This morning I spoke to my CTO James at work. We were the only two in the office, it was early, and we got to talking about some of the blog posts I have been writing recently. He praised the Just Make a Decision one, and then we ended up on the topic of leadership. I asked him something that has been on my mind: how would you write about leadership? What really qualifies as a good leadership article?
His answer was that leadership is very hard to write about because it depends so much on context. Of course, most of us sort of know this. But when you think a little deeper about it, you realize just how much that matters. It is not just different from organization to organization. It is different from team to team, from dynamic to dynamic, from person to person.
You see a bunch of this content online. A bunch of courses, processes, frameworks, all kinds of things. And a lot of these things simply do not apply to a given team in a given context at a given size. It does not transfer. It looks good on paper, or in a LinkedIn post, or in a book, and then it falls apart the moment you try to use it somewhere specific. This reminds me of the article I wrote a couple of days ago called Make $5, which was about go-to-market strategy from a founder meetup I went to. It is more or less the same problem. For some companies, something is going to work. For others it is not going to even remotely be the same. It might not even be similar. It might actually be harmful. The advice that saves one team will break another.
It seems absurd when you watch some of the courses or go to some of the leadership conferences or read some of the popular leadership content. A lot of it is formulated in a way that feels like the only truth. Like this is how you lead, this is what works. In retrospect, I do not know if that is actually done on purpose, if these people believe that, or maybe they are assuming that their readers will understand that the advice is context-specific. Either way, when you read a lot of it, it reads as if it was the ultimate guide to leadership.
Maybe leadership, when it is read through a lot of these articles written based on the experience of others, should be observed exactly like that. As a story. This is also what James was saying this morning. He prefers to read articles where people write about their experiences of certain things, whether that is leadership or infrastructure or programming. He said he likes to read examples where people did something that they either failed at or succeeded at. Not guidelines. Stories.
Maybe leadership content should be consumed that way too. Maybe aligning with certain experiences is more useful than aligning with general principles. For instance, reading about experiences from teams of a similar size, or in similar circumstances, might work better because you can actually see yourself in those situations. You can connect the advice to something concrete.
It seems to me that no matter what subject we discuss, whether that is leadership or programming or code reviews or anything else, all of it becomes very abstract and very general if not applied to a given problem, a given context, a given example. Maybe even I, writing these articles, should add more context. As James said, maybe talk more about personal examples, personal experiences. If you try to write about leadership in a very general way, it might attract some people, but it might also push a lot of people away, because you just might sound as wrong as you sound right.
The question of how you quantify this
So the question becomes, how do you quantify this? I have read many good leadership articles. I want to become better as a person and in my career as I work towards being an engineering manager. You can read all of this content. You can apply to courses. I am currently taking the LeadDev Together: Pillars of Engineering Management course through work. And as I discussed this morning with James, there are so many principles out there that are simply made for larger scale. For enterprises. For organizations with layers and layers of management.
When you are on a small team, a lot of it does not apply. Some of it is counterproductive. Processes designed for 200-person engineering orgs create overhead that kills a 10-person team. Feedback frameworks built for formal review cycles feel absurd when you sit two meters from the person every day.
It is almost ridiculous in a way. It is almost ridiculous writing about this. Because some of the things that I might write about might be completely obvious to some people. Might be obviously wrong to others. Each one of these rules, each one of these dynamics really boils down to the context, to your team, to your organization, to the timeline when it is executed, to the circumstances, and to the competences that people have in a given company.
A toolbox, not a manual
I think, as I get more and more into leadership, I think more and more that the only rule worth following is to apply certain tools in a given context at a given time. Leadership is a toolbox. Being very open to change. Being open to ambiguity and lack of clarity. But also trying to use advice as a set of tools rather than something that must be applied in a certain order.
Take something as simple as direct feedback. In one team, very direct feedback can build trust because everyone knows the intent is good and nobody is playing politics. In another team, if trust is weak or people already feel unsafe, the exact same approach can create more distance and more damage. Same principle. Different context. Completely different outcome.
One could say that a lot of these leadership principles or rules or advice could literally be consumed as functions. And then being able to remind yourself of these functions when the time comes, when the situation calls for it. Each function has its own conditions. Each one works in some situations and not in others. Your job is to know which one to reach for. No course teaches you that part. That comes from working with people long enough to start recognizing the patterns.
What is underneath all of this
If I try to summarize my thoughts, and if we think about leadership meaning essentially just working with people, it boils down to this. In all of the sea of various principles and strategies, what you are really trying to build is judgment. More social intelligence as a person. More strategy. More patience. Less rush to judge.
That means gaining enough experience to recognize certain events when they happen. Certain disagreements. Certain frictions. Certain conflicts. And then being able to handle them as they appear, not as a framework told you they should appear.
That is the part nobody can teach you. You can read about it. You can take courses on it. Those things help, the same way studying music theory helps a musician. But the actual skill comes from being in the room when things go wrong. From being there when people disagree, when nobody knows the right answer. And learning to act anyway.
The reading gives you vocabulary. The work gives you judgment.