Selling a company can be a very emotional moment, especially if it’s been held for a long period of time including across multiple generations. For many owners this has been their livelihood, this has defined their life and it’s not an easy thing to let go of.

A key is to understand why the owner really wants to sell. If it doesn’t feel strong enough, seller’s remorse could kick in and you’re left at the altar and back to ground zero on the acquisition trail.

So when might you be most at risk for a transaction that could fall through:

1. The owner’s looking to retire however the owner might not really have to retire quite so soon.

2. The owner’s eggs are all in one basket. This is his only company. This is where he or she’s been spending most of their time and there doesn’t appear to be much in the way of outside interest.

3. He only began with high expectations on the valuation. Even though you’ve got to negotiate down to a more realistic level that nagging thought may still be in the back of the owner’s mind.

4. The owner is selling due to a financial crunch. What if another source of money suddenly appears so the owner doesn’t have to sell?

5. Optimism. The owner might feel that if sales volume was up just a bit more they wouldn’t have to sell and then they might feel a sudden surge of optimism that that big account is just around the corner before you’re ready to close.

6. Employees. If the owner has a big heart and cares deeply about the employees, which is terrific, but like any terrific thing in life there can be a point where it goes to far and the owner is so attached to the people that it’s tough to let go.

Of course, there are lots of legitimate reasons for selling a company, but often the real underlying reason is not what’s stated. Make sure you get below the surface and know if you’re on solid ground. Otherwise you could be on a shaky foundation and the odds may be against the transaction getting done.