LLenny's Podcast
← All episodes
Ada Chen Rekhi (Notejoy, LinkedIn, SurveyMonkey)16 April 2023

How to make better decisions and build a joyful career

6Frameworks
14Insights

Frameworks in this episode

Strategy4 steps

Curiosity Loops

Turn a hard decision into structured, contextual advice by asking the right people the right question.

Read →
Mindset4 steps

Don't Be the Frog: The Learning Trajectory Test

Judge whether to stay in a job by the direction of your learning curve, not by inertia.

Read →
Peak Performance4 steps

Eating Your Vegetables: The 10-12 Exposure Rule

Do a hard, avoided skill 10-12 deliberate times before judging whether you actually dislike it.

Read →
Strategy4 steps

Explore and Exploit Career Strategy

Explore widely with a thesis early, then exploit a role for the specific learnings your next goal needs.

Read →
Self-Mastery4 steps

Inner vs Outer Scorecard Values Filter

Rank your real values, then test whether a decision optimizes for them instead of for status.

Read →
Leadership5 steps

The Anti-Sell Coach Decision Framework

Most people don't need a coach — test the goal against cheaper alternatives, then select for vibe over credentials.

Read →

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take35:30

The Resume Trap: Your Life Is the Resume You're Living

Lenny and Ada dissect the pull to keep chasing the next impressive logo, title, and role to make a resume look great. The point: there is no finish line where the resume is finally done — you retire and die, and that resume-chasing was your actual life. Ada names the failure mode of waking up late-career, financially trapped, and unhappy with the job in the mirror.

  • There's no endpoint to making your resume more impressive — the treadmill never stops
  • The roles and logos you chase are the life you're actually living
  • The worst outcome is late-career entrapment: locked in by lifestyle and expectations, unhappy at work
  • Get intentional about who you're actually optimizing for

“And I find that just like like you do that long enough in your life, you get you you end up like you're you retire…”

Lenny · 35:30

“it's a terrible outcome to wake up one day and be sort of late career, and feel trapped because you have a certain lifestyle, or…”

Ada · 37:30
#career#status#meaning#values
Hot Take42:30

A Coach's Hot Take: Most People Don't Need a Coach

As an executive coach, Ada opens with the counterintuitive claim that the vast majority of people don't need a coach. She pushes prospective clients to define concrete six-month goals and then compare a coach against cheaper alternatives. A coach is a poor mentor because it's one person's opinion — a curiosity loop or a Reforge course often delivers more.

  • Most people considering a coach are really feeling stuck or trying to solve a specific problem
  • Ask: roll it forward six months — what did coaching actually get done, and what were the alternatives?
  • A coach is a bad mentor because it's just one person's opinion
  • For learning a topic, a course or community often beats one coach's limited experience

“but my hot take is that for the vast majority of people, they probably do not need a coach.”

Ada · 42:30

“the thing that people don't really think about is if you're looking for a mentor, a coach is actually a terrible mentor in some ways…”

Ada · 43:30
#coaching#mentorship#learning#advice

Story· 4

Story29:00

She Joined LinkedIn to Learn, Not to Get Promoted

Ada recounts her fast early-career run from an entry-level Microsoft sales job to SVP of marketing at SurveyMonkey in about seven years. The pivotal move was treating her post-acquisition time at LinkedIn as a deliberate apprenticeship: she told her manager up front she was there to learn to be a better founder, and chased growth and subscriptions experience instead of the biggest title. That unusual combination of skills is what caused SurveyMonkey to recruit her.

  • Went from entry-level Microsoft AdCenter to SVP of marketing at SurveyMonkey in ~7 years
  • At LinkedIn she optimized for specific learnings (growth, pricing, subscriptions) over promotion or title
  • Explicitly told her manager she was there to learn to be a better founder
  • The rare mix of founder + big-company + growth + subs + product-marketing experience is what got her recruited

“I even told my manager this when I first came in. I'm here to learn to be a better founder.”

Ada · 29:00

“but I wouldn't have gotten those opportunities if I just let them promote me, or I followed a strategy where I was just focused on…”

Ada · 30:30
#career#learning#founder#intentionality
Story52:30

The Feedback No One Gives: A Woman Founder Story

Ada tells the story of a sharp seed-stage founder whose casual in-person appearance clashed with the competent operator Ada knew over Zoom. She gave the hard feedback that these controllable elements could trigger biases right before fundraising, and the founder was grateful no one had ever connected the dots. Her larger point: reaching executive or funded-founder roles is Olympic-level, but no one tells you the rules of the game.

  • A brilliant founder had never been told how her casual appearance shaped first impressions
  • Managers almost never give women this feedback because there's 'no winning' in it
  • Getting to executive or funded-founder roles is like an Olympic sport with hidden rules
  • You're not powerless: study the rigged game, help each other, surface the rules, and find ways around them

“But the difficulty of this game is that no one tells you the rules of the game.”

