Why Asking the Right Questions Matters More Than the Price

 

Right now, millions of baby boomer business owners are aging out. Many are exhausted. Many are emotionally attached. Many are unprepared for a clean exit.

 

That creates opportunity, but only for buyers who can separate story from substance.

 

Here’s the hard truth most acquisition advice skips:

Sellers don’t lie nearly as often as buyers fail to ask follow-up questions.

 

When you don’t ask, you assume.

When you assume, you overpay.

When you overpay, the business owns you.

 

Your job as an acquisition entrepreneur isn’t to interrogate, it’s to professionally understand the business, the seller, and the future you’re stepping into.

 

A Lesson Most Buyers Learn Too Late

Early in my career, I reviewed a deal that looked perfect on paper.

• Strong revenue.
• Consistent cash flow.
• Owner “ready to retire.”

 

But one question changed everything:

 

“What are your plans after the sale?”

 

The seller paused. Then said, “Honestly? I don’t know what I’d do if I wasn’t here every day.”

 

That single sentence told me more than the P&L ever could.

 

The business wasn’t owner-operated; it was owner-dependent.

 

No org chart would fix that overnight.

 

That’s why the questions below aren’t random. They’re sequenced. Each one builds context. Each one reduces uncertainty.

 

 

The Core Questions Every Buyer Must Ask a Business Seller

 

Think of this as your first-line acquisition filter, before LOIs, before bankers, before attorneys.

 

Identity, Ownership, and Motivation

 

Start with the human being across the table.

• Who am I speaking with—and who’s actually been leading this business?
  
  
• What’s your full name and role today?
  
  
• How many years have you owned the business?
  
  
• What’s the complete ownership history?
  
  

These questions establish authority and continuity. You’re confirming that the person negotiating actually controls the asset.

 

Then move to motivation:

• What’s your main reason for selling?
  
  
• Why now, not last year or next year?
  
  
• What are your plans after the sale?
  
  
• What are your long-term personal or professional goals?

 

Motivation determines flexibility.

Sellers retiring often prioritize certainty.
Burned-out sellers prioritize speed.
Strategic sellers prioritize price.

Your deal structure should match their motivation, not fight it.

 

Deal Flexibility and Alignment

 

Once motivation is clear, explore alignment.

 

• Would you consider an earnout?
  If yes, what portion of the price feels reasonable to tie to future performance?
  
  
• Are you open to seller financing?
  If so, what percentage of the deal would you consider financing?

These questions don’t commit either side, but they reveal whether the seller believes in the future of the business beyond closing day.

 

A seller unwilling to share post-close risk is telling you something.

 

Business Structure and Legal Reality

 

Before emotion comes accuracy.

• What is the business’s exact legal entity name?
  
  
• What industry do you operate in, and how do you define your niche?
  
  

Precision matters here. Sloppy answers often indicate sloppy records, which always surface later.

 

Pricing and Financial Logic

 

Never argue price first. Understand logic first.

• What’s your asking price?
  
  
• How did you arrive at that number?
  
  
• Was it based on a valuation, multiple, broker opinion, or intuition?
  
  

This tells you whether the seller is anchored to math or emotion.

Then get performance context:

• What were your gross sales last year?
  
  
• Is the business professionally managed or owner-operated?
  
  
• Who truly runs day-to-day operations?

Owner-operated businesses can be great acquisitions, but only if you price in the transition risk.

 

Transition and Continuity

 

Now assess post-close stability.

• Would you consider staying on as an employee or consultant?
  
  
• In what capacity and for how long?

This isn’t about dependency. It’s about knowledge transfer.

 

Assets, IP, and Balance Sheet Reality

 

Clarify what you’re actually buying.

• Does the business own any patents, trademarks, copyrights, or trade secrets?
  
  
• How much cash is currently in the business?

Then inventory the asset base:

• Accounts receivable
  
  
• Notes receivable
  
  
• Inventory or work-in-progress
  
  
• Equipment, vehicles, real estate
  
  
• Furniture, fixtures, machinery

Assets create optionality. Liabilities create surprises.

 

Which brings us to:

• Does the business have any liabilities?
  
  
• Any loans, notes payable, private debt, or off-book obligations?

If a seller hesitates here, slow down.

 

Unit Economics and Growth Intelligence

 

This is where buyers separate themselves.

• What’s your customer acquisition cost (CAC)?
  
  
• What’s your average order value (AOV)?
  
  
• Do you have recurring revenue (MRR or ARR)?
  
  
• What’s your customer lifetime value (LTV)?
  
  
• What’s your retention and churn rate?
  
  
• How many active customers do you have today?

These numbers determine scalability, not just survival.

 

 

Marketing, Sales, and Revenue Engines

 

Understand where growth actually comes from.

• Which marketing channels drive revenue today?
  
  
• Which sales methods are currently used?
  

A business with diversified channels is resilient.
A business with one channel is fragile, no matter how profitable it looks today.

 

Financial Records and Professionalism

Finally, verify readiness.

• Do you have financial records available?
  
  
• Are income statements, balance sheets, cash flow statements, and tax returns audited or unaudited?
  
  

This tells you how close the business is to being financeable and how much cleanup is required.

 

The Real Objective Behind These Questions

You’re not checking boxes.

You’re answering one core question:

 

Can this business thrive without the seller and reward capital honestly?

When the answers line up, deals close faster, financing becomes easier, and post-close stress drops dramatically.

 

An Acquisition Artistry Story: The Lantern Keeper

 

There was once a traveler seeking to buy an inn at the edge of a long road.

 

The inn looked beautiful by daylight. Full rooms. Steady traffic. A friendly owner ready to move on.

 

Before signing, the traveler asked the innkeeper one final question:

 

“How do you light the inn at night?”

 

The innkeeper smiled and said, “I carry the lantern myself.”

 

The traveler walked away.

 

Months later, another buyer took the deal, only to discover that without the innkeeper, the lights never came on, guests stopped arriving, and the road went dark.

 

The lesson is simple:

 

Never buy a business illuminated by someone else’s lantern unless you know how to light it yourself.

 

That is Acquisition Artistry.