Strategy
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November 5, 2026

Pitch to how the buyer actually thinks

At my old agency, we figured out how every lead thinks before the first call. The same proposal lands or dies on it, and it's the one reason a pitch dies that I control.

At my old agency, we had a habit before every first call. A lead would come in, and before anybody talked about money, we'd try to figure out how that person thinks.

Most people who called us didn't really know what they were looking for, so we'd sort them into one of two camps. If they were a big-picture person, we could talk big ideas, let the conversation twist and turn and come back around, and save the budget for later. If they were a detail person, they needed the five steps we were going to take and the budget, broken out all the way down to an hourly rate per person.

I learned to do that the hard way. Around 30 I started reading about personality types to figure out why I struggled to talk to people. At the same time I was running my first real business, a scooter brand. I flew to China, found a manufacturer, figured out shipping and customs, and built the website and what I called the brand. My business partner and I could not communicate. Neither of us was wrong. We just thought in completely different ways. The company went under, mostly from over-ordering inventory, but the two of us never once got on the same page.

Then I met the owner of the creative agency next door. He knew more about personality types than anyone I'd met, and he invited me in. He could put all the pieces in order. I had the ideas. And we started using what we knew on every lead that came through the door.

Same proposal, different buyer

I think in big pictures. Most of the people I sell to don't. The owner-operators who call me are good at their craft, and they think in concrete terms: what are you making, what does it cost, when is it done. If I walk in with possibilities (maybe this, maybe we could try that) I've lost them before I get to the good part.

That's why the same proposal can land with one person and die with the next, and nothing in it changed. Hand a big-picture buyer five steps and an hourly breakdown and they feel like they're being sold a spreadsheet. Hand a detail buyer the big idea and they feel like they're being sold a daydream.

Even José Caballer ran into it. When he came on my podcast, he said the frameworks he's known for were built mainly for nonlinear people like the two of us. "People that are linear, which I added later, needed the six steps for each exercise." The person who taught half the industry how to sell creative work had to go back and add the steps for the buyers who think in steps.

Words do the same damage. A founder once liked my recommendation and still didn't trust it, because of the language. "All you brand guys are all the same." He'd heard that vocabulary before, from people who didn't deliver. I sell strategy for a living, and strategy is exactly the kind of word that sounds like a daydream to a detail buyer. A lot of my fights over the years have been against budgets and against people who don't know the words I'm saying. Some of that was on me for using the words.

One reason, not the reason

A pitch dies for all kinds of reasons. The budget isn't there. The timing is wrong. They weren't a fit and I wrote the proposal anyway. Most often, they just decide to do nothing. Getting the buyer's mode wrong is only one of those reasons, but it's the only one I fully control.

At the agency it was easier. There were two of us, and between us we covered both kinds of buyer. Now it's me. I pick up the phone with a client, go back to the computer to do strategy, then try to do some design. Nobody down the hall is going to build the step-by-step version for me.

So the detail version is the part I have to do on purpose, because it isn't how I think. The big idea comes out of me on its own. The five steps and the budget by the hour have to be ready before the call, because a detail buyer isn't going to wait while I find them.

None of this saves a pitch that was going to die anyway. It just means that when one dies, it isn't because I walked a detail person through my daydream.

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