Ask first, then talk for fifteen minutes
Most people have this backwards, and it costs them the deal before they get to the good part.
You have something you have built over decades, and when somebody finally asks about it, the instinct is to tell them everything. The problem is that you now know nothing about them, and you have spent all of the attention you were given.
"Stephen Covey passed away, but he said to be more influential you need to be influenced first, by asking questions. You could talk to an investor for two hours straight about everything that you're doing that's exciting in your platform. But if you ask questions first, then you can talk for 15 minutes about what they actually care about. And now you know that investor better, they respect you more, and they're going to be influenced more by what you say."
Two hours of you talking is worse than fifteen minutes of you talking, and the fifteen minutes only works if the questions came first.
The part that is actually strategic
This is not a rapport technique. The questions are how you find out which version of your deal to present.
"You can identify things in their answers that allow you to take the seven or two deal structures you could present to them, and just present to them a deal structure with a small tweak. That's exactly what they're asking for, and said that they prefer, because you were thoughtful in asking questions first."
A small tweak. Not a different business, not a different valuation. The same opportunity, arranged the way this particular person needs it arranged.
One family office needs current income and does not care about the back end. One needs their money back before anybody else gets a dollar. One cannot have a bank in the deal at all because of something that happened to them in 2009. Same company, same numbers, three different structures, and the only way to know which one is to ask.
If you walk in with one structure, you are hoping the person across the table happens to be the one it fits. Most of the time they are not, and you never learn why, because people do not tell you the real reason they passed.
Five questions worth asking before you present anything
Why family business owners in particular resist this
Because you know your business better than anyone in the room, and that is true. It is also the trap.
Forty years of knowing something cold makes explaining it feel like the valuable thing you have to offer, and in most contexts it is. In this one it is not. The person across the table already assumes you know your business. What they do not know is whether you will listen to them once their money is in it, and the meeting is the only evidence they get.
I am not sure there is a way to fake this... people can tell. But the mechanical version works even when you are bad at it, because a real question with a pause after it does most of the work.