How to make better decisions and build a joyful career | Ada Chen Rekhi (Notejoy, LinkedIn)

1. 0:00 – 3:17

   Ada’s background

   1. ARAda Chen Rekhi0:00

      You know, 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 a certain expectation that the people around you, that you have to go work this job, but then you look at yourself in the mirror and you're not happy going in there. I think that's a terrible trap that we should all try to avoid as we kind of navigate our career paths, and find the thing that's sort of most optimal for us, which is usually a mix of career success but also meaningfulness and sort of alignment in the work that we're doing with our values. (instrumental music)

   2. LRLenny Rachitsky0:36

      Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard-won experiences building and growing today's most successful products. Today my guest is Ada Chen Rekhi. Ada is an executive coach and also the co-founder of a product called Notejoy. In her coaching practice, she focuses on helping founders scale themselves. Before starting her company, she was senior vice president of marketing at SurveyMonkey. Before that, she started a contact management startup that was acquired by LinkedIn, where she ended up leading LinkedIn's marketing efforts for their growth team. Two fun facts about Ada. One, she started her current company with her husband, which we chat about whether that's a good idea or not. Also, her brother is Andrew Chen of A16Z fame. In our conversation, Ada explains how to make better decisions with a framework she calls curiosity loops. We do a live exercise around my own personal values. She shares a bunch of advice on how to intentionally and proactively build your early career path, how to thrive as a woman in Silicon Valley, when to get a coach and what you can do on your own without one, and a ton more. Enjoy this episode with Ada Chen Rekhi after a short word from our sponsors. (instrumental music) This episode is brought to you by Sprig. Next-generation product teams like Robinhood, Notion, and Loom rely on Sprig to uncover blind spots in their product development process. Sprig lets product teams collect user insights fast, allowing you to better understand why users take certain actions and how they feel about the experience. One of the things I love most about Sprig is that they're all about getting product teams the specific insights they need in the timeframe that they need it. And as of today, Sprig is making that even easier with a new and improved templates library. On this podcast, you've heard a lot about how useful templates are for companies as they grow. Sprig partnered with some of the top product teams and product thinkers to build proven playbooks specifically to solve the biggest challenges facing product teams today. From how to optimize an existing feature, to improving a conversion flow, to troubleshooting drop-off, Sprig helps you build better products. Sprig now has a library of more than 85 templates that you can use to get started collecting user insights quickly, right in your app. I especially love that Sprig builds templates specifically for product teams, and I was really excited when they asked me to create a template around product sense. One of the questions I get most is how to develop your product sense, and so I decided to build a playbook along with Sprig on how to do that based on my experience at Airbnb and from what I've learned interviewing top product folks like Jules Walter, who wrote a whole guest post on how to build your product sense. Explore my product sense playbook and the entire Sprig templates library and build better products faster. Check it out today at sprig.com/templates. That's S-P-R-I-G.com/templates. (instrumental music)

2. 3:17 – 11:39

   What a curiosity loop is and when to use one

   1. LRLenny Rachitsky3:17

      Ada, welcome to the podcast.

   2. ARAda Chen Rekhi3:20

      Thanks. I'm excited to be here.

   3. LRLenny Rachitsky3:22

      So, I've heard such great things about you from a lot of people, including a bunch of guests that have been on the podcast, and you also have this really great Venn diagram of maybe an ideal guest for the podcast. You've done growth. You've done product. You've started a company. You're also an executive coach to founders. And so there's a variety of topics I'm excited to dig into, and so thanks again for being here.

   4. ARAda Chen Rekhi3:44

      Yeah, I'm excited to be here.

   5. LRLenny Rachitsky3:45

      An interesting thing that I'll start with is that when we were chatting about what to focus on in our conversation, we were emailing about this, and you did something that I thought was really interesting. You ran something called a curiosity loop where you Pinged a bunch of your friends and asked them for input in this really structured way. And so I thought I'd start there. Could you just share what this process is so that we can learn how to maybe do it ourselves, this idea of a curiosity loop?

   6. ARAda Chen Rekhi4:08

      A curiosity loop is essentially, you know, going to a whole bunch of people, in this case I sent out an email very quickly to about 10 or 11 people and asking them, "Hey, you know, here are nine topics for Lenny's podcast. What are two or three of the topics that resonate with you and why?" And I got back such an incredible amount of information for about 20 minutes of work. And I don't normally do this, but I actually showed you some of the anonymized feedback from people-

   7. LRLenny Rachitsky4:34

      Mm-hmm.

   8. ARAda Chen Rekhi4:34

      ... really just talking about what resonated and what didn't. And so I came out of it just so much smarter, and, um, curiosity loops are kind of my method of doing so.

   9. LRLenny Rachitsky4:42

      Often people ask for friend... Ask friends for advice on just, like, "Hey, what should I do here? What can... What can I maybe talk about on this podcast?" Your approach had a lot of structure to it, and so maybe two questions, just, like, what is the actual structure to this concept? And then, two, just, like, you know people... You can often ask friends for advice, but you also don't want to over-bug them with questions.

   10. ARAda Chen Rekhi5:02

       Yeah. Yeah.

   11. LRLenny Rachitsky5:03

       How do you think about just, like, not over... Like, asking everyone questions all the time about all decisions you wanna make?

   12. ARAda Chen Rekhi5:08

       Yeah.

   13. LRLenny Rachitsky5:08

       And I guess... So I guess the question is when do you use this versus just, like, not?

   14. ARAda Chen Rekhi5:12

       I think that there are sort of heavyweight and lightweight ways to use this. So the heavyweight way was sort of what I just exemplified by saying I sent an email and I made a doc, and on the other side I had all of this really interesting and rich data. The lightweight way to do this is really just sort of make it your ongoing theme of what you're curious about as you interact with people. And so maybe it's this thing where every single day as you talk to people, if you have sort of a social topic, you might just bring up the same question over and over again and start looking for are there any differences or surprises in what people are telling you. And, you know, one of the big reasons why I think curiosity loops are really useful is that it really fights the fact that there's a lot of bad advice out there.

   15. LRLenny Rachitsky5:53

       Hmm.

   16. ARAda Chen Rekhi5:54

       And it's not bad because it's not well-intentioned, but it's bad because it's not contextual. So when someone tells you to quit your job and chase your dreams-... or they tell you to sit tight and grind through and build some experience before you go off and go start the company that you've always been thinking about starting, which piece of advice do you actually take, right? And a lot of it kind of depends on your situation, what you're considering, what skills and experience you actually have. And curiosity loops actually are this way of really thinking about, how do you make your advice contextual? So I'll break it down a bit, in terms of how-

   17. LRLenny Rachitsky6:27

       Yeah, let's do that.

   18. ARAda Chen Rekhi6:27

       ... I think about structuring it. So the first piece of a curiosity loop is really just thinking about asking a good question. In the time when I was working at SurveyMonkey in the past, I had this opportunity to spend a lot of time with the survey researchers, and we really talked a lot about what makes a question good. And so in this case, 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 wanna please you or to agree with you. And so a good example... Well, let me start with a bad example of a question. A bad example of a question is, "What should I do with my career next?" And it's just such a poorly formed question because it's really vague, it's not specific, it puts a lot of cognitive load on other people, and you know, the kind of output that you're going to get from it is probably going to be similarly bad. You know, garbage in, garbage out. A better example of a question might be something like, "Hey, you know me, I'm a marketer. I've been thinking about doing this web dev thing. So my plan is to quit my job, do a web dev bootcamp, and then go find a job elsewhere. Do you think that's a good idea?" And there's just so much rich data to actually explore with that. First, you know, are you suited to being a developer? Are web dev bootcamps effective? What's the state of the economy and the hiring market right now for junior web developers? And you know, that's an example of maybe a question that's a little bit more specific and gives people something to anchor on. So that's, that's the first piece. The next piece is really around, how do you curate who you ask? And I think there are two dimensions of this. The first one is the obvious one, which is a subject matter expert who really knows something about the topic at hand. So maybe a web dev themselves, right? For my example question. Another one, and this dimension I think is really important, is someone who knows you really well-

   19. LRLenny Rachitsky8:28

       Mm-hmm.

   20. ARAda Chen Rekhi8:29

       ... and can provide insight on, how well does that work for you? And then after that, you know, you really wanna ask the question, and this touches on sort of what you said about how do you make it really lightweight. Ask the question in a way that really gets you a useful constructive answer, but doesn't put too much weight on people. And so what I usually like to do is just make it very lightweight. So in your case I said, "Here are nine topics. Can you pick your top two and tell me why you like them?" And some people went above and beyond, and scrolled through and gave me feedback on every single topic. And some of them just said, "Here are my top two, and here's one I think you should avoid." I wanted to design it in a way where if you're a busy founder, you're a busy product person, which is sort of the list that I chose for this curiosity loop, you would be able to sort of sit down on your couch at the end of the night, read this sort of interesting email and tap out a quick reply and sort of give me that answer, because the risk that you're running is either you're getting poor answers or you're getting a really low response rate because you've given them way too much cognitive load in terms of answering it. And then finally, to kind of close the loop, I think a big piece of it is processing that information and then thanking them for it.

