Sometimes Leaders Have to Go Back to School

May 27, 2026
Massachusetts Institute of Technology’s iconic main building features grand columns and a central dome, framed by bare trees in a serene setting.

One of the hardest things for experienced leaders to admit is that the world has changed again.

Not a little.

Not in theory.

But enough that yesterday’s experience is no longer sufficient by itself.

That does not mean our experience has no value.

It means our experience must be refreshed, challenged, and strengthened so we can continue leading with relevance.

There are seasons in life and leadership when we have to go back to school.

Sometimes that school is a formal program.

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Sometimes it is a certification course.

Sometimes it is a stack of books.

Sometimes it is YouTube University.

Sometimes it is a conversation with someone younger, faster, or closer to the edge of what is changing.

The point is not the classroom.

The point is the posture.

A leader must be willing to become a student again.

I have been thinking about this often as I continue leading my company through an AI transformation.

I have been in technology for decades. I have built a company, survived multiple market shifts, served the federal government, and navigated the many disruptions that come with entrepreneurship.

And yet, when artificial intelligence began reshaping the world around us, I knew I could not lead my company into that future by relying only on what I already knew.

So I went back to school.

I enrolled in executive learning programs.

I studied.

I listened.

I experimented.

I became uncomfortable.

And I am still learning.

That last part is important.

Because learning is not always clean.

Sometimes it exposes what we do not yet understand.

Sometimes it reminds us that being experienced is not the same as being current.

Sometimes it humbles us enough to ask better questions.

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For leaders, this matters deeply.

You can delegate execution.

You can hire talent.

You can bring in specialists.

You can assign responsibility.

But you cannot responsibly lead a transformation you are unwilling to understand.

You do not have to be the person pushing every button.

But you do need enough foundation to know what questions to ask, what risks to watch, what standards to set, and what direction to give.

That is the difference between delegation and abdication.

Delegation says:

“I understand enough to establish direction, and I trust you to execute.”

Abdication says:

“I do not understand this, so someone else should handle it.”

Those are not the same.

As leaders, owners, and builders, we must know the difference.

This does not mean we become experts in everything.

That is impossible.

It means we remain serious enough about our responsibilities to keep learning when the environment changes.

It means we do not allow our titles, years of experience, or past success to keep us from becoming students again.

In this current season, AI is one of those areas for me.

I am not uncomfortable with AI because I fear it.

I am uncomfortable because I respect its power.

I know it can accelerate thinking, improve quality, strengthen systems, and open doors for people who may not otherwise get a seat at the table.

But I also know that AI must be governed.

It must reflect our values.

It must strengthen our voice, not replace it.

It must serve the organization, not quietly reshape it without leadership understanding.

That is why I continue learning.

Because once a leader understands something deeply enough, they lead differently.

They ask better questions.

They set clearer boundaries.

They build better systems.

They develop better people.

And they are less likely to be led by the tools they were supposed to govern.

The same is true in every area of leadership.

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Finance.

Security.

Operations.

Marketing.

Technology.

Compliance.

Culture.

When the world changes, leaders must decide whether they will protect the past or prepare for the future.

Sometimes preparation looks like humility.

Sometimes it looks like slowing down long enough to learn.

Sometimes it looks like going back to school after everyone assumes you already know enough.

But that is what responsible leadership requires.

Because once you know, you lead differently.

And once you know that you do not yet know enough, the most powerful thing you can do is begin learning again.

— Margaret Wood
Founder, LightKeeper TV
CEO, WOOD Federal Solutions, Inc.

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