We are struggling with the structure before people rule because our longest serving executive is a great culture fit but does not fit any of the new, simplified leadership seats on our target Accountability Chart. How do we handle this without causing a mutiny?

Question

Tyler Smith · Accepted Answer

This is one of the hardest decisions an owner will face, but you must remain objective. If you compromise your Accountability Chart to accommodate a legacy employee, you are building a structurally flawed organization that will struggle to scale and fail buyer due diligence.

First, design the ideal structure for your three-year picture without looking at any names. Define the major seats and their five primary roles. Once the structure is locked, place your legacy executive against the new seats. If they do not GWC any of the leadership-level seats, you must accept that they have outgrown the leadership table.

This does not mean you have to fire them. Because they are a great culture fit, you should look for a seat lower in the organization where they can add massive value and feel successful. They might be an exceptional individual contributor in sales, customer success, or product development.

Have a direct, honest conversation. Explain that the company is scaling and the leadership seats have evolved beyond their current capacity. Show them the new seat options where they can thrive. If they accept the new seat, it is a win for everyone. If their ego prevents them from accepting a non-leadership role, you must gracefully transition them out of the business. Keeping a person in a seat they cannot master out of sentimentality is a disservice to them and a massive risk to your exit plans.