Selling Isn’t Convincing. It’s Connecting.

A few years ago I was standing in front of the dairy case at Safeway, trying to choose a whipped cream. A man beside me asked how I even decided - fat content, hydrogenated oils, all of it. I sized him up, decided he was harmless, and we got talking. Food, health, the small science of a grocery aisle. I enjoyed it. Strangers in a city don't usually stop to look at each other, let alone talk.

Then he asked the question.

"So - you're interested in health, hey?"

You know that pulse of recognition, the half-second where you realize that what you thought was happening was not what was happening. I felt it land in my stomach. He smoothly segued into his real intent letting me know he represented a great line of products he was sure I'd be interested in. I said no as gracefully as I could and walked off with that slightly winded feeling. In a single sentence the whole thing had flipped. He hadn't been curious about me. He'd been looking for common ground so he could sell me something.

An ulterior motive is always exactly that. Ulterior. The conversation was never the point. I was the point.

For a long time I drew the obvious lesson from that morning: I am not a salesman. I don't have the stomach for it. I wore the fact that I don't like manipulating people as a small badge of honour, the way decent people do.

The trouble is I kept building things. Programs. Products. Eventually a whole practice. Things I genuinely believed would help the people who used them. And every single time, I hit the same wall - the one nobody warns you about when you're busy making something good. The best thing in the world does not sell itself. Someone has to put it in front of someone else. And when that someone was me, I froze. Because in my head, selling meant becoming the man at the dairy case.

So I did what any reasonable person looking to learn a new skill does. I went to YouTube. I typed in "sales techniques" and watched a man sell vegetable peelers in Times Square. I watched his patter. I watched actual people hand over actual money for a peeler they had not woken up wanting. It was mesmerizing, and it half-confirmed my fear - this is a trick, and I don't have it in me.

But I kept watching, and reading, and I eventually found sales aligned with integrity and honesty. My perspective began to slowly turn. The distinction that changed the work for me, when it finally arrived, was almost embarrassingly simple.

What kept me out of sales for years was thinking sales meant convincing someone to do something they didn't want to do. It doesn't. And it has nothing to do with polish. It's where you start. Good selling begins by meeting the person - listening closely and understanding their real need. Then trying to solve it. That work is honest. You can either meet that need or not, in fact a great salesperson will even be the first to say, "I don't have what you need" - and then tell them who does.

The other kind of selling is all about manufacturing the want. Not meeting anyone's need but your own.

Don't get me wrong - a good salesperson gets their need met too; they make the sale. Just never at the cost of the person across from them. I'd been so afraid of being the smooth (as whipped cream) salesman that I'd refused to sell, even when I needed to.

Here's why this matters far past the grocery store, and far past anyone with "sales" in their title. If you lead anything, you are influencing people all day. You ask a board for a yes. You ask a funder to believe you. You ask a tired team for one more good week. And if you've decided, like I did, that influence means convincing people to do what they don't want to do, you'll do one of two things with it. You'll avoid it - and watch good work die for lack of a champion. Or you'll do it badly, with a pressure in your voice that people can feel, the way I felt it over the whipped cream.

Honest influence starts on the other foot entirely. Not "how do I get them to want this," but "what do they need, and can I meet it?" If the answer is yes, your job isn't to convince. It's to connect. If the answer is no, then the honest move is to stop selling - which, it turns out, is also the thing that makes people come back.

When I relearned that, the work got easier. Not because I got better at persuading anyone. Because I stopped believing I needed to convince anyone to do something they didn't want to do.

The Leadership Check-In won't teach you to sell. It'll show you how your influence actually lands - whether the people on the other side of you feel connected to something real, or quietly feel approached. Most of us can't tell the difference from the inside. That's the whole point of a check-in.

En route, but aren't we all.