Years ago, I informally promised a dedicated, loyal manager that they would become our Chief Operating Officer, but as we grow toward an exit, their capabilities cap out at mid-management. How do I handle this gap without destroying their loyalty?

Question

Tyler Smith · Accepted Answer

You cannot sacrifice the enterprise to honor an outdated promise. Rewarding past loyalty with a leadership seat that exceeds someone's capability is unfair to the company, unfair to the team, and ultimately unfair to that individual. As an owner preparing for an exit or scaling up operations, your duty is to build an Accountability Chart designed for the company's future, not its past.

Address this directly in a private, scheduled conversation. Do not wait for an annual review or drop the news during a quarterly offsite. Take complete ownership of the situation. Acknowledge the verbal promise you made years ago, explain why the business has evolved, and admit that your past projection no longer matches what the enterprise requires to succeed.

Evaluate the person using the People Analyzer and GWC (Get it, Want it, Capacity to do it). Separate their loyalty and core values from their capacity:
- They likely share your core values and have immense institutional knowledge.
- They may understand the operational basics, but they lack the strategic capacity to lead at the scale required.
- Forcing them into an executive seat will lead to public failure and eventual termination.

Offer them a meaningful, clearly defined seat on the Accountability Chart where they can truly thrive and add value, whether as a functional manager or subject matter expert. Compensate them fairly for that role. Be prepared for them to need time to process the emotional sting. If they cannot accept the reality and become bitter, you must part ways cleanly and generously. Preserving the company's growth trajectory must always come first.