We Lost the Deal

A while back, we got the kind of opportunity that's exciting for about five seconds before it turns terrifying: a full RFP for a big logo, due in a handful of days. The team's first reaction was the honest one. There's no way. It was too much, in too little time, and whatever we sent would be half-baked. And they weren't wrong on the facts - it was a lot, and the clock was real.

So I did what I've learned to do when a room has decided something is impossible: I opened a blank document. I spent about an hour on it. Just drafting. A few ideas, a rough shape, the bones of what a strong response could look like (of course with the help of Claude). Then I brought it to the people leading the deal and said, more or less: look, this took me an hour, and I think it's already enough of a skeleton. If we split the work well and use AI efficiently, we can all make it. It won't be 100%. It'll be 80%. But 80% does the job - and whether we win this or not, what we learn building it will be worth more than the deal.

Here's the part I still think about. It took maybe ten or fifteen minutes of talking it through before the mood in the room turned. You could feel it. First it was "okay, maybe this is possible." Then "actually, we could do this well." And then, quietly, the thing I was really hoping for: "wait - we might even win this."

We didn't win it.

And I was as proud as if we had.

Because somewhere in those few days I watched people do some of the best work I'd seen from them. They put in some extra hours to get it over the line, but nobody complained about it. They were invested in what they were building. I saw contributions I didn't know were in there. I saw a team that clicked. And somehow, a process that should have been stressful and miserable turned out to be genuinely, ridiculously enjoyable. We didn't get the logo. But I got to see what that team was capable of when they stopped thinking about whether they could do it and started figuring out how.

For most of my career, I thought leadership was about being impressive. Being the one with the answer, the one who could figure it out, the sharpest person in the room. But that RFP is the whole thing in miniature. My job that week wasn't to write the best response (trust me, their output was far better than mine). It was to change what the team believed was possible - and then get out of the way so they could go prove it. I didn't make them impressed with me. I made them braver.

That's the shift no one hands you a memo about. Impressing people is about you. Making people braver is about them. One gets you admired. The other gets you followed - and, for what it's worth, tends to produce far better work.

And you can't fake the belief. People can smell a pep talk from a mile away. What moved that room wasn't my enthusiasm, exactly - it was that I genuinely believed we could do it, and I was willing to go first, blank document and all. Belief is contagious, but only the real kind. You carry it for people until they can carry it themselves. And then they surprise you. I love that.

The best feedback I ever got in twelve years had nothing to do with a number I hit or a project I completed. It was people telling me I'd made them braver. That I believed in them before they believed in themselves. I used to file that under the soft, nice-to-have part of the job. Now I think it was the job.

And don't read any of this as me being at peace with losing. I still wanted that logo - I'm competitive, and winning will always matter to me. But a team that walks out of a loss sharper, closer, and more sure of what it can do doesn't stay on the losing side for long. What we learned in those few days is exactly what wins the next ones. You either take the deal, or you take the lesson that goes and gets you the next three.

We lost the deal. But I still think about those few days as one of the wins.

What's a "we lost, but I'd do it all again" moment in your own work - something that didn't work out that you're still proud of? I'd love to hear.

See you next Friday, -Laurie 🤍