I’ve been thinking a lot about leadership lately, for no reason at all connected to the news or the state of social media or the way we’ve constructed an economic sytem that allows petulant man-children to set billions of dollars on metaphorical fire because strangers on the internet made fun of him while simultaneously pretending that homelessness is an intractable inevitability that can only be solved by brutalizing the unhoused rather than taking away those billions of dollars from aforementioned megalomaniacs.

Sorry, where was I.

I’ve been thinking a lot about leadership lately, and I’m starting to think that the single most important trait of a good leader is the ability to listen to someone who has less power than you do about the ways in which you’ve fucked up.

I realize it’s folly to distill anything as complex as leadership down to a single dimension, which is definitely not going to stop me. The literature on leadership can and has filled many an underused MBA library. I won’t pretend to have read more than half a dozen of these because business psychology books give me hives, but I did go to business school and I have been forced to sit through many an anodyne TED talk in the name of professional development, so I feel somewhat qualified to pontificate on this.

There are lots of parameters you can use to gauge someone’s effectiveness as a leader. These might include whether they inspire, whether they communicate well, whether they raise up those around them, whether they can shift between strategic and tactical thinking, whether they understand how to measure success, whether they have the executive capacity to be decisive about the right things, whether they have the courage to take risks, or any number of other impressive-sounding traits.

Different ventures will need more or less of each of these things from its leaders. But sooner or later, a leader will fuck up. Leaders are only human, and humans fuck up all the time, and the fuck-ups of leaders are proportionately that much more impactful given their structural power.

It is unreasonable and unfair to expect a leader not to make mistakes. It is, however, extremely fair to expect a leader to own up to those mistakes when they happen and to take steps to correct those mistakes. I don’t care how well you practice the tenets of servant leadership if you can’t admit when you’ve picked the wrong person to empower, or how good you are at being strategic if you’re oblivious to signals that the execution of that strategy is harming people1.

The structure of leadership makes it difficult for you to receive high quality signals about your performance, particularly if you’re someone with significant privilege. As you advance in any given hierarchy, the people around you are more likely to look and think like you and less likely to feel the impact of any harm you cause. As you advance, the likelihood that your good opinion can improve someone’s life increases, and the incentive to risk that good opinion for the sake of telling the truth decreases. The higher up you climb, the more it takes active, daily effort to seek out the truthtellers among those you lead and to open yourself to their critiques.

If you can’t remember the last time a subordinate told you to your face that you did something wrong, it’s probably time to check to see whether you’ve surrounded yourself only with people who tell you what you want to hear. If you always have a perfectly rational reason (smart people are great at rationalizing) for why someone isn’t worth listening to, remember that the expected return of critiquing someone with power over you is generally pretty terrible, and people who do so are generally trying to help, so it’s probably time to try a little curiosity rather than immediately dismissing them. If you can’t remember ever being wrong at all, it’s probably time to—I don’t know—go to therapy or something and figure out why the prospect of admitting fault feels so threatening to your ego that you would rather run an organization aground than feel the slightest loss of pride.

Otherwise you lose all sense of perspective and end up buying a social media website in the hopes of gaining the approval of a bunch of white supremacists only for everyone on that platform to unite for the first time in sixteen years to cyberbully you.

Well, probably not that, specifically. But we all have our Twitter.

  1. Assuming harming people wasn’t the goal. If it was, we have different issues to talk about.