Before pursuing an off-market business, a buyer should know why the owner might sell, on what timeline, roughly what the business earns, how much it depends on the owner, and whether it truly fits the buy box. Off-market owners haven't prepared a sale package, so these answers come from conversation, and getting them early saves weeks on deals that were never right.
Motivation and timing
- What would you want to do after a sale, and why now (or why not yet)?
- Is anyone else involved in the decision: a partner, a spouse, family in the business?
- Have you talked to a broker, another buyer or an advisor about selling?
- What would a good outcome look like for you, beyond the price?
An owner without a reason to sell is a long-term relationship, not a deal this quarter. That's fine, as long as you know which one it is.
The business
- What does the business do, and who are its main customers?
- Roughly what are revenue and earnings, and how have they moved over the last few years?
- How much of the revenue is recurring or under contract?
- Does any single customer make up a large share of sales?
You don't need audited numbers on a first call. You need enough to know whether the business could fit your size range and financing.
Dependence on the owner
- What does your week look like, and who handles it when you're away?
- Which customer and supplier relationships run through you personally?
- Who are the key employees, and would they stay?
- Are there licenses or certifications held in your name?
A business that can't run without its owner is harder to finance and harder to keep after closing.
Fit and practicalities
- Is the real estate owned or leased, and would it be part of a sale?
- Are there debts, disputes or liabilities a buyer should know about early?
- Would you consider staying on for a transition period, or financing part of the price?
Then check the answers against your buy box. A good business that doesn't fit is still a pass.
How to ask
These aren't a questionnaire to read out. The first call is about building trust: explain who you are and why the business interests you, listen more than you talk, and save detailed financial questions for after an NDA if the owner wants one. Our process puts a qualification call like this before any owner is introduced to a buyer. For building the list these conversations come from, see how searchers build an acquisition target list.
Common questions
Should I sign an NDA before the first call?
Not usually for an introductory call. An NDA becomes useful when the owner is ready to share detailed financials or customer information. Offer one when the conversation gets there.
What if the owner won't share numbers yet?
That's common early on. Ask for ranges, or what a typical year looks like, and come back to specifics once there's more trust. An owner who never shares numbers is a signal in itself.
When should I bring in advisors?
Once there's real interest on both sides and you're moving toward valuation and terms. Your attorney, accountant and lender should guide the letter of intent, diligence and structure.