Regretful leadership

I

Did you know that during the Vietnam War, there were almost 1000 cases of military personnel killing their superior or commanding officer with grenades? And even more suspected cases of friendly fire from firearms. It was so common that they came up with a word for it — "fragging".

I'm sure every one of those cases had their own unique constellation of actors with their own unique constellation of motives. But man, it sure fits the broader narrative of the Vietnam War, doesn't it? It's just a complete breakdown of hierarchy.

It's not too hard to think about a prototypical fragging case. You have an officer on some kind of power trip, making decisions that are actively dangerous to troops on the ground. Individuals are forced to choose between their own safety and the impossible objectives of a disconnected leadership. Most often this just led to lying — platoons claiming they completed missions that they definitely didn't, or soldiers reporting kills that didn't happen. But once or twice, a grenade may go missing and a tent may get vaporized in the night.

Or, I guess, 1000 times.

After Vietnam, military leadership was rightfully excoriated for their complete lack of awareness of the situation on the ground. There was a gulf between the experiences of the average soldier and the generals and politicians making the calls. And in that gulf, a festering wound¹.

II

I love Office Space. For those who haven't seen it, Office Space is a 90s workplace comedy told from the perspective of the ever-put-down peons, the bottom of the hierarchy. After years of mistreatment, the three main characters decide to retaliate by stealing from the company.

It's a hilarious movie on its own merits, but I think part of the reason it has had such staying power is because it speaks to real experience. The main antagonist of the movie is represented by this punchable schmuck:

Bill Lumbergh. A guy who exists to make the protagonists miserable with his ridiculous requests, invariably followed up with "that would be great". Bill is not openly malicious. But he is passive aggressive and disconnected. And as a result he can't or won't understand why his employees might not want to come into work on a Sunday.

My hunch is that every average office worker in any industry has met this guy, or at least has heard of him. Even at Google, where for the most part managers were fantastic, there were endless complaints about how executive leadership just didn't understand what was happening on the ground. I think in general, there's a natural gap between those who do and those who (ostensibly) lead. And when that gap gets too large, things start going sideways.

III

Recently I've been turning over a concept in my head that I call "regretful leadership". The basic sketch of the idea is that the best leaders are those who make hard decisions, but regret having to make them.

This concept came out of some of my observations as a startup founder, and conversations with Mia and Ganesh² while hiking in the San Diego desert.

When you're running a startup, you very quickly learn to appreciate high quality information. There are ten million decisions that need to be made, any one of them can have significant impacts for the future, there just isn't enough time to reason from first principles about everything. Having a good gut instinct can take you pretty far, but having a good signal is game changing. As a result, a lot of operators build heuristics and intuition about what to look for in different situations. Scar tissue transfer is incredibly valuable. And the best operators are always, always, seeking more information.

More information leads to better choices. But it also leads to a deeper understanding of the costs of your choices. And in any leadership position that matters, those costs are going to be deeply personal ones.

Put bluntly: someone will get hurt as a direct result of your decision making.

Here's a motivating example, relevant to startup world. As an engineering manager, you may one day have to deal with someone who has been around for a while, who isn't performing as well as they should. This happens more often than not — startups and their needs often change faster than the people who run them, and a superstar in one environment is a needs-improvement in another. But firing is costly. Not just, or even mostly, in terms of expertise. The biggest cost is invariably to the team culture, because on a small team everyone (including you!) is pretty closely bonded together. And if you've done your due diligence and fully understood all the reasons why someone may be underperforming, you will likely have to deal with the fact that firing them is going to make their life significantly worse. Sometimes the right move is still to fire someone. But it hurts. It should hurt.

Sometimes we have to do layoffs, but we want the C-Suite to be aware of the lives that have been thrown into turmoil. Sometimes we have to implement austerity measures, but we want our politicians to think about every parent who can't feed their family as a result. Sometimes we have to go to war, but we want our generals to deeply feel the weight of deciding to send young men and women to their deaths³. And so on, up the chain⁴.

Thus, regretful leadership.

IV

I think someone could reasonably push back. Maybe it's a good thing if leadership is a bit distanced from the rank and file, especially if it will ensure that they can make hard decisions when the time comes.

Seems reasonable. But when I think through how that distance might happen, I start to doubt.

One way this could happen is that leadership actually just doesn't actually have all the relevant information. That is, because they don't fully know all the costs, it's easier to make a "hard" decision because it seems less hard.

