GCR problem #8: Leaders weaken themselves with misapplied epistemic humility
Most leaders in this cohort under-rate their own authority. They trust their self-criticism more than their confidence. They convert authority they demonstrably already hold into hesitation, asking whether they’re allowed to decide a thing that is plainly theirs to decide.1
This shows up so often among GCR leaders because epistemic humility is the field’s core virtue. Rightly so. Humility about whether you’re right soaks through the question of whether you’re allowed to lead. These are different questions. Collapsing them stalls a capable leader who waits for permission a) they already have or b) they simply can’t get (because they are the founder/boss – they are the ones who have to make the low-information, high-stakes decisions, the decisions you can’t get timely, epistemically pure, and authoritative answers for).
Fixing this requires separating the two questions.
Humility about the truth: keep it, it’s a strength.
Uncertainty about your authority to decide and to direct: this is miscalibrated and it costs your team in ways that aren’t in your line of sight. Your right to make a call is not a claim that you’re the smartest person in the room. That right rests on your accountability for the performance and well-being of the whole endeavor. If you’re the founder/executive, you’re the only one who carries that responsibility.
Once you’ve set these questions apart from each other, take outside data at face value. You get a 360 review because you have unfixable blind spots. Your ability to self-assess is limited. The epistemically humble leader will often tilt their self-assessment downward. So when the feedback says you’re more capable, more respected, or more authoritative than you feel, you should take that as signal rather than flattery. Treat the gap between how you see yourself and how a dozen colleagues see you as information to act on, not a discrepancy to explain away.
And for the reverse error: if you find yourself sorting reviewers into the ones who “get you” and the ones who don’t, immediately after a 360 landed uncomfortably: stop. The reviewers who surprise you are usually the ones with something to teach you.
-ben
Related: acting on blind-spot feedback and one sign your feedback culture is strong.
Teach them to think like you do > teach them to do like you do
A leader I work with wrote out a beautiful set of frameworks that were adopted across the organization. Across a few hundred people, the team applied her tools confidently. Alas, they were doing this in the wrong situations and for the wrong reasons.
Ex: Somebody wrote a one-page script for a tough conversation with a direct report that included the phrase, “I want to reassure you that you’re not in trouble” five separate times. If you have to tell someone five times they’re not in trouble, they know they’re in enormous trouble.
Leaders will sometimes fault a framework for low performance and then offer more frameworks to the person floundering. If the diagnosis is that people are being too literal about frameworks, telling them to use more frameworks reproduces the bug at higher volume.
To fix all this, it helps to imagine yourself as a ninth-grade English teacher. Imagine you teach your students that a good thesis statement addresses a core theme of the book, takes an argumentative stance on it, and makes clear that’s the focus of the essay. Everybody nods and gets it and tries it. Then every thesis statement you read looks like this: In this paper, I will show that a core theme of this book is [ ].
The students in this hypothetical learn the formal convention but not the point of that convention, the reason it should be deployed. An argumentative essay exists because a reader wants a controversial take from you, backed up with good evidence or reasoning. The real skill at the hear of it is generating a clear argument you can support. But the students learn to mimic the shape of a particular kind of sentence instead.
The failure mode in coaching adults is quite similar. When people apply your expertise clumsily or in the wrong context, they aren’t thinking like you think. They’re pattern-matching to things they’ve watched you do. They grab whatever you told them most recently and apply it to whatever’s in front of them.
A way past this is to change the question you tell them to ask themselves. Instead of “What have I seen my (trusted, expert) leader do in situations like this?” they should try “What advice would the (trusted, expert) leader give me about the situation I’m in?”. Better still: “What questions would she ask before giving any advice at all?”
-ben
transcribe your way through the darkness
When you are managing a big project, like putting on an event, and you are dutifully exercising productive paranoia, I suggest keeping your hands off the keyboard, at least to start. Instead, turn on the transcriber (Otter, Granola, Zoom, iphone voice memo, whatever suits your fancy) and say everything that comes to mind. All the details, the rabbit holes, the worries - get it all out there and don’t worry about keeping it linear, hierarchical, crisp. This is a messy first draft on purpose.
Then copy that transcript into your LLM of choice (Claude Opus 5.5 around here, for now) and ask that LLM to impose order upon it. Turn the transcript into an action plan or a set of communications to all the relevant people, stack ranked in order of priority, that you can review and send.
In this mode, you’re hiring Claude as a Chief of Staff. You’re sparing your actual staff the crazy-making burden of translating your anxious stream of consciousness, inferring what’s important from your tone of voice and the weird things your eyebrows do when you’re stressed.
In this mode, you’re likely also saving yourself significant low-output low-value time rejiggering the cells of a table or spreadsheet. Don’t fool around with paint swatches when you’re still mixing the concrete for the foundation.
Transcribe your way through the darkness.
-eric
COMPELLING QUOTATIONS
Critic Henry Oliver takes a road trip:
And who knows what else is coming? Drive the suburbs and see the great variety of houses, the bizarre Halloween decorations, the endless businesses; drive the highways and see the blaring and sublime advertisements that line all the roads—NOW HIRING, WE BUY GOLD, CHEAPEST CIGARETTES FOR MILES, SHE WANTS THE DECK, WORLD’S LARGEST FIREWORK SUPERMARKET, WE SELL FLAMETHROWERS—go to the supermarkets and see the great variety of life, go to the Piggly Wiggly, which was the first self-service market, and is now a living museum, with the old beige shelves, brands from the 1960s, and the typography your grandmother would have known. Nothing is boring in America.
Journalist Bob Woodward on the connection between paper and power:
So much of the U.S. government ran on paper. What Darman understood better than most was the flow of paper, what it said and what it left out. Darman introduced me to one of my most important channels of information: the staff secretary. “A key to understanding what goes on in any White House,” he told me, “is the staff secretary.”
The position sounded to me like a paper pusher, a mindless cog in the bureaucracy. In fact, as Darman tutored me, the staff secretary sees and controls all information that goes to the President.
Poet Ocean Vuong on poet Anne Carson:
For decades, Carson’s unapologetically erudite work has centered strangeness and mystery as methods of human revelation. And its myriad and restless formal enactments have granted endless permissions to multiple generations of writers. Like the best work out there, it fosters others as it forges new ways to be and think for itself.
There’s also a smaller group in the sector that has the opposite failure mode. These leaders see themselves as low-ego and humble while their 360 review flatly contradicts that view. These same leaders hunt through the 360 for reviewers that “read them well” so they can discount the unpleasant, inconvenient data.