   21. LRLenny Rachitsky9:41

       Yeah.

   22. ARAda Chen Rekhi9:42

       So, a big misconception that people have when they're really getting into this work of asking for advice or input from other people in the community is often that it's really one-sided, right? "I'm asking you for help, and you're getting nothing out of it." The reminder that I would have for all of you is that it feels really good to help someone. It feels really good to be heard and give input, and a big piece of that is if someone comes to you and they said, "You gave me this advice. It changed my life," you know, maybe it's not at that level, (laughs) but, "It really affected my decision and here's how it turned out. Thank you so much." That feels so good, especially if you only spent a few minutes giving them the input that enabled them to make a better decision.

   23. LRLenny Rachitsky10:21

       So to summarize, I wrote these pieces down. Uh, they, the concept broadly is if you want, um, advice on a decision you're trying to make, pick some friends, and this is, I guess I'll go through the four things you just mentioned and, and part two is actually pick the right sort of friends. But one is just, like, come up with a question that's specific, isn't just like, "What should I do with my life?" But more, "Should I take this specific role at this specific company?" Figure out the people that know you well and maybe have some context on this decision. And how many people do you usually email for this sort of thing? Like, what's like a number?

   24. ARAda Chen Rekhi10:55

       I would try to optimize for getting at least three or four responses. And it kind of just depends on the nature of the loop, and then you... Yeah, then you think about what is your ex- response rate? So you know, if you're emailing really busy people, maybe you would assume that, that you don't know very well, maybe you would assume that you only get half of people to respond.

   25. LRLenny Rachitsky11:14

       Got it.

   26. ARAda Chen Rekhi11:14

       And if you're emailing people you know really well and it's really lightweight, like yes or no and here's why, then you might just send out a handful.

   27. LRLenny Rachitsky11:22

       Okay, awesome. So it's like five to 10 people bro- broadly sounds like. And then, um, oh yeah, you wanna make it really quick and easy. So it's like a, like here's 10 things. "Which of these two do you think I should focus on?" So it's like a quick ask, y- is something you recommend and then just like thank them for it after you finish? Is that broadly

3. 11:39 – 14:13

   Using curiosity loops in your personal life

   1. LRLenny Rachitsky11:39

      the approach?

   2. ARAda Chen Rekhi11:39

      Yep, that's the approach. One thing I wanna note is that it's actually really useful for personal things as well. So...

   3. LRLenny Rachitsky11:45

      Mm-hmm.

   4. ARAda Chen Rekhi11:45

      ... we framed it in this professional context of, "I'm trying to change a job." But you know, one example that I have is when we had our daughter, who's now three years old, one of the debates that my partner and I were having was, how do we actually set up our estate planning in terms of if, God forbid, something happened to both of us? How should she inherit?... this date, and, you know, my partner was basically saying 18 years old, she gets everything fully unlocked.

   5. LRLenny Rachitsky12:13

      Hmm.

   6. ARAda Chen Rekhi12:13

      And I was saying, "Oh, well, you know, maybe 25." And we're at this impasse, and we actually just started to tell each other why don't we, in our day-to-day conversations with folks that we trust in our family, people that we think are smart that have kids, ask people what their perspective is on it? And one thing was really telling. No one, out of everyone we asked, said 18, and so that really, like dragged my partner up.

   7. LRLenny Rachitsky12:35

      Hmm.

   8. ARAda Chen Rekhi12:35

      And then the other thing that was really interesting was that we learned a little bit about executive function and the research around it. And so executive function, which is your ability to make decisions and plans and be thoughtful, peaks at the age of 30.

   9. LRLenny Rachitsky12:49

      Hm.

   10. ARAda Chen Rekhi12:49

       And it's all downhill from there, so bad news for people like me that are older. Um-

   11. LRLenny Rachitsky12:54

       Yeah, me either. Shit, man.

   12. ARAda Chen Rekhi12:55

       (laughs) Yeah, exactly.

   13. LRLenny Rachitsky12:56

       Game over. Have to start crying.

   14. ARAda Chen Rekhi12:57

       But, you know, if you're thinking about 18, like, you know, you are so far from your peak, and so it kind of dragged us both up in terms of what our set point was to make a decision like that. But we wouldn't have figured that out without a curiosity loop because it's just, it's too much work to kind of dig through papers or research or whatever else to try to come to a good decision on it.

   15. LRLenny Rachitsky13:14

       So the, like the core lesson here is just versus just emailing a bunch of people with a, like asking for advice, which I imagine people often do, just like, "Hey, what should I do here?" Creating a little bit of a structure and even ca- calling it a curiosity loop, I bet helps people feel like they wanna be a part of this and participate and help.

   16. ARAda Chen Rekhi13:31

       Yeah, definitely. I mean, one of the things that I always try to do is I try to explain to people in my ask-

   17. LRLenny Rachitsky13:37

       Mm-hmm.

   18. ARAda Chen Rekhi13:37

       ... "Here's why I picked you."

   19. LRLenny Rachitsky13:38

       Mm. Yeah. That's a great idea.

   20. ARAda Chen Rekhi13:39

       So for example, you know, "I picked you because I really trust you to be a sound source of truthful advice and give me some feedback."

   21. LRLenny Rachitsky13:47

       I like that a lot.

   22. ARAda Chen Rekhi13:48

       And so I really value that. "Do you mind spending a couple minutes and just giving me some thoughts on this?"

   23. LRLenny Rachitsky13:53

       And how often are you (laughs) pinging people? Like if you're a friend of Ada, are you, uh, are you getting curiosity looped every week or how often? (laughs) what's your rate limit?

   24. ARAda Chen Rekhi14:02

       I usually reserve it for bigger things, so probably quarterly or, you know, anything where I'm having a big debate and I'm feeling really indecisive.

   25. LRLenny Rachitsky14:12

       Awesome.

4. 14:13 – 16:30

   How curiosity loops are like customer advisory councils

   1. LRLenny Rachitsky14:13

      It also makes me think about, about this idea of a personal board of directors, and this feels like an asynchronous approach to that sort of concept, or instead of like a call every, I don't know, quarter month with like small group, it's asynchronous. Here's an ask I have.

   2. ARAda Chen Rekhi14:24

      Totally. Yep. I think this is really based off of the, the marketing concept of customer advisory councils.

   3. LRLenny Rachitsky14:30

      Mm-hmm.

   4. ARAda Chen Rekhi14:30

      And so when I was working in marketing and product at a startup, one of the things we would always have is a group of our top customers on DM basically, and if we had really interesting product conflicts, we would actually just go ping a couple of them and ask them, "Hey, we're debating this. Do you mind just like giving us your quick thoughts and telling us why?"

   5. LRLenny Rachitsky14:49

      Mm-hmm.

   6. ARAda Chen Rekhi14:49

      And then being able to, as a marketer, come back to the product conversation and say, "Here is the literal voice of the customer."

   7. LRLenny Rachitsky14:56

      Mm-hmm.

   8. ARAda Chen Rekhi14:56

      And four or five different verbatims on what people think about this really, you know, enabled me as a marketer to have a seat at the table, and the insight and the helpfulness of that was really something I wanted to bring to my personal life as well.

   9. LRLenny Rachitsky15:07

      That's really interesting. It's like basically user research for your life. Like, you know, with user research you're, you're told don't do what people tell you to do, and I guess it's the same thing here where it's just like, here's advice, and then you end up making the decision for your, for your home life.

   10. ARAda Chen Rekhi15:19

       Right. Right. Yes. That is the big caveat. Don't do what people tell you to do. Take it as an input-

   11. LRLenny Rachitsky15:25

       Yeah.

   12. ARAda Chen Rekhi15:25

       ... and, you know, look for, look for the hard feedback.

   13. LRLenny Rachitsky15:29

       Mm-hmm.

   14. ARAda Chen Rekhi15:29

       Look for things that you strongly disagree with or are surprises to you because, you know, to me, I think 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.

   15. LRLenny Rachitsky15:43

       Sweet. Uh, you said that people told you what not, what we should not talk about. They were like, "Don't cover this." What was, what was in that list?

   16. ARAda Chen Rekhi15:49

       (laughs) So I think there were two topics on the list. The first one was, um, it was just, you know, how do you onboard and hire and sort of bring people onto the team and, you know, the feedback I got there was like, "There are just so many people who have done this. I'm sure you have some interesting concepts, but I personally wouldn't be that interested in hearing it," and that was really useful to me. And then the other one was actually just about being a woman in Silicon Valley and the experience of that, and I actually had someone write, and you probably read this, Lenny, "No, stay far away from this. There's no winning on this topic."

   17. LRLenny Rachitsky16:24

       Oh my god. Okay. Let's, let's touch on that topic later then.

   18. ARAda Chen Rekhi16:27

       (laughs)

   19. LRLenny Rachitsky16:27

       It's gonna be great.

   20. ARAda Chen Rekhi16:27

       Yeah. So let's ignore the advice.

