Ask why now
Start with the reason for sale, how long the owner has considered selling and what they would do if the business did not sell. The answer is not proof of anything, but it frames the incentives behind the listing.
Ask how the numbers are produced
Which systems generate revenue and expense data? What costs have been added back? Which months are unusual? What changed recently? Ask to reconcile answers to source records later.
Use the live marketplace to compare real listings against the criteria in this guide.
Ask what could break
Which customer, supplier, platform, employee, contractor or traffic source would hurt most if lost? What has failed before? Which metrics have worsened even if headline revenue grew?
Ask what the owner actually does
Request a weekly task list with hours, tools and decision rights. Owner dependence is often clearer when work is described operationally rather than with a single “hours per week” number.
Ask what does not transfer
Which accounts, relationships, licenses, contracts, data or processes require third-party approval or a new application? A sale can be attractive economically and still fail technically at transfer.
Ask what the buyer still needs to prove
End every seller call by listing the claims that remain unverified. Then request the evidence required to test them rather than letting conversation substitute for diligence.