Curiosity Loops: Ada Chen Rekhi's Method for Better Decisions and a Career You Won't Regret

Chen Rekhi explains that a curiosity loop is a way of going to a group of people with the same question and learning from their answers. To prepare for the episode she emailed about ten people nine possible topics and asked which two or three resonated and why, which took around 20 minutes and produced a great deal of information. She uses it because there is a lot of well-intended advice that is bad because it is not contextual: quit and chase your dreams, or stay and grind.

The loop has four parts. First, ask a good question: specific, rationale-soliciting and unbiased, informed by what she learned from survey researchers at SurveyMonkey. A question like "what should I do with my career next?" is vague and creates cognitive load, whereas laying out a plan to leave marketing for a web-dev bootcamp gives people something to anchor on. Second, curate who you ask, mixing subject-matter experts with people who know you well.

Third, make the ask lightweight, since a heavy request lowers response rates, and fourth, close the loop by processing the answers and thanking people. She notes that helping someone feels good, especially when they come back to say the advice affected their decision. She aims for three or four responses, uses loops for big or indecisive moments roughly quarterly, and compares them to marketing's customer advisory councils and to user research for your life, where you take input but make your own decision.

A personal example involved estate planning for her daughter. She and her partner disagreed on when the child should inherit, and informal asking showed that nobody they asked said 18. They also learned that executive function peaks around age 30, which moved both of them toward a later age.

Chen Rekhi gives her coaching clients, and gave Lenny, a 10 to 15 minute values exercise. You pick words that resonate from a long list, group and stack-rank them, and end with three to five sentences describing your values. She likes that it is an internal scorecard in contrast to the external scorecard of status, money and others' perceptions. Lenny's list included choosing adventure, staying optimistic, treating others as you want to be treated, getting better, acting generously and his grandma's rule to first do what you need to do, then what you want.

Applying them live to Lenny's current decision of what to say yes or no to, such as a book or pausing angel investing, revealed that he wants to do less and simplify. Chen Rekhi suggests decomposing what adventure really means to him, since a project can stop feeling like an adventure after the start. Lenny adds that writing a book or teaching a course felt like the obvious next step but did not bring him joy.

She says values help ground you against obvious next steps. In her own life, climbing the executive ladder gave way to prioritizing relationships, knowledge and growth on her own terms, and independence and autonomy rose after she started a family. The list is not fixed, and it can be changed over time as you notice what matters, as Lenny noticed simplicity.

Chen Rekhi describes her early career as an explore-and-exploit story. Over seven years she went from an entry-level sales job at Microsoft adCenter, where she stayed 367 days and found corporate life too slow, to a marketing role at a startup called Mochi Media, and then to founding Connected, a personal CRM later acquired by LinkedIn. At 23 she decided she had little to lose and kept exploring with a thesis, such as trying to be a founder.

After the acquisition she switched to exploit mode and told her manager she was at LinkedIn to learn to be a better founder. She sought growth marketing and subscriptions experience, which she lacked, instead of chasing the biggest title. That mix of founder, big-company, growth and subscription experience is what led SurveyMonkey to recruit her as head of marketing around age 27 or 28.

Asked how long to stick with a job that does not feel good, she uses the boiling frog story. It is easy to be a victim of inertia, so watch whether the temperature of the water is trending up, and judge a role by what you are learning and how you are growing. If you hit a wall, have a proactive conversation with your manager about projects, or treat the spare time as a gift to build relationships or learn something new.

Lenny observes that people can keep optimizing a resume forever, forgetting to ask whether they enjoy it. Chen Rekhi says she has experienced this herself, shaped by tiger-parent expectations around Ivy League schools, recognizable companies and titles. She took the values exercise over a decade ago, extended her current path forward and asked how well it satisfied her values.

She warns that a terrible outcome is waking up late in your career, trapped by lifestyle and expectations, unhappy going in. The best path usually mixes career success with meaning and alignment with values. A trigger was a high-profile opportunity that required demanding travel and grueling hours in a space she was not excited about, and when a friend had her apply the values exercise, the job failed her top three values.

