What If Leaders Went Back to School? Five Questions Worth Revisiting This Fall

There’s something about September that has always felt like a fresh start.

Kids head back to school. New routines begin. New notebooks get opened. And after the slower pace of summer, things seem to shift back into gear.

For students, going back to school comes with a pretty simple expectation:

You’re going to learn something.

Which got me thinking.

What if leaders approached the fall the same way?

Not by signing up for another leadership course. Not by ordering a stack of business books. And probably not by buying a new backpack.

But by taking some time to reflect on what they’ve learned, question what they think they know, and decide where they need to focus next.

Because leaders spend a lot of time asking their organizations and their people to learn, change, and adapt.

Good leadership requires the same thing.

So, as everyone heads back to school, here are five questions leaders might want to take with them.

1. What Have I Learned This Year?

We’re already eight months into the year.

Think about everything that has happened since January.

Decisions have been made. Strategies have been implemented. People have joined and left. Customers have changed. Problems have emerged. Some things have worked better than expected.

Others probably haven’t.

All of those experiences create opportunities to learn. But experience doesn’t automatically become learning.

That requires reflection.

Ask yourself:

What do I understand today that I didn’t understand in January?

Then take it one step further:

What am I going to do differently because of it?

Learning becomes valuable when it changes what we do.

2. What Assumption Should I Reconsider?

Every leader operates with assumptions.

We have assumptions about what customers want.

What motivates employees.

How work should get done.

What makes someone a strong performer.

What our organization is good at.

Which capabilities will matter in the future.

Many of those assumptions may be right.

But some of them may have been right.

There’s an important difference.

Markets change. Technology changes. Employees change. Organizations change.

Experience is valuable because it helps us recognize patterns. But it can become a limitation when yesterday’s experience prevents us from seeing that today’s circumstances are different.

So periodically ask:

What do I believe to be true that might no longer be true?

You don’t need to abandon your experience.

Just stay curious enough to question it.

3. What Does My Team Need to Learn Next?

Organizations spend a lot of time thinking about the skills people need to perform their jobs today.

That’s important.

But leaders also need to look ahead.

What will our people need to be good at next?

Maybe it’s working differently with AI.

Maybe it’s stronger cross-functional collaboration.

Maybe it’s better decision-making.

Maybe it’s managing greater complexity.

Maybe it’s a capability specific to where your business is heading.

Whatever it is, development shouldn’t only respond to today’s skill gaps.

It should prepare people for tomorrow’s work.

And that means leaders need to think about capability before the gap becomes urgent.

4. What Should We Stop Doing?

Learning isn’t always about adding something new.

Sometimes learning means recognizing that something old no longer serves us.

Organizations accumulate things.

• Meetings.

• Reports.

• Processes.

• Policies.

• Priorities.

• Ways of working.

Leaders accumulate habits too.

Eventually, some of those things become disconnected from the reason they existed in the first place.

So ask:

What are we still doing because it matters, and what are we doing simply because we’ve always done it?

Making room for something new sometimes requires being willing to let something old go.

5. What Deserves More of My Attention This Fall?

A leader’s attention is limited.

The demand for it isn’t.

There will always be another meeting, another email, another problem, another decision, and another issue requiring your attention.

The challenge isn’t finding things that need your attention.

Almost everything can make that case.

The better question is:

What deserves more of my attention than it’s getting today?

Maybe it’s a strategic priority that keeps getting pushed aside by urgent work.

Maybe it’s developing someone on your team.

Maybe it’s spending more time with customers.

Maybe it’s fixing an organizational problem everyone has learned to work around.

Or maybe it’s simply creating more space to think.

Where leaders spend their attention tells an organization what really matters.

Back to School

Going back to school comes with an assumption:

We’re here to learn.

Maybe that’s an assumption leaders should carry into the fall as well.

Experience matters. Expertise matters. Having answers matters.

But so does staying curious enough to reconsider them.

So you probably don’t need a new backpack, pencil case, or fresh box of crayons this September.

But five questions might be worth taking with you:

1. What have I learned?

2. What assumption should I reconsider?

3. What does my team need to learn next?

4. What should we stop doing?

5. What deserves more of my attention?

Because perhaps one of the most important things leaders can demonstrate is that learning isn’t something we expect from everyone else.

It’s something we continue doing ourselves.