He was calm, senior, and unimpressed. A global CISO. One of our biggest prospects.
And he wanted a feature that didn’t exist.
“We’d need custom X, but built into the UI. Auditable. Editable by non-admins. Can you do that?”
Old me would say yes.
I froze for a second. Because technically—yes. Our engineers could build it. But should we? Not even close.
We were six months post-launch, shipping fast, fragile in places. A detour like this would pull two sprints, maybe three, just to satisfy one buyer. And one whose contract wasn’t signed.
Still, saying “no” to a whale is career risky. Especially when you’re the one in the room.
So I asked him: “Can I show you why we don’t have that?”
I pulled up a whiteboard and mapped what would break.
Auditing delays.
Shadow admin creep.
Support overload.
Complexity no one would maintain after onboarding. I didn’t defend the roadmap, I explained the tradeoffs.
Then I asked: “What problem are you really trying to solve with this feature?”
He paused. “Accountability.”
We talked through three simpler ways to get alerts, logs, permissions templates. All things we already had. No roadmap detour needed.
The call ended with, “This makes sense. I’ll adjust our requirements.”
We closed two weeks later. No feature added.
What I learned: selling isn’t just about listening. Sometimes it’s about challenging. Not with ego but with insight.
That day, I didn’t just protect the roadmap. I earned credibility. With him, with my team, and with myself.
And yeah, saved my job, too.
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