any social media platform at all, even Strava, even LinkedIn, we can succumb to an infinite scroll of others demanding, demanding, demanding, that we pay attention which is to say, in some way, that we pay.

With that in mind, it’s funny to me how much I still pretend that media I push out in the world have a safe, orderly conveyor belt to rest upon, one with clean edges and some relationship to familiar precepts of friction and gravity. I pretend that there is such a thing as a “season” of a show or a “launch” of something. Irrationally, I stress about tuning those correctly, in accord with rules that stopped applying some time in the last 15-20 years. A show isn’t a seasonal good anymore. It’s a bolus you sample or binge. For your “launch” to have the character of a splashy, attention-catching debut of old, you have to spend an immense amount of money and even that is no guarantee.

On one hand, this is a bummer. There’s nostalgic comfort for me in the idea that I’d tune in with a sizable chunk of America to experience the same new thing at the same time. That we’d all be lucky and safe enough to have the chance to experience it together. There’s a thrill imagining that a sizable chunk might experience something I made. For almost 100 years, mass media worked more or less like that.

On the other hand, this seasonlessness is an opportunity. I can experiment and adjust ongoing. I can respond to an audience – my community – and make my thing better for them without waiting for the seasons to turn. I can make more stuff.

I often feel great vexation with philanthropies because they assign themselves the problems and constraints of government agencies. They opt into tortured inertia. But the structure of my madness is similar. Little creator/designer/product launcher me – I assign myself the problems and constraints of a big corporation in the broadcast era.

No need for that. Nimbler doing, happier thinking await in the space beyond.

-eric

Pencil and paper as technology

As Claude has gradually become my most consistent coworker, I’ve found myself getting increasing satisfaction and value out of a much older, cruder technology: pencil and paper.

Before flinging a prompt out at the most powerful computer in human history, I like experiencing the discipline a sketchbook forces. Unlike a galaxy of chips and pixels, the discrete inches of the page require decisions. The ratio of output and input is tighter. I can one-shot a line, not a whole piece of software. Relationships between the elements on the page are visible; they’re right there.

Given what Claude can do and “see”, my sketch is interoperable. My hand-drawn sketch, the wobbly first butterfly, can shape and steer the rest of the thinking that follows, whether I’m doing all of it or I’m doing it in tandem with Claude, or Claude is taking it and running.

-eric

COMPELLING QUOTATIONS

Poet Emily Dickinson on filling a gap:

To fill a Gap

Insert the Thing that caused it—

Block it up

With Other—and ‘twill yawn the more—

You cannot solder an Abyss

With Air.

Writer Han Ong on the comedy of our shortcomings:

Life being a comedy, of course, you never escape even those folks whose skulls you have imaginatively crushed in your writing; their signature epithets and reflexive unkindness may suddenly erupt from inside your own skull.

Critic Louis Menand on the point of Lady Chatterley’s Lover:

The whole point is that they love each other. If you don’t get that, you don’t get the book. People who love each other often have sex. So, in “Lady Chetterley,” the lovers have sex, and Lawrence describes it.

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Affordances

Good design of objects and UI takes advantage of affordances. Psychologist James Gibson came up with the term and defined it this way:

The affordances of the environment are what it offers the animal, what it provides or furnishes, either for good or ill. ... It implies the complementarity of the animal and the environment.

Examples abound. A handle on a mug is an affordance. It makes a hand-shaped hole with an insulated arc that’s sitting next to very hot stuff. You see the handle and it makes sense to reach for the handle instead of the body of the mug. On your computer screen, a button changes color when you hover over it. This tells you “hey, this button is clickable.”

When you’re the leader, you very often encounter people not doing stuff you want them to do. This will really bug you when the stuff we’re talking about is stuff everyone here on the team agreed we’d do. It will puzzle you when the stuff is a customer or community member not doing things that they said in a focus group or casual conversation they really wanted to do. What gives?

The answer here might be that you need an affordance. Make it easy for your people to do the thing by making it intuitive to do that thing when the time comes. Don’t put a reminder in a standard business envelope (which reads as “this is trash, throw me away”; send a postcard instead (a postcard is the mail without the envelope). If the goal of your retreat is for people to build trusting relationships, don’t sit them in rows of chairs facing a giant projector screen for hours. If you want people to follow a particular financial policy, don’t bury the policy ⅔ of the way through the .pdf of the employee handbook.

