Our head of customer support has been with us since the garage days and perfectly embodies our core values, but as we scale toward a transition, she lacks the capability to manage the AI-driven ticketing systems we need to implement. How do I resolve this conflict between loyalty and the business need for high-level capability?

Question

Tyler Smith · Accepted Answer

This is one of the hardest challenges for a founder. Loyalty is admirable, but keeping someone in a seat they cannot fulfill is actually disloyal to their future and the health of the company. It drags down the entire leadership team and stalls your preparation for a clean exit.

First, separate the person from the seat. Use the GWC™ tool. Does she truly get, want, and have the capacity to lead a modern, automated customer support department? Capacity includes the mental bandwidth, skills, and time to manage the new technology. If she does not GWC™ the seat at our current and future scale, she must step out of it.

However, because she is a core values fit, you should look for a different seat on your Accountability Chart. Can you create a high-value individual contributor role, such as customer success champion, where her deep relationships and legacy knowledge are utilized without the burden of technical management?

If there is no suitable seat where she GWCs, you must transition her out of the company with dignity and a generous severance. True loyalty means treating people with respect while making the hard decisions necessary to build a healthy, cohesive, and functional leadership team that can execute the company's long-term vision.