First-Time Buyers
What questions should I ask the owner?
Get past the pitch — ask about transitions, customers, team, and the worst year.
Practical Explanation
Good buyer questions surface what isn't in the CIM: Why are you really selling? What does the business look like without you? Who are your top 10 customers, and what's the risk of losing them? What was your worst year and what caused it? Who on your team could leave and break the business? What grows the business 20% if I do nothing?
Real-World Example
A buyer learns the seller is leaving because their largest customer (35% of revenue) is shifting to a competitor — a discovery that re-prices the deal entirely.
Typical cash required
N/A.
Experience required
Asking real questions doesn't take experience, it takes preparation.
Advantages
- ✓Reveals hidden risks
- ✓Surfaces growth levers
- ✓Builds rapport
Risks
- !Asking adversarial questions early can sour the relationship
Frequently Asked Questions
Should I ask why they're selling?
Yes — and triangulate by talking to employees, customers, and vendors when given the chance.
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