   21. LRLenny Rachitsky16:28

       Mm-hmm. Yeah, let's ignore

5. 16:30 – 25:30

   A values exercise

   1. LRLenny Rachitsky16:30

      it. Before we get to that, I wanted to, uh, first talk about you, you gave me some homework also ahead of this chat, and, uh, the homework was around helping me figure out values and personal values for myself, and I did the exercise. So first of all, can you just maybe talk about what this exercise was and what the, what the goal of it is, and then I'll share, share what I come up, came up with.

   2. ARAda Chen Rekhi16:50

      Yeah. So the homework that I gave you is similar homework that I give to everyone that I work with in coaching, and it's this values exercise. It's this 10 to 15 minute exercise where you're presented with a list of words that might encompass potential values. And it's pretty lightweight. You just go down the list and you pick out all the words that resonate with you, and then we filter them down into groups of values, and then we filter them down into a stack rank and sort of a list, and the output on the end is basically three to five sentences that cover what are the values stack ranked that are important to you right now in your personal and professional life? And what I really like is 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's this great way to look back and see how well do decisions or how well do my situations in life align with my values?

   3. LRLenny Rachitsky17:53

      Sweet. Yeah. And what I liked about it is if someone were to be like, "Hey, come up with your values," I'd be like, "Oh my God, I'm just sitting here thinking about words and concepts." And it was really helpful because it was basically multiple choice. Here's all the options across tons of categories, just like keep picking and then helps you kind of whittle 'em down. I ended up with six. I think I feel like that's one too many. I actually added a bonus one 'cause it's just one that I really like.But, uh, should I read through what I came up with?

   4. ARAda Chen Rekhi18:18

      Yeah. That sounds great.

   5. LRLenny Rachitsky18:19

      So here's what... Yeah, my values, I guess. Uh, choose adventure, stay optimistic, treat others like you want to be treated, classic, keep getting better, act generously, and added one that my grandma taught me back in the day that has stuck with me that had nothing to do with this exercise but I just wanted to have on this list, which is first do what you need to do, and then do what you want to do.

   6. ARAda Chen Rekhi18:43

      I love it. What a great list of values. And what stands out to me from that list too, Lenny, is, you know, this, this idea of achievement or status or success, like a lot of the things that we talk about publicly, right, like what your LinkedIn feed might look like, don't actually show up in your values, and it must reflect in some of the choices that you've made in your life.

   7. LRLenny Rachitsky19:04

      Yes. I hope so. (laughs)

   8. ARAda Chen Rekhi19:08

      So let me ask you this. Um, let's try to apply some of the values in-

   9. LRLenny Rachitsky19:12

      Mm.

   10. ARAda Chen Rekhi19:12

       ... real time as an experiment.

   11. LRLenny Rachitsky19:14

       Oh, boy.

   12. ARAda Chen Rekhi19:14

       If, if you think about a recent decision that you've had to make or a decision that you're facing coming up, can you share what that decision might be? And then let's try to apply the values to it to kind of think about if you were living up to these values, what choice would you make and maybe some of the pressures you might feel to choose otherwise.

   13. LRLenny Rachitsky19:37

       So like an ongoing decision I have is I have all these opportunities of things I can be doing, additional things I can be doing, like the podcast. This actually was a good example of I never wanted to do a podcast, because I really wanted to... Like I was living in, like life is good. I write, was writing this newsletter. I was doing great making a living doing a new, like one great email a week, and I was like, "Why would I do anything more?" This is good. And so constantly resisted the... I resisted the podcast for two, three years, and then eventually succumbed, and it was a great decision in the end, but now I have other things that I, um, I'm trying to not do, but they're kind of like always pushing, pushing into my mind space, like a book, for example. I had a course at one point, and I paused that just so I could have more time for the podcast. So I guess the decision is just like what should I say yes to versus say no to? And I'm looking at my values a little bit, and like one of them is choose adventure, which you would think would be like, just do stuff, just try stuff out. But I feel like e- maybe it's just like a missing bullet point here of just like I just want, I just wanna li- do less. I don't want... I'm trying to take on less and do less and-

   14. ARAda Chen Rekhi20:43

       Mm. That's really interesting.

   15. LRLenny Rachitsky20:44

       ... cut out and simplify. Yeah, 'cause there's just like endless things I could be doing, and I wanna like, you know, spend time with my wife and my new child, who's, uh, coming in a couple months if all goes well. So that's where my mind goes when you ask that.

   16. ARAda Chen Rekhi20:57

       Yeah. Yeah. And then maybe, you know, if you were to decompose adventure-

   17. LRLenny Rachitsky21:01

       Hmm.

   18. ARAda Chen Rekhi21:02

       ... what adventure actually means to you-

   19. LRLenny Rachitsky21:04

       Hmm.

   20. ARAda Chen Rekhi21:04

       ... and you go into that word list, you might actually just find that some of these opportunities, like writing a book, at some point it doesn't feel like an adventure.

   21. LRLenny Rachitsky21:13

       Right. That's so true. Like the beginning of it is an adventure, and then it... That's such a good point because, yeah, once you start a thing... Something I always say about like this content creation life is like it's easy to start; it's hard to keep it going.

   22. ARAda Chen Rekhi21:25

       Yeah. Yeah.

   23. LRLenny Rachitsky21:25

       And it becomes just like this treadmill of just you have to keep creating awesome stuff basically for the rest of your life. I don't know how you get off this treadmill. Not that I'm complaining, but that's just like a reality of this, uh, path. And so that is such a good point that it becomes not adventurous very quickly. So that's really interesting.

   24. ARAda Chen Rekhi21:41

       I love it.

   25. LRLenny Rachitsky21:42

       I guess the other thing is just like what to cut off, like what am I... Like I do a bunch of angel investing, and so I'm thinking about just like stopping that for a while just so I can have more time with my new, new child and just, uh, carve out things that maybe aren't as essential.

   26. ARAda Chen Rekhi21:55

       So on the values exercise, I think what you've done a really good job of is just really delineating here are some examples of choices that you have to make, and I think that there are some points in our lives where, like writing a book, it just seems really obvious. It's good for your career. It's sort of the next level in terms of where you go from the community, the newsletter, the podcast, and sort of getting to that next level. But, you know, where I think there is value is these lists of values can help ground us from those obvious decisions. And so in my life, to kind of share a mini-example of this, there have been a lot of cases where the next obvious step for me might be to go be an executive at a big company and to kind of go chase the dream and, you know, continue on sort of the latter climb of my career. And as I've examined my own personal values, a big piece of it has really been around prioritizing relationships, right-

   27. LRLenny Rachitsky22:46

       Mm.

   28. ARAda Chen Rekhi22:46

       ... and really pursuing knowledge and growth on my own terms. And things like independence and autonomy have started to creep up over time, especially once I started a family, and it became very clear to me that sometimes the external scorecard of what people think you should go do is very much an opposition of what I actually want to do, and even though it might be objectively better, you know, depending on what scorecard you actually use, I would actually be less happy with some of those outcomes. And so I think values are sort of this really nice useful tool to think about how do you make better decisions again to maximize for your own alignment with life.

   29. LRLenny Rachitsky23:23

       That's such an important point, and it connects back to the course that I taught and then this potential book of like it just feels like an obvious thing I should do, and it was, it was great, but it just didn't bring me joy, and other things bring me more joy. And so it was a really good reminder of just like, "Do I really want to be doing this or is this just like a thing that feels like a smart thing to do but, uh, maybe isn't for me psychologically?" And so I love the, just the reminder of like coming back to values as a lens to decide if you wanna do a thing versus just like what are people tell- telling you is smart or-

   30. ARAda Chen Rekhi23:57

       Yeah. Yeah.
6. 25:30 – 31:28

   Ada’s “explore and exploit” framework

   1. LRLenny Rachitsky25:30

      You talked about your career and how you avoid... You kind of resisted these shiny object opportunities to focus on the thing that you were excited about and wanted to do. So maybe a couple questions there. One is just, like, early career advice. You coach a lot of founders. You had a really inc- incredible career doing all kinds of interesting things. What have you learned about what works best for optimizing in your early career?

   2. ARAda Chen Rekhi25:55

      My early career was pretty wild. So I had a really fast run. Over the course of seven years, I went from my first job, which was basically this entry-level sales job at Microsoft, working on Microsoft Ad Center to SVP of marketing at SurveyMonkey, leading a global team. And when I reflect back on what worked across my early career, it really kind of comes down in a nutshell to this career concept of explore and exploit, which actually sounds kind of dark now that I'm saying it out loud, but, um...

   3. LRLenny Rachitsky26:27

      No, sounds great. I, I, I love it.

