Buying a Business? 3 Questions to Vet the Seller First

Sometimes when you're in the middle of evaluating a business opportunity, everything on paper looks fine — but your gut is telling you something’s off.

And that instinct? It’s worth listening to.

But in addition to trusting your gut, you need to ask smart, strategic questions that help you uncover what the seller isn’tsaying out loud. Surface-level answers won’t protect your investment — but the right questions can reveal inconsistencies, pressure points, and hidden risks that might otherwise slip through the cracks.

Here are 3 powerful questions to ask any seller if something doesn’t feel right — and what to watch out for in their answers.

1. “Can you walk me through any recent changes in revenue or expenses?”

This question puts the spotlight directly on any fluctuations in performance. Whether it’s a sudden dip in sales or a spike in operating costs, you want to hear why it happened and whether it’s a one-off or part of a trend.

This forces the seller to either reinforce the story behind their financials — or reveal red flags that contradict the numbers.

Red Flag: Vague or overly optimistic answers like “We just had a great month” with no documentation or explanation to support the claim.

2. “Is there any reason you wouldn’t want to keep this business yourself?”

This flips the script and puts the seller in your shoes — which can be revealing. A motivated seller with nothing to hide will give you a thoughtful answer about life circumstances or a genuine pivot.

But someone trying to unload a struggling business might dodge the question or give a rehearsed response.

Red Flag: Generalities like “I’m just moving on” with no personal or financial context. Watch for hesitation or answers that feel too smooth.

3. “What would you fix or improve if you were staying another year?”

This is one of the most underrated questions you can ask. It gently invites the seller to talk about what’s not working — whether that’s outdated systems, high turnover, or operational inefficiencies — without putting them on the defensive.

A thoughtful answer here gives you insight into the areas that might require attention post-sale.

Red Flag: A response like “Nothing, really.” That’s rarely the full truth. Every business has areas for improvement — and if they can’t name one, they’re likely withholding something.

Final Thought: Good Questions Reveal Hidden Truths

These questions aren’t just clever conversation starters — they’re due diligence tools. When used strategically, they help you:

• Detect misalignment between the story and the numbers

• Spot gaps in operations, staffing, or systems

• Uncover issues the seller may not volunteer

Pro Tip: If the answers feel vague, defensive, or too perfect — don’t ignore the feeling. Dig deeper, ask for documentation, and if needed, bring in an attorney or advisor to guide the process.

Please contact Serna Legal Services at 312-601-9859 or info@sernalegalservices.com if you’d like to learn more about what questions to ask a seller. We can help you review the deal, spot hidden risks, and protect your interests every step of the way!

This content is published by Serna Legal Services, LLC and is available for informational purposes only and is not considered legal advice on any subject matter. By viewing this content, the reader understands there is no attorney-client relationship between the reader and the publisher. The content should not be used as a substitute for legal advice from a licensed professional attorney, and readers are urged to consult their own legal counsel on any specific legal questions concerning a specific situation