What are the real execution risks you’ve uncovered during diligence that didn’t show up in the CIM or financials?
November 25, 2025
by a professional from University of California, Hastings College of Law in Petaluma, California, United States
Question for the community as we head into 2026: What are the real execution risks you’ve uncovered during diligence that didn’t show up in the CIM or financials?
I’ve been comparing notes across a number of searchers and deal teams, and these 5 themes come up repeatedly:
1) GTM durability questions
Revenue looks good, but the engine isn’t as repeatable as expected.
2) Key employee fit concerns
Great tenure… but unclear post-close adaptability.
3) Operational cadence gaps
KPIs, reporting rhythm, and handoffs aren’t as standardized as the numbers suggest.
4) Pricing inconsistencies
Pricing decisions often based on feel, not data — creating hidden risk or hidden upside.
5) Buyer/operator bandwidth load
Search CEO capacity is tested much earlier than expected.
Curious for the community, since we are aiming to learn & refine if we should add to this list:
- Which of these have you faced?
- What surprised you the most during diligence?
- (And if there’s a pattern you’ve seen that isn’t on this list, I’d love to learn from it.)
— Stephanie, Five Experts