A buyer questions for the seller checklist organizes the direct questions worth asking across a Canadian business purchase — about operations, customers, staff and the seller’s own plans — as a question bank for calls and meetings throughout the process, not only the first conversation, with a note on what a vague or evasive answer to each one usually signals.
Reviewed
This checklist is a bank of direct questions worth asking a Canadian business seller across the buying process, distinct from Deavo’s first meeting checklist, which covers how to conduct that conversation rather than what to actually ask. Use these across several conversations, not all at once — a seller who is asked everything in a single sitting tends to give shorter, more guarded answers than one given room to actually think.
Ask about how the business actually runs
Ask what a typical week looks like for the owner personallyA specific, detailed answer suggests an owner who genuinely knows their own operation; a vague one can mean the real answer is less flattering than they would like to admit.
Ask what is currently broken or overdue that has not been fixed yetEvery real business has something like this, and an owner who names one honestly is more credible than one who insists nothing is currently a problem.
Ask what would happen to the business if the owner were unexpectedly unavailable for a monthAn owner who has genuinely thought through this answer is describing a business with real depth; one who has never considered it is describing one that depends entirely on them.
Ask about customers and competitors
Ask how many customers the owner would say they know personally by nameA high number in a business that should run on repeat, anonymous transactions can point to a level of personal relationship risk the financials alone will not show.
Ask which competitor worries them most, and whyAn owner with no real answer may be underestimating a genuine competitive threat, while a detailed answer usually reflects an owner paying close attention to the market.
Ask what the business has lost a customer over in the past, and what changed afterwardA specific story with a lesson attached suggests an owner who learns from setbacks; a shrug in response suggests problems may be recurring without being addressed.
Ask about staff and culture
Ask whether staff would be surprised to learn a sale is being consideredA confident no from an owner who has already had honest conversations with the team is a different signal than a nervous no from one who has avoided the topic entirely.
Ask who on the team the owner would be most reluctant to loseA clear, immediate answer points to a genuinely key employee worth understanding better; hesitation or an inability to name anyone raises its own separate question.
Ask how the business handles a slow month for cash flowA calm, specific answer suggests a business with real financial discipline behind it; an evasive one can mean cash flow is more fragile than the annual numbers suggest.
Ask about the seller’s own experience and plans
Ask what the owner wishes they had known before they started the businessA thoughtful, specific answer here often surfaces real operational lessons that never show up in a data room, however good the documents themselves are.
Ask what they consider the biggest mistake they have made running itAn owner willing to name a genuine mistake, rather than deflecting the question entirely, is generally more trustworthy on everything else they tell you.
Ask what they actually plan to do after the sale closesAn owner with no real plan for after the sale may be more likely to linger, second-guess the deal, or struggle to let go during the transition than one with a clear next chapter.
Deavo is an advertising and listings platform, not a brokerage, law firm or valuation firm. This page is general information, not legal, tax, accounting or valuation advice, and rules differ by province. Confirm anything you rely on with a qualified professional before you act on it.