Questions That Sniff Out Seller Motivation
The seller’s story matters more than the spreadsheet. You’re not just buying numbers — you’re buying someone else’s choices, habits, and problems. Ask these questions before the deal smiles at you and stabs you in the back.
1. So… why are you actually selling?
This isn’t small talk — it’s the one question that unlocks everything.
If they say “retirement,” fine. But what they don’t say matters more.
Do they pause? Get vague? Launch into a monologue about “new opportunities”?
You’re either catching someone mid-exit… or mid-escape.
💡 CPA Take: Sellers rarely tell you the whole story. “Family time” is the classic decoy — what they’re really saying is: I’m exhausted, revenue’s sliding, and the walls are closing in. Always match their story to the financials. If it doesn’t add up, assume the business is bleeding.
What you’re really listening for:
- Are they running toward something (a planned exit)?
- Or running away from a sinking ship?
Follow-up questions that tighten the screws:
- If the business is still doing well, why not hire a manager and keep the income?
- What changed in the last 12 months that made you want to sell?
- What would make you not sell right now?
If they flinch on this, dig. This is where the real due diligence starts.
2. How many hours a week are you actually working?
Skip the theoretical BS. You want numbers.
“Only about 10 hours a week” sounds great… until you realize they’re including late-night emails, emergency phone calls, and Sunday inventory runs.
This is your life you’re buying — not just a profit line.
💡 CPA Take: When sellers say “part-time,” ask what that really means. One guy I met was still teaching students, handling customer support, and doing payroll himself. That’s not part-time — that’s unpaid labor disguised as freedom.
Why it matters:
A business that runs without the owner is valuable.
A business that needs the owner is a trap with receipts.
Follow-ups that expose the truth:
- Walk me through your typical week — day by day.
- Who handles operations when you’re on vacation?
- When was the last time the business ran for 7 days without you doing anything?
If they can’t answer with confidence, it’s not passive — it’s just unpaid overtime waiting for a new name.
3. What’s the part of this business you hate the most?
This is your pressure test. It catches them off-guard and tells you what’s broken.
You’re not looking for cute answers like “Oh, bookkeeping.”
You’re looking for pain. The kind they don’t put in the listing.
Bad answers:
- “Hiring’s a nightmare.” → High turnover, low morale
- “We always get stuck with late shipments.” → Supply chain problems
- “I’m sick of chasing customers for money.” → Cash flow warning ahead
💡 CPA Take: A friend of mine asked a seller about her biggest headache, it was flaky staff. When they asked what she’d tried to fix it, she shrugged. That’s not a red flag — it’s a neon sign. If they’re checked out, you’re inheriting both the problem and the apathy.
Follow-up gut punches:
- What have you done to fix that?
- What would happen if that problem got worse?
- Why hasn’t it been solved yet?
The gold is in the silence.
If they stall? You just found your leverage.
If they get defensive? You just hit a nerve.
Recap: What This Section Tells You
These aren’t throwaway questions — they’re your pressure points.
They tell you:
- If the seller’s motivated or desperate
- If the business is self-sustaining or held together by willpower
- If you're walking into opportunity — or walking into fire with your eyes closed
If the story doesn’t line up with the spreadsheets? Walk. Or negotiate like hell.
Money Questions That Actually Matter
Everyone looks at revenue. Smart buyers ask what’s left after the dust settles — and how clean those numbers really are.
4. How much do you actually take home after all the bills?
This is your real baseline — not the inflated “seller’s discretionary earnings” figure they found on Google.
You want to know:
- How much cash they’re pocketing after rent, staff, subscriptions, and overhead
- Whether they’ve padded the numbers with personal perks (spoiler: they have)
💡 CPA Take: That SDE might look solid — until you realize it includes private school tuition, a luxury SUV lease, and “strategic planning” in Maui. That’s not margin. That’s camouflage.
Follow-up gut checks:
- Can you show me which expenses you added back to get that number?
- If I owned the business as-is, with no changes, how much would I take home in Year 1?
- Are there any personal expenses in here I shouldn’t count as income?
What you’re really asking: Is this a healthy business — or a financial optical illusion?
5. Can I see your revenue and expenses month-by-month — not just yearly totals?
Annual summaries hide sins. One great month can cover up eleven mediocre ones. You want the rhythm: when the money flows, when it doesn’t, and how often they sweat payroll.
