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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AI for culture audits

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

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

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

Culture audit prompt:

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

-eric

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

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

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

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

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

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

-eric

A fun emergency plan

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

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

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

Two benefits I hope come out of this for you:

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

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

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

-eric

COMPELLING QUOTATIONS

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

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

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

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

Poet David Whyte on witness:

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

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Sketches of fantasy and maintenance

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

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

Fantasy is envisioning the greener grass.

Reality is mowing it.

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

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

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

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

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

What is the tending your pretending will require?

-eric

Using AI to find blind spots

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

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

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

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

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

-eric

Thinking of in person work as a retreat

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

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

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

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

-ben and eric

COMPELLING QUOTATIONS

Writer Julia Freeland Fisher on making up machine rules

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

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

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

Novelist Zadie Smith on art:

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

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

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

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

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

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

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

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

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

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

-eric and ben

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

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

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

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

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

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

-ben and eric

Micromove: naming contributions and naming contributors

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

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

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

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

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

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

-eric

COMPELLING QUOTATIONS

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

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

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

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

Writer C.S. Lewis on types of pain:

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

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

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

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

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

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

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

-eric

Insider fit beats specialist fit

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

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

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

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

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

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

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

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

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

-ben & eric

Do you have to hire true believers?

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

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

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

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

-eric & ben

COMPELLING QUOTATIONS

AI chronicler Zvi Mowshowitz on getting AIs to write well:

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

Philosopher Krista Lawlor on being reasonable:

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

US Secretary of Education Linda McMahon on steak sauce:

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

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

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

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

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

Two things usually become clear when you do this:

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

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

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

-ben

An alternative view of spare CEO capacity

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

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

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

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

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

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

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

-ben

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

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

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

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

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

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

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

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

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

-ben & eric

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COMPELLING QUOTATIONS

Poet Ocean Vuong on the writer’s job:

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

Songwriter John Darnielle on writers’ errands:

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

Poet Pablo Neruda on loving:

I love the handful of earth you are.

Building identity and agreement on day -1

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

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

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

I suggest two moves to get this agreement set:

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

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

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

-ben

A thought experiment using younger you

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

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

• Thinner network

• More physical energy

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

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

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

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

• Use OOMs to unlock possibilities

• Cosplay to get unstuck

-eric

AI and ClipArt: a millennial tale of taste

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

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

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

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

-eric

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

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COMPELLING QUOTATIONS

Poet and lawyer Reginald Dwayne Betts on time in prison:

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

Of prison home. Awakened to guards keeping tabs

On my breath. Bartered with every kind of madness,

The state’s mandatory minimums and my own callus.

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

Wrecked cars; drank whisky straight; nothing suffices –

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

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

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

Mississippian Wright Thompson on New Orleans in 2015:

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

1. Power v clarity

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

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

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

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

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

-eric

2. Executive coaching reduced to three questions

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

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

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

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

ben & eric

3. Using small success to build big identity

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

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

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

2. Naming the impact it had

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

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

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

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

-eric

COMPELLING QUOTATIONS (back by popular demand!)

Anonymous, in Tehran, on living in a war:

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

Novelist Hilary Mantel describing the experience of a beheading:

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

Commentator Chuck Klosterman on movies:

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

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1. Product development: a simplified journey

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

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

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

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

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

-eric

2. Enrolling those you wish to persuade

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

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

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

-eric

3. A suggested replacement

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

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

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

-eric

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

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

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

-ben

2. Making good use of a rough patch

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

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

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

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

-eric

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

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

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

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

-eric

COMPELLING QUOTATIONS

Writer George Saunders on connection:

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

Writer Imani Perry on prayer:

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

Butterfly enthusiast Vladimir Nabokov on art and nature:

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

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

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

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

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

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

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

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

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

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

But this doesn’t happen without your intentional framing.

-ben

2. Growth mindset meets pragmatism

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

I simplify that to two questions.

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

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

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

-ben

3. Unpacking and overcoming a bureaucratic “no”

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

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

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

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

-eric

COMPELLING QUOTATIONS

Artist of noticing Rob Walker on the “unshazamable”:

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

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

Writer Wright Thompson on land and creation in the Delta:

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

Poet WS Merwin on early middle age:

It sounds unconvincing to say When I was young

Though I have long wondered what it would be like

To be me now

No older at all it seems from here

As far from myself as ever

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

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

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

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

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

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

-ben

2. Servant leadership, trust but verify, and training

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

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

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

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

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

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

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

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

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

-ben

3. Setting people up for direct feedback during hiring

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

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

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

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

-ben

COMPELLING QUOTATIONS

Founder-ologist Paul Graham on branding:

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

Writer Sam Kriss on the difference between Americans and Brits:

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

Novelist Fyodor Dostoevsky

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

1. Before you fire someone

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

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

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

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

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

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

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

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

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

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

-ben

2. After you fire someone

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

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

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

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

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

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3. Refreshing feedback when it gets perfunctory

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

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

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

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

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

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COMPELLING QUOTATIONS

Former NFL coach Bill Parcells on deceptive routines:

Don’t confuse routine and commitment.

Former CEO of Hallmark Don Hall on brutality:

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

Earth cataloguer Stewart Brand on realism about repair:

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

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

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

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

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

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

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

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

-ben

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

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

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

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

Care Personally, Challenge Directly

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

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

Three Things That Build the Culture

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

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

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

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

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3. Structures for a steady stream of feedback

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

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

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

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

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

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

And: the question that builds culture

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

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

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

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

-ben

COMPELLING QUOTATIONS

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

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

Painter Francisco Goya on cause and effect:

The sleep of reason produces monsters.

Supreme Court Justice Anthony Kennedy on learning:

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