The Executive Who Got You Here May Be the Executive To Get You There

There is an old piece of conventional wisdom in business:

“The executive who got you here may not be the executive who gets you there.”

I’ve heard some version of that throughout my career in executive search.

Sometimes it’s exactly right.

But sometimes we treat it as an assumption when it should be the conclusion of an assessment.

In private equity-backed and growth-stage companies, that distinction matters.

The investment thesis requires something different from the business. More EBITDA. Margin improvement. Better cash conversion. An acquisition strategy. New markets. More sophisticated systems and leadership. Eventually, perhaps, an exit.

Naturally, the leadership team gets evaluated against what comes next. And one of the most common ways to reduce the perceived risk is to hire someone who has already been there.

There is logic in that.

But there is a distinction I think matters.

The larger-company executive may have seen scale. The smaller-company executive may have actually built toward it.

Those are different forms of experience. And neither, by itself, tells me which executive is more likely to create value in the next stage of the business. Recruiting for Private Equity Portfolio Companies: What Hiring Actually Looks Like covers what that evaluation looks like across an entire portfolio company, not just one seat.

Experience at the destination is only part of the evidence

If the value creation plan requires a more sophisticated finance organization, prior experience inside one matters. If the company expects significant M&A, having lived through integrations matters. If the likely exit path requires a particular level of reporting, controls, forecasting or capital-markets sophistication, experience matters.

I’m not arguing against any of that.

What matters more is understanding what the executive actually built, changed or improved while they were there.

A CFO from a much larger company may have operated with systems, processes and leadership depth already in place. Another CFO may have spent the last five years building those things.

When I’m assessing executives, I want to understand the difference. CFO 2.0: How Financial Leadership Is Evolving in the Age of Automation is a good example of how much that difference matters in practice.

But expanding scope isn’t the same as expanding capability

This is where I think executive assessment gets harder.

It’s relatively easy for an executive to describe a career in which their scope continually increased. The company grew. Their team got bigger. Responsibilities expanded. Perhaps acquisitions added businesses or functions underneath them.

But expanding scope doesn’t necessarily mean the executive expanded with it. Sometimes responsibility grows because the organization grows.

What I want to understand is what happened to the executive’s judgment as the complexity increased.

When I talk with executives, I sometimes describe it as the ability to see around corners.

Did they simply get better at solving increasingly complex problems, or did they begin seeing those problems before they arrived? Did they recognize what the business would need next and start building toward it before the need became urgent?

Did they build leaders underneath themselves, or did more decisions continue flowing upward? Did they create systems and operating disciplines that made the organization less dependent on individual heroics? Did their influence with the CEO and board expand because they were bringing better enterprise judgment to the table?

Ultimately, I want to know:

What became possible because this executive was there?

That question tells me considerably more about someone’s ability to scale than the size of the company printed on their resume. Why Hiring at Scale Requires a Different Operating Model makes the same case about what has to change beneath an executive as the company grows.

The incumbent deserves the same scrutiny as the outside candidate

There is risk in assuming an executive will continue scaling simply because they have done so before.

Some don’t.

The approaches that worked at one stage stop working at another. Informal decision-making becomes a bottleneck. A leader who once built aggressively begins protecting what they created. The organization becomes more complex, but the executive’s operating model doesn’t.

At that point, the business may genuinely need different leadership.

But the outside candidate deserves equally serious scrutiny.

A resume that says someone has already operated at the scale you’re trying to reach can create a comforting sense that the risk has been removed.

It hasn’t.

How much of that executive’s success travels with them when the infrastructure is thinner and they have to build rather than inherit?

That’s an expensive distinction to discover after the hire. Watch CFO Behavior Before You Watch CFO Exits tracks the specific warning signs that show up long before that discovery becomes expensive.

Replacement isn’t the only answer

Leadership decisions don’t always have to resolve into keep or replace.

Sometimes the right answer is augmentation.

A CFO who has been instrumental in building the business may need a stronger FP&A leader underneath them. A CEO may need a COO who can institutionalize execution without replacing the entrepreneurial strengths that got the company this far. The Rise of the Chief Operating Partner: Why Operations Deserve a Seat at the Strategy Table covers exactly that kind of role.

An executive may need a clearly defined period to demonstrate that they can build the capabilities required by the next phase of the value creation plan.

Sometimes you don’t need to replace the executive. You need to change what’s around them.

And in a PE-backed business, these decisions are being made against a clock. Waiting indefinitely for an executive to grow into the next stage isn’t a strategy either.

As an executive recruiter, a replacement creates a search.

But replacement isn’t always the right answer.

Sometimes the better leadership decision is identifying what the incumbent does exceptionally well, determining what the next stage requires, and closing the gap around them.

That’s where judgment enters the equation

For private equity operating partners, boards and portfolio-company CEOs, the harder question isn’t whether an executive’s background looks right. It’s what that experience actually tells you about their ability to create value in this business.

And if the incumbent doesn’t yet possess everything the next phase requires, is the gap fundamental, or can it be built around?

After twenty-five years in executive search, those are the questions I’ve become much more interested in.

Because executive assessment shouldn’t simply determine whether someone has already been where the business is going.

It should help determine whether they have demonstrated the ability to get the business there.

Past scale is evidence. Trajectory is evidence. Knowing how to interpret the difference is judgment.