Colin Dowling

When I was younger I played a lot of poker. At casinos, with friends, online. And I learned a universal truth most poker players understand: I can't remember the biggest pots I ever won, but I remember with excruciating detail every bad beat I ever suffered.

In the last 25 years of B2B selling, I've won some incredible deals — including GoDaddy's largest-ever enterprise contract, WP Engine's first five-figure monthly hosting contract, and Alembic's first true enterprise deal. And still, the details I remember most clearly are the deals I didn't win. The ones where I felt blindsided at the finish line. Where I had the verbal approval for an order form that never came. The ones where I later learned a deal I had committed to the board had gone to a competitor.

Sell for long enough and your own "bad beats" start to stack up. If you've made it this far, they probably already have.

For a long time I thought the better salesperson won. I’d lose a deal, take it personally, and go looking for what I could have done differently in the room.

Then I inherited enough broken motions to see it differently. The deals I lost weren’t lost in the room. They were lost upstream — in an ICP nobody had tightened, in a stage definition that meant four different things to four reps, in a forecast built on deals that were already dead, in positioning that made us interchangeable before the first call.

The rep gets blamed for an outcome that was set weeks earlier by a motion nobody had rebuilt in years. That’s the bad beat, and it’s structural.