   4. ARAda Chen Rekhi26:29

      Explore and exploit, if you're familiar with it from, you know, growth background, is really just around what mode you're in. You're either in a mode of explore where you have a bunch of unknowns and you're testing to see whether or not you like it, how well it works, whether or not it fits for you. Or you're exploiting, where you actually have found something that's really rich and really deep and then you're just trying to get more. 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. So coming out of school, my first job was at Microsoft, I was at Ad Center. The big thing I learned from the 367 days that I was there was that (laughs) corporate life at that point in my career was just a little bit too slow-paced for me, and I was really hungry to go do something else. But I also learned quite a lot about marketing and advertising, and I had the suspicion that not only did I wanna try something smaller, but I also wanted to try marketing. And so I moved to this Series A startup where I had to assemble my desk on the first day, called Mochi Media, and I was in a marketing role at a startup and had this great run there over three years where I learned all kinds of things and even tried product at some point. And, you know, what I learned from that experience was then I love marketing, games was pretty fun, and, you know, being in a smaller team was really dynamic. And it was this choice on do I exploit and sort of go deeper into the industry or do I explore more? I was 23 at the time, so I decided, "I have so little to lose, let me continue exploring." And my big thesis was, "Let me try being a founder." And so then I founded Connected, and Connected was this personal CRM that's a little bit like, um, Clay, if you've seen Clay now recently in terms of how do you do a better job of managing and building your professional and personal network. And, uh-

   5. LRLenny Rachitsky28:22

      Yeah. It's a beautiful product.

   6. ARAda Chen Rekhi28:23

      Yeah, it's a beautiful product. Much more beautiful than what we built at the time.

   7. LRLenny Rachitsky28:26

      (laughs) .

   8. ARAda Chen Rekhi28:27

      (laughs) And it was such a great learning experience to discover what it was like to be a founder of a company and an entrepreneur, and my personal learning out of all of those things was really just that I was continuously optimizing, you know, that I loved marketing, I loved being a founder, I, um, really like small teams. There are pros and cons to sort of this corporate life where maybe things are really slow-paced, but the scale is really important. And so that was really what carried me through a lot of my early career. And after Connected was acquired by LinkedIn, I kind of moved into this exploit mode. So I was at LinkedIn for a period of time while I was investing and I really wanted to be intentional about the time that I spent there in terms of how I wanted to exploit it. So unlike a traditional path where you're really focused on trying to get the biggest title, a big team, set yourself up to kind of run a big org., my role at LinkedIn was really explicit. I even told my manager this when I first came in, "I'm here to learn to be a better founder." So there were a lot of things when I started Connected which I didn't know how to do very well. I didn't understand growth, I was, you know, fair to middling at pricing, I really didn't understand how to build a subscriptions business and how to price it. And so if I can make my LinkedIn experiences match to that, that would be a huge win for me independent of promotion or compensation or a whole bunch of those things because the plan afterward is actually to go off and start another company. And so I managed to get into this great role leading growth marketing for LinkedIn, working with their growth team from 100 million to 200 million members, read every experiment brief that I could, spent a lot of time with the team really understanding their process, and then shifted into the subscription side where I worked on LinkedIn subscriptions and ran their sales subscriptions business at scale through the online channel and kind of saw how all of those pieces and r- worked together from a financial planning and analysis stage to all of the optimizations that they did. And it was just such a rare opportunity, 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 trying to get the biggest title. Instead, I was focused on those learnings and those experiences, and ultimately, the fact that I was...... a startup founder. I had big company experience, I had growth experience, and I had subs experience, and I was a product marketer. That was actually the winning combination that caused SurveyMonkey to send me a LinkedIn InMail, start a conversation, and ultimately bring it, bring me in as their head of marketing at the age of, I think I was 27 or 28 at the time. Because their rationale was, "You have all these experiences that we really need, and you don't have the management experience, but we have plenty of that. We're happy to teach that to you."

   9. LRLenny Rachitsky31:12

      I really like this framework, I've never heard it described this way, of exploit, explore and exploit. Connects a lot with what I always recommend, which is early on, is to optimize for a variety of experience so that you can figure out where you actually-

   10. ARAda Chen Rekhi31:24

       Mm-hmm.

   11. LRLenny Rachitsky31:24

       ... have a good time, and what you're interested in, versus, uh, getting stuck on

7. 31:28 – 35:37

   When it’s time to leave your job

   1. LRLenny Rachitsky31:28

      the first thing. Something, I, I don't know if you'll have a im- im- an immediate answer to this, but I'm curious, many people don't know how long to stick with something that maybe doesn't feel good, but may lead to something. Like, someone may be in a job right now just like, "Uh, I really don't like what I'm, I really don't like this job, but I feel like it'll lead to something great, and I don't wanna give up too quickly." So, I guess the question is, what are heuristics that tell you to, like, stick it out and stick with something that you think will lead to something great versus, like, pull the ripcord and, and get out?

   2. ARAda Chen Rekhi32:01

      That's a great question, and it's a really tough one that is kind of contextual on the person that you are.

   3. LRLenny Rachitsky32:06

      Yeah.

   4. ARAda Chen Rekhi32:06

      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. And so, if you are familiar with the story of the frog, it's this idea of boiling the frog. So (laughs) if you take a frog and you throw it in a pot of boiling water, it'll jump out. But if you take a frog and you put it in a pot-

   5. LRLenny Rachitsky32:27

      Mm-hmm.

   6. ARAda Chen Rekhi32:27

      ... and you increase the temperature degree, by degree, by degree, the frog doesn't notice. And before it knows it, it's boiled alive. And how I apply this to kind of your question-

   7. LRLenny Rachitsky32:38

      Mm-hmm.

   8. ARAda Chen Rekhi32:39

      ... to come back and circle back to it, is that it's really easy to be a victim of inertia. It's really easy for all of us to be the frog, where there are little things that make us uncomfortable and, you know, we kind of sit with them or we think, you know, "Gosh, it'll get better. The next manager will get better. I'm always one conversation or one promotion away from kind of getting to that next step." But you really have to be aware of your surroundings. You have to be aware of which way is the direction of the te- you know, the temperature of the water trending. And that's what kind of makes the advice really contextual. I really kind of look at it from the lens of learning. What can I learn here, and how am I growing and developing? 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 single day, you're being really challenged, you're learning new things, you're deriving a lot of meaningful enjoyment out of your work, and, you know, you're kind of this happy frog that's hanging out, realizing that things are good and the temperature is not rising. But there are also situations where you might encounter just some really hard walls, where you don't get along with the thesis of the company, right? Like, you don't agree with the direction of the company that you're in. There are fundamental aspects of the role which are limiting to you, or you're not learning a lot, frankly, and I think that happens a lot, where you're pr- providing a lot of value and doing a good job at a company, but you might not be learning things that kind of stretch you and grow you to achieve your ultimate goal. And, you know, when you are aware of that learning, I think that's sort of the point at which you have to say, "How do I change that? How do I kind of be an agent in my own career and make a difference in that?" And it doesn't necessarily mean that the strategy is to quit your job and do something catastrophic and then, you know, go, go do something else, take a course or sign up for something new. It might actually mean a proactive conversation with your manager-

   9. LRLenny Rachitsky34:35

      Mm-hmm.

   10. ARAda Chen Rekhi34:35

       ... or the leadership, to say, "I love what I'm doing here, and I would also like to learn a little bit more, and here's what I'm interested in." And then try to find a way to either land the right project, so in my case it was really growth in subscriptions, right, that experience that I really wanted. Or, to even, let's say you hit a black wa- a blank wall there, even take it as a gift of time, which is great. I'm not going to be able to get this from my company, but now that I have sort of this extra time because I'm so optimized at this job, how am I going to choose to use that time? And it might be around building relationships with some of the key people at the company-

   11. LRLenny Rachitsky35:13

       Mm-hmm.

   12. ARAda Chen Rekhi35:13

       ... or learning something new on your own time that you can leverage in another way.

   13. LRLenny Rachitsky35:17

       I like that. Make the most of the time, even if it's not, like, the k- the best opportunity for you. Also love the frog boiling metaphor.

   14. ARAda Chen Rekhi35:23

       A little gory.

   15. LRLenny Rachitsky35:24

       No, it's, it's great. So, I guess the lesson there is think about, are you that frog being boiled right now? And think a- think ahead. Is this gonna be-

   16. ARAda Chen Rekhi35:31

       Right.

   17. LRLenny Rachitsky35:31

       ... the end of the-

   18. ARAda Chen Rekhi35:32

       Like, keep an eye on your environment and which way is it trending.

   19. LRLenny Rachitsky35:34

       Mm-hmm. Yeah. The temperature and the thermostat in your office.

8. 35:37 – 39:30

   Logo collecting and why you should optimize for your values instead

   1. LRLenny Rachitsky35:37

      Uh, the other thing this makes me think about is, it's, like, so easy to get caught up in making your resume look amazing and continuing to just like, "Oh, if I get this next role, my resume's gonna look so great. I can have this other logo and this cool title and role." And I find that just, like, like, you do that long enough in your life, you get, you, you end up re- like, you're re- you retire and then you die. Like-

   2. ARAda Chen Rekhi36:00

      Yeah.

   3. LRLenny Rachitsky36:00

      Life is that resume, right? Like, that is your life you're living, and there's not gonna be a point at which, like... Like, you have to realize, "Okay, I've done all the things to make my resume awesome. Like, what do I actually wanna do? Am I, like, enjoying this?" 'Cause it'll never end. You're never gonna end trying to make a better resume and a o- more awesome background for yourself. Do you experience that with yourself or other people you work with, of just, like, over optimizing to make an awesome series of-

   4. ARAda Chen Rekhi36:25

      Mm-hmm.