Lenny shares a friend's idea of an ego monster shouting from the corner of the room. Chen Rekhi uses Warren Buffett's inner versus outer scorecard: the outer one is wealth, status and titles, while the inner one asks how you spent your day, whether you were kind and whether you had an adventure. Asking whether you won at the cost of kindness helps you trade off against external pressure.

Chen Rekhi's hot take is that most people probably do not need a coach. She asks prospective clients what they want from coaching in six months and whether another approach would achieve it. A coach is a poor mentor because it is one person's opinion, so a curiosity loop gives you several minds, a course such as Reforge gives a survey of a field, and a community gives lasting emotional support.

Coaching helps most in hyper-growth, where founders face chaos, justified imposter syndrome and sharp highs and lows with little time to learn, and on sensitive topics like interpersonal conflict. Lenny compares it to athletes, who all have coaches. She recommends talking to two or three coaches first, as her research with over 80 people found that half of founders hired the first coach they spoke to.

The surprise from her interviews was that personal connection and feeling safe mattered more than credentials or perfect experience. She also suggests treating coaches like a menu, with short-term specialists for things like pitching, writing or speaking, since high performers often have more than one. Lenny jokes about hiring coaches for the podcast, newsletter, writing, parenting and life.

Friends advised against covering being a woman in Silicon Valley, with one saying there is no winning on that topic. Chen Rekhi approaches it with respect for the real challenges and an emphasis on agency. She tells of a seed-stage founder she coached, whom she admired as an operator, who showed up to a weekday lunch dressed very casually, and who was about to start fundraising.

After taking a deep breath, she shared the disparity between how she came across in person and her competence. The founder said no one had ever connected the dots for her, and then made changes to her appearance with friends and reported more positive comments. Chen Rekhi says it was hard to give even with trust, and that most managers will not offer such feedback because there is no winning in doing so.

Her broader point is that reaching executive or funded-founder roles is like an Olympic sport where nobody tells you the rules. Whether someone is judged as too young, too old, or the wrong gender or race, we are not powerless, since we can study the game, help each other and call out the rules. Lenny links it to Radical Candor and Sheryl Sandberg telling Kim Scott that saying "um" made her sound stupid, a story Chen Rekhi says shows the real risk of giving feedback.

Chen Rekhi's key advice is what she calls eating your vegetables. Researchers say children need ten or twelve exposures before they like a vegetable, and she says the lesson is to separate dislike that comes from being new or bad at something from genuine dislike after real practice. She notes a statistic that 75 to 80 percent of podcasts never get past the first episode.

As a networker she was awkward after moving to Silicon Valley, so she gave herself a rule: go to an external event once a week, hand out ten business cards to new people and touch the back wall of the venue before leaving. It was awful at first, but familiar faces made it easier and some of those relationships became foundational to her network. Lenny likes the physicality of touching the back wall.

Other examples include a LinkedIn 30 challenge of posting every day for 30 days and, in modern networking, repeatedly messaging interesting people. Lenny suggests posting to crystallize a thought rather than to chase likes, and Chen Rekhi adds the advice to write for an audience of one. Both agree readers can tell when you are being genuine.

Chen Rekhi says that at first she would have enthusiastically recommended starting a company with your partner, but now adds asterisks, since mixing romance with the volatility of founding seems to go either very well or very badly. She and her husband Sachin have started two companies together, and because founders are obsessed with their business, she preferred to share that obsession. She set 30, 60 and 90 day check-ins that asked whether the work was affecting their relationship.

Two things made it work. They have complementary domains, with Sachin on product, design and engineering and Chen Rekhi on marketing, operations, finance and the rest, so decision rights are clear. They also practice constructive conflict, attacking the problem rather than each other and assuming the most respectful interpretation of feedback.

In the lightning round she recommends a Cialdini book on persuasion and Designing Your Life by Bill Burnett and Dave Evans, and she names Notejoy, Captio and the Arc browser. Her interview question is to ask what common misconception people have about you. Her productivity tip is to pick one thing the night before and give it just five minutes at the first opportunity, which usually turns into an hour.