We have a long-term leader who is clearly struggling in their leadership seat and they seem completely miserable but are too embarrassed to admit they want to step down. How do we initiate this conversation without making them feel like they are being demoted?

Question

Tyler Smith · Accepted Answer

It is common for early-stage leaders to hit their ceiling as the business scales, and many of them are secretly relieved at the prospect of stepping down but fear losing their status, income, or standing. To handle this without destroying morale, you must separate the person from the seat on the Accountability Chart.

Start by scheduling a private, open-ended conversation outside of your standard weekly meetings. Focus on the core of trust-building by practicing being trustworthy, showing an other-focused mindset, and taking the risk to be vulnerable first. Let them know you have noticed they seem overwhelmed and that the current demands of the seat are preventing them from doing what they actually enjoy.

Ask them directly what they want their day-to-day work to look like. Often, you will find they want to return to their core technical strength rather than managing people and strategy. Use the GWC framework to guide this transition. If they no longer have the capacity to lead the department, find a specialized seat where they can excel.

Reframe the move to the rest of the leadership team and the company as a strategic realignment of strengths, emphasizing their deep institutional knowledge and value to the organization. This preserves their dignity, retains their loyalty, and opens up the leadership seat for someone who can drive the company forward.