What separates years of leadership from years of growth
There’s an assumption we make about experience that I’m not sure holds up.
We assume that the longer someone leads, the better leader they become. Certainly, experience matters. There are situations I handle differently today simply because I’ve seen some version of them before. You begin to recognize patterns. You know which problems need immediate attention and which ones probably need a little time. You get more comfortable having difficult conversations and making decisions when you don’t have all the information you would like.
But experience and growth aren’t necessarily the same thing.
I’ve worked with leaders who have been doing this for twenty years and leaders who have been doing it for two. Sometimes the person with less experience is learning faster because they are paying closer attention to what their experiences are teaching them. The other person may have far more experience, but they’ve also become very comfortable with the way they see things.
That’s an important distinction.
We can spend years reinforcing the same assumptions, reacting to situations the same way, and getting frustrated by the same problems. Eventually, we stop questioning those patterns because experience has given us confidence in them.
That’s why I think leadership reflection matters. Experience gives us something to work with, but reflection is where we begin to understand what the experience should teach us.
The Question We Usually Ask First
Think about what normally happens when something goes wrong at work.
A deadline gets missed. A meeting goes poorly. Someone doesn’t follow through on an expectation. A decision we made creates a problem we didn’t anticipate.
We start trying to figure out what happened.
That’s part of leadership. We need to understand the problem and determine what needs to happen next. But I’ve noticed how quickly that process can become an examination of everyone else.
The employee didn’t communicate. The team wasn’t prepared. Another department dropped the ball. Someone should have raised the issue sooner.
Maybe all of that is true.
I don’t believe good leadership means assuming everything that happens is somehow the leader’s fault. People have responsibilities. Standards matter. Accountability matters. Sometimes someone simply didn’t do what they were supposed to do, and we shouldn’t manufacture a leadership failure where there wasn’t one.
But there is another question worth asking before we move on.
What was my part in it?
Maybe the expectation wasn’t as clear as I thought it was. Maybe I saw the problem developing and waited too long to address it. Maybe someone tried to tell me something and I had already made up my mind. Maybe I stepped in and solved the problem so many times that I shouldn’t have been surprised when the team waited for me to solve this one too.
That question doesn’t remove anyone else’s responsibility. It simply forces me to examine mine.
I think some of the best growth I’ve seen in leaders starts there.
Reflection Isn’t the Same as Replaying What Happened
Most leaders think about work long after the workday ends. We replay conversations on the drive home. We think about what we should have said. We wonder why someone reacted the way they did. We revisit decisions and sometimes argue our case again in our own heads.
I’m not sure I’d call most of that reflection.
A lot of it is just replay.
There’s a difference between thinking about an experience and examining it. If I replay a difficult conversation five times and every version ends with me being right and the other person being wrong, I probably haven’t learned very much.
Michael Bungay Stanier makes a useful point in The Coaching Habit about learning. People don’t really learn simply because they are told something or even because they experience something. Learning starts when they have an opportunity to recall and reflect on what happened.
That idea has stuck with me because leadership gives us plenty of experiences and very little natural space to examine them.
A meeting ends and the next one starts. We deal with an employee issue and then answer ten emails. We make a decision, solve the immediate problem, and move on because there are five other things waiting.
There’s nothing inherently wrong with that. It’s the reality of leadership. The problem comes when moving on becomes our normal response to everything.
We may be gaining experience, but are we actually learning from it?
Sometimes Success Teaches Us the Wrong Lesson
We tend to associate reflection with mistakes. Something goes badly, so we look backward and try to figure out what we should have done differently.
I think we should also reflect when things go well.
Years ago, I started paying more attention to the difference between the result of a decision and the quality of the decision itself. They aren’t always the same.
You can make a poor decision and get a good result.
Maybe you made the call too quickly. You didn’t ask the people closest to the work. Someone raised a legitimate concern and you dismissed it. You didn’t have enough information, but you went forward anyway.
And it worked.
What do we normally learn from that?
We tell ourselves we made a good decision.
Now imagine doing that several times. Eventually, the leader starts believing that moving quickly without involving others is one of their strengths. Experience appears to support the belief because the outcomes have been good.
Until one isn’t.
