Looking back: April 2026
Early in my career selling into medical technology, I lost a deal I thought I’d won. Not a deal slipped — a deal lost, definitively. The lesson has shaped how I think about enterprise selling ever since.
The deal was with a regional hospital system. The clinical champion was enthusiastic. The department head had quietly approved. The CMO had met with me twice and was leaning in. Everything looked right. Legal had the redlines. I was forecasting it to close that quarter.
Then IT got involved.
What Happened
The hospital ran an electronic medical records system I’d assumed would interoperate cleanly with our device. It didn’t. Specifically, the HL7 messaging format my clinical data needed to export into was implemented slightly differently in their EMR than in the two reference hospitals I’d cited. The integration wasn’t impossible — it was non-trivial, required their IT team’s involvement, and would add two to three months to the implementation timeline.
None of this had come up in discovery. Not because I hadn’t asked — because I’d asked the wrong people. I’d asked the clinical champion about integration and she’d answered based on her general understanding, which was “our IT team handles that kind of thing.” That answer was technically true and functionally useless.
The deal didn’t die. It slipped two quarters while the integration questions got worked through. But the damage was done: my CMO champion got frustrated with the timeline, my clinical champion started getting pressure from her department to explore alternatives, and by the time we got to a workable integration plan, a competitor had re-entered the conversation with a solution that had already been proven in that EMR environment.
We got the deal back, eventually. But it closed six months late at a 20% discount I wouldn’t have had to give if I’d identified the HL7 issue in discovery.
What I Learned
Three things, which I now teach anyone I mentor in enterprise selling:
1. Every enterprise deal has a silent second stakeholder.
It’s never the champion. It’s not the economic buyer. It’s the person whose job is to say “hold on” at some technical, legal, or operational layer. In medtech, it was IT. In telecom, it’s facilities or network ops. In construction, it’s the bonding company. In consulting, it’s procurement. The pattern is universal.
2. The silent stakeholder must be surfaced in discovery, not at close.
The cost of finding them early is 15 minutes of conversation with your champion, asking “when this goes to [X], what’s the first question they’ll have?” The cost of finding them late is a slipped quarter, a discount, and sometimes a lost deal.
3. Your champion’s answers about the silent stakeholder are almost always wrong.
Not because your champion is wrong about their own job. Because they’re answering based on how they’d want the process to go, not how it actually goes. “Our IT team will handle that” is directional truth. It is not actionable intelligence. You have to get to the IT team yourself — not through the champion’s interpretation of what IT will need.
Why This Pattern Matters So Much
Looking back, the HL7 problem was probably the single most expensive lesson of my medtech career. But the principle it taught — silent stakeholders exist in every enterprise deal, they must be surfaced early, and your champion can’t fully characterize them — is something I now apply in every deal review, in every deal I’m in directly, and in every coaching conversation I have with someone earlier in their career.
I’ve watched sellers in construction learn this lesson with bonding companies. In consulting, with procurement. In telecom, with network operations. The industry changes; the pattern doesn’t.
The irony is that the fix is cheap. A seller who asks two or three specific questions in discovery about the silent stakeholders will catch most of these issues before they compound. But most sellers don’t ask, because the questions feel awkward, and because the champion is giving them warm signals that make the deal feel safe.
Warm signals from the champion are not the same as visibility into the full buying process. I learned that once. I don’t forget it.
If you’re selling enterprise anything and you haven’t identified your silent stakeholders in discovery, you don’t have a deal yet. You have a relationship that might become a deal, pending surprise.
Don’t be surprised. Ask early. Ask specifically. Get past the champion’s version of the process to the actual one.
That’s the HL7 lesson. It cost me a quarter. It’s saved me many more.