What are the real execution risks you’ve uncovered during diligence that didn’t show up in the CIM or financials?

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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
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