5 warning signs it’s time to make a change to your executive team

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I once hired an executive—we’ll call her Alice—who elevated our company overnight. She helped shape our strategy, built a great team, and brought instant credibility to our brand. Our growth accelerated. The board respected her. The team loved her. I felt lucky to have her.

But five years later, things had changed. Alice looked exhausted. She was short-tempered in meetings. One of her best people left. The team’s performance stalled. She wasn’t making obvious mistakes, but she was slowing the business down. Looking back, the signs were there, but I looked past them—like many CEOs do. When an executive has been a major contributor to success, it’s easy to let loyalty, optimism, or past achievements cloud your judgment.

When I finally sat down with Alice and told her I thought it was time for a change, she seemed hurt—but also relieved. She knew it, too. The conversation was difficult but necessary.

If you’re a CEO, this moment will come for you, too. Changing executives isn’t about whether someone is capable or not. More often, it’s about whether the executive who was right for yesterday is still right for tomorrow. The hardest part isn’t making the call when the numbers are bad, the team is frustrated, or the board is raising concerns. By then, the answer is obvious but the damage—to both the business and the individual—has already been done. The real challenge is recognizing the early warning signs before failure happens.

Here are five signals to watch for:

1. They Hire for Yesterday, Not Tomorrow

Great executives hire people who push them, challenge them, and bring new capabilities into the organization. But when an executive stops scaling, their hiring reflects it. Instead of bringing in talent that stretches the company’s future potential, they hire for what they already know—people with skill sets that made sense in the last stage of growth, not the next one.

Even worse, they may avoid hiring people who are more experienced than they are, fearing they’ll be outshined. This is one of the subtlest but most telling signs that an executive isn’t evolving with the business. Strong leaders aren’t threatened by A-players; they seek them out.

2. They’re Getting Caught Flat-Footed

Early in a company’s growth, a strong executive is ahead of the curve. They anticipate problems before they arise and see opportunities before the competition does. But as the company scales, things get more complex—market dynamics shift, operations grow more intricate, and leadership requires a different level of execution.

An executive who once led with foresight can suddenly find themselves constantly reacting, caught off guard in ways they never were before. Often, it’s not that they’ve lost their strategic instincts—it’s that the business has entered a stage they’ve never navigated before, and their previous playbook no longer applies.

3. Their Team Doesn’t Know Where They’re Going

A key role of any executive is ensuring their team understands the company’s strategy and how it translates into their function. In a small company, this is relatively straightforward—the strategy is narrow, and the CEO is often close to employees, reinforcing the vision directly.

But as the company grows, that changes. The strategy becomes more complex, and executives—not the CEO—become responsible for making sure their teams understand how their work connects to the bigger picture. If employees seem unclear on the company’s direction or their role in it, it’s a sign that their leader isn’t effectively setting strategic clarity. And it’s not just about communication; it’s about an executive’s ability to process complexity, distill it into actionable priorities, and inspire alignment.

4. They Struggle to Translate Strategy into Execution

Similarly, in a company’s early stages, translating strategy into action is relatively simple: The organization is smaller and the steps to execution are clear. But as the company grows, the gap between strategy and execution widens. Success requires more than just understanding company goals; it requires breaking them down into operational plans with clear milestones, defined ownership, and built-in accountability.

An executive who once thrived in a lean, fast-moving environment may start to struggle as the organization becomes more complex. If they can no longer connect long-term strategy to day-to-day execution, teams lose focus, decisions get delayed, and momentum fades.

5. They’re in Nonstop Operational Meetings

Great executives elevate themselves over time. They move from being operators to being leaders—setting direction, aligning the team, empowering their managers, and ensuring execution through others.

But when an executive can’t scale, they get pulled deeper into the weeds. Instead of creating an environment where the strategy, expectations, and processes are in place for the team to operate, they’re stuck firefighting. If they’re constantly in meetings troubleshooting operational issues, solving tactical problems, or micromanaging details, it’s a sign that the business is running them—not the other way around.

What Do You Do When You See These Signs?

These are the warning signs I’ve learned to watch for, but spotting them doesn’t always mean an executive needs to go. If an executive is struggling to translate company strategy for their team, for example, it could be a sign that the strategy itself isn’t well-defined. And if they’re micromanaging, it may be a reflection of the expectations, culture, or tone set by the CEO. That’s why the first step should always be feedback and coaching.

But if the same patterns persist despite candid conversations and support, waiting longer won’t fix the problem. It will just delay the inevitable. Companies don’t move backward.

Some leaders recognize these gaps and rise to the challenge. Others don’t. And when they don’t, it’s not a failure—it’s simply that their strengths align with an earlier stage of the company’s journey, not where it’s headed next.

Making an executive change is disruptive. It’s expensive. It can be risky. But failing to make a change is often exponentially more so. The CEOs who scale companies successfully are the ones who make these calls early—before the business, the team, or the results force their hand.

When it comes to evolving the executive team, like many other areas of leadership, knowing what to do is rarely the hardest part. Knowing when to act is.

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