Day 425 of 1095: Finding the right partners to design your product and pilot requires asking the right questions
425 days into this journey.
Roughly 39% through the 3-year window we gave ourselves.
And yet—some days, it still feels like day one.
That moment when you're staring at your product board, your Notion doc, or a messy Miro map, asking:
"Who can actually help me shape this into something real?"
I used to think it was about who’s the best designer. The fastest coder. The sharpest strategist.
But now I realize:
The real differentiator is who’s sitting next to you when you ask the right questions—and who knows how to sit in the discomfort of not having the answers yet.
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The breakthrough came during a 17-minute call.
A potential partner looked at our pilot concept and asked:
"What if this isn’t the problem your users actually care about?"
It wasn’t a criticism. It was curiosity.
And it changed everything.
We redesigned the flow. Simplified the ask.
And most importantly—we stopped assuming.
Since then, I’ve started measuring partners not by how fast they say "yes", but by the quality of the questions they ask.
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Here are 10 questions I now ask before choosing a product or pilot partner:
1. What’s a recent pilot you ran that didn’t go as expected?
2. How do you define success before building anything?
3. How do you challenge assumptions—yours and mine?
4. What does “iteration” mean to you in practice?
5. Are you comfortable killing your own ideas?
6. What’s a product decision you regret—and what did you learn?
7. How do you involve users before launch?
8. What happens when we disagree on direction?
9. How do you balance speed vs. certainty?
10. Can you handle silence while we're figuring things out?
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Closing Thought:
Finding the right people is not just about talent—it’s about alignment of thought process, emotional resilience, and timing.
Ask better questions. Sit with better people.
And the right answers will start revealing themselves.
— Eliav Ser
