You did everything right and still lost the deal

Four years ago I was working a deal in New York that had everything going for it.

Strong champion. Full MEDDIC run. POC completed. Price agreed. Around $150-200k ACV. The kind of deal that feels, at a certain point, like it's just a matter of paperwork.

Then came the decision call.

They were going a different way. A competitor. I was upset, and I wanted to understand why. So I dug in.

It turned out the CEO's investors were also invested in the competing vendor. The decision had nothing to do with our product, our price, or our sales cycle. It was made in a boardroom conversation I was never part of and could never have influenced.

That one stung for a long time.

I was about four years into my sales career, working an enterprise deal in New York. The company was a solid prospect — good fit, real budget, a champion who genuinely believed in the product. We had done everything by the book. Qualified hard, ran a proper POC, built a business case, agreed on price. By the time we got to the decision call, I was confident.

Then we lost.

I went back and tried to understand the root cause. What I found out was this: the CEO's investors were also invested in our competitor. The decision had been made in a room I was never in, based on motivations that had nothing to do with our product, our price, or anything I had done.

There was nothing I could have done differently. The deal was never really ours to lose.

That one stung for a long time. And it was one of the first times I started seriously thinking about what I actually have control over in a sales cycle — and what I don't.

There is a concept I keep coming back to, one my VP introduced me to: controlling the controllables. It maps almost perfectly onto something the Stoic philosopher Epictetus wrote about over two thousand years ago. The idea is simple: some things are in your power, and some things are not.

The mistake most salespeople make — especially earlier in their careers — is attaching their sense of performance to outcomes they cannot fully control. The result is only one data point. The quality of your execution is a much better measure of how well you are actually doing the job.

Josh Braun, who writes a lot about this, puts it well: detach from the outcome, not the effort.

If you want to go deeper on this, I strongly recommend picking up The Art of Living by Epictetus. It is an introduction to Stoicism, and a huge part of Stoicism is exactly what we are talking about here — detachment, or as my VP puts it, controlling the controllables. It is something every salesperson should at the very least be aware of. I cannot recommend it enough.

After every significant loss now, I run a quick personal audit. Two questions only: what was in my control in this deal, and what wasn't? If the honest answer to the second question is "most of it", I give myself permission to move on faster than I naturally would. That is not laziness — it is protecting your energy for the next opportunity.

The other thing I do differently is try to identify, during qualification, what forces exist above or outside my champion that I cannot influence. Investor relationships, pending reorgs, board-level mandates. I cannot always find them, but asking the question keeps me honest about the risk in my pipeline.

Execute the sales cycle to the best of your ability. Use every resource, framework, and relationship available to you. Then let go of what you cannot control — because holding onto it does not change it. It just costs you sleep, focus, and over time, your enjoyment of the job.

The goal is not to stop caring. It is to care about the right things.

If something happened outside your control that cost you a deal, I'd genuinely like to hear about it. Hit reply and tell me.