The Question More CEOs Are Quietly Asking: Why Can't I Step Away?

Dana Campbell, PCC

CEO | Leadership Coach | Advisor | Speaker | Change Leader | Stress Resiliency Expert

TL;DR

One of the biggest assumptions organizations make is that hiring exceptional executives will naturally build an exceptional executive team.

It doesn't.

As organizations grow, the work changes. Success depends less on the strength of individual functions and more on the executive team's ability to lead the business together. That's a transition very few organizations intentionally develop.

Earlier this year, we facilitated an executive team offsite where the CEO challenged her team to:

"Play from the front of the jersey."

The metaphor was crystal clear. How the leaders would play that way was far less so.

The business had reached a point where its biggest challenges no longer belonged to one function. Product couldn't solve them alone. Sales couldn't solve them alone. Operations couldn't solve them alone. Every meaningful decision required leaders to think beyond their own departments and make choices based on what was best for the business. It was exactly the leadership challenge the organization needed to solve.

But it's one thing to ask executives to play from the front of the jersey; it's another thing entirely to expect they already know how. Because very few executives are ever taught how to make that transition.

Most executives earn a seat at the leadership table because they're exceptional at leading a function. They're promoted because they're outstanding operators, builders, strategists, and leaders within their discipline.

Then something quietly changes. The job they're asked to do is no longer the job that got them there. The biggest transition in an executive's career isn't becoming responsible for more people.

It's becoming responsible for something bigger than their function.

The problem is that almost nobody acknowledges that the job has fundamentally changed. Organizations continue evaluating executives by functional excellence while simultaneously expecting them to think and operate at the enterprise level. Those aren't the same capability.

Harvard Business Review has written that one of the defining shifts in executive leadership is that a leader's value no longer comes primarily from making great decisions themselves. It comes from creating the conditions where other leaders can make great decisions.

Gartner's research points in a similar direction. High-performing organizations don't just develop individual executives. They intentionally develop the executive team.

Those are two different investments.

And I think they point to the same conclusion.

Organizations spend years developing leaders to run functions. They spend remarkably little time helping those leaders learn how to lead a business together.

This is where we see organizations get stuck.

As companies grow, they naturally become more interconnected. It's not just that decisions in one function increasingly affect every other function. Nor is it simply that AI is changing workflows across every function. The challenges the business has to solve in order to stay ahead of competitors become increasingly more complex and require product, engineering, finance, operations, sales, marketing (and all the functions) to think in new ways together to unlock new levels of problem solving.

What we have seen across so many of the organizations we work with is that while the business experiences greater complexity, which drives more integration, the leadership team lags behind.  Leading from the back of the jersey instead of the front.

Not because the executives aren't capable.

Because they're still operating from the perspective that made them successful in the first place. Optimizing for their vertical.  Hyper-focused on helping their function excel and succeed. Individually, they might be making good decisions. Collectively, those decisions don't always add up to what's best for the enterprise.

Playing from the back of the jersey not only inhibits the speed that's so critical to staying ahead, but it also cuts teams off from finding breakthrough solutions to complex business problems.

One of the questions that comes up regularly in our coaching work with CEOs and C-suite leaders sounds deceptively simple.

"Can I trust my team enough to step out of the weeds?"

It's usually followed by another question.

"If I do, what happens?"

On the surface, it feels like a trust problem. Underneath, it's usually an organizational design problem.

When an executive team hasn't developed a shared way of interpreting the business, weighing competing priorities, and navigating enterprise tradeoffs, someone still has to integrate all of those perspectives into one coherent direction.

This role falls back on the CEO, which not only makes them the Chief Integration Officer, but because the other dynamics of playing from the front of the jersey haven't been attended to, also places them at the center of a hub-and-spoke structure that is difficult to break out of because the organization hasn’t created another way for the executive team to execute together.

Most CEOs we work with are eager to “let go” and let the executives lead the business more. It may look like they can’t let go.  When in reality the CEO is compensating for a capability the organization never intentionally built.

When a client asks:

"Can I trust my executives enough to step away?"

We think the question they really should be asking is:

Have we invested as much in developing our executive team as we have in developing the executives on it?

Those are very different things. One builds exceptional leaders. The other builds an exceptional leadership team.

My working hypothesis is that high-performing executive teams aren't built simply by hiring great executives.

They're built by helping great executives make the transition from functional leadership to enterprise leadership. Not by teaching them to think alike. But by helping them develop a common way of understanding the business—one that allows them to bring different expertise, challenge one another's assumptions, and integrate those perspectives into better enterprise decisions.

Every CEO eventually reaches the point where the business outgrows functional leadership. The organizations that continue to scale aren't necessarily the ones with the smartest executives. They're the ones that figure out how to help those executives become something different. I don't think we have good language for that transition yet. But I do think it's one of the most important leadership challenges organizations will face over the next decade.