Peter Drucker wrote that the most important thing a manager could have was 'character'. I've asked myself "What is character?", and the best answer I've come up with is: "The willingness to do the right thing regardless of negative consequences to oneself." When I look at myself, I don't believe I have character. I want to be liked too much, and in my emotional core, I'm frightened. I don't think I'm alone in this. I think a lot of people in managerial roles have little or no character, and are unwilling to take on the monster of 'the system', whatever that means in their context, because in general their superiors don't want to hear the bad news a manager with character might deliver. I've worked for managers who were complicit in hiding the dilution of stock options; who failed to push back on higher-management policies that were eroding the morale of their subordinates; who failed to be straight with subordinates about things they could improve; Who accepted ridiculous schedule demands on their teams, allowing death marches. You've probably got many examples of your own.

I wish there were some easy solution to this problem, but I don't see one. I do recommend the NASA document "What Made Apollo A Success". https://ntrs.nasa.gov/citations/19720005243

> When I look at myself, I don't believe I have character. I want to be liked too much, and in my emotional core, I'm frightened.

First of all, thank you for the honesty. It shows good character!

I think you are right that good character is the core of being a good manager. It’s the core of being a good person. Virtue and duty. Unfashionable words, but the secret to “happiness” (the good life). The ancient greeks understood this, and it’s been the heart of western philosophy.

We are all works in progress.

I feel like the solution is ultimately going to be some kind of trust-less or low-trust system that ultimately incentivizes every individual to do the right thing, no matter where they might be in the hierarchy. We can't rely on top-down leadership spontaneously getting it right, let alone bottom-up leadership. This is why we need an external system that can incentivize people effectively, while being fully observable, trustable, reproducible, etc.

Thanks for the vulnerability and full marks for self awareness.

> I want to be liked too much, and in my emotional core, I'm frightened. I don't think I'm alone in this.

This makes at least the two of us. Of late, I’ve been observing how frightened my inner child becomes when it perceives not being liked. I’m straddling the line between the temptation to feel relieved by being liked and the survival-level fear when faced with disapproval. Breathe in, breathe out, breathe in, breathe out.

I’m certainly not an expert, but just based on my personal experiences, I think “character” is the distillation of a lot of different aspects of self, some of which are binary haves/don’t haves (“people listen when you speak”) and others that are more of a spectrum (a “willingness to speak up” is easier when the consequences are low).

That is to say, it’s really really hard to pinpoint exactly what makes up character and whether someone has it. So when we DO cross paths with those who clearly have character it’s all the more reason to network, communicate, and keep those people in our orbit, so that we might learn from them and maybe have a little bit of their character rub off on us.

I think your definition of character is useful, and I tend to agree with Drucker that it's the most important thing, because otherwise a manager will subject to whatever political winds are blowing higher up without any grounding or point of view on what should be pushed back on. On the other hand though, "do[ing] the right thing regardless of negative consequences to oneself" is easily stated, but in practice is not effective without influence—if you are constantly saying no, you'll quickly be replaced.

The uncomfortable truth is that "the right thing" depends a lot on the point of view and narrative at hand. In large organizations political capital is inherently limited, even in very senior positions. It's especially challenging in large scale software development because ground-level expertise really is needed to determine "the right thing", but human communication inherently has limits. I would say most people, and especially most software engineers, have strong opinions about how things "should" be, but if they were put in charge they would quickly realize that when they describe that a hundred person org they would get a hundred different interpretations. It's hard to grok the difficulty of alignment of smart, independent thinkers at scale. When goals and roles are clear (like Apollo), that's easy mode for organizational politics. When you're building arbitrary software for humans each with their own needs and perspective, it's infinitely harder. That's what leads to saccharine corporate comms, tone deaf leaders, and the "moral mazes" Robert Jackall described 30+ years ago.

> I want to be liked too much, and in my emotional core, I'm frightened

Many such people, dare I say most similar don't ever end up realizing this during their entire lives. They just live in mode which is subpar for them and their surroundings without ever having chance to understand. So bravo for that!

Even if it may not allow you to fully conquer it, unknown monster became known, described, and this can bring some inner peace which is also source of further strength in other areas.