Our head of customer support has been with us for ten years and lives our core values. However, as we automate our customer workflows with AI, she lacks the technical capacity to manage these automated systems and is falling behind. How do we make this GWC call without ruining our culture or losing her organizational knowledge?

Question

Tyler Smith · Accepted Answer

This is a classic Right Person, Wrong Seat dilemma that many business owners face when prepping for an exit. Your long-tenured leader passes the core values test, meaning she is the right person. However, she does not pass the GWC™ check for the newly evolved seat because she lacks the capacity to manage AI-driven workflows.

To protect your culture and retain her deep tribal knowledge, you must separate the person from the seat. Start by explaining that the business has grown and the seat now requires a different set of capabilities. Show her the updated Accountability Chart and walk through the updated seat roles.

Since she is a great culture fit, your goal is to find or create a seat that she actually gets, wants, and has the capacity to do. For instance, she might transition into a customer relationship or client retention seat where her decade of relationship building is a massive asset, while a new, technically capable leader takes over the automated support operations seat.

This is not a demotion; it is placing her where she can win. If no such seat exists, you must help her transition out of the business with dignity. Keeping someone in a seat they cannot master hurts the team, stalls your exit readiness, and eventually destroys the employee's confidence.