There’s a strange thing that happens as you gain experience.
You become better at recognising patterns. You become quicker at spotting problems. You develop instincts that weren’t there before.
And yet, at the same time, you can become more aware of how little you actually know.
That used to surprise me.
Earlier in my career, I thought experience was supposed to make you certain.
The more you did something, the more you understood it.
The more you understood it, the easier it should become.
After more than 20 years of teaching, choreographing, working on productions and building businesses, I don’t think that’s how it works.
Experience hasn’t made everything clearer.
It has made me more curious about what isn’t immediately obvious.
And that has changed the way I approach people, problems, leadership and decisions.
Experience doesn’t give you more answers.
It gives you better questions.
The Confidence To Question What You See
When you’re less experienced, it’s natural to look for the right answer.
You want to understand the rules. You want to know what successful people do. You want to recognise the process and get it right.
There is nothing wrong with that.
Experience matters because it gives you knowledge, perspective and a deeper understanding of what tends to work.
But it also teaches you that very few situations are exactly what they first appear to be.
Someone who seems difficult might be under pressure.
Someone who appears disengaged might not understand what is expected of them.
A team that looks unmotivated might have lost clarity rather than motivation.
And sometimes a problem that seems obvious has very little to do with the thing you first noticed.
The more experience you gain, the more you learn to distinguish between what you see and what you assume.
That distinction can change everything.
When Experience Becomes A Trap
Experience is powerful.
But it can also create blind spots.
When you’ve dealt with the same types of problems repeatedly, your brain naturally looks for familiar patterns.
You see something and think:
I’ve seen this before.
I know what this is.
I know what needs to happen next.
That instinct can save time.
But it can also make you stop looking.
A familiar situation isn’t necessarily the same situation.
The person in front of you isn’t the person you dealt with five years ago.
The business you’re leading today isn’t the business you were leading before.
And you aren’t necessarily the same person who made those previous decisions.
Some of the most valuable lessons I’ve learned have come from moments when my first interpretation turned out to be incomplete.
Not completely wrong.
Just incomplete.
And there is an important difference.
The Problem Beneath The Problem
One of the things experience has taught me is that the problem people bring you isn’t always the problem they actually need to solve.
Someone might say:
“I don’t know what decision to make.”
But perhaps the real issue is that they’re afraid of making the wrong decision.
Someone might say:
“My team isn’t listening.”
But perhaps expectations haven’t been made clear.
Someone might say:
“I don’t enjoy my work anymore.”
But perhaps the problem isn’t the work itself. Perhaps their definition of success has changed.
This is why asking why something is happening can be more useful than immediately asking how do we fix it?
The first looks for an answer.
The second looks for understanding.
And understanding usually needs more time.
Good Leadership Isn’t About Having Every Answer
This becomes particularly important as you become more senior.
The more responsibility you have, the more people look to you for answers.
Your team expects direction. Your clients expect decisions. Your business needs movement.
And because you’ve built experience, people may assume you should know what to do.
But good leadership isn’t about proving that you have the answer.
Sometimes it means making the decision.
Sometimes it means asking another question.
Sometimes it means listening.
And sometimes it means admitting:
“I don’t know yet.”
That isn’t necessarily a weakness.
You can be uncertain about the answer while still being confident in your ability to work it out.
I’ve found that there is often more value in creating the space to understand something properly than rushing to demonstrate that you already know what to do.
Better Questions Change What You See
A better question doesn’t necessarily produce an immediate answer.
It changes the way you look at the situation.
Instead of asking:
“What’s wrong?”
You might ask:
“What’s really happening?”
Instead of:
“Why are they behaving like this?”
Try:
“What might I not understand about their perspective?”
Instead of:
“How do I fix this?”
Ask:
“Am I solving the right problem?”
Instead of:
“What should I do?”
Ask:
“What matters most here?”
And sometimes the most useful question is one we don’t particularly want to answer:
“What if my current way of looking at this isn’t the whole story?”
That question requires humility.
But it also creates possibility.
Five Questions Worth Asking More Often
You don’t need a complicated framework to become more curious.
Sometimes it starts with a few simple questions:
1. What am I assuming?
Separate what you know from the story you’ve created around it.
2. What might I be missing?
There may be information, context or emotion you haven’t considered.
3. Is this the real problem?
Before solving something, make sure you’re solving the right thing.
4. What would change if I looked at this differently?
A different perspective can reveal options that weren’t visible before.
5. Do I need to answer this — or understand it first?
Not every situation needs an immediate response.
Some need a little more attention.
Final Thoughts
Experience is valuable.
It gives us knowledge. It gives us perspective. It gives us instincts.
But perhaps the greatest value of experience is not becoming someone who always knows the answer.
It’s becoming someone who knows when to look again.
To question the first interpretation.
To listen to another perspective.
To recognise that familiar doesn’t always mean identical.
And to understand that sometimes the thing standing between you and clarity isn’t a lack of answers.
It’s asking the wrong question.
I’ve become less interested in being the person who has the quickest answer.
I’m more interested in asking the question that helps reveal what actually matters.
Because the right question can change the conversation.
It can change a decision.
It can change how you see another person.
And sometimes, it can change how you see yourself.
Experience doesn’t give you more answers.
It gives you better questions.
Frequently Asked Questions
What does experience teach us?
Experience can develop knowledge, judgement and perspective. It can also teach us to recognise complexity and question our initial assumptions rather than automatically relying on familiar solutions.
Why is curiosity important in leadership?
Curiosity helps leaders look beyond the obvious explanation. It encourages them to understand different perspectives, challenge assumptions and make decisions based on a fuller picture.
Can experienced leaders become too confident in their judgement?
Yes. Experience can make pattern recognition faster, but familiar patterns can sometimes lead to assumptions. Remaining open to new information helps experienced leaders avoid treating every situation as something they’ve seen before.
How can I become better at asking questions?
Start by slowing down your first reaction. Before giving an answer, consider what you know, what you’re assuming and what you might be missing. Open questions that encourage reflection can often reveal more than questions designed to confirm what you already believe.
How can coaching help people develop better perspectives?
Coaching creates dedicated space to step back from immediate challenges and explore thoughts, assumptions, behaviours and patterns. Through reflective questioning, people can often uncover perspectives and possibilities that are difficult to see when they are inside the situation.
