Alright folks, settle in. My name’s Gary Miller, and I’m your host here at the Average Sales Guy blog. If you’re looking for secrets to hitting 300% of quota, scaling your outbound to infinity, or becoming a sales ninja warrior, you’ve probably clicked the wrong link. My goal is simpler: share stories from the trenches that make you think, “Yep, that sounds about right,” or “Okay, maybe my sales life isn’t that weird.”
This week’s installment comes courtesy of a deal I officially waved goodbye to just a few days ago. It was a good one, nothing earth-shattering, but solid. You know the kind – good fit, engaged champion, seemed to understand the value proposition, competitive landscape felt manageable. It was the kind of deal you pencil into the “probable commit” column, maybe even let yourself daydream about the commission check for a solid 30 seconds before shaking your head and remembering Rule #1: It Ain’t Over ‘Til the Paper’s Signed (And Sometimes Not Even Then).
We were there. The finish line was in sight. Legal seemed happy (a minor miracle in itself). Procurement wasn’t raising any red flags (another sign the universe was maybe, possibly, briefly aligning). My internal champion was responsive, asking about next steps for implementation. I was feeling pretty good. Maybe even… confident? (Rookie mistake, I know).
And then it happened. The email landed.
It wasn’t from my champion. It was from someone new they’d looped in – apparently a stakeholder who needed a final look. Their question was polite enough, but it hit like a sudden hailstorm on a sunny day. It was about a feature. A small one. Like, really small. Think the digital equivalent of needing a very specific color of staple remover. Something we honestly rarely get asked about. Something that had never, ever, once come up in the dozens of conversations we’d had over months.
My immediate thought process went something like this: “Huh? That feature? Do we… have that? Surely we do. That seems… basic? Or maybe super niche? No, wait, is that even our product? Is this a competitor spec? Let me quickly check the internal wiki that’s definitely out of date…”
Cue the frantic internal scramble. Pinging the poor, overworked SE who probably gets 50 ridiculous questions from AE’s a day. “Hey, Bob! Feature X! Do we have it? Like, specifically how they’re asking?” Hitting up Product Management chat groups. Sifting through old battlecards. There was a brief, desperate hope it was a misunderstanding. A simple configuration change. A setting toggled in the admin panel.
The reality hit back with the force of a wet noodle. Nope. We did not have Feature X. Not in the current release. Not in the next release. Not even really on the drawing board because, frankly, almost no one asks for the darn thing.
Delivering that news to the customer was… fun. “So, about Feature X… turns out, yeah, that’s not something we currently offer.”
Their response was swift and decisive. “Oh. Well, that’s actually a hard requirement for us now. We, uh, just realized how critical it is for [insert slightly vague, sudden use case here]. Guess we’ll have to go with Competitor Y. Thanks for your time!”
And just like that, poof. Months of work, gone. Not because our core product wasn’t a fit. Not because pricing was off. Not because of a major gap. Because of the digital equivalent of a specific color of staple remover that suddenly became the linchpin of their entire operation the day before signing.
Trying to explain that on the forecast call was… an experience. “Yeah, so, [Deal Name] is a closed/lost. Reason? Missing feature.” Cue the follow-up questions: “Which feature? Was it a known gap? Was it on the roadmap?” Explaining that it was a sudden, last-minute requirement that appeared out of nowhere just earns you the sympathetic, slightly bewildered stares of colleagues who’ve undoubtedly experienced their own version of this particular sales hell.
Look, I’m not going to pretend I wasn’t annoyed. Losing a deal that way stings. It feels absurd. Like the sales gods are just messing with you. But after almost two decades in this game, you also develop a certain… acceptance. This stuff happens. Deals are fragile ecosystems, and a butterfly flapping its wings in a customer’s engineering department can apparently cause a hurricane in your pipeline.
You dust yourself off. You update the CRM (while muttering under your breath). You try to find the slightly dark humor in the situation. And you move on to the next opportunity, knowing, deep down, that it too will present its own unique, probably equally absurd, challenge.
That’s just life for the Average Sales Guy.