The Demo Only Works In One Order

Every car I've owned has had one thing like this — a door that only locks if you jiggle the handle a certain way, a window that sticks unless you push the top corner first. You learn the order and stop thinking about it. You just do it.

We had a demo build like that once. Every feature in it was real, nothing was faked, but it only held together if you clicked through in the sequence we'd rehearsed. Click the wrong thing first and something would lock up or throw an error that had nothing to do with what the prospect actually cared about.

Everyone on our side knew. Sales knew, I knew, the engineers building it knew. What got to me was that most prospects who clicked wrong didn't say anything — they just went quiet, assumed it was them, and moved on. A few asked, carefully, like they'd caught us. Nobody ever said out loud "does this only work one way," even though I'm sure plenty of them suspected it.

I started just telling people up front. This build has an order to it, here's roughly why, ask me anything you want about it. It felt exposing the first few times — like I was handing someone a reason to walk. A couple of people on our side thought I was talking us out of deals we hadn't lost yet. I don't have a clean answer for whether they were right. I've watched it land two completely different ways: sometimes it buys trust, sometimes I can see the prospect's confidence drop a notch and never come back.

I'd been doing a worse version of this for years before I found out there's a whole idea about admitting the fault yourself before someone else finds it and holds it over you. My worse version was more anxious — blurting the flaw defensively, half-apologizing for a product that mostly worked fine. The difference I'm still working on is saying it flat, once, without the apology attached to it.

What I haven't figured out is the line between disclosure and undermining yourself before you've even started. Say too little and you're the person who let them find out the hard way. Say too much and you've talked yourself out of a deal that was never going to hit that edge case anyway.

If you sell or demo product for a living — have you ever told a prospect about a known flaw and watched it cost you the deal outright?