Leadership Lessons: The Difference Between Running the Business and Understanding It

As leaders advance, they naturally spend less time doing the work and more time leading the people who do it. The mistake isn't becoming less involved in the day-to-day—it's becoming so detached that you no longer understand how your business creates value. Great leaders stop doing the work, but they never stop learning it.

Carter Cathey

8/17/20263 min read

One of the biggest transitions in leadership happens gradually. The higher you rise in an organization, the further you move from the day-to-day work. That's natural. In fact, it's necessary.

As an executive, your job increasingly becomes about hiring leaders, setting priorities, allocating resources, resolving conflicts, developing talent, and creating strategy. My wife used to joke that some days my calls sounded more like I was a therapist than a sales executive.

She wasn't entirely wrong. Much of executive leadership is helping people solve problems.

But over the years, I've seen leaders drift too far in the other direction. They stop understanding the business they're leading. And I think that's just as dangerous as micromanagement.

The Two Extremes

I've seen executives who spend every day buried in tactical decisions.

They're involved in every customer issue.
Every pricing decision.
Every hiring conversation.
Every project.
Every approval.

They become the bottleneck. The organization can't grow because every important decision still depends on one person.

I've written before about why that doesn't scale. But there's another extreme that's just as problematic.

The executive who no longer understands how the business actually works.

I've met CEOs who couldn't comfortably discuss a client project.
Sales leaders who couldn't coach a difficult sales situation.
Operational leaders who couldn't explain how work actually moved through their own department.
Years into the role, they understood budgets.
They understood reporting.
They understood organizational charts.

But they no longer understood the work.

Doing the Work Isn't the Same as Understanding It

As leaders grow, they should stop doing everyone's job. That doesn't mean they should stop understanding everyone's job. There's an important distinction.

A CEO doesn't need to manage projects, but they should understand the customer experience.
A CRO shouldn't negotiate every contract, but they should understand enough to coach a struggling salesperson.
An engineering executive shouldn't write production code, but they should understand how software gets built, where bottlenecks occur, and why technical teams raise certain concerns.

Operational understanding allows leaders to ask better questions. Not because they're pretending to be experts. Because they're genuinely curious.

Every Leader Learns Somewhere

One of the challenges I've observed repeatedly is that every executive learned leadership somewhere.

Every leader develops instincts.
Patterns.
Frameworks.
Solutions.

Those experiences become incredibly valuable. They also become dangerous.

When leaders don't invest time learning their new business, they often default to solving the problems they already understand. The result?

They spend their first year solving their previous company's problems instead of learning their current company's.

I've seen enterprise leaders bring heavyweight processes into agile organizations.
I've seen startup leaders dismiss governance that mature businesses genuinely needed.
I've seen leaders redesign functions before they fully understood why they operated the way they did.

Experience is valuable. Assumptions are dangerous.

Curiosity Is an Executive Skill

The best executives I've worked with weren't the people who always had the answers. They were the people who kept asking questions.

How does this process actually work?
Where do customers struggle?
What frustrates employees?
Why was this system designed this way?
What problem was it originally solving?

Curiosity keeps experience honest. It prevents leaders from assuming they already understand. It replaces certainty with learning.

Strategy Depends on Understanding

People often say executives should spend their time working on the business rather than in the business.

I agree. With one important addition. "You can't effectively work on a business you no longer understand."

How can you improve customer experience if you don't understand how customers experience the company?
How can you improve operations if you don't understand where work gets stuck?
How can you create clarity if you don't understand where confusion exists?

Strategy built on assumptions eventually becomes disconnected from reality.

Stay Curious

One of the defining characteristics of great executives is that their responsibilities grow without their curiosity shrinking.

They ask thoughtful questions.
They spend time with customers.
They talk to frontline employees.
They seek to understand before they seek to change.

As organizations grow, leaders naturally become more removed from the work. That's healthy. What isn't healthy is becoming more removed from understanding it.

Great leaders eventually stop doing the work. They should never stop trying to understand it.

Because experience tells you how you solved yesterday's problems. Curiosity helps you discover today's.