I guess it's definitely possible for an executive to make the "right" call without fully understanding how that decision will impact folks downstream. Maybe a CEO shouldn't know how many children are getting screwed because of each employee being laid off. But I think without the additional information you increase the risk of simply making the wrong call, inflicting damage that could just be avoided or not working as hard to find alternatives. Going back to the Vietnam example, because the top brass didn't understand the psyche of their troops they ended up thinking they were winning a war all the way up until they lost. If the Pentagon fully internalized the costs of war, they may have run the war differently, or at the least pulled out much sooner (still a win condition, given how many lives that would save on both sides!).

Another way this could happen is that leadership is aware of the costs, but just doesn't care.

The problem here is that people leadership is about people. And in reality, people know what their leaders are like. If you have to give a team bad news, it'll go over much more easily if they respect you, think that you understand them, and believe that you have exhausted all other options before making a tough choice. I had to do this at least once at my startup — we were running out of money, and I asked the team to take pay cuts, and every person took a cut, on average 50%. The only reason that company still exists is because my team believed that I wasn't trying to screw them over, that I really did regret having to even ask to lower their pay. And, on my end, that regret also led me to work much harder towards a compromise that everyone could accept.

More broadly, I think I personally just don't want to be led by sociopaths. I think a society in which leaders are servants who are trying to improve things is better than a society where leaders only care about themselves. Maybe you can have a disinterested, fully informed leader who is also working towards the greater good. But I don't think there are many examples of this; any servant leader will regret something.

V

So far I've avoided writing about politics on this substack, but there's a first time for everything. I have a lot of opinions about the 2024 election, and I may write a longer post at some point. But for now, I'll stay on theme.

Fair warning for folks who would rather avoid the politics — skip to the end.

One of the things I liked about Biden, Romney, Obama, and McCain (before that I was too young to really remember much about politics) was that I got the sense they understood the gravity of the station they were running for. They knew they were going to have to make tough decisions, and they were going to regret having to make them, and in some ways that shared regret came from a lot of common ground, a desire to do good and improve the country coupled with the harsh truth that not everyone can win.

Maybe critics will call me naive, or nostalgic, or a hack. And maybe all of that is true. But regardless of my rose colored glasses for a past political era, I think it's very clear that both candidates on offer in '24 lacked any indication that they deeply felt the pain their policy choices may cause to their constituents.

And since we're talking politics, I'll go further. Trump, in particular, strikes me as never having regret anything in his entire life. It's part of his brand. Trump believes that Trump is always right, is always making the best choices, and the only reason anything ever goes wrong is because some other people (who were wrong) got in the way of Trump's utopia, because Trump is right.

This is obviously delusional. Many current Trump supporters openly say that the man is first and foremost self interested, motivated by greed and ego⁵.

Look, maybe tariffs are the right economic choice. Maybe we really should gut the DoE or VA or social security. Maybe cutting food stamps is what the country needs. But part of why I'm so skeptical is that it's obvious that Trump has zero understanding (or interest in understanding) what the results of his policies are in terms of human suffering. He hasn't priced in the costs. And as a result, he can't regret the choices that he has to make, the pain that he has to cause.

VI

As of November 2024, I'm well on my way to starting a second company. I've been trying to consolidate a lot of what I learned the first time around. And maybe more importantly, I've been trying to define my own management philosophy. Spoiler: it's a lot of servant leadership. Startups require so much trust and so much autonomy, how could it be anything else? Every employee worth a damn is taking a massive risk to be there. They need to believe in their leadership; and their leadership needs to draw out every bit of ability to make it all work. But I don't want to emphasize the practical aspects too much. Yes, it's true that I care about my employees because it's a practical necessity of a startup. But also, I care because I want to care. And yes, I think that attachment will lead to some hard decisions down the road. Decisions I'll regret having to make.

I think I'll be better for the regret.

1. WWI had a similar problem of disconnected leadership throwing waves of soldiers over trenches to capture feet of territory. There, though, war was still glorious and most people just died.

2. Writes All New Mistakes.

3. As an aside, I think this is also why it's generally a good idea to have folks with real armed combat experience in positions of leadership (the presidency, obviously, but also in the Senate/House). Some things are hard to internalize unless you've done it yourself.

4. I think there's a longer post in here somewhere about how our leaders have abandoned regret — they are too isolated, too atomized, that the people bearing the costs of their decisions are just statistics. Maybe another time.

5. Folks from his previous administration only have worse things to say.