   5. LRLenny Rachitsky36:25

      ... roles and logos and then forgetting, like, "Do I actually enjoy any of this? What am I doing?"

   6. ARAda Chen Rekhi36:30

      I have, I have experienced that personally-

   7. LRLenny Rachitsky36:32

      Mm-hmm.

   8. ARAda Chen Rekhi36:33

      ... um, a lot. I think that it may be sort of a, a generational thing or it just may be my background, but having grown up with sort of the Asian tiger parenting-

   9. LRLenny Rachitsky36:42

      Mm-hmm.

   10. ARAda Chen Rekhi36:42

       It's very focused on logos, or certain accomplishments, or certain achievements like going to an Ivy League school, working at a company that someone's heard of, being able to have a certain title. And at a certain point, you know, I kind of bailed out a bit, and I really started to think about who am I trying to please and optimize for. And that values exercise that I had you do, Lenny, is actually a big piece of that. So I probably took it for the first time over a decade ago at this point, and I looked at those values and I said, "Well, if I draw a straight line from where I am right now and just sort of extend it forward and play the rest of the movie as it plays out given the current plotline, how well does that optimize for those values?" Like that's great, you know, my parents might be happy about my resume or other people might look upon me in a certain way because I've managed these achievements, but in my day-to-day life what really matters to me, what's really meaningful to me, only some of this stuff really matters. And so, you know, kind of getting very intentional about that and being clear about who your audience is as you navigate your career, I think, you know, 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 a certain expectation that the people around you that you have to go work this job, but then you look at yourself in the mirror and you're not happy going in there. I think that's a terrible trap that we should all try to avoid as we kind of navigate our career paths and find the thing that's sort of most optimal for us, which is usually a mix of career success but also meaningfulness and sort of alignment in the work that we're doing with our values.

   11. LRLenny Rachitsky38:25

       I love this topic. Thank you for sharing that. This episode is brought to you by Sprig. You already heard me talk about how Sprig helps you uncover blind spots in your product development process, allowing you to better understand why users take certain actions and how they feel about the experience. And just this week, they launched their brand new templates library which you can find at sprig.com/templates, which helps you plug and play proven playbooks for helping you identify and solve the biggest challenges facing product teams today, from how to optimize an existing feature, to improving a conversion flow, to troubleshooting drop-off. One of the questions I get most on this podcast and in my newsletter is how to develop your product sense. So I decided to work with Sprig to build a playbook for how to do just that based on my experience at Airbnb and what I learned from interviewing top product people like Jules Walter, who wrote a whole guest post on how to develop your product sense, which informed this template that you'll find. Just go to sprig.com/templates to find this playbook and 85 more. That is sprig.com/templates. S-P-R-I-G.com/templates.

9. 39:30 – 42:10

   What triggered Ada to reevaluate her career path

   1. LRLenny Rachitsky39:31

      What triggered your reevaluation of that path? Was there just like a, "Oh, man, I need to really rethink where I'm going"? And then I have a follow-up question.

   2. ARAda Chen Rekhi39:40

      Really just a, a career opportunity, and it was sort of this step where I could do something that was at the time, like, really high profile and really exciting and felt great, but also involved demanding travel and sort of grueling hours and wasn't in a space that I was excited about, but it'd look amazing on my resume. And I was talking to a friend about it, and they actually introduced me to this values exercise to say like, "Ada, go through and fill out this values exercise and apply it to this job." And, uh, what I realized at the time after I did it was that my top three values, like the things that I cared about this job would categorically just fail at, because I would be gone all the time in pursuit of sort of glory that I didn't really care about. And instead, you know, my current path, at the time, was something that if I persisted in it would actually be able to potentially fulfill all of those values.

   3. LRLenny Rachitsky40:36

      It reminds me of a friend who has this metaphor of this ego monster sitting in the corner of the room that's always yelling at them when they're... Like, to do the thing that's impressive and, like, take on the really cool role and just, like, get an awesome title and do something really impressive that's just, like, sitting and just, like, yelling at them from the corner. And my friend's just kind of learned to just like, "Okay, that's the ego monster pulling at me. I don't have to listen to that. Doesn't mean I'm gonna be happy if I listen to this, to this guy." And that's been really helpful to my friend just to kind of disassociate that part of the brain.

   4. ARAda Chen Rekhi41:10

      Yeah. The, the, the ego monster is a great way to put it. I use, um, something that Warren Buffett has talked about which is-

   5. LRLenny Rachitsky41:17

      Mm-hmm.

   6. ARAda Chen Rekhi41:17

      ... inner scorecard versus outer scorecard.

   7. LRLenny Rachitsky41:19

      Hmm. Good work.

   8. ARAda Chen Rekhi41:21

      So he talks about how there's an outer scorecard which is how the rest of the world evaluates you, how you keep score in terms of external factors, so top 10 lists, wealth, status, title, maybe, you know, things that people really care about. And then your inner scorecard is things that actually matter to you. You know, how you spent your day, how good of a person you are. Did you have an adventure today, Lenny? Were you kind?

   9. LRLenny Rachitsky41:46

      Mm-hmm.

   10. ARAda Chen Rekhi41:47

       And there are a lot of things that maybe are in opposition to each other, 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 you really wanted? I think really thinking about it in that lens kind of helps you sort of trade off against some of that external pressure and the ego

10. 42:10 – 44:59

    Why most people don’t actually need a coach

    1. ARAda Chen Rekhi42:10

       monster.

    2. LRLenny Rachitsky42:11

       This might be a good segue to chat about coaching. I imagine a lot of people listening to this are like, "Yes, I wanna do that. I want to measure myself according to my values and check in on this, and am I doing the wrong path?" And it's hard to do just like on your own, I find, and I think that's one of the benefits of an executive coach. And so maybe we just chat about what should people know about coaching and getting a coach, and does everyone need a coach, and how to think about the idea of getting a coach at some point in their career.

    3. ARAda Chen Rekhi42:42

       I'll have a hot take on this-

    4. LRLenny Rachitsky42:43

       Okay.

    5. ARAda Chen Rekhi42:43

       ... and it's something that I share to people when I talk to them about coaching. But-My hot take is that for the vast majority of people, they probably do not need a coach.

    6. LRLenny Rachitsky42:54

       Right.

    7. ARAda Chen Rekhi42:54

       And what I often push people on is if you're thinking about getting a coach, which is usually an indication that they have a feeling of being stuck or they have a problem that they're trying to solve, I ask them, "What are your goals when it comes to coaching? Like, roll it forward six months. What have you gotten done in your coaching experience?"

    8. LRLenny Rachitsky43:17

       Hmm.

    9. ARAda Chen Rekhi43:18

       "And you know, what have you accomplished and you're just, it's like a home run? And then look at all of the potential alternatives in terms of how you could've spent your valuable time, and you know, often pricey fees to achieve the same goal, but maybe in a better way." And you know, 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 because it's just one person's opinion. It's actually way better to run a curiosity loop, for example, and get the benefit of a couple different minds on a specific topic and you know, hit their wheelhouse of things that they know about than to go ask one person, "What do you think I should do in this situation?" If you're trying to learn about a topic in a really robust way, let's say you wanna learn about growth, maybe you should take a Reforge course and get access to all of the resources and the insights of the EIRs and you know, the growth advisors at Reforge, and get sort of an overview and survey of the landscape instead of one person's experience and the handful of companies that they might have worked with. And likewise, you know, if you're just feeling like you're a little emotionally overcome, I think coaches are sort of this great resource around that, but it's actually better to kind of pay it forward and build a tribe and a community of people around you that you can rely on for support, because that's the kind of thing that lasts you for years and years, right? And so one of the first things that I do when people talk to me about coaching is I challenge them and say, "Have you explored all of these other opportunities first? And do you really need a coach, and is a coach actually the best option for you?" Kind of like an anti-sell, just so that they know what they're getting themselves into, because I don't necessarily think that it's useful for all things, even though it can be helpful.

11. 44:59 – 47:20

    When coaching is valuable

    1. ARAda Chen Rekhi44:59

    2. LRLenny Rachitsky44:59

       And then when do you find that it is actually, actually important and valuable and something someone should try to get?

    3. ARAda Chen Rekhi45:06

       I wouldn't be a coach if I didn't think that it wasn't important and valuable.

    4. LRLenny Rachitsky45:10

       Mm-hmm. Mm-hmm. Yeah.

    5. ARAda Chen Rekhi45:10

       Um, I think that in, in certain contexts it can be super helpful. So when you have situations where you're in a state of hypergrowth and you need very accelerated learning, and you kind of need someone...

    6. LRLenny Rachitsky45:23

       Mm-hmm.

    7. ARAda Chen Rekhi45:23

       ... who can point you in the right direction, I think coaches can be really helpful. So I work with founders, for example, and founders are just kind of in this unique state where everything is chaos. They have no structure. They don't know what their jobs are.

