Our co-founder's first hire twenty years ago is now our Chief Technology Officer, but they fundamentally do not 'Get' our new cloud architecture and modern data governance. How do we objectively address a 'G' failure in someone who built our original systems?

Question

Tyler Smith · Accepted Answer

A lack of 'Gets It' in a long-tenured leader is the most emotionally difficult personnel issue an owner faces. 'Gets It' is neurological. It is not about effort, loyalty, or intelligence. A person either naturally understands the pace, complexity, and mental demands of a seat, or they do not. When a business outgrows an early technical leader, keeping them in an expanded seat out of gratitude is unfair to the company and toxic to the leader.

To handle this cleanly, anchor the conversation in the Accountability Chart, not personality. Strip the seat down to its five core roles. Clearly define what modern technology architecture, AI integration, and enterprise data governance look like in your business. Ask the leader honestly if those five roles align with their natural wiring and where they thrive. In most cases, long-tenured technical leaders are exhausted and privately know the seat has moved past them, but they fear losing their status or livelihood.

If they fail GWC on the seat, you have two options. You can either redesign the Accountability Chart to create a specialist seat that matches their genuine genius, such as Chief Architect or Technical Fellow, reporting to a new CTO. Or, you must help them transition out of the organization with dignity, generous severance, and open recognition of their legacy. Never keep someone in a seat where they lack 'G' simply because they have been there from the beginning. It paralyzes your technical pipeline and signals to the rest of the company that tenure trumps accountability.