One of the most common things we hear from CEOs who’ve made changes to their leadership team is, “I wish I had done it sooner.” Making these decisions is rarely easy, but putting them off often creates more challenges down the road. At Katahdin, our CEO members often find that their peers give them the push they need to make these tough decisions, and acting early tends to lead to better outcomes for both the team and the business.

Your role as CEO is to build a strong, aligned leadership team that can grow and evolve with your company. If you’ve been wrestling with concerns about a team member’s fit, it’s usually a sign that action is needed. 

Here are 7 signs it might be time to make a change:

1. They’re outpaced by the company’s growth - As your company evolves, so must your leadership team. CEOs often face the challenge of realizing when a team member’s skills can no longer meet the demands of a growing business. What worked during an earlier phase of growth may no longer be enough to support the company’s future. If you sense this misalignment, it could be time to bring in someone whose capabilities are better suited to the company’s evolving needs.
   
   
2. Recurring issues aren't being solved - If you find yourself addressing the same problems with a team member over and over again, it could signal a deeper issue. While some mistakes are normal, persistent challenges suggest a poor fit.
   
   
3. You don’t have visibility into their work - If you often wonder what a team member is doing with their time, it could indicate they’re not managing up effectively. A good executive will make sure you’re aware of their progress and priorities.
   
   
4. Meetings with them leave you frustrated - Interactions with your leadership team should energize and inspire you. If certain meetings feel draining or consistently frustrating, that’s a sign the dynamic may be off—and it’s likely affecting the rest of your team too.
   
   
5. Communication feels strained or unproductive - Healthy communication is essential for any executive team. If conversations with a particular executive consistently feel strained, unproductive, or leave you feeling like they don’t fully understand or support your vision, it could be a sign that something’s off. Strong leaders should help drive alignment, and if that’s not happening, it may be time to rethink their role on the team.
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6. There’s a lack of personality fit - Beyond skills and experience, it’s essential that your executives mesh well with you and the rest of the exec team. Leadership teams thrive when there’s a natural flow and ease in communication and collaboration. If working with a particular executive feels forced or uncomfortable, or if there’s ongoing tension that disrupts the team’s dynamic, it may be a sign that the personality fit isn’t quite right.A strong leadership team requires not only competence but also chemistry. If someone doesn’t align with the culture or communication style of the group, it can hold everyone back, even if their skill set is strong.
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7. They have strained relationships with their team - An executive’s effectiveness isn’t just measured by how they interact with you, the CEO, but also by the relationships they build with their direct reports and teams. If you notice that their team seems disengaged, unmotivated, or if there are recurring conflicts, it’s a sign that this executive might not be fostering a healthy or productive working environment. Strong leaders should inspire trust, respect, and collaboration from those they manage.

At the end of the day, a strong, aligned leadership team is what will help move the business forward (or not). If you’ve given it your best and the issues persist, it may be time to act. While it’s a painful process, your business and your team will thank you for it.

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