The Leaflet #131: teaching judgment, 1990s television, pencil and paper as technology
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.





