Five years ago, a buyer’s diligence list read like a familiar recipe: financials, contracts, litigation, key employees, a look at customer concentration, maybe a light IT review at the end. If the numbers held up and the lawyers didn’t flinch, the deal moved.
Buyers in 2026 open the data room with questions that would have sounded wild in 2021, and sellers who show up unprepared are watching valuations get re-cut at the eleventh hour.
These aren’t add-on questions anymore. They sit next to EBITDA.
If you’re thinking about selling in the next 24 months, learn what buyers are probing so you can answer before they ask.
What Does the Target Actually Do With AI? Can it Prove it?
This question didn’t exist on a diligence list in 2021, and now it sits near the top. Buyers want to see the AI stack the way they used to want to see the cap table: model by model, license by license, dataset by dataset. A Deloitte overview frames AI diligence as part of the investment thesis itself, not a footnote, because substitution risk and margin erosion from AI-native competitors can erode what the business is worth. What they’re really testing:
- Capability vs. marketing. Does the product use AI the way the pitch deck claims, or is a third-party API doing the heavy lifting behind a thin wrapper? Overstated AI capability has become common enough that buyers now assume they’ll find some of it.
- Data provenance. Where did the training data come from, who owns it, and can the target keep using it after change of control?
- Model licenses. Every foundation model has terms. Commercial use, fine-tuning rights, and output ownership vary widely, and inherited restrictions travel with the deal.
How Exposed Is the Business to a Cyber Incident Nobody’s Found Yet?
Cybersecurity used to be a checkbox handled during IT diligence. It’s now its own workstream, with its own specialists and its own line in the risk register. Buyers assume most targets have unresolved vulnerabilities and, in some cases, active intrusions the seller doesn’t know about. An EY analysis of cyber diligence in M&A points to how often serious exposures surface only when a buyer looks carefully, which is exactly why the workstream keeps expanding.
Expect questions about incident history the seller may have resolved without disclosure, third-party access from vendors and contractors, and how identity and access controls hold up under a real audit. A finding here doesn’t usually kill a deal, but it can lead to repricing.
Will This Business Actually Integrate, or Just Look Like It Should?
Integration readiness has moved forward in the process. Buyers no longer wait until post-signing to discover that the target’s cloud architecture, identity systems, and data pipelines don’t fit theirs. They ask now. That includes questions about tech debt, key-person dependency on a single engineer who knows how everything is wired, and whether the target’s systems can survive a migration without breaking.
For owners, get in front of it. Understanding the range where your business realistically trades, using something like a business valuation calculator, is a useful starting point. The harder work is making sure the answers to the new questions are ready before a buyer starts asking.
The deals that close cleanly in 2026 belong to sellers who saw the list change and updated their file.