    8. LRLenny Rachitsky45:37

       Mm-hmm.

    9. ARAda Chen Rekhi45:37

       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. And there's really intense highs and lows. And so for a founder, it might make a lot of sense to get a coach because they have to learn a lot of stuff really quickly and time is of the essence, and so a coach might be a really helpful shortcut for them to get there. Related to that, I think it's also really helpful on sensitive topics.

    10. LRLenny Rachitsky46:01

        Hm.

    11. ARAda Chen Rekhi46:01

        So there are a lot of things that we wanna be coached on where either it takes a lot of time for us to work through and sort of like, you know, progress because it's a long-term project, for example, or it's something very sensitive, like people issues and interpersonal conflicts. Coaches can be especially helpful in those cases because it's this really safe space for you to work through things, but also have someone who's really rational to help guide you through them with potentially some frameworks and extra advice.

    12. LRLenny Rachitsky46:30

        So I had a couple coaches in my career, and what made me feel like I should pursue that is when you think about a sports, sports athlete, uh, or an- (laughs) I don't know, an athlete, like no one not, does not have a coach. Like, the best athletes have coaches and they get great because they have somebody helping them get better. It's not just like an accident. They don't just learn on their own. And as, you know, it just makes you realize that other people in your profession that have a coach helping them out are just gonna be more successful because innately they have someone helping them learn how to do the job better. So that made me realize, man, I should really, I should probably get a coach to help me out with stuff, even though there wasn't anything super specific, I'm like, "Oh, I need to fix this problem." It's just like, well, it just intellectually makes sense. And so that was a- it was actually really important and transformative

12. 47:20 – 51:38

    How to find the right coach

    1. LRLenny Rachitsky47:20

       for me.

    2. ARAda Chen Rekhi47:21

       If you go to my site, I actually have this guide...

    3. LRLenny Rachitsky47:23

       Mm-hmm.

    4. ARAda Chen Rekhi47:23

       ... that I've written over time on both my take on how do you find a coach, and you know, the TL;DR there is actually that I strongly recommend to everyone, if you're thinking about getting a coach, talk to two or three different coaches and really get a sense of their vibe and how well you get to know them, and it's surprising because I did this piece of research, which I also wrote about and we can link to, but I talked to over 80 people about their experiences with a coach. I talked- including coaches, including, um, 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 first coach that they talked to.

    5. LRLenny Rachitsky48:02

       Hmm.

    6. ARAda Chen Rekhi48:03

       It's that your buddy said, "I work with this great coach," and then you go and you hire b- your buddy's coach. I think that's a totally fine way to go find a coach, but I would actually really just urge people to talk to a couple, because what works for your friend may not work for you, and just being able to see some of the variance in terms of the style and how people get along, I think that can make a huge difference in terms of, you know, kind of this reflection of, how do you learn best, right? When you think about acquiring a new skill, do you love structure? Do you not like structure? Do you like it when someone really teaches you and walks you through specific examples, or do you like frameworks? Coaches kind of come in all of those different flavors, and so I think it's really worth it to kind of explore before you get into, you know, such a deep relationship with someone just so that both people can feel really sure about it.

    7. LRLenny Rachitsky48:51

       What's one thing that people may not think about, or just like, it's something that you find really important that maybe is, uh, is unexpected when you're looking for a coach?

    8. ARAda Chen Rekhi49:00

       I thought that credentials and sort of the relevant experience of the coach was a huge factor in terms of how you should go about your coach selection. But part of the interviews that I did was talking to founders that had had experiences with coaches and asking them to reflect back. And these founders and executives, when they thought about it, they actually said so much more about it was actually this amorphous sense of vibe with the person-

    9. LRLenny Rachitsky49:27

       Mm-hmm.

    10. ARAda Chen Rekhi49:27

        ... how safe you felt with them-

    11. LRLenny Rachitsky49:28

        Mm-hmm.

    12. ARAda Chen Rekhi49:28

        ... how deeply you could explore with them, and how well they got you and sort of remembered the pieces of the conversation and help you put it together, way more than potentially some experiences that they'd had where this person had the perfect background but they just never really kind of connected on that level. So, it was unintuitive to me that there was such a big piece of it that was around personal connection, which is why I've now pushed people to try to, you know, talk to a couple different people. And then the other thing which kind of comes back to the sports coaching analogy is that there are different coaches that are really good at different things. And so just like how if you're a star tennis player, you might actually have multiple coaches working with you-

    13. LRLenny Rachitsky50:10

        Mm-hmm.

    14. ARAda Chen Rekhi50:10

        ... maybe like an offensive coach or a defensive coach or working on a particular swing, it actually makes sense when you're really performing at a high level to consider having coaches that work with you on shorter term basis to really just, you know, work on your speaking or, you know, help you with getting into your groove on writing or help you achieve a specific goal, and you shouldn't think about it as sort of this long-term commitment to stay with one person, but instead, you know, more choosing off of a menu and thinking about what goal are you trying to achieve right now.

    15. LRLenny Rachitsky50:39

        Does anyone ever get multiple executive coaches? That... I like how we went from "You don't need a coach," to, "Maybe you need-"

    16. ARAda Chen Rekhi50:44

        Mm-hmm.

    17. LRLenny Rachitsky50:46

        "... a coach for your hamstrings."

    18. ARAda Chen Rekhi50:46

        I, I know, um, yes, I know of multiple people that I've talked to, usually CEOs, that either have had a series of coaches or have multiple coaches. And, you know, it makes a lot more sense, Lenny, when you think about someone who's getting a pitch coach because they're about to get into fundraising.

    19. LRLenny Rachitsky51:03

        Mm. Got it.

    20. ARAda Chen Rekhi51:04

        Right.

    21. LRLenny Rachitsky51:04

        Very, like, niche-

    22. ARAda Chen Rekhi51:05

        Right-

    23. LRLenny Rachitsky51:05

        ... skills.

    24. ARAda Chen Rekhi51:06

        ... with very niche things, um-

    25. LRLenny Rachitsky51:07

        Oh, man.

    26. ARAda Chen Rekhi51:07

        ... because they, they're about to enter a process, or someone who's trying to get into a writing coach, right?

    27. LRLenny Rachitsky51:12

        Got it. Yeah.

    28. ARAda Chen Rekhi51:13

        In addition to some of their executive and leadership work that they might be doing.

    29. LRLenny Rachitsky51:17

        Okay. That makes sense. I love it. I'm gonna get four coaches, one for every-

    30. ARAda Chen Rekhi51:21

        (laughs)
13. 51:38 – 1:00:08

    Advice for women in Silicon Valley

    1. LRLenny Rachitsky51:38

       (laughs) Okay. So let's touch on the thing that your friend said we shouldn't touch on, which is, uh, being a woman in leadership in Silicon Valley, and I, I guess I'll just frame it simply. I imagine there's many young women listening to this podcast, and many may, uh, dream of a career like yours with all the things you've shared. What advice do you have for young women just starting out in their career hoping to kind of find a similar path?

    2. ARAda Chen Rekhi52:03

       This is a really delicate subject, and it's interesting because when I try to decompose why people gave me the feedback they gave me on this topic, I think a big piece of it is just that you wanna have respect for the inherent challenges of being, you know, sort of a non-stereotypically great fit for leadership roles or certain career success roles in Silicon Valley and acknowledge that, and also, you know, try to push for some of the agency of the things that you can do. So, I'm gonna start with just like this quick story about someone that I worked with who's given me permission to share this in a coaching context and then sort of back out. So, I was working with this seed stage founder, and she's so smart. She is really dynamic, very, very focused, really, really great at taking feedback and actioning it. She's one of those people that is just stellar, and I have no doubt that she's gonna make a huge dent in the universe. And we'd been working together on Zoom for a couple months, and I'd sort of built this great respect for her competence as an operator, and sort of the way that she thought and took apart problems and then acted on them. And then we met together for the first time in person at lunch. And the disparity, and I feel almost nervous talking about this here, the disparity between sort of my sense of who she was as an operator and how she came across to me initially at this lunch was really striking in that it was a weekday lunch and she was kind of dressed as if she was hanging out on the weekend. So, you know, old T-shirt, hair back in a claw, bra straps were showing, and, you know, she was just incredibly casual in terms of her pers- her physical appearance. And it took me almost, like, a little bit of a step back to kind of reevaluate and think, "Oh, you know, this is the same person, but she actually just presents so differently." And so then I took the step after we met, and I gave her that feedback in one of our next coaching sessions where we invited each other to give each other feedback, and I shared a lot of my impressions with her. And I told her, "I respect you so much as an operator, and I want to tell you that in the physical app- meeting that we had together, you know, there was kind of like this disparity on how I would've potentially perceived you when I first met you in person versus what I've come to know from about you from the months that we spent together." And her reaction was like, "Oh my god, Ada, no one has ever connected the dots for me. Thank you so much. It has never explicitly been told to me that some of these elements which you describe, and they're very easy for me to fix, and I'm motivated to fix them, are things that might actually trigger certain impressions or biases, and like, no one's actually said it to me before. And I'm about to go into fundraising."And it's actually super helpful for me to hear this, that these are controllable elements of my physical attire or my appearance that might actually just affect the way that people perceive me, and then it gives me this extra hump to get over in terms of getting to this point of credibility for them to see me as the seasoned operator that I am. And she took it so well, but what was interesting about it was actually that she'd made it all this way in her career, she'd even raised funding, and no one had ever given her this feedback. And so this is, sort of, I think one of the big challenges of being a woman in Silicon Valley, because getting to an executive role or getting to a funded founder role, it's kind of like an Olympic level sport. You have to get all the way through the funnel and become one of the few that are really chosen to do that. But the difficulty of this game is that no one tells you the rules of the game. You actually don't really know, like, what are the rules on how to get intros or give intros? What's the right way to follow-up? You know, what are the impressions that people have about you? And 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 the vast majority of them will just never do it, 'cause there's no winning, which is similar to the feedback that I got. And so, you know, where I kind of lean in is to say, "We're not powerless," and, you know, there's something that all of us can do if we're in a position where we feel like it's not even about being female, it's about being perceived as too young or too old, too tall, too short, not the right race. You know, whatever reason that you feel people may be disqualifying you or not seeing you. 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 to call out some of those rules and then find ways around them. And, you know, in this case for the founder in this example, she really, you know, turned to her friends and did, you know, kind of like a mini makeover-

