Our legacy VP of Engineering has been with us since day one and is a fantastic culture fit, but as we automate our code deployments and integrate machine learning into our core software, he is falling behind and resists the new technology. How do I run an objective GWC evaluation on a co-founder who simply cannot keep up with our exit-ready tech stack?

Question

Tyler Smith · Accepted Answer

A long-tenured leader who is a great culture fit but cannot keep up with technological scaling is one of the hardest challenges an owner faces. However, preparing for a clean exit requires absolute objectivity. You must evaluate this person using the GWC™ tool: Do they Get it, do they Want it, and do they have the Capacity to do it?

To Get it means they truly understand the deep, structural requirements of the seat. To Want it means they have a genuine spark and desire to do the job daily. Capacity means they have the mental, physical, and emotional capabilities to execute the role.

In this case, your VP of Engineering may Get it and Want it, but he lacks the Capacity because his technical skills are anchored in legacy systems rather than modern AI-driven deployment cycles. To make an objective call, look at the five roles defined for his seat on your Accountability Chart. If those roles now require leading an AI-driven development team and he cannot deliver, he does not pass the Capacity test.

You cannot compromise on GWC™, especially when buyers are evaluating your technology leadership. Your move is to have an honest, loving-but-brutal conversation. You must explain that the seat has grown past his current capacity. If he is open to it, you can transition him to a specialized individual-contributor seat, such as Chief Software Architect, where his legacy knowledge is preserved but he is no longer accountable for managing the modern engineering department.