9 Comments

Man, this one is really well-written. And I say that as someone with so little integrity that none of this especially bothers me, so I’m not just automatically aligned with the content!

I think some of this dilemma is a function of -you guessed it- scale: there are things that enliven and motivate you that would not work on others, and vice versa, and what seems most impossible about being e.g. a CEO is the need to say things that work for all types at once. Some people, like you I’d assume, demand and require reality: substantive, honest, unvarnished reality; not only can you “take it,” you need it to be real and to be yourself. Others, of course, are different, and for all kinds of reasons. A single All Hands speech cannot appeal to both constituencies, and you probably cannot build a company out of just one constituency (both for hiring reasons and because it really does take all types!!!). But maybe this is all just cope!

Anyway: loved this one.

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Man, pluralism is really hard to argue against, huh? I think you’re right (as usual) but I do find the constant cradling to be condescending and the outcomes are... numbing? There must be another way.

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I like to hope that it’s possible to square all these things; I think believing you can is important to getting as close as possible. And I do think *many* leaders / companies do this really incompetently, so we should separate the abstract situation from the typical reality, which is: shit jobs of balancing these things and a lot of lazy lies and so on.

One thing is like: you can have relationships with your colleagues in 1:1 or small group contexts that are realer. Therefore the % of “culture” that unfolds in public vs private contexts is relaxant to this. A company that insists on “transparency” will gravitate towards public contexts where truths get suppressed, sadly, so those virtues are already in tension, and there are more!

It’s exhausting lmfao.

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“A company that insists on “transparency” will gravitate towards public contexts where truths get suppressed” -- what makes you say this? You must know something (so many things) that I don’t.

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Well, transparency basically means “doing things in public.” The CEO can (1) have conversations with small groups / teams in which they can be real, but every conversation will be different and there will be silos of variant knowledge and so on; or (2) the CEO can speak to the entire company, in an All Hands or an email to everyone or whatever. And that latter path is more “transparent,” meaning that more people can see the same thing / access the same information, but that just means what they access / the information has to be “for everyone,” which practically means “for the lowest common denominator.” The content will need to be safe for the broadest pool of employees; the messages will have to be somewhat bland and indirect; nasty, nuanced elements will need to be avoided, as there’s simply no way to get into the weeds with large groups efficiently / sanely.

So demands for transparency and communication often lead to these outcomes where low information content / lies are selected for. The “realest” companies I’ve been at, and Substack is one, have the least transparency (we do okay on that front, but I’d say we do better on “realness” than on transparency / comms). Tradeoffs everywhere 😤😤😤🤮🤮🤮

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That makes sense! I guess I’d argue that leaders often steep far lower than the lowest common denominator and those denominators at the bottom are well aware that they’re being fed an inauthentic message. Why do this waltz?

You see this in politics all the time: nobody says what they mean and everyone knows it. It’s like we’re all writing, reading, and interpreting The Bible all the time. I’d like to believe that there’s a way to address a large group of adults as adults and present them with tough, ambiguous problems without obvious solutions. They can handle it as well as you or me or any other leaders can.

(Man this Russian nesting dolls of replies is wild! Software is hard 🙃)

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No this is a perfect interface. We started from first principles, we took a step back, we imagined and empathized, and this is the result: a flawless user experience for all purposes.

I think what you’re anchored on is the important point, and it’s very real. David Deutsch has this line about most compromises being “no one’s idea of what will work,” which is related: when you average out ideas, messages, concepts, when you compromise them for these scale reasons, you can wind up with content that’s “no one’s idea of what’s true or good.” And that is weird: how much time we spend being told things that no one believes or takes seriously. I would argue that that is a failure on the part of leadership; at least one constituency should be happy with your messages!

(In politics, the situation is slightly different because one constituency will always be happy with you, so it’s more about avoiding things that would alienate them; so like 99% of what they all say is totally, totally empty, and everyone knows it as you say!!!).

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Just re-read this. Best thing I’ve read this year.

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👏🏼👏🏼👏🏼 Aries szn is here and it’s 🌶️🌶️🌶️

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