A Deal I Lost Last Week That’s Still Bothering Me

I lost a deal last week.

That’s not unusual. I’ve lost hundreds of deals over thirty years. You win some, you lose some. That’s the job. You’re supposed to shake it off and move on.

But this one is still sitting with me. I keep replaying the conversations. Going back through my notes. Trying to figure out where it went wrong.

Because here’s the thing: I did everything right.

The Setup

Mid-market software company. About 400 employees. They had a real problem – I won’t get into specifics, but it was costing them money every month. Real, measurable money. Not theoretical.

I had a champion. She was bought in. She brought me to her VP. The VP was nodding along. They gave me access to their data so I could build a custom business case. They introduced me to procurement early – which is usually a good sign.

I built the ROI model. The numbers were strong. 14-month payback. Clear cost savings. I even got a reference customer in their industry to take a call with them.

Textbook. Everything by the book.

The Loss

They went with the competitor.

Not because the competitor was cheaper. They weren’t. Not because they had better features. They didn’t. Not because of some relationship I didn’t know about. I asked.

My champion told me – and I could hear how uncomfortable she was – that they just “felt more confident” in the other solution.

Felt. More. Confident.

That’s what I lost to. A feeling.

What I Keep Coming Back To

I’ve been going back through my notes from every call. And something keeps jumping out at me.

Our team talked too much.

In every call, I can see it. We had the answers. We knew the product. We knew the market. We knew the business case cold. And so we talked. We explained. We presented. We answered every question thoroughly – probably too thoroughly.

We were so focused on proving the value that we never shut up long enough to let them own it.

Looking back, the VP barely spoke in our calls. I took that as a good sign at the time – no objections, right? But now I’m wondering: was he quiet because he was convinced, or because he never felt like it was his idea?

The Competitor

I found out a little about what the competitor did differently.

Apparently their rep asked a lot more questions. Let longer silences hang. Made the VP do more of the work in the conversation. My champion said their demo was actually less polished than ours – but the VP came out of it with pages of notes he’d written himself.

Notes he’d written himself.

I handed them a beautiful deck. He handed them a pen.

I Don’t Know What This Means Yet

I’m not drawing any grand conclusions here. It’s one deal. Could be an anomaly.

But it connects to something I’ve been thinking about. This idea that maybe selling harder isn’t the answer. That maybe being too prepared, too polished, too ready with the answers… actually works against you.

The competitor didn’t out-sell me. They out-listened me. They made the buyer do the work. And somehow that made the buyer more committed to the decision.

I don’t fully understand it yet. But I can’t stop thinking about it.

The Question I’m Sitting With

What if I lost that deal not because I did something wrong, but because I did too much right?

What if all that preparation – the ROI model, the reference call, the polished deck – actually made it feel less like their decision and more like mine?

What if the buyer needs to struggle a little? Needs to work for it? Needs to convince themselves?

I don’t know. I’m just writing this down because I can’t shake it.

Maybe it’s nothing. Maybe I’m reading too much into one loss.

But that VP with his pages of notes keeps coming back to me. He did the work. He owned it. And he signed with the other guy.

I’ve seen this before.

There’s something there. I just can’t name it yet.