Average Sales Guy

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The Over-Promising Sales Leader: When “Yes” Becomes “Gary’s Problem”

people at theater

Gary Miller here, and let me tell you, there’s a special kind of dread that washes over you when your manager, or even worse, a VP, hops on a customer call and starts… improvising. Not improvising a sales pitch, mind you. Improvising product features. Improvising delivery timelines. Improvising everything.

You’re sitting there, nodding along, contributing where you can, feeling like the deal is progressing nicely. And then, it happens. Your esteemed sales leader, in their zeal to close the deal, utters those fateful words: “Absolutely, Mr. Prospect, we can definitely do X, Y, and Z for you! Consider it done by next Tuesday!”

X, Y, and Z, of course, are things that you, the Average Sales Guy on the ground, know for a fact are:

  1. Not currently possible with the product.
  2. On a roadmap for Q4… of next year.
  3. Something that would require an act of Congress and a team of 10 engineers working around the clock.

My eyes widen. My blood runs cold. My internal monologue screams, “NO! NO, THEY CAN’T! PLEASE DON’T SAY THAT!” But it’s too late. The promise is out there, hanging in the digital air, shiny and completely undeliverable.

The call ends. The customer is delighted. Your manager is beaming, high-fiving you virtually. “Great job, Gary! See, all they needed was a firm commitment!”

And then begins the slow, painful process of reality setting in. For me, that usually involves a quick internal Slack message to our overburdened Sales Engineer: “Hey, remember how [VP’s Name] just promised [Impossible Feature X] by next week? How much trouble are we in?” The reply is usually a single emoji: 💀 or a GIF of a dumpster fire.

Then comes the walk of shame (or the Slack message of shame) to Product Management. “So, about that thing we just committed to… is there, uh, any way we could perhaps… fast-track that, maybe?” Product looks at me like I’ve suggested we teleport the customer’s entire data center to the moon. They remind me, patiently, of development cycles, resource allocation, and the small matter of physics.

So, who gets to deliver the bad news? Who gets to explain to the now-delighted customer that the moon they were just promised is actually a very long-term project, pending budget approval, and requires significant client-side resources? That’s right. Gary Miller.

It’s a delicate dance of walking back promises without making your own company look incompetent or, worse, deceitful. You try to spin it: “What [VP’s Name] meant was that we are highly committed to exploring solutions for your needs within our future roadmap framework, subject to mutual prioritization…” It’s exhausting. It feels like you’re constantly playing damage control for someone else’s over-enthusiasm.

It’s not malice, usually. It’s just the pressure of the deal, the desire to win, and sometimes, a slight disconnect from the ground-level reality of product development. But for the Average Sales Guy, it’s a direct highway to awkward customer conversations and strained internal relationships.

You learn to preempt. You learn to subtly interject on calls (“…and we can explore those advanced capabilities as part of a phased approach, post-implementation!”). You learn to send follow-up emails immediately, clarifying (“Just to reiterate from the call, our standard implementation includes A, B, and C, with X, Y, and Z being part of our future strategic development…”).

Because ultimately, the buck stops with the rep. And in the world of sales, an over-promised feature today is just Gary’s problem tomorrow.

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