-eric

Prototyping to end a leadership team tug-of-war

I give leadership advice for a living. That means I’m often talking to people who are part of leadership teams at their organizations. Maybe this is weird or wrong, but I found this part of being a leader one of the worst parts. This was true even in cases where I admired, respected, and enjoyed the other people on the leadership team (lucky for me, this has been most cases). We’re all badasses here – why is this not working???

A reason this has been hard for me is these teams tend to have the least-defined decision rights and processes of any team. When there’s one boss and a bunch of reports, things can be relatively clear even without clear definitions. Leadership teams, though, tend to be teams of peers and can also be places where the members want to take a break from being the big deciders all the time. So the hierarchy is still there but it’s sorta on pause and the resulting politics are stuttering and strange.

This is a lot of words to say: I got frustrated by how little leadership teams got done and how long we got stuck in unresolved debates.

A path out of such debates is a prototype. Build and test some version of a proposal that’s under consideration. Make it as quick and dirty as your context requires. Using an LLM or coding agent can be great for this – you might learn everything you need from something that stands in rather than stands out.

A thing I like about the prototype path is anyone can suggest it and, thanks to our LLM friends, almost anyone can own it. When you pitch a prototype, you might find that the rest of your leadership team is grateful to you, no matter how crummy or cool your prototype ends up being, because you ended a debate without anyone having to lose face.

-eric

If you run a non-profit, you’re no longer at the mercy of your software

Some of the work I enjoy most is with the lil Davids of the social change world. The 5-person non-profit slinging rocks at the meanest giants they can find.

The Davids that inspire me most have become elite slingers. They have developed good aim and damaged many an ogre. But these same Davids are often annotating receipts by hand because the HR software only accepts this one weird file type that they don’t have a license for the native software of that makes it and also that one spreadsheet tab is broken because that really smart woman from the local university who built it well she was only here for that one summer and then someone deleted the contents of that cell by accident dear god above why is the world like this we have this heap of lethal stones and these artisanal leathern slings and rotator cuffs like whoa and do you KNOW how many giants are gnawing the sleeves off their tunics just the other side of that hill, hungry for Davidian gristle? We definitely don’t have time to fix this, so let me see here, $9.58 for gas for travel to semi-annual team dinner, yep.

Listen, Dave. You aren’t at the mercy of your software anymore. Not even the cuddly-interfaced non-profit-marketed software. If you’re having to do something manual, if there is tedious repetition, if one of your programs doesn’t talk to the other one – that can be fixed and fixed cheap. You can do it yourself with Claude Code, or you can hire a college student to fix it for you with Claude Code, or you can apply to have Anthropic give you $10,000 so that they can also give you someone to work for you for a year to fix it.

The meme two years ago when generative AI was taking off was a thing about computers getting to do all the art and the humans being stuck with the spreadsheets. Flip that, David. The bots haven’t been trained to make great art. But damn can they make some software.

-eric

COMPELLING QUOTATIONS

Octogenarian Bob Dylan on being an octogenarian:

You don’t chase the parade anymore. You’re an old king from some vanished country. You’re harder to program. You’re not rushing to become anything and you’re not haunted by things that you did. You’re haunted by how little of it really mattered in the way you thought it would.

Guy who eventually cut stuff out of paper Henri Matisse on what he was up to:

I do not paint things, I paint only the differences between things

Poet Victor Hugo on the loss of life in war:

Fugitives, wounded men, and dying,

In caissons, stretchers, and sleds, overloading

The bridges, falling asleep by the ten thousand,

Woke up, hundreds, or less.

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A second hand on the wheel (yours)

When your organization is growing and you’re chasing a big mission, you’re going to encounter new chunks of work that need leaders. There will be more of those chunks than available, seasoned leaders. Someone young or relatively untested is going to get a chunk.

Some execs bend over backwards to avoid this. They spend big money to go to market and find a shiny veteran leader they can patch in. They outsource to consultants who can’t fully own the chunk but give adult-in-the-room vibes (or slides), at least.

A better approach is to use this situation to make your young leader nearly as capable as you are, with the confidence to match. To achieve that, the young leader needs to be the named and legitimate owner of the chunk of work. They are in the driver’s seat, holding the steering wheel.

