Curiosity Loops, Inner Scorecards &
Designing Your Career by Values

Ada Chen Rekhi

Executive Coach · Co-founder, Notejoy
Fmr. SVP Marketing, SurveyMonkey · Fmr. LinkedIn

LENNY'S PODCAST

The Framework

The Curiosity Loop

"A curiosity loop is really just going to a whole bunch of people, asking them a specific question, and coming out so much smarter, for about 20 minutes of work."

Fights bad advice that's well-intentioned but not contextual
Lightweight version: ask the same question in daily conversations
Reserve heavyweight loops for quarterly or high-stakes decisions
Feels good to be asked, give people the credit of helping you

Career Design

Inner Scorecard vs. Outer Scorecard

Warren Buffett's inner scorecard: how you actually spent your day, were you kind, did you have an adventure
The values exercise: 10–15 min, pick resonant words, stack rank to 3–5 core values
"Play the movie forward", does your current path satisfy those values in 5 years?
Tiger parenting trap: optimizing for logos and titles that don't match your actual values

3–5

core values to identify

age executive function peaks

The values test Ada turned down a high-profile, travel-heavy role after doing the values exercise. Her top 3 values would have "categorically failed" in that job, but looked incredible on a résumé.

The frog-boiling warning "It's a terrible outcome to wake up one day and be late career and feel trapped… you look in the mirror and you're not happy going in there."

Mechanics

What Makes a Question Actually Good

❌ Bad question

"What should I do with my career next?"

Vague, no anchor, huge cognitive load, garbage in, garbage out.

✓ Better question

"I'm a marketer thinking of doing a webdev bootcamp. Is that a good move?"

Specific, gives context, invites real expertise and personal knowledge of you.

Specific: gives people something concrete to anchor on
Solicits rationale: ask why, not just yes/no
Not biased: don't lead with "I think X", people will agree to please you
Who to ask: subject matter experts AND people who know you well, both dimensions matter
5–10 people: optimise for 3–4 responses minimum; adjust for your expected reply rate

"These loops are more about looking around the corner and seeing if there's anything you missed in terms of the integrity of your decision making process."

Origin Born from marketing's customer advisory councils, Ada brought the same "voice of the customer" method into her personal life and career decisions.

Hot Take

Most People Don't Actually Need a Coach

"My hot take is that for the vast majority of people, they probably do not need a coach."

Want a mentor? A curiosity loop beats one person's narrow opinion
Want to learn growth? A Reforge course beats a coach who worked at 3 companies
Feeling overwhelmed emotionally? Build a tribe, that lasts years, not just your coaching engagement
When coaching IS worth it: hyper-growth stage, feeling stuck with a specific problem, need an accountability partner who challenges you

Ada's anti-sell test Before taking on a client, she asks: "Have you explored all the alternatives first?" Roll forward 6 months, what's the actual outcome you want, and is coaching the best path to get there?

Contrarian

Ada's Counterintuitive Career Truths

✗ Ask friends "What should I do?" for big decisions INSTEAD → ✓ Structure a curiosity loop: give them options, ask for top 2 and a reason why. Unstructured asks get polite, useless answers.

✗ Optimize your résumé for the most impressive logos INSTEAD → ✓ Optimize for your inner scorecard. "Play the movie forward", an impressive résumé you hate is the trap, not the goal.

✗ If you're stuck in your career, hire a coach INSTEAD → ✓ First try: a curiosity loop, a peer community, a good course, or a mentor. Coaching is powerful in specific contexts, not a default fix for feeling lost.

✗ Good advice is just good advice, take it INSTEAD → ✓ Most advice is well-intentioned but not contextual. "Quit and chase your dreams" vs. "grind and build experience", both can be right. Curiosity loops make advice contextual to you.