💡 CPA Take: If they say it’s “in QuickBooks” but can’t tell you when they last opened it — run. That’s not financial hygiene. That’s neglect.
What you’re looking for:
- Seasonal swings
- Revenue plateaus
- Expense spikes (e.g., insurance renewals, tax payments, surprise repairs)
Follow-up clarity checks:
- Which months were your best — and why?
- What are your highest fixed expenses?
- Have any vendors raised prices recently?
Smart buyers spot trends. Lazy buyers stare at totals.
6. Were there any one-time boosts or weird spikes in revenue I should know about?
This is where the truth hides.
Government loans. A massive one-off contract. A COVID bump. A hail Mary marketing win that won’t repeat. If the current numbers look sexy, ask: “Will that happen again?”
💡 CPA Take: Think you're buying a booming pet supply store? The ‘boom’ might only be a one-time bulk order from a government shelter. Post-close — there's no growth story.
Follow-up detection tools:
- Was that revenue tied to a contract or was it just a lucky month?
- Have any customers stopped ordering since then?
- What % of last year’s revenue came from repeat customers?
Ask this. Hard. Twice. In writing. You’re not buying lightning in a bottle.
7. Do people owe you money — or do you owe anyone money?
Translation: What’s the accounts receivable (AR) and accounts payable (AP) situation?
Don’t let them frame this like it’s “all normal.” If they’re waiting on $100K from three flaky clients — or owe a vendor $60K — that’s your problem after the handshake.
💡 CPA Take: Don't get blindsided by a $40K vendor dispute that the seller “forgot” to mention. That could easily wipe out Month 2’s cash flow. Ask questions.
Follow-ups that matter:
- What’s the average time it takes for customers to pay you?
- Are there any unpaid invoices more than 60 days old?
- Do you prepay for any major expenses?
Think of this like buying a car — and realizing it still has someone else’s parking tickets taped to the windshield.
8. What exactly am I getting for the purchase price?
Inventory? Equipment? Goodwill? A customer list? A domain name? Spell it out — line by line.
💡 CPA Take: Don't be a rookie and assume “everything” is included — even the logo. Small detail - if the seller never legally transferred it, that’s not a deal, that’s a lawsuit starter kit.
Follow-up deal shapers:
- Is the inventory current — or is some of it dead stock?
- Is any of the equipment leased or under financing?
- Are there customer contracts or just handshakes?
If you can’t list the assets and their value — you’re buying hope, not a business.
Recap: What This Section Tells You
You’re not here to be impressed by shiny topline numbers. You’re here to:
- Follow the money
- Find the dead weight
- Separate facts from fluff
If the seller can’t clearly show where the profit is — they either don’t know, or they don’t want you to know. Either way: your signal to dig deeper… or walk.
Operations — Will This Thing Survive Without Them?
Buying a business is one thing. Running it without the previous owner holding your hand is another. Here’s how you figure out whether you’re buying a system — or stepping into someone else’s burnout.
9. What happens if you disappear for two weeks?
Say nothing else. Let it hang.
If they laugh and say, “Nothing — my team’s got it,” you might be in luck. If they start describing a long list of daily tasks they handle? You just found your first panic button.
💡 CPA Take: I asked this during a café deal. The owner listed 12 daily tasks only he could do — including ordering inventory and resetting the POS. No manager. No backup. I walked.
Follow-up to separate fact from fiction:
- When was the last time you actually took two weeks off?
- Who’s trained to run things if you're out?
- Is there a written manual for anything?
If there’s no clear backup plan, the business is a bottleneck — and you’re about to become the bottleneck.
10. If your best employee quit tomorrow, what breaks?
Every business has one MVP. The question is: do they know it — and are you dependent on them?
This question flushes out:
- Single points of failure
- Whether processes are documented
- What kind of emotional blackmail you’re inheriting (“we can’t lose Sarah…”)
💡 CPA Take: If the manager runs scheduling, payroll, and handles every complaint, what happens when he walks? You're not just losing an employee — you're losing the brain trust. He probably knows every password, every vendor, and every fire drill fix.
Follow-up hammers:
- Is there a backup trained on their role?
- Have they mentioned leaving or getting recruited?
- Do they have an equity stake — or just loyalty?
