Our Head of Operations was our first employee ten years ago and is beloved by everyone, but as we scaled past twenty million dollars, the seat outgrew him and he no longer has GWC. How do we address this Right Person, Wrong Seat reality without crushing company culture?

Question

Tyler Smith · Accepted Answer

This is one of the most agonizing leadership challenges in business: the Right Person, Wrong Seat. Your Head of Operations matches your Core Values completely, but he lacks GWC for the complexity of a twenty-million-dollar company. He gets it and wants it, but he simply lacks the mental or organizational capacity to manage the expanded scope.

Leaving him in the seat out of sentimental loyalty is not kind. It is managerial cowardice. It burns him out, forces his peers to cover for operational failures, and sends a signal to your entire company that performance does not matter as long as you are well-liked.

You have two options. The first is to redesign your lower-level Accountability Chart to see if there is a genuine seat where he has complete GWC. Can he step into a focused role, such as Special Projects Lead, Facilities Director, or Senior Account Manager, while you recruit an experienced Head of Operations above him? If such a seat exists and genuinely serves the business, offer it with transparency and dignity.

The second option is to help him transition out of the company cleanly. If no seat fits his capacity, or if his ego cannot tolerate reporting to a new executive, you must part ways with generous severance and deep gratitude.

Frame the conversation around the seat, not his worth as a human. The seat required ten years ago was a five-person coordination job. The seat today requires enterprise systems architecture. Respect his historical contribution by being honest about the gap rather than allowing him to slowly fail in public.