Making the squishy legible

Someone great at this catches the small signals instead of punting them into the background of our noisy mental chatter. Michael Lopp calls the sense that something is off a “Twinge,” arriving in the unstructured way experience speaks to you [4]. His line belongs on the wall: “your failure to heed your Twinge is a management failure.” Lopp means it about the whole organization; the version that matters here is the twinge about a person, especially the unpleasant one.

Noticing is only the beginning. You feel the reaction, you act on it, you put your finger on the specific thing, and then you make it legible to everyone else with a label made of words other people hear and repeat, saying, “Yes, my god, that’s it!” You circulate it, you teach the team why it matters, you win their buy-in, and you codify it into a filter the team actually uses. Private clarity does not get you there; the team has to be able to run the filter without you.

And the great ones own their preferences without laundering them and without apology, interrogating them for fairness as well, yes. That is the golden mean of confidence: you own your read without apologizing for it and without going rotten into an arrogance that assumes you have nothing left to learn and no biases at all.

At Management Craft, we chart each competency on an abridged version of the Dreyfus Model, a system developed in the 1980s to chart how humans develop skills. The original model has six rungs, going from novice to master, but for simplicity’s sake we’ve simplified it to three: novice, competent, and expert (corresponding to 1, 3, and 5 on the Dreyfus Model). Read the proficiency rubric below for this competency and try your best to honestly assess where you sit on the spectrum from novice to expert.

You do not need a decade of scar tissue to start, though most first-time founders think they do: “I’ve only been doing this a year, how would I know what works?” My friend, you have been a human far longer than you have been a founder. You have built friendships, you have talked people into joining you, and you already carry a great deal of hard-won data about who lifts you up and who lands you in trouble.

Author Alan Weiss put it well: “Confidence is the honest-to-God belief that you can help others. Arrogance is the belief that you have nothing left to learn. And smugness is arrogance without the talent.” [5] Steve Magness adds that real confidence is self-knowledge rather than delusion, “being vulnerable, not delusional” [6]. Confidence here is just self-trust, and you have more grounds for it than you think. As Alain de Botton observes, “it might be brutishness, not confidence, that we hate.” [7]

So, go forth and heed the Twinge. Treat the strong reactions, to the things that make you say, “I fucking love that guy,” and the ones that cause you to wrestle with intrusive thoughts of throwing someone out a window, as legitimate signals rather than noises to suppress.

Put your finger on it. Move from “I don’t like this person” to the specific behavior. Someone sucks the air out of every room; you dig, and the real thing is that they never take responsibility and always blame someone else.

Name the positive version. Flip the aversive into the appetitive you actually want. “Blames everyone” becomes “high agency, takes responsibility.” Do this especially for the traits you admire, since those are the ones you are least practiced at naming.

Mine your network for the test. Use the Calibration Call: ask people who have hired for this how they interview for it. When I was trying to screen for high agency, an investor of mine gave me a question I still use: tell me about a time you felt slighted or treated unfairly, and what you did about it. Most candidates tell on themselves by blaming whoever wronged them. We all eventually find ourselves in unfair situations. The difference between people is how they respond.

The best answer I ever got came from a guy who shared a quota with a teammate who went out on parental leave. He asked his boss whether his number would come down, and was told no, so suddenly he had to hit double. I asked him what he did. He said, “I hit the fucking quota.” He was not going to let an unfair situation keep him from performing.

Build it into the filter, and run it as a hypothesis. Interview for the trait, reward it once people are inside, and stay open to being wrong and re-tuning.

Most importantly, close the loop. You will not be perfect at this. When a hire goes wrong, or someone quits, stop and ask what squishy thing stayed illegible, the thing you never interviewed for, filtered for, or rewarded. Then fix the system so it does not happen again.

The main way founders get this wrong is simple: they don’t do it. They sit at the novice level and decide that is fine. I have watched founders let themselves be treated like shit by people they hired and pay. The failure to make the squishy legible always shows up as underperformance eventually, because if you never filter for what actually works, you’ll hire ineffective people. Q.E.D.

Part of what makes it hard is that nobody warns you how becoming a founder is tantamount to unwittingly enrolling yourself in a crash course in knowing yourself. The whole premise of a lot of psychotherapy is that there’s a boatload of self we don’t see, sitting beneath the waterline of our own self-awareness, and plenty of people go a lifetime skimming the surface. Build a team and you lose that option. You have to work out what your preferences are, trust them, and learn to filter for them, or else the team pays for the parts of you that went unexamined, at the brutal cost of failure, sadness, and regret.

Another failure mode is darkly ironic. A good leader knows exactly how explicit you have to be when you communicate, and then forgets the rule applies to them on the one message that matters most: who belongs here and who does not.

And the darkest pitfall has to do with tolerance. When the team is not working, founders tend to conclude they need to become more tolerant of a wider range of people. Usually the opposite is true. They need to become more intolerant, which is a deeply uncomfortable idea to even propose.

Molly Graham, writing about founder mode, is blunt about how badly most of us start out. “Most new founders can’t identify the right kind of hire,” she writes, “let alone onboard them in a way that sets clear expectations or delegate in a way that makes their strong preferences or desires clear. This is why ‘hire great people and give them room’ is such overly optimistic, toxic advice.” [8] She tells a story from a conversation with Mark Zuckerberg, who said everyone thought he was a terrible manager. Her answer was that he simply had to find people who thrive working for him, because every manager has a type. Working for Mark, she writes, meant no performance reviews but “robust, sometimes bash your head against the wall debate about ideas” and a lot of direct, sometimes searing feedback. It was not for everyone, and he built a team of people who thrived in exactly that. Ed Batista wrote a whole essay whose title is the rest of the advice: don’t wait [9].

The mean here is its own kind of golden mean, with a vice on each side. Under-do it and you are too flexible: you hold no line, you tolerate what quietly corrodes the team, and you apologize for preferences you should own. Over-do it and you are too rigid: so fluent in your own preferences that you leave no room for anyone to fall short, forgetting that every hire is a trade, and you take some weaknesses to get the strengths you were really after.

The thread through all of it is a little tragic and a little funny. A CEO holds every lever of power in the company and is somehow still a tortured soul, and the torturer is them. They are the warden of their own prison yet again. The way out is inner work: figuring out what you like and what you don’t, and holding it with enough confidence to draw the line and enough grace not to demand perfection. People say founders should go to therapy to find this. Maybe. But being a founder is one of the few roles that forces the door to that self-knowledge open. All you have to do is have the courage to walk through it.