Two of our key executives have deep interpersonal friction and unresolved resentment, which threatens to derail our upcoming quarterly offsite. How should we handle this executive conflict heading into our offsite so the session remains productive?

Question

Tyler Smith · Accepted Answer

Never enter a leadership team offsite hoping that interpersonal animosity will resolve itself over dinner and drinks. A quarterly or annual session requires intense focus, radical candor, and vulnerability. If two leaders arrive carrying passive-aggressive tension or defensive posturing, the offsite will dissolve into political posturing, and the rest of the team will check out.

The Integrator must confront the issue at least one week before the session. Pull both executives into a room and put the relationship on the table. Point out the specific behavioral patterns damaging team cohesion, such as defensive commentary in meetings, withholding information, or backchannel complaints to direct reports. Clarify that personal friendship is not required, but total functional respect and enterprise-first collaboration are non-negotiable conditions for keeping their seats.

Require them to surface their core friction using the IDS process before the offsite. Identify whether the root cause is structural ambiguity on the Accountability Chart, conflicting department Scorecard metrics, or broken personal trust. Force them to agree on behavioral boundaries and operational handoffs ahead of time.

If the issue remains raw when the offsite begins, address it during the opening health check. Acknowledge that the team cannot solve company-wide strategy while executive relationships are fractured. Use tools like the Five Dysfunctions framework to realign the room around vulnerability-based trust. When leaders realize that executive friction appears as a canyon to the frontline employees watching them, they usually drop their defensive shields and commit to doing what is right for the enterprise.