The long dark
I want to tell you guys about one of the scariest parts of selling a product to another business.
In fact, my buddy has a name for it—he calls it “the long dark”.
The long dark starts the moment a prospect verbally says, “yes, we are going to buy your product” and ends when they sign a legally binding agreement to do it.
If you don’t work in sales, you might think the time between those two events is short and straightforward. They said they’d buy it, so surely they’ll just go do that?
It’s called the long dark for a reason. It can take weeks or months, and many things can happen that are out of your control to bring it to completion.
The procurement process could be a nightmare. Hidden decision makers might veto the deal at the last minute. Budget could get unexpectedly revoked. Your agreement could get unreasonably red-lined. Or my favorite: maybe the person who said “we have a deal” never had the authority to say that in the first place!
It’s a fragile space to be in.
9 out of 10 times I come out unscathed. But sometimes I don’t, and it’s about the most painful part of the work I do. The real problem—for me at least—is that it’s tempting to mentally equate someone verbally saying “we have a deal” as having actually closed the deal. Because when you do that, anything that goes wrong—whether you can control it or not—makes you feel like you lost something you never actually had.
The lesson I learn, and keep relearning, is that the end game in sales is its own skill. The agreement isn’t done until there’s ink on the page, and as much as you can, you need to keep doing the fundamentals well: driving alignment with your prospect, remaining helpful with whatever obstacles come up, and seeking out all the decision makers on the other side of the table.
As long as I work in sales, the long dark will never go away. But as I get a little more disciplined about the end game, I can move through it more calmly.


One of the best, messiest parts of the job. So many random texts and ad hoc meetings flare up in a series of negotiation mini games.
These are the times I question why I didn't build a product customers just buy by clicking a button on a website 😆