Most people who lead others never took a course on leadership. They didn’t attend a program, read a textbook, or sit through a workshop before they found themselves responsible for a team. This is simply how it happens in most organizations. Someone performs well in their role, gets noticed, and gradually takes on more responsibility. At some point, they’re managing people. The formal training, if it comes at all, arrives after they’ve already started.
What I’ve observed over years of working in and around organizations is that the learning happens in a specific sequence, and it rarely looks like what leadership development programs assume. People don’t start with theory and apply it. They start with friction – situations where their old approach stops working. A person who was effective as an individual contributor discovers that the same habits that made them successful no longer fit. They have to figure out what does.
The gap between what someone knows how to do alone and what they need to do when responsible for others creates a kind of productive discomfort. This is where real learning begins. It’s not comfortable, and it’s not always recognized as learning while it’s happening. Often it feels like failure or confusion.
Learning through proximity and observation
One of the most consistent patterns I’ve seen is that people learn leadership by watching someone else do it. Not by being told about it. They work for or alongside a manager or leader who handles situations in a way that makes sense to them, and they absorb the approach. This happens almost invisibly. A person might not even realize they’re learning.
The quality of this learning depends entirely on who they’re watching. If they work for someone who manages through clarity and consistency, they tend to learn that approach. If they work for someone who leads through relationship and trust-building, that’s what they internalize. If they work for someone who avoids difficult conversations, they often inherit that pattern too. The learning is deep because it’s embedded in real behavior, not abstract principles.
This is why the first manager or leader someone works closely with often shapes their leadership style for years afterward. It’s not the only influence, but it’s significant. People rarely unlearn what they absorbed early through daily observation. They might refine it or consciously modify it later, but the foundation is there.
What’s rarely discussed is that this kind of learning requires the person to be paying attention. Some people are naturally observant about how others operate. They notice what works and what doesn’t. Others are focused on their own tasks and don’t absorb much from their environment. The people who learn leadership fastest tend to be the ones who are curious about how things actually work, not just about completing their own work.
Responsibility as a teacher
When someone takes on their first leadership role, the real education accelerates. They have to make decisions about how to allocate work, how to respond when someone underperforms, how to handle conflict between team members. These situations don’t have textbook answers. The person has to figure out what to do based on what they’ve seen, what they think is fair, and what they think will work.
Early mistakes in this phase are common and often necessary. A new manager might be too lenient, then swing too hard toward control. They might avoid a difficult conversation and watch the problem grow. They might try to be friends with their team and discover that doesn’t work when they need to make unpopular decisions. These experiences teach faster than any course because the stakes are real.
What matters during this phase is whether the person has someone they can process these experiences with. A peer who’s also managing, a mentor, or even just someone willing to listen and reflect back what they’re seeing. Without that, people often internalize lessons that are too narrow or draw the wrong conclusions from their mistakes. With it, they can extract the actual learning from the experience.
I’ve noticed that people who learn well in this phase tend to be the ones who are willing to admit they don’t know what they’re doing and ask questions. The ones who pretend to have it figured out tend to repeat their mistakes longer. There’s something about the willingness to be uncertain that allows for genuine learning.
The role of failure and adjustment
Leadership development without formal training is largely a process of discovering what doesn’t work and adjusting. A person tries an approach, it fails or succeeds, and they adjust their behavior based on the result. Over time, they develop a sense of what works in their context with their team and their organization.
The speed of this learning varies. Some people are reflective and extract lessons quickly. Others repeat the same mistake multiple times before it registers. Some are naturally flexible and willing to try different approaches. Others are rigid and keep doing what they’ve always done, just harder.
One thing I’ve seen consistently is that people who read widely tend to learn faster. Not because they’re learning leadership from books, but because they’re exposed to different frameworks and ways of thinking about problems. When they encounter a situation at work, they have more mental models to draw from. They can think, “Oh, this is like that thing I read about,” and try a different angle. It accelerates the learning cycle.
The people who struggle most are often those who are isolated – either because they work in a small organization with no peers, or because they’re not connected to anyone who can help them think through what’s happening. They’re left to figure everything out alone, and the learning is slower and often more painful.
Accumulation over time
Leadership capability built this way is often stronger than what comes from formal training because it’s rooted in real experience. A person who has managed through a hiring cycle, a budget cut, a team conflict, and a major project has learned something that can’t be taught in a classroom. They’ve felt the weight of their decisions affecting other people. They’ve had to sit with the discomfort of not knowing what to do. They’ve had to recover from mistakes.
What tends to happen is that over five to ten years, a person who’s been paying attention, making mistakes, reflecting, and adjusting develops a fairly sophisticated sense of how to work with people and move work forward. They might never have read a book on emotional intelligence or systems thinking, but they’ve lived it. They understand their own patterns and how they affect others. They can read a room and adjust their approach.
The limitation of this kind of learning is that it’s often specific to the person’s context. Someone who learned to lead in a startup might struggle in a large organization. Someone who managed a small team might not know how to scale their approach. Someone who worked in a high-trust environment might not have developed the systems and clarity needed in a less trusting context. They have to learn again in the new setting.
Formal training, when it does come, tends to work best for people who already have some experience. They can connect the concepts to situations they’ve lived through. They can question what they’re being taught and figure out what applies to them. Without that foundation of real experience, training often feels abstract and disconnected from the actual work of managing people.
