Apr 16, 2023 · 1h 18m · lennys-podcast
How to make better decisions and build a joyful career | Ada Chen Rekhi (Notejoy, LinkedIn)
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Executive coach and entrepreneur Ada Chen Rekhi joins Lenny Rachitsky to share battle-tested frameworks for intentional career progression, structured decision-making, and executive growth. Through mental models like Curiosity Loops, Explore vs. Exploit, and radical candor, Ada provides actionable guidance on building an impactful, values-aligned career.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Lenny holds 29.5% of the talking time here. How this is scored →
Lenny as informed peer 3.9 Guest teaching 6.4 Guest disagreement 0.8 Lenny pushing back 1.4
speaking balance: gold is Lenny, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 42:42 Ada's anti-sell take against hiring executive coaches
Ada leads with a strong contrarian premise, asserting that the vast majority of people asking for coaching actually do not need a coach and are wasting time and money.
Hardest push from Lenny ▶ 1:13:09 Lenny challenging Ada's take on conflict-free Star Trek episodesLenny pushes back against Ada's assertion that Star Trek episodes are purely happy and without danger, pointing out that dramatic narrative structure fundamentally requires conflict.
Biggest teaching moment ▶ 54:30 Ada breaking down the unspoken rules and taboo feedback for womenAda delivers a masterclass on how corporate safety dynamics prevent managers from giving women crucial, actionable feedback about presentation and presence.
Lenny holds their own ▶ 59:05 Lenny connecting Ada's story to Radical Candor and Sheryl SandbergLenny demonstrates deep command of leadership literature by spontaneously contextualizing Ada's coaching anecdote within Kim Scott's Radical Candor framework.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Lenny as informed peer | Guest teaching | Guest disagreement | Lenny pushing back | Why |
|---|---|---|---|---|---|---|
| Making Better Decisions with Curiosity Loops | 4 | 6 | 1 | 2 | Ada explains the mechanics and structure of 'curiosity loops' for contextual decision-making. Lenny actively synthesizes her steps into actionable takeaways and connects the concept to customer advisory boards and asynchronous boards of directors. | |
| Personal Values Exercise and Real-Time Decision Audit | 5 | 6 | 1 | 1 | Ada coaches Lenny in real-time on auditing his personal career values against pending commitments like writing a book or angel investing. Lenny vulnerably explores his need for simplicity, and Ada helps him deconstruct what 'adventure' truly means in his work. | |
| Early Career Strategy: Explore vs. Exploit | 3 | 7 | 0 | 1 | Ada breaks down her rapid career progression using the explore vs. exploit framework, explaining how she intentionally prioritized foundational skills at LinkedIn rather than chasing titles. Lenny validates the framework and asks for heuristics on when to persevere versus move on. | |
| Avoiding the Boiling Frog Trap and Resisting Ego Monsters | 4 | 6 | 1 | 1 | Ada presents the boiling frog metaphor for career inertia and warns against chasing external prestige. Lenny contributes with his friend's 'ego monster' metaphor, and Ada ties it back to Warren Buffett's inner versus outer scorecard distinction. | |
| Sponsor Message: Sprig (Mid-Roll) | 4 | 7 | 2 | 3 | Ada opens with a contrarian take that most people do not need an executive coach and should exhaust peer networks first. Lenny offers his perspective comparing executive coaching to professional athletic training, prompting Ada to detail how to interview and select coaches. | |
| Navigating Silicon Valley as a Woman and Giving Radical Candor | 5 | 8 | 1 | 1 | Ada details a sensitive coaching experience where she delivered candid feedback on personal presentation to a female founder, highlighting the unspoken rules of Silicon Valley. Lenny demonstrates his knowledge by linking this directly to Kim Scott's Radical Candor framework and Sheryl Sandberg's famous feedback. | |
| The 'Eating Your Vegetables' Rule and Modern Networking | 4 | 6 | 0 | 1 | Ada introduces the 'eating your vegetables' rule for overcoming initial awkwardness in networking and content creation. Lenny shares practical tactical reframings for LinkedIn posting and modern outreach to avoid feeling self-promotional. | |
| Frameworks for Co-Founding a Startup with Your Spouse | 3 | 7 | 0 | 1 | Ada outlines key operating principles for co-founding companies with a spouse, emphasizing separate functional ownership and depersonalizing constructive criticism. Lenny expresses admiration for her self-awareness and suggests she write a dedicated guide on the topic. | |
| Lightning Round: Books, Media, Tools, and Overcoming Procrastination | 3 | 5 | 1 | 2 | In the rapid-fire round, Ada recommends books, tools like Captio, and a five-minute micro-commitment strategy to defeat productive procrastination. Lenny playfully challenges Ada's description of low-stakes Star Trek plots with classic narrative theory before connecting her routine to the book Make Time. |
Statements from this episode (15)
How to ask for advice without triggering confirmation bias
“A question's good if it's specific, if it solicits rationale, and, you know, it's not biased, right? You don't want to start a question with, here's what I think, because people have this tendency to want to please you or to agree with you.”