You’re not just buying a business — you’re inheriting its drama. Ask like it.
11. Are your processes actually written down?
This is your SOP gut check. If they say “yeah, it’s all in our heads,” what they mean is: you’ll be guessing at everything after closing.
💡 CPA Take: Seller tells you “our training is hands-on.” Translation: chaos with charisma. No checklist. No docs. No thanks.
What you want:
- Simple checklists
- Documented workflows
- A Google Drive, Notion, or dusty binder — anything
Follow-up drills:
- Can I see your onboarding doc for new employees?
- How do you train someone to do [task]?
- Do you track repeat mistakes or process issues?
If they can’t hand over a playbook, you’re buying improv theater — not a business.
12. What software/tools do you use — and who manages them?
You’re sniffing for two things here:
- Whether the business runs on systems
- Whether the owner is the only one who understands them
💡 CPA Take: I reviewed a warehouse biz running six tools — but only the owner had the logins. No password manager. No documentation. Don't let the owner walk out with the keys to the kingdom.
Follow-up clarity checks:
- Do you have admin access stored anywhere safely?
- Does your team actually use the tools — or is it just you?
- How much of this could I run from a laptop?
Bonus points if they use tools like QuickBooks, Slack, Shopify, Notion, or anything with built-in reporting. Red flags if everything’s in Excel and verbal memory.
Recap: What This Section Tells You
Operations are where deals go to die quietly.
You want a business that:
- Doesn’t panic when someone calls in sick
- Has playbooks instead of memory banks
- Can run without the founder clinging to it like a baby monitor
If every answer starts with “I usually…” — you're not buying a business. You’re buying someone’s inbox with a lease.
Customers, Sales & Growth — Where’s the Money Really Coming From?
If you don’t know who buys, why they buy, and how they found the front door — you’re flying blind. This is where good businesses become great ones… or where decent revenue hides deep rot.
13. “Who are your top 3 customers — and how much of your revenue comes from them?”
This is the customer concentration test. You’re not just asking for names — you’re mapping dependency risk.
💡 CPA Take: I once saw a digital agency with $1M in revenue… and $720K came from one client. That’s not a business — that’s a paycheck with overhead.
Follow-up reality checks:
- If one of them left, how long could the business stay afloat?
- Are they locked in by contract or just habit?
- What’s the longest customer you’ve kept — and why?
If three customers are propping up the entire business, you’re not buying growth — you’re buying a cliff.
14. “How do most new customers find you?”
This question sounds polite — but it’s pure strategy.
It tells you:
- Whether the business has a repeatable sales engine
- Or if it’s just coasting on word of mouth and luck
💡 CPA Take: If the seller says “most people just find us.” Translation: zero predictable lead gen. When those referrals dry up, so does the pipeline.
Follow-up flashlights:
- What’s your average cost to acquire a new customer?
- Do you spend anything on marketing — or just wait?
- What’s worked and what flopped?
You’re looking for systems. Not sorcery.
15. “What happens if I raise prices by 10%?”
This is a subtle trapdoor question. You’re testing:
- How confident they are in their value
- How price-sensitive the customer base is
- Whether they’ve ever tested pricing
💡 CPA Take: I once asked a seller this and they laughed nervously — “we haven’t raised prices in five years.” That's easy money left on the table for half a decade.
Follow-ups to make them squirm (and reveal gold):
- When was the last time you raised prices?
- How did customers react?
- Is there anything stopping you from charging more?
A strong business can flex price. A weak one begs to stay afloat.
16. “If you weren’t selling, what would you do to grow this thing?”
You’re not just looking for ideas — you’re measuring vision.
This is your free roadmap. If the seller’s been in the game, they already know the untapped levers. And if they say “not sure”… that’s a red flag too.
💡 CPA Take: I once heard, “I’d start an online store but never got around to it.” Build that post-close and tap into additional revenue streams.
Follow-up excavation:
- What’s stopped you from doing that already?
- What’s the easiest win the next owner could unlock?
- Where’s the upside the next buyer shouldn’t miss?
Growth potential lives in the ideas sellers never acted on.
You’re buying what they left on the table.
Recap: What This Section Tells You
This is where you separate the wheat from the wishful thinking.
You’re buying:
- A customer base (how loyal?)
- A marketing engine (how repeatable?)
