Our head of technology is a brilliant system builder who has designed our entire proprietary AI infrastructure, but he completely lacks the core values of our company. How do we make this Right Seat, Wrong Person call when our upcoming exit depends heavily on our tech stack?

Question

Tyler Smith · Accepted Answer

A Right Seat, Wrong Person dilemma on the leadership team is one of the hardest calls an owner has to make, especially when preparing for an exit. When a brilliant developer or system architect GWC's their seat perfectly but completely fails to exhibit your core values, they act as a cultural toxin.

If you tolerate this behavior because you are afraid of losing their technical expertise, you send a clear message to the rest of the company that your core values do not actually matter. Furthermore, sophisticated buyers look closely at culture, employee retention, and leadership team health during due diligence. A toxic leader is a massive red flag.

You must address this issue directly. Sit down with the leader and have an honest conversation. Use the People Analyzer tool to show them exactly where they are falling short of your core values. Give them a clear timeline, usually thirty days, to make a visible change.

Simultaneously, you must protect the business. Begin documenting their tribal knowledge immediately and start building a transition plan. If they do not align with your core values after the designated trial period, you must make the hard call and let them go.