    3. LRLenny Rachitsky57:01

       Hmm.

    4. ARAda Chen Rekhi57:01

       ... and, you know, amped up her appearance, and she came back and she reported, "A lot of people have been giving me really positive feedback that something about me feels more confident and more energetic," and they can't figure out why. But actually, she was getting, like, a ton of people noticing that something was really different about her in a positive way simply because, you know, I was in this great position as her coach to give her some of these pieces of hard feedback that she had never heard before. So, it's really on us to try to find those and then try to, kind of, adapt ourselves to play that game if you wanna play at that level.

    5. LRLenny Rachitsky57:33

       How nervous were you, uh, giving her that sort of feedback?

    6. ARAda Chen Rekhi57:37

       I was so nervous. I actually, um, almost didn't do it and then-

    7. LRLenny Rachitsky57:41

       Mm-hmm.

    8. ARAda Chen Rekhi57:41

       ... took a deep breath, and then decided, you know, "What the heck, I think she's great, I think she would really benefit from doing it," and I gave it. And even in a position where I'm in a relationship with her where I can have that trust, it was super, super difficult, so I can only imagine how hard it is for people to give feedback like that in another context. But how else are people going to hear it?

    9. LRLenny Rachitsky58:03

       I think it was a company culture where they talk about how you're s- you're being selfish not giving someone hard feedback, because you don't wanna be stressed or risk causing damage to your own reputation, but you're not helping them. And so, it's a really interesting insight of just, like, don't be selfish. Like, do something that's hard when you think it's gonna help someone else.

    10. ARAda Chen Rekhi58:26

        Right, right. But I think on the topic of being female or on the topic of physical appearance or, you know, maybe even some of the topics around being an immigrant, right?

    11. LRLenny Rachitsky58:35

        Mm-hmm.

    12. ARAda Chen Rekhi58:35

        If you're in a position where you can give that feedback, I think the struggle is often-

    13. LRLenny Rachitsky58:39

        Yeah.

    14. ARAda Chen Rekhi58:39

        ... will it be well received? You know?

    15. LRLenny Rachitsky58:42

        Yeah.

    16. ARAda Chen Rekhi58:42

        And, and that's where the feedback comes for me from the curiosity loop for this piece, which was there's almost no winning in doing it, because the upside is something great happens for them.

    17. LRLenny Rachitsky58:53

        Yeah.

    18. ARAda Chen Rekhi58:53

        But, you know, there's just so many downsides to giving advice or giving someone input like that that, you know, the default course is just to avoid. But then, you know, that person never learns the rules of the game.

    19. LRLenny Rachitsky59:05

        Yeah. Absolutely. It makes me think also a little bit about, um, Radical Candor. Like, basically, I don't know if you read that book, but-

    20. ARAda Chen Rekhi59:13

        Yeah. Kim Malone Scott, I think.

    21. LRLenny Rachitsky59:16

        Yeah. And Sheryl Sandberg had a similar story where w- she, I think Sheryl Sandberg gave her really hard feedback and she didn't take it that well, actually. I think you did a better job where-

    22. ARAda Chen Rekhi59:25

        (laughs)

    23. LRLenny Rachitsky59:25

        ... your friend actually took the feedback and, uh, did something with it. I think, uh, the whole book was just like, how to actually do this where people actually listen? And I think the framework is you gotta communicate that you care deeply about the person, but you want to challenge them directly also at the same time.

    24. ARAda Chen Rekhi59:40

        Yeah. It's, it's a great story. I think Sheryl Sandberg took her aside after one of her meetings and basically told her that, "If you say 'um,' it makes you sound stupid." (laughs)

    25. LRLenny Rachitsky59:51

        Hmm.

    26. ARAda Chen Rekhi59:53

        And she didn't take that well.

    27. LRLenny Rachitsky59:55

        Yeah.

    28. ARAda Chen Rekhi59:55

        But at the same time, later on in retrospect, you know, she reflected that it was so brave and so helpful of someone like Sheryl to go give that feedback, because there's a real cost to it, there's real risk to it.

14. 1:00:08 – 1:05:07

    Eating your vegetables—why you need to power through things you find challenging

    1. ARAda Chen Rekhi1:00:09

    2. LRLenny Rachitsky1:00:09

       Any other thoughts or advice along these lines that you wanna leave people with?

    3. ARAda Chen Rekhi1:00:13

       The biggest piece of advice that I have that comes to mind is really around trying to be really thoughtful on something I call eating your vegetables.

    4. LRLenny Rachitsky1:00:24

       Hmm. Yep.

    5. ARAda Chen Rekhi1:00:24

       And so, (laughs) I feel like I, I have all these branded terms for things. But, um-

    6. LRLenny Rachitsky1:00:30

       It's great.

    7. ARAda Chen Rekhi1:00:30

       ... 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. And so the researchers say, you know, expose kids to vegetables 10 or 12 times, even if they don't like it, because that's what it takes to get someone to like something. And so, when I think about career strategy and when I think about improving yourself and I kind of think about, you know, how do we look for some of the hard feedback, 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 d- genuine dislike where you've done it and you really don't like it?

    8. LRLenny Rachitsky1:01:13

       Mm-hmm.

    9. ARAda Chen Rekhi1:01:14

       And so, you know, to make it a little bit real, if we think about the world of podcasts, Lenny, I think it's something like 75 or 80% of podcasts never make it past the first podcast.

    10. LRLenny Rachitsky1:01:25

        Hmm. Yeah.

    11. ARAda Chen Rekhi1:01:27

        And, you know, you have to do things a number of times before you really develop an affinity for it, because the first time you do it, you're just not gonna be good. And so, you know, my mini-example of that was early on in my career I was really awkward and not very good at networking, and I moved to Silicon Valley. And one of the things that people told me about Silicon Valley was that it's really important to grow your network, it's all about the people. Totally agree about that. However, I didn't know anyone, and I didn't really understand this networking thing. 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 ten business cards.

    12. LRLenny Rachitsky1:02:05

        Hmm.

    13. ARAda Chen Rekhi1:02:05

        And the rule was I had to hand out all ten of those business cards by introducing myself to people that were new, and touch the back wall of the venue of that event, and then I could leave.

    14. LRLenny Rachitsky1:02:14

        Hmm.

    15. ARAda Chen Rekhi1:02:15

        And I did that a couple weeks in a row, and it was horrible, it was really awful, but it got a lot better. And what I realized about that was actually two things. One, that as I started going and I saw familiar faces, it became a lot easier for me to just break in and meet people, just by seeing who people I knew already were talking to. And then second, I got a lot better at just breaking in and introducing myself and kind of understanding how this intro and sort of networking thing worked in terms of meeting people and moving through a crowd. And some of those relationships now from that first job and those first couple months are s- pretty much foundational to the network and sort of the people that I know today. And so it really paid off for me, because I really focused on eating my vegetables and kind of powering through that initial discomfort. And so, to kind of title back when it comes to thinking about how do you progress in your career, think about the obvious things that maybe you're not very good at, and then think about what are some of the actions that you can do to kind of be very deliberate and intentional about practicing it, to get to the point where, you know, you're, you have some faculty at it. 'Cause it's just really important in some cases to be good at certain skills.

    16. LRLenny Rachitsky1:03:24

        I really like that. I r- I also really like the physicality of that, uh, rule of touching the back wall. It kind of just forces you to go through a room and not just, like, escape really quickly. Is there any other examples of things you've seen or recommend for doing thing, like eating vegetables, like that was a really good example, just forcing yourself to go to a networking event and touch the back wall.

    17. ARAda Chen Rekhi1:03:46

        Yeah. Yeah.

    18. LRLenny Rachitsky1:03:46

        Is there anything else, any other examples that come to mind that you've recommended or found useful? Doing something really hard that was really impactful?

