Tip
Ada Chen Rekhi talks about Curiosity Loops—sending a focused question to 5-10 people and triangulating their perspectives. She used it prepping for Lenny’s podcast: sent 9 topics to 10 contacts, asked which 2 they’d pick and why. One person said “stay far away from this topic—there’s no winning.” She listened.
Turns out major career decisions work the same way.
You’re staring down the Chief AI Officer role at the enterprise company versus staying put to build the AI practice at your startup. Or pivoting to consulting versus doubling down on product leadership. Don’t poll one person. Don’t trust your own analysis alone. You need triangulation.
Pick 5-10 people: some who know you deeply, others with domain expertise in the exact choice you’re making. Send them a structured question—not “what should I do?” but “here are 3 options, which 2 would you choose and why?” Make it lightweight. They can answer from their couch in 5 minutes.
This is advisory board thinking for personal decisions. You’ve run stakeholder councils for product strategy, competitive positioning, pricing. You know how to triangulate perspectives, filter signal from noise, synthesize conflicting input. Same discipline, different domain.
The network matters. Younger colleagues might have 3-5 people to ask. You have dozens—former managers, peers who went on to run divisions, specialists you respect. When you ask, they respond. That’s the compounding return on years of relationship capital. You’re not learning this method. You’re recognizing you already have the infrastructure to run it.
Context
Ada Chen Rekhi, co-founder of Notejoy and executive coach, adapted Curiosity Loops from customer advisory councils she ran at LinkedIn and SurveyMonkey. The method only works if you’ve invested years building genuine relationships across functions, companies, and expertise areas.
For experienced professionals, this transforms scattered networking into strategic advantage—you have the relationships, the credibility, and the synthesis skills.