Every COO can build a system. The harder part is deciding what to do when it involves someone they genuinely care about.

In our July mastermind, COO Alliance members sat with a question most leadership content avoids. What is the hardest people decision you have made as a COO.

When Loyalty and Alignment Diverge

The same story kept surfacing in different forms. Someone talented, someone trusted, sometimes even a friend, reaches a point where they no longer fit where the organization needs to go.

One COO waited too long to let go of a VP he had worked alongside for years, a close friend who had quietly become a cultural problem. Another stepped into a COO role and had to tell a ten year employee they would not get the position they expected, then stayed present through the conversation until that person found a role built for their real strengths.

A third member had to fire the person who originally hired them, once that relationship became a direct report with real performance issues.

Why Avoiding The Decision Backfires

Stewardship kept coming up as the word that defined this work. Leadership is not loyalty to individuals. It is stewardship of the whole organization.

Leaving someone in a role where they cannot succeed rarely counts as kindness. It usually slows them down along with everyone around them. Avoiding the decision does not make it gentler either, it just makes the outcome harder for everyone involved.

What The Best COOs Do Differently

Most experienced COOs already know what needs to happen. What makes these moments hard is the relationship they built along the way.

• They have the honest conversation instead of delaying it
• They give the other person real clarity, not vague signals
• They sit with the discomfort instead of rushing past it

Bottom Line

These decisions do not get easier with more experience. They just get handled with more intention.

If conversations like this happen in a monthly online mastermind, imagine what unfolds in a room full of COOs for three straight days. Distance disappears, guards come down, and people share stories that never make it into a video call.

Our Boston event is one month away and already sold out, which says a lot about how much operators value this kind of room. 

Cameron Herold founded COO Alliance as a global membership organization for COOs and second in command executives, built around exactly these conversations. Explore COO Alliance to be part of it.