    19. ARAda Chen Rekhi1:03:53

        Yeah. So, um, there, there are actually a few of them. A lot of them are around content creation, because it's just so hard.

    20. LRLenny Rachitsky1:03:59

        Mm-hmm.

    21. ARAda Chen Rekhi1:03:59

        So, you know, one of them that comes to mind is I know a lot of people have talked about doing a LinkedIn 30. And so 30 days of posting something on LinkedIn in terms of content every day for 30 days straight, and just getting past that barrier of sharing, and then looking at it over time and seeing out of the things that you posted what really resonated.

    22. LRLenny Rachitsky1:04:18

        Mm-hmm.

    23. ARAda Chen Rekhi1:04:19

        I also think it's helpful to start thinking about things like getting into DMs, right? Like, it takes a lot of work to sort of think about, oh, this person's really smart, let me DM them, let me try to strike up a conversation, because we're well out of the world of physical business cards. I don't think anyone has those anymore.

    24. LRLenny Rachitsky1:04:35

        Yeah.

    25. ARAda Chen Rekhi1:04:35

        But, you know, modern networking is finding people that are really interesting on the internet and then finding some way to connect with them. It takes a certain amount of extroversion in that case to start meeting up with people and having conversations with them. So, forcing yourself in some way to really think about, well, instead of having one outreach and then failing at it and saying, "I'm never doing that again," how do I actually create a pattern where I can learn, or a sequence of trying to do this 10 or 12 times, right, and see what I get out of it? Because that's really how you learn and how you grow.

15. 1:05:07 – 1:06:54

    Why you should write to crystallize knowledge, rather than for likes

    1. ARAda Chen Rekhi1:05:07

    2. LRLenny Rachitsky1:05:07

       The LinkedIn 30 idea I like a lot. And something that I'll share as a tip is when you hear that, I bet a lot of people are just like, "Oh, my God, got link, post on LinkedIn's so cringey. Oh, I don't wanna be this, like, self-promotion-y LinkedIn person." But what I find is if you reframe it to, "I just wanna crystallize a thought that I have and just, like, share something that is useful to me, or an insight I've had," and not think of it from, like, "I'm trying to get as many likes. I'm trying to go viral with this post," or, "I'm trying to just, like, build some following," just, like, don't think of it that way. Think of it as just want to communicate a thought I have and use this opportunity to crystallize in a really simple way. That helps motivate. That, like, at least works for me, and it also ends up being useful for me. It's not like I'm trying to, you know, grow some kind of following as a result of that.

    3. ARAda Chen Rekhi1:05:59

       I find that really helpful as well. One piece of advice that's similar to that that I've heard is write for an audience of one.

    4. LRLenny Rachitsky1:06:05

       Mm-hmm.

    5. ARAda Chen Rekhi1:06:05

       Like, imagine you're just talking to a friend, or you're trying to talk to someone that's a trusted colleague.

    6. LRLenny Rachitsky1:06:10

       Mm-hmm.

    7. ARAda Chen Rekhi1:06:10

       And just write for them. I think that's really helpful. And it kind of helps us with this, the problem of getting in over your skis, right?

    8. LRLenny Rachitsky1:06:18

       Mm-hmm.

    9. ARAda Chen Rekhi1:06:18

       Like, really over-fixating on the outcome of-

    10. LRLenny Rachitsky1:06:21

        Yeah.

    11. ARAda Chen Rekhi1:06:21

        ... "I did a post and I didn't get my 5,000 followers." And instead just thinking about, "I did a post because I wanted to share an interesting idea. And then how cool, some people resonated with it."

    12. LRLenny Rachitsky1:06:31

        Yeah. I love that. And you could just even say, like, "Something I found useful, day one," and just approach it that way. And that's the stuff that end ups, being most interesting to people. The less it feels like you're trying to be thirsty for followers and likes and all that stuff, and the more it's just like, "Here's a thing I found useful. Enjoy it if you can."

    13. ARAda Chen Rekhi1:06:49

        Yeah. Yeah. People can really tell when you're being genuine and authentic online.

    14. LRLenny Rachitsky1:06:52

        Abso- absolutely. More and

16. 1:06:54 – 1:11:07

    How to successfully build a company with your spouse

    1. LRLenny Rachitsky1:06:54

       more. Maybe a last question. You started a company with your partner. You're both co-founders, you and your husband. And, uh, I'm curious, what's your take on that approach to starting a company would you recommend for other folks or, or not?

    2. ARAda Chen Rekhi1:07:10

       If you had asked me when I first started the company, it would have been an enthusiastic, hell yes, I totally recommend. Now I have a couple asterisks on top of it. (laughs) And...

    3. LRLenny Rachitsky1:07:22

       Go on.

    4. ARAda Chen Rekhi1:07:23

       I think it really just goes back to what I was talking about earlier, where 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 romance into the mix, it's just this really volatile combination. And so 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. And the asterisks are there because we've actually had a couple friends try it, and it's been such a mixed bag of results.

    5. LRLenny Rachitsky1:07:52

       Hmm.

    6. ARAda Chen Rekhi1:07:52

       So my personal experience is I love it. My partner, Sachin, and I work really well together, and the main benefit that we have is that the act of founding is such an act of obsession that you spend so much of your time thinking about your business and the concepts of your business and whatever problem you happen to be facing, that when I had this thesis of I want to be a founder too, we kind of, you know, played it out and said, "Well, okay, now we're gonna walk around being obsessed about two completely different things. We may never see each other, and so why not try the same thing?" And so our first experiment was actually trying it together, and we were kind of nuts. I actually had a 30, 60, and 90 day plan where we would have check-ins-

    7. LRLenny Rachitsky1:08:33

       Hm.

    8. ARAda Chen Rekhi1:08:33

       ... and some of the explicit questions in the check-in is, is this affecting our relationship? 'Cause I just wanted to make sure we were putting our relationship first, and it worked well for us to the extent that we've done two companies together, and then when we were at LinkedIn, we actually moved across multiple teams in the company and continued to be counterparts in product and marketing together. So it's-

    9. LRLenny Rachitsky1:08:54

       Wow.

    10. ARAda Chen Rekhi1:08:54

        ... it's been phenomenal. The thing that I would say really helps us in terms of making it a successful relationship was kind of things that I think apply to anyone that's thinking about should you work with a person and should you be a co-founder with this person. We had a very, very good set of complementary domains and skill sets, so we had really clear decision-making rights. Sachin does product design and engineering. I focus on marketing, operations, finance, kind of everything else on the business side, and because of that, it's really clear that we take input from each other, but ultimately, who makes the call and, you know, who's driving and owning that project? So that was really helpful for us. And then the big part that I think is sort of the, the murky mire for couples, and maybe even for close friends working together, is how do you engage in constructive conflict? How do you get to the point where you're attacking the problem and not each other? And so if your partner comes to you and says, "That work was not good. That marketing plan or, you know, that product roadmap that you put together, not good," do you take it as the plan is not good and let's talk about what we can actually do to fix it? Or do you take it as, oh gosh, they think I'm not good, they think I'm too lazy, I saw that look that they were giving me, and you know, sort of take it as this personal offense? So 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 you have to think about if you're gonna work with anyone, much less your partner or a close friend, on starting a company and what's really worked for us.

    11. LRLenny Rachitsky1:10:37

        I am, uh, very impressed with how you're able to execute on this. I don't think I could do this with my wife. That would not go well, I think. You should probably write a-

    12. ARAda Chen Rekhi1:10:44

        That's self-awareness. (laughs)

    13. LRLenny Rachitsky1:10:46

        Yeah. No, we're, we're aware. You should write a post on like how to successfully build a company with your partner. That seems like you have a lot of really interesting frameworks and, uh, insights on how it's worked, the fact that you've-

    14. ARAda Chen Rekhi1:10:57

        That's a great idea.

    15. LRLenny Rachitsky1:10:57

        ... worked together for so long. Yeah. Could be its own little book. Um, is there anything else you wanted to share or touch on before we get to our very exciting lightning round?

    16. ARAda Chen Rekhi1:11:06

        I think you

17. 1:11:07 – 1:11:40

    Lightning round

    1. ARAda Chen Rekhi1:11:07

       covered most of it, Lenny.

    2. LRLenny Rachitsky1:11:08

       With that then, we have reached our very exciting lightning round.

    3. ARAda Chen Rekhi1:11:11

       (laughs)

    4. LRLenny Rachitsky1:11:11

       I've got five questions for you. Are you ready?

    5. ARAda Chen Rekhi1:11:15

       I am ready.

    6. LRLenny Rachitsky1:11:17

       What are two or three books that you've recommended most to other people?

    7. ARAda Chen Rekhi1:11:20

       Persuasion by Robert Cialdini. I think it's a great book if you're a marketer, it's a great book if you're a founder or product person, but it really kind of is a breakdown of what are the different strategies to get people to say yes and help persuade them towards things, and I think it really helps in terms of thinking through that and designing a product or business around it. The-

Episode duration: 1:18:27