Hear it straight from our PE partners
What failed, what was missed, and what they’d do differently to align leaders for value creation early.
The most valuable talent insights come from experience… and often from the deals that didn’t go quite as planned.
Leadership missteps can be among the costliest in private equity, yet they remain among the most preventable.
So we asked PE leaders in our network to look back at past deals and share what they got wrong and what they would do differently. Apply these lessons to sharpen your leadership assessments, accelerate alignment, and protect value from day one.
Too often, evaluation gets anchored on how someone shows up — the interpersonal, the cultural read, and the presence in a room. What gets missed is whether any of that actually correlates with results.
The challenge is that everyone defines executive presence differently. It’s a feeling. And feelings are hard to stress-test in diligence. I think we can over-index on that feeling. Strength and results don’t always indicate each other.
There’s a version of this that plays out more often than anyone wants to admit: a CEO gets placed shortly after close because the momentum of the deal carries them into the role. The hard questions about fit, about capability under a new ownership structure, and about whether they can actually partner with investors don’t get asked until there’s already a problem.
Too often we take what the CEO tells us at face value. I’ve seen it: gotten into positions shortly after close where we had to make a change. The only other ones I can think of who weren’t caught flat-footed were the ones who asked the hard questions before the investment was made.
The firms that avoid the most painful leadership transitions are the ones that over-communicate from the start about what the exit looks like, what the scenarios are, and what’s expected of the team at each stage. Surprises in year two almost always trace back to assumptions that were never made explicit at close.
You have to ensure that you’ve outlined from the very beginning what the economics of the exit are so there’s absolutely no confusion. You have to align on those things as early as possible. We’ve seen how it’s one of the most important things you can do.
Prolonged CEO uncertainty takes a quiet but serious toll on culture. Without clear leadership (and sustained over time), teams lose alignment, informal power structures can emerge, and morale erodes as employees grow anxious about the company’s direction. A culture shaped by this ambiguity is harder to reset and the incoming CEO inherits not just a role, but the residue of a sprawling organization.
We learned a lot of lessons on timing and what happens when you wait too long on a CEO decision, whether that’s hiring or exiting. Delay can be costly in so many ways. You may need up to 90 days to really assess, but shouldn’t drift beyond that.
Hunt Club is the executive search partner VC and PE-backed high-growth companies trust to identify and secure the right hires for the job. We’ve built an integrated search platform and exclusive network to access talent traditional firms can’t reach.
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