Let them say no
Most people selling something spend the whole conversation trying to keep the other person from saying no. The people worth buying from do the opposite. They hand you the no early, out loud, and they mean it.
It sounds like a good way to lose the sale. It isn't. Pressure rarely gets you a real yes. It gets you "let me think about it," which is usually a no that was too polite to come out. Once someone feels cornered, every question you ask sounds like a trap, so they stop telling you the truth. Take the pressure off and the truth comes back. A real no is useful. A fake maybe costs you both.
The move: let them say no.
I've sold on commission for 10 years, so I understand why this feels backwards. Here is what it sounds like in three places. These are made-up examples, but if you've ever sold anything, or been sold to, you'll recognize every one of them.
You've just walked a homeowner through a quote at their kitchen table, and they go quiet. The reflex is to fill the silence, or to say the price is only good until Friday. Letting them say no sounds like: "If this isn't the right fit, or the right time, you can just tell me." Now the silence has somewhere to go.
Someone books a first call about your coaching, and halfway through they start hedging. The reflex is to answer every doubt before they finish saying it. Letting them say no sounds like: "You don't have to decide anything today, and if it's not for you, that's a fine answer." You haven't given up. You've made it safe for them to tell you what the hedge is really about.
A proposal you sent has gone quiet, and you're about to write "just checking in" for the third time. The reflex is to keep nudging. Letting them say no sounds like a short note: "Should I close this out? A no is a perfectly good answer, and it means I'll stop following up." It's easy to answer, because it's the first message that doesn't ask them to feel bad about not answering.
Notice what you didn't do. You didn't drop your price. You took the fear out of one word. Once no is safe, you hear the real reason: the timing, the money, a partner who hasn't seen it yet. You can work with that. You can't work with "let me think about it."
There is one way to ruin it: offer the no, then fight it. If they take the easy no and you start arguing, you've shown them it was a trick. When they say no, thank them and ask one question: "What would have made this a yes?" Then let it go.
Steal this line: If this isn't right for you, it's completely fine to say no, and I'd rather hear it now than guess.
The thread: people tell you the truth once they feel free to disagree, which is also why saying their side first works in an argument. A sales call isn't an argument, though: you're not on opposite sides, you're finding out together whether it fits, so a no here isn't a position to beat, it's an answer to respect.
That's the move. Last week was politics, this week is sales. This letter covers five areas: politics, sales, marketing, AI and building a business, one move from one of them each Tuesday.
Hit reply: what's the one yes you're waiting on right now?
Gunnar
P.S. Know someone who sells for a living and hates feeling pushy? Forward this to them.
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