Ada · 55:30

“We're not powerless even though this game is rigged, right? We can study the game, we can help each other, and we can actually start…”

Ada · 56:30
#women-in-tech#feedback#leadership#silicon-valley
Story1:00:00

Eating Your Vegetables: The Business-Card Networking Rule

Ada's 'eating your vegetables' idea borrows from research that kids need 10–12 exposures before liking a vegetable — the same is true for career skills. New in Silicon Valley and awful at networking, she made a rule: once a week, hand out all 10 business cards to strangers and touch the back wall before leaving. It was horrible at first but built foundational relationships and taught her to distinguish being bad at something from genuinely disliking it.

  • Kids need 10–12 exposures to appreciate a vegetable; skills work the same way
  • Her rule: hand out 10 business cards to new people and touch the back wall before leaving
  • The first weeks were awful, but it got dramatically easier and built a lasting network
  • Exposure helps you tell 'bad because I'm new' apart from genuine dislike

“eating your vegetables is really this idea around how little kids don't really develop an appreciation for vegetables until they're 10 or 12 exposures in.”

Ada · 1:00:30

“And the rule was I had to hand out all 10 of those business cards by introducing myself to people that were new and touch…”

Ada · 1:02:00
#networking#skills#career#practice
Story1:06:30

Starting a Company With Your Spouse: The Asterisks

Ada co-founded companies with her husband Sachin and now recommends it only with caveats: founding is a traumatic, volatile experience, and adding romance makes it either go really well or really badly with little in between. What made it work for them was complementary skill sets with clear decision rights, plus explicit 30/60/90-day check-ins asking whether the venture was harming the relationship. The core skill is constructive conflict.

  • Founding plus romance is volatile — it tends to go very well or very badly, rarely in between
  • They ran explicit 30/60/90-day check-ins to protect the relationship first
  • Complementary domains and clear decision-making rights were essential (he owns product/eng, she owns marketing/ops/finance)
  • The crux is constructive conflict: attack the problem, not each other

“being a founder is such a traumatic and crazy experience with all these intense highs and lows and lack of structure that when you throw…”

Ada · 1:07:00

“How do you get to the point where you're attacking the problem and not each other?”

Ada · 1:09:30
#co-founders#relationships#startups#conflict

Q&A· 1

Q&A45:00

When a Coach Actually Is Worth It

Ada explains the contexts where coaching genuinely pays off: states of hyper-growth demanding accelerated learning, and sensitive or interpersonal topics that need a safe, rational sounding board. Founders are a prime case — chaos, no structure, justified imposter syndrome, and intense highs and lows mean a coach can be a real shortcut.

  • Coaching is valuable in hyper-growth states where you must learn fast and time is short
  • Founders benefit because their role is chaos with no structure and huge emotional swings
  • Coaches are especially useful on sensitive, long-term, or interpersonal issues
  • It works as a safe space plus a rational guide with frameworks and advice

“when you have situations where you're in a state of hyper-growth and you need very accelerated learning and you kind of need someone who can…”

Ada · 45:00

“they have fully justified imposter syndrome where no one in their right mind would objectively have hired them for the position that they're in.”

Ada · 45:30
#coaching#founders#growth#leadership

Tool· 2

Tool1:11:00

Book Picks: Persuasion and Designing Your Life

In the lightning round, Ada recommends Robert Cialdini's Persuasion (formerly Influence) as valuable for marketers, founders, and product people — a breakdown of strategies for getting people to say yes. She also recommends Designing Your Life by Stanford D-School professors Bill Burnett and Dave Evans, which applies design principles to mapping a meaningful, fulfilling career.

  • Persuasion by Robert Cialdini — strategies for getting people to say yes, useful for marketers, founders, and PMs
  • Designing Your Life by Bill Burnett and Dave Evans (Stanford D-School)
  • Designing Your Life applies design principles to career and life design
  • Ada points people to Designing Your Life when they're stuck on career strategy

“Persuasion by Robert Cialdini.”

Ada · 1:11:00

“The next book that I also recommend is a book called Designing Your Life. And it's out of the Stanford Design School”

Ada · 1:11:30
#books#persuasion#career#design
Tool1:14:00

Product Picks: Notejoy, Captio, Arc, and Note to Self

Ada shares the tools she uses: Notejoy (her own fast, focused notes app for individuals and teams), and Captio, a minimalist iOS app that's a blank notepad with one button that emails whatever you dump into it. She also just downloaded Arc, the new browser. Lenny counters with Note to Self, an even simpler app that sits on his dock for emailing himself a thought.

  • Notejoy — fast, focused notes app for individuals and teams (Ada's company)
  • Captio — an iOS blank notepad with one button that emails your note to yourself for later processing
  • Arc — the new browser Ada is excited about for rethinking browser tabs
  • Note to Self — Lenny's even simpler dock app for emailing yourself a quick thought

“it's a blank notepad. You can dump your brain into it, and there's one button and it emails it to you.”