- A price point (how flexible?)
- And a growth story (how believable?)
If they can’t answer these cleanly — or haven’t tried to grow at all — you’re buying a hamster wheel, not a launchpad.
Red Flags, Legal Landmines & Deal-Breaker Gut Checks
This is where you flush out the stuff they didn’t mention on the listing. You’re not being paranoid — you’re protecting your ass.
17. “Any lawsuits, complaints, or nasty surprises I should know about?”
Ask this one deadpan. Don’t soften it.
Lawsuits. Unpaid taxes. Landlord disputes. Employee HR issues. Bad Google reviews.
You want it all. And you want it early.
💡 CPA Take: Everything looked clean — until I threw a direct jab: “Any legal issues I should know about?” The seller shrugged. “Just a small thing.” That “small thing” was a $40K lawsuit and two employees walking out before close.
Follow-up firestarters:
- Any complaints with regulators or health departments?
- Have you had to fire anyone in the last year — and did they leave clean?
- Any past disputes with your landlord or vendors?
If they say “no,” pause… and then ask again later in the convo.
Sometimes people don’t lie — they just conveniently forget.
18. “Has anyone else made an offer on the business?”
Sounds innocent. It’s not.
You’re probing for:
- How long it’s been sitting on the market
- Why others walked
- What objections have come up already
💡 CPA Take: I asked the owner if anyone else was interested in investing in his business. “Yeah,” he said, “A few were interested, but couldn’t get financing.” Later I found out: three were already invested and trying to get their money out — and two had already bailed after seeing the books.
Follow-up disarmers:
- What feedback did they give you?
- Did any of them make it past financial review?
- Would you sell to them now if they came back?
This is your backdoor to the real story of the deal.
19. “What kind of transition support are you offering — and how long will you be around?”
This is where expectations die if you don’t spell it out.
You might assume the seller will stick around and help.
They might assume they’re handing you the keys and bouncing.
💡 CPA Take: Make sure you don't get stuck with only 7 days of help after buying a $900K business. That's not support — that's abandonment.
Follow-up clarifiers:
- Can we agree on X weeks of hands-on support?
- Would you be available part-time for the first quarter?
- What’s your availability if I hit issues six months in?
Get it in writing. Verbal promises disappear faster than a seller’s inbox post-closing.
20. “If you were buying this business, what would you be nervous about?”
This is the closer. The truth extractor. Ask it late, when they’re relaxed.
It’s unexpected. It’s disarming. And it often reveals the one thing they were hoping you wouldn’t ask about.
💡 CPA Take: I asked this once and the seller paused. Then said: “Honestly? The lease is up in 6 months and I haven’t renegotiated.” That changed the entire deal. But he wouldn’t have told me unless I hit him with this curveball.
No follow-ups. Just shut up and let them answer.
What you hear here may not kill the deal — but it’ll tell you where the cracks are.
Recap: What This Section Tells You
This is the stuff that doesn’t show up on a P&L:
- Pending lawsuits
- Sketchy exits
- Flaky sellers
- Ghosts in the lease or legal docs
If the answers start getting vague, slow, or defensive — pay attention.
That’s your signal. Not to run — but to renegotiate, restructure, or re-evaluate.
Wrap It Up: Ask Hard. Ask Early. Ask Twice.
Most first-time buyers worry about sounding rude. Screw that.
You’re about to invest six or seven figures into something with moving parts, unpredictable people, and no guarantees. You don’t need to be rude — but you do need to be relentless.
And if the seller doesn’t like the questions? That’s not a deal. That’s a cover-up in a cash flow costume.
This guide just gave you the questions that separate amateurs from assassins.
Use it. Share it. Or forward it to that friend who’s about to overpay for a coffee shop.
Ready to stop guessing and start screening smarter?
Acquidex helps you spot red flags, overhyped listings, and financial fiction — before you waste your time or your down payment.
Disclaimer
This article is for informational purposes only and does not constitute financial, legal, or investment advice. Always consult with a qualified professional before making any acquisition decisions.
Avery Hastings, CPA
Avery Hastings, CPA lives in Tokyo, helping first-time buyers cut through the noise and avoid bad deals. When she's not tearing apart small biz P&Ls, you’ll find her sipping a Pauillac red or carving through powder on her snowboard in the Japanese Alps.