Gary Miller here, wondering why I thought selling software would be easier than this.
So I’m three months into what should have been a straightforward $150K deal with a manufacturing company. Started simple enough – three people on the buying committee: the IT director, operations manager, and CFO. We’d been having good conversations on our video calls, they liked our software, and I’m thinking this closes by month-end.
Then I get a message: “Hey Gary, we’re expanding the evaluation team. Can you do a demo for the full group next week?”
Full group? I’m thinking maybe we add the CEO and a department head. Makes sense for a deal this size.
I dial into the video call and there are twelve people staring back at me. Twelve. The original three, plus the CEO, two VPs, three department managers, the head of procurement, someone from legal, and – I kid you not – an intern named Tyler who’s apparently “helping with the technical evaluation.”
The IT director introduces everyone and says, “We want to make sure all stakeholders have input on this decision.”
Stakeholders. Right.
So I’m doing my demo, explaining how our software handles their inventory management, and Tyler – the intern – raises his hand. “Does this connect to TikTok?”
I pause. “I’m sorry, what?”
“TikTok. For like, social media integration?”
The IT director looks embarrassed. “Tyler, this is inventory management software.”
“Oh. Cool, cool.”
Then the legal person jumps in with twenty minutes of compliance questions. The procurement head wants to negotiate terms I can’t even approve. One of the VPs keeps asking about features we don’t have and probably never will.
Meanwhile, my original three champions are just sitting there looking as confused as I feel.
Two hours later, I finally escape the call. The IT director messages me privately: “Sorry about that. The CEO read an article about ‘inclusive decision-making’ and decided we needed more voices.”
More voices. In a twelve-person committee that now includes someone who thought inventory software should connect to TikTok.
Three weeks and four more group calls later, they’re still “evaluating.” Tyler keeps asking questions that make me question my career choices. The legal person found seventeen new concerns. And the procurement head is now demanding a 30% discount because “the evaluation process has been so resource-intensive.”
My original champions are apologizing in private messages while being completely silent in the group calls. Classic.
Last week, the CFO – one of my original three – messages me: “Gary, I think we need to push this to next quarter. The committee wants to evaluate two more vendors.”
Of course they do.
Here’s what I’ve learned: in 2025, every three-person decision apparently needs a twelve-person committee. And somehow, there’s always an intern who thinks business software should connect to social media.
Some days I miss when deals were just complicated, not crowded.
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