Human executive function peaks at age 30, says Ada Chen Rekhi
“Executive function, which is your ability to make decisions and plans and be thoughtful, peaks at the age of 30.”
Personal values provide an internal scorecard against external status pressures
“It's sort of like this internal scorecard of what really matters to you in your decision-making process, as opposed to the external scorecard of status, money, wealth, how other people perceive you. That, you know, often we feel really pressured by, and so it'…”
Content creation is an endless treadmill, says Lenny Rachitsky
“Something I always say about like this content creation life is like, it's easy to start. It's hard to keep it going. And it becomes just like this treadmill of just, you have to keep creating awesome stuff basically for the rest of your life.”
Early careers should prioritize hypothesis-driven exploration over exploitation
“And when I think about explore and exploit for early career, it's all about exploration. You really haven't experienced that much, but you're doing it with a thesis. You're doing it kind of with that growth mindset where you have a hypothesis.”
The vast majority of people do not need an executive coach
“My hot take is that for the vast majority of people, they probably do not need a coach.”
Half of coaching clients hire the first coach they interview
“I talked to over 80 people about their experiences with a coach. I talked including coaches, including founders, including executives, and there's this sort of shocking data point in there where half of people that found their coach literally went with the fir…”
Why managers avoid giving appearance feedback to young female employees
“It turns out that in a career context, it's so unsafe for your manager to turn to a young woman on the team and say, here, let me give you feedback on your physical appearance and how it affects your competence and how you're perceived in the workforce, that t…”
Practice uncomfortable skills to distinguish inexperience from genuine dislike
“Eating your vegetables is this really important component of it because it's about how do you identify dislike for something because you're bad at it or you're new to it or you've never done it before compared to genuine dislike where you've done it and you re…”
Up to 80% of podcasts never publish past episode one
“Lenny, I think it's something like, 75 or 80% of podcasts never make it past the first podcast.”
Overcome networking anxiety with the 10-card, back-wall rule
“So I gave myself this rule where I had to go out once a week for a couple months, go to an external event, and I would count out 10 business cards. And the rule was I had to hand out all 10 of those business cards by introducing myself to people that were new …”
Co-founding a company with your spouse has no middle ground
“What I found is that it seems like it either goes really well. Or it goes really badly, and there's kind of no in-between.”
Generous interpretation of feedback is crucial when co-founding with a spouse
“The ability to be really truth seeking and kind of take the most respectful interpretation when you're giving feedback to focus on trying to get to a smart, good outcome that benefits the business. I think that's actually one of the most crucial things that yo…”
Ask candidates about common misconceptions to test self-awareness and reset bias
“What's a common misconception people have about you? And I usually like to throw that in toward the end of the interview, and the reason why I think it's really useful is it's a way for me to kind of reset my bias. I may have had a certain impression about the…”
Overcome procrastination by working on your top task for just five minutes
“Figure out, maybe the night before, The one thing that you want to get done in your day. And then at the earliest opportunity, just try to give yourself five minutes on it. Just five minutes. And the reason why I say five minutes is that there is sort of this …”