Their work has real stakes. They make the decisions, they eat the crow, and they earn the credit. When the project is urgent and stakes-y enough, you are not abandoning them to the open road. Rather, your hand rests lightly on top of theirs on the wheel. You’re not driving or backseat-driving. You are near enough that a learning mistake doesn’t become a crisis.

Importantly, you gotta tell the young leader and the team what’s happening here. It can help to be quite concrete about this, eg,

“while [Young Up and Comer] is taking on [Gnarly Important Project] you’ll probably see me off camera in meetings they’re leading. You’ll see me show up in documents they’re writing and reviewing. You might even see me whispering in their ear real-time during meetings. Don’t take any of those as bad signs or a lack of trust in [Young Up and Comer]. Instead, I invite you to see those moves the same way I do: votes of confidence in [Young Up and Comer]’s growth.”

If you do this well, you get a compounding return on your effort. Instead of just having a problem solved, you also have a new leader capable of solving problems. Instead of a script that kills one particular bug, you have an agent who can find and kill other bugs independently.

-ben and eric

Inoculation to ambiguity and volatility aka change

When you’re in startup or turnaround mode, the rate and weight of change at your organization are high. People might have titles, but each role is more like a beach bag than a cellophane-sealed container. There’s lots of stuff in there, some of it is covered in sand, some of it leaks, some of it doesn’t make sense but there just wasn’t anywhere else to put it.

Good hiring practice includes a clear, detailed forecast of the hardest parts of the job. If you’re hiring for these beach bag kind of roles, you might not really know what exactly their job is going to entail in 3-6 months.

This means you should go one layer up with your forecast. Rather than describing particular tasks that might be hard, describe this pattern of volatility, ambiguity, and change. This person needs to be ready for – ideally, excited about – running into the unknown. If you can, illustrate what that might look like:

• “Things change fast around here. That means you might work super hard on something for weeks, only to find that we’ve decided to shift course. That thing you worked on gets shelved and you’re going to have to attack the next thing with just as much energy.”

• “We aren’t yet in a mode where we can accommodate preferences of work task and work style. You may have noticed we don’t really have an office yet. Don’t take this job unless you’re excited about becoming more versatile and trying new ways of working.”

The point of these warnings is getting folks on the team who opt in to growth in the face of your particular kinds of adversity. They will work harder and feel better that folks who get backed or bamboozled into that adversity.

-ben and eric

Make it a falsifiable experiment with a refresh date

The move I reach for when I suspect I’m right but can’t fully prove it and don’t have the data yet is almost embarrassingly simple: Could we try it for X amount of time? And at the end of X, I’ll put a reminder in our one-on-one to look at what we’ve learned/seen and check whether it’s still worth doing. This can unwind a stalemate and keep you from pulling an ugly power move involving some version of “because I said so.”

This approach can be especially useful when you’re working with a brilliant skeptic. This kind of person can balk at acting on an unproven judgment because, to them, acting without a first principles justification feels like surrendering rigor.

A time-boxed experiment with explicit success criteria can be rigorous without delaying you or sending you on philosophical birdwalks. Set up a hypothesis, a test, a decision rule, and a time to review. With this premise, they don’t have to abandon good epistemics; instead, they apply those epistemics to your bet.

You protect your ability to move nimbly in the face of uncertainty. Nobody has to say “because I say so,” because nobody has to win the prospective, theoretical argument. You just have to agree on how you’ll find out.

-ben and eric

COMPELLING QUOTATIONS

Former intelligence officer Shane Parrish on skill:

What looks like skill is mostly just a lot of work in the dark.

Investor Charlie Munger on ideology:

I have what I call an iron prescription that helps me keep sane when I naturally drift toward preferring one ideology over another. And that is I say ‘I’m not entitled to have an opinion on this subject unless I can state the arguments against my position better than the people do who are supporting it.’ I think only when I reach that stage am I qualified to speak.

AI observer Ethan Mollick on working with the wizard:

Last year I called this working with a wizard: you chant the spell and something happens. With Fable the spell has gotten powerful enough that I am no longer sure I am the wizard. I am closer to a patron. I describe what I want, I pay for it, and I judge the result. The conjuring happens somewhere I cannot watch, in hundreds of small choices I never get a vote on. The work has shifted from process to outcome. I no longer steer; I commission.

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