When I sit down with a seller for the first time, I know that the conversation will shape the entire deal. Financial statements and documents come later, but that first meeting gives me insights no spreadsheet can provide. It reveals motivation, culture, and the human side of the business.
Over the years, I’ve developed a set of questions I always ask in that first meeting. These aren’t about drilling the seller with numbers; they’re about understanding the story behind the company and whether the deal has a chance of working for both of us.
In this article, I’ll walk through the first questions I ask, why they matter, and the lessons I’ve learned from conversations that went well and those that didn’t.
Why the First Questions Matter
That first conversation sets the tone. If I ask the right questions, I learn:
- Why is the seller motivated to exit.
- How the business actually runs day to day.
- Where hidden risks and opportunities might be.
- Whether the seller is someone I can work with during the transition.
If I skip these questions, I risk missing key information and misjudging whether the deal is viable.
Question 1: Why Are You Selling?
This is always my first question. Motivation drives everything. A seller retiring after 30 years has very different expectations than one burned out after five.
If they’re selling because of personal health or retirement, I expect a cooperative transition. If they’re selling because the business is struggling, I know to dig deeper into problems.
This question also reveals whether the seller truly wants to let go or whether they may have second thoughts down the road.
Question 2: What Do You See as the Biggest Strengths of Your Business?
I want to hear the seller’s perspective on what makes the company successful. Their answers highlight the areas they’re most proud of customer relationships, employees, systems, or brand reputation.
These strengths aren’t just about bragging; they tell me what’s most valuable to preserve.
Question 3: What Do You See as the Weaknesses?
Sellers often hesitate here, but the honest ones provide valuable insight. Weaknesses might include customer concentration, lack of documented systems, or reliance on the owner.
I take careful note, because what they admit usually scratches the surface of larger issues I’ll need to explore in diligence.
Question 4: How Do Customers Describe Your Business?
I love this question because it reveals culture and brand reputation. If sellers answer confidently, it usually means they know their market well. If they stumble, it suggests they may not have a pulse on customer perception.
Question 5: Who Are Your Key Employees?
I want to know which employees are essential, how long they’ve been with the company, and how loyal they are. Employee stability or fragility tells me a lot about transition risk.
Question 6: What Keeps You Up at Night About This Business?
This question often disarms sellers. It gets them to drop the polished pitch and reveal their real concerns. Sometimes it’s cash flow, sometimes competition, sometimes burnout. Their answer always gives me valuable context.
Question 7: How Do You See Your Role in Transition?
I ask this early because expectations can differ. Some sellers want to walk away on day one. Others expect to stay for months or even years. I want clarity upfront, so there are no surprises later.
Question 8: What Would You Do Differently If You Were Starting Over?
This question reveals blind spots. It tells me what the seller has learned from experience and where they see opportunities that I might seize after taking over.
Mistakes I’ve Made in Early Conversations
I’ve made mistakes by rushing into numbers too quickly. In one meeting, I asked about financials before building rapport. The seller became guarded, and the relationship never recovered.
I’ve also failed to ask why the seller was exiting early in my career. Only later did I learn the business had major operational problems. That mistake taught me to always start with motivation.
Why These Questions Build Trust
Asking thoughtful questions does more than gather information; it builds trust. Sellers want to feel understood. When I ask about their legacy, their employees, and their concerns, they see that I care about more than just numbers.
That trust often makes the difference between winning a deal and losing it to another buyer.
Final Thoughts
The first questions I ask when meeting a seller are about motivation, strengths, weaknesses, culture, employees, and transition. They set the tone for the entire relationship.
I’ve learned that deals succeed or fail as much on trust and alignment as on financials. That’s why I treat the first conversation with care. It’s my chance to understand not just the business, but the human being who built it.
I continue sharing my acquisition playbook, lessons, and strategies at DrConnorRobertson.com, where I document the realities of buying and growing businesses.