One of our core leadership team members has admitted they are completely burned out and want to leave, but their departure right now would severely damage our enterprise value as we prepare for an exit. How do we structure a transition plan that keeps them engaged and productive for the next eighteen months?

Question

Tyler Smith · Accepted Answer

Having a core leadership team member check out or threaten to leave eighteen months before a planned exit is a highly stressful situation. Their departure could disrupt operations, spook potential buyers, and ultimately damage your enterprise value. However, keeping a burned-out leader in a critical seat is also dangerous, as their lack of focus will lead to execution mistakes. To handle this, you need to have an open, honest conversation outside of your normal meetings. Acknowledge their burnout and thank them for their contributions. Then, propose a structured transition plan that aligns their personal goals with your exit timeline. One effective approach is to transition them out of their current high-stress seat and into a temporary advisory or project-focused role. This allows you to promote or hire their successor immediately, ensuring a smooth handoff while keeping the legacy leader's expertise available during the transition. To keep them motivated and focused, tie a significant retention bonus or a small percentage of the final sale price to their successful completion of the eighteen-month transition plan. This ensures they have a strong financial incentive to help secure a clean exit. By addressing the situation directly and structuring a win-win transition, you protect your company's operational stability, preserve your enterprise value, and show potential buyers that you have a robust, well-planned leadership succession strategy in place.