The opposite is also true. Sometimes we do the work. We gather the information available to us, involve the right people, consider the risks, and make what appears to be the best decision we can make at the time.
Then it fails.
That doesn’t automatically mean the decision was bad.
There are too many things outside our control for good judgment to guarantee good outcomes. Markets change. People make unexpected choices. Information we couldn’t have known becomes available later. Sometimes things simply don’t work.
If we judge every decision only by the result, we can end up learning the wrong lessons from both success and failure.
A better reflection is to go back to what we knew when the decision was made. Did we ask good questions? What assumptions were we making? Did we listen when someone challenged our thinking? Were we responding to the facts we had or to the story we had already created about them?
That’s a much harder examination than asking whether we won or lost.
But it tells us far more about our judgment.
The Stoics Were Constantly Examining Their Judgments
This is where Stoicism becomes especially practical for leadership.
One of the ideas that comes up repeatedly in Stoic philosophy is the distinction between what happens and the judgment we make about what happens. We experience something, and almost immediately we begin interpreting it.
Someone doesn’t respond to our email.
That’s what happened.
“They don’t respect the urgency of this” is something we’ve added.
An employee questions a decision during a meeting.
That’s what happened.
“They’re being resistant” may be our judgment about what happened.
A team struggles with a new process.
That’s what happened.
“They don’t want to change” is an interpretation.
Sometimes those interpretations turn out to be correct. The problem is how quickly we begin treating them as facts.
I’ve done it. I’ve watched other leaders do it. Someone says or does something, and within seconds we’ve built a fairly complete explanation of their motives. Then we respond to the explanation we’ve created rather than getting curious about whether it’s actually true.
Reflection gives us a chance to go back and separate those things.
What actually happened?
What did I believe was happening?
And how did what I believed affect what I did next?
That is a very Stoic exercise because it brings our attention back to our own judgment. I can’t control another person’s motives, attitude, or reaction. I can examine the conclusions I reached, the questions I asked, the words I chose, and how I responded.
That’s where my responsibility is.
It is also where my ability to improve is.
What Are You Starting to Notice?
I don’t think reflection needs to become another leadership program or another elaborate process we have to manage. Most of us don’t need another system.
What we need is enough space to notice patterns.
After an important conversation or decision, I might ask what actually happened, what I contributed, and what I would do differently if I had the same situation tomorrow. If something went particularly well, I want to understand that too. What did we do that made this work? Was there something about how I approached the conversation that I should repeat?
Over time, you begin seeing things that are difficult to notice in isolation.
Maybe you realize that when pressure increases, you stop asking questions and start giving answers. Maybe you notice that you’re very comfortable holding people accountable for missed expectations but less comfortable acknowledging when your expectations weren’t clear. Maybe you discover that your team brings you more problems than solutions because you’ve trained them, without realizing it, that you’ll eventually provide the answer.
Or you may notice something you’re doing well. Maybe the best conversations with your team happen when you resist the urge to fill the silence. Maybe people bring you bad news sooner because of the way you’ve responded to it in the past. Maybe someone you have been coaching is beginning to make decisions without looking to you for approval.
Those things are worth noticing too.
Reflection shouldn’t become an exercise in finding everything we’re doing wrong. The point is to understand ourselves a little better so we can become more intentional about what we do next.
Experience Gives Us the Material
There is a reason experience matters in leadership. You can’t learn everything from a book, a class, or someone else’s advice.
Eventually, you have to lead.
You have to make the decision when the information isn’t complete. You have to sit across from someone during the difficult conversation. You have to deal with the consequences when your plan doesn’t work. You have to decide when to step in and when to let someone struggle long enough to figure something out themselves.
Those experiences matter.
But I don’t think experience automatically makes us wiser.
We still have to be willing to look at what happened without immediately defending ourselves. We have to separate the outcome from the quality of our judgment. We have to question the stories we tell ourselves about other people. And every once in a while, we have to be willing to consider that the thing needing to change might be us.
That isn’t always comfortable.
It is, however, within our control.
The leaders I’ve seen grow the most aren’t necessarily the ones who have experienced the most. They’re the ones who seem unwilling to waste the experiences they’ve been given.
Maybe that’s a better way to think about wisdom.
Experience gives us the material.
Reflection is what we choose to do with it.