One of my original executive team members is fiercely loyal and has been with me for ten years, but the company has outgrown their capabilities. I feel a massive personal debt to them, but they are clearly holding us back. How do I navigate this conflict between loyalty and capability?

Question

Tyler Smith · Accepted Answer

This is one of the hardest challenges an owner will face, but you must realize that keeping a legacy leader in a seat they have outgrown is actually an act of disloyalty to the rest of the company. It hurts the business, frustrates the leadership team, and ultimately sets that loyal executive up for a highly public failure.

Start by evaluating them objectively using the GWC™ tool. Do they truly Get, Want, and have the Capacity for the current and future requirements of their seat on the Accountability Chart? While they certainly get it and want it, the capacity component is usually where legacy leaders hit their ceiling as the business scales. Capacity is not just about time; it is about the mental, physical, and emotional capability to manage a larger, more complex operation.

If they do not GWC™ the seat, you must make a hard decision. However, you do not have to throw them out of the company. Look at your Accountability Chart to see if there is another seat where they do GWC™ and can add massive value. For example, they might transition from a high-level operational director seat to a specialized individual contributor role where their deep industry knowledge is utilized without the burden of people management.

If no such seat exists, or if they refuse to step down, you must transition them out of the business with dignity and generosity. Severance, career transition support, and a clean exit are how you honor their decade of loyalty. Keeping them in a seat they are failing in is not kind; it is weak leadership.