At some point in most holds, the plan the CEO signed up for at close stops being the right plan, and someone has to have the conversation about changing it. This is one of the more delicate moments in the operating partner relationship, because how it’s handled determines whether the CEO experiences it as a genuine reset or as a quiet vote of no confidence in them personally. 

The mistake I see most often is treating the renegotiation as primarily an analytical exercise. Build the case, show the data, present the revised numbers, expect the CEO to simply update their view because the evidence is sound. Sometimes that works. More often, it doesn’t, because the CEO isn’t purely evaluating the analysis, they’re also evaluating what the request to change the plan says about how the board sees their performance so far, and that’s a much more personal read than the deck accounts for. 

The better approach starts before the numbers, not with them. Have an honest, private conversation with the CEO about what’s changed and why, framed around shared circumstances rather than CEO performance specifically. Markets shifted, an assumption in the original model turned out to be wrong, a competitor moved faster than anticipated, whatever the actual driver is. The goal isn’t to avoid accountability where it’s genuinely warranted, it’s to make sure the CEO experiences the renegotiation as something being done with them, based on new information, rather than something being done to them, based on a verdict about their performance. 

Once that framing is genuinely shared, the numbers conversation becomes much easier, because you’re now jointly solving a problem rather than negotiating across a table. CEOs who feel the plan revision was collaborative tend to execute the new plan with real conviction. CEOs who feel it was imposed tend to execute it adequately and no more, and adequate execution of a revised plan is rarely enough to hit a revised target.