He might be the most talented interviewer I’ve worked with. The kind of founder who can walk into a room, ask a few careful questions, and have you explaining your own business back to yourself in a way you’d never quite managed on your own. Watching him run a call is a genuine pleasure.
He was also losing. Not dramatically. Quietly. Curious buyers, good calls, second meetings, and then silence. Deals that felt alive right until the moment they weren’t.
Somewhere in the hardest session we did together, he stopped and said the truest thing a founder has said to me in a long time.
“I know all this. And yet I still don’t do it.”
That sentence is the whole job. Not the framework, not the tactics. The distance between what a founder knows and what they actually do when there’s a real buyer in front of them and the pressure is on.
He came to me thinking his problem was pipeline. Most founders think their problem is pipeline. Usually there’s some truth to it, but it’s rarely the thing worth fixing first. If you can’t close what’s already in front of you, more pipeline doesn’t save you. It just hands you more deals to lose the same way. When I watched his calls, the real problem was the same one on every single one of them, and it was hiding inside his greatest strength.
Every time a buyer handed him the real pain, the thing they actually lie awake about, he turned it into a question. He took the moment that mattered and politely asked the buyer to describe it back to him. On one call a buyer said the quiet part out loud and named the exact thing his own boss judges him on. That is not a feature request. That is the deal, handed over. And my founder said, more or less, “right, so we can make that more efficient.”
He took the one moment that gets an executive to lean in and turned it into a pitch about saving time. He had a painkiller in his hand and he sold it like a vitamin.
I stopped him there, because that is the whole game. People don’t spend money to get better. They spend money to stop getting worse. Executives don’t buy efficiency. “More efficient” usually means the same people work a little more, and nobody upstairs ever feels it. What executives buy is the removal of pain that has their name on it. The number slipping. The target missed. The board asking questions they can’t answer. Show them you can stop the bleeding and they’ll find the budget. Tell them you’ll save their team some clicks and they’ll take the meeting and forget you by lunch.
So we went to work. I run every founder I coach through the same framework, and it pressure-tests the whole motion end to end. We moved him off the vague, everything-to-everyone positioning that put him in a fight with every competitor and every weekend hobbyist building the same thing. We anchored on the one problem his buyers already agreed they had. We built an opening that lands in the first ninety seconds, a statement rather than a question, the kind that makes a buyer think this person has been inside businesses like mine. We got specific about who he sells to and who he doesn’t. And we surfaced the objection he was never actually hearing out loud, so he could put it on the table before the buyer ever did.
But we didn’t spend the week teaching him any of that. Here is the part worth sitting with. He already knew all of it. He knew you shouldn’t sell features. He knew painkillers beat vitamins. He had read the posts. He could have written the posts. And under pressure, on a live call, he reached for the thing that felt safe instead of the thing that works.
That is not a knowledge problem, and you cannot read your way out of it. He defaulted to asking questions because asking questions was comfortable, and saying the hard thing first, planting a flag, being a little confrontational, risking being wrong before he was sure, was not. That instinct runs exactly backwards in sales. In most professional life, being wrong is the thing you avoid, so you wait until you’re sure. In sales, waiting until you’re sure is the only real mistake. Put a hypothesis out loud and one of two things happens. You’re right, and the buyer feels understood and you’re off. You’re wrong, and the buyer corrects you, and now you have the real answer you’d otherwise have spent three calls trying to pry loose. Both of those are wins. The only way to lose is to not take the shot, because you were still busy making sure.
I have had some version of this conversation with more than three hundred founders across forty-eight countries now. Different products, different markets, the same trap every time. The founder’s greatest strength, the thing that carried them this far, turns out to be the exact thing capping their ceiling. For him it was the questions. For the next founder it is the demo they cannot stop giving, or the likability they lean on instead of leading, or the enormous market they refuse to narrow because narrowing feels like walking away from money.
The strength is never the problem. Leaning on the strength past the point where it still serves you is the problem. Nobody warns you about that, because online everybody already has all the answers.
We fixed his motion in a week. What we actually did that week was close the distance between what he knew and what he did when it got hard.
That distance is where the deals are.
Stop wondering why the good calls go quiet. That gap between knowing and doing is exactly what I fix. Let's talk → daverubinstein.com