Ada · 1:14:30
#tools#productivity#apps#note-taking

Takeaway· 5

Takeaway32:00

Don't Be the Frog: When to Stay in a Job vs Leave

Ada uses the boiling-frog metaphor to explain how people fall victim to inertia in a job, tolerating small discomforts while telling themselves it will get better. Her heuristic is to watch which way the temperature is trending and judge everything through the lens of learning and growth. Staying a decade can be right if you're genuinely challenged; stalling out on learning is the signal to act.

  • Inertia is the trap — you sit with small discomforts assuming the next manager or promotion fixes it
  • The real question is which direction the 'temperature' is trending
  • Judge a job by the lens of learning and growth, not just comfort
  • Acting doesn't have to mean quitting — a proactive conversation with your manager or repurposing spare time can work

“So one of the things that I like to share is sort of this idea of um it's a little gory. Don't be the frog.”

Ada · 32:00

“So, there might be an argument for you to stay at a job for a decade, for two decades. If it turns out that every…”

Ada · 33:00
#career#decision-making#jobs#growth
Takeaway40:30

The Ego Monster and Warren Buffett's Inner vs Outer Scorecard

Lenny shares a friend's metaphor of an 'ego monster' in the corner yelling at you to take the impressive role and title. Ada pairs it with Warren Buffett's inner scorecard vs outer scorecard: the outer scorecard is how the world ranks you (status, wealth, titles, top-10 lists), the inner one is what actually matters to you. The two are often in direct opposition.

  • The 'ego monster' is the internal voice pushing you toward impressive-looking choices
  • Outer scorecard = how the world evaluates you (status, title, wealth)
  • Inner scorecard = how you spent your day, whether you were kind, whether you had an adventure
  • Naming the ego monster lets you dissociate from it and weigh the real trade-offs

“I use um something that Warren Buffett has talked about which is inner scorecard versus outer scorecard.”

Ada · 41:00

“So, really thinking about did you win at the cost of kindness? Did you succeed at the cost of losing access to the adventure that…”

Ada · 41:30
#values#decision-making#psychology#meaning
Takeaway47:30

How to Find a Coach: Vibe Beats Credentials

Ada interviewed over 80 people about their coaching experiences and found that half hired the very first coach they talked to. Her advice is to talk to two or three and compare, because what worked for a friend may not work for you. Surprisingly, credentials and relevant experience mattered less than an amorphous sense of vibe, safety, and how deeply the person got you.

  • Half of people who found a coach went with the first coach they spoke to
  • Talk to two or three coaches before committing — what works for a friend may not fit you
  • Credentials mattered far less than expected in what made coaching work
  • Founders valued vibe, feeling safe, depth of exploration, and being truly understood most

“There's of shocking data point in there where half of people that found their coach literally went with the first coach that they talked to.”

Ada · 47:30

“they actually said so much more about it was actually this amorphous sense of vibe with the person, how safe you felt with them, how…”

Ada · 49:00
#coaching#hiring#advice#relationships
Takeaway1:04:30

Beat the Cringe: Post to Crystallize a Thought, Write for an Audience of One

On overcoming the awkwardness of posting publicly (like a LinkedIn 30-day challenge), Lenny reframes it as simply crystallizing a thought rather than chasing likes or followers. Ada adds the classic advice to write for an audience of one — imagine talking to a trusted friend. Both note that the less thirsty for followers you are, the more genuine and interesting the content becomes.

  • Reframe posting as crystallizing an idea for yourself, not going viral
  • Write for an audience of one — imagine a single trusted friend or colleague
  • This defuses over-fixation on outcomes like follower counts
  • Genuine, non-thirsty content is what people can tell is authentic and resonates most

“what I find is if you reframe it to I just want to crystallize a thought that I have and just like share something that…”

Lenny · 1:05:00

“One piece of advice that's similar to that that I've heard is write for an audience of one. Like imagine you're just talking to a…”

Lenny · 1:06:00
#content-creation#writing#linkedin#authenticity
Takeaway1:15:30

The 5-Minute Rule to Beat Productive Procrastination

Ada's productivity tip: decide the night before the one thing you want to get done, then give yourself just 5 minutes on it at the earliest opportunity. The tiny commitment gets past 'productive procrastination' — doing other useful tasks to avoid the important one — and those 5 minutes usually turn into a solid, accomplished hour. Lenny links it to the 'highlight' concept from the book Make Time.

  • Pick the one thing the night before, then commit to just 5 minutes on it early
  • Productive procrastination is doing other useful work to avoid the important thing
  • The 5-minute start usually snowballs into a productive hour and a sense of accomplishment
  • Related to the 'highlight' framework in the book Make Time

“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…”

Ada · 1:15:30

“productive procrastination. Even though I know something is really important that needs to get done, I will often do other things that are useful and…”

Ada · 1:16:00
#productivity#procrastination#habits#focus