April 16, 2023

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

Brought to you by Sprig—Product insights that drive product success.

Ada Chen Rekhi is an executive coach and co-founder of Notejoy. She helps founders scale themselves alongside their teams. She has over a decade of experience leading teams through periods of rapid transition, from the chaos of founding early-stage startups to leadership roles in growing SurveyMonkey and LinkedIn. In today’s podcast, we discuss:

• How utilizing a “curiosity loop” can aid you in decision-making

• A values exercise that can help determine if your life choices align with your personal values

• Ada’s “explore and exploit” framework for making the most of your job opportunities

• The advantages of seeking an executive coach and useful tips on finding one

• Tips for women navigating working in Silicon Valley

• Why it’s so important to provide constructive feedback

Where to find Ada Chen Rekhi:

• Website: https://www.adachen.com/

• Twitter: https://twitter.com/adachen

• LinkedIn: https://www.linkedin.com/in/adachen/

Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• Twitter: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

In this episode, we cover:

(00:00) Ada’s background

(03:17) What a curiosity loop is and when to use one

(11:39) Using curiosity loops in your personal life

(14:13) How curiosity loops are like customer advisory councils

(16:30) A values exercise

(25:30) Ada’s “explore and exploit” framework

(31:28) When it’s time to leave your job

(35:37) Logo collecting and why you should optimize for your values instead

(39:30) What triggered Ada to reevaluate her career path

(42:10) Why most people don’t actually need a coach

(44:59) When coaching is valuable

(47:20) How to find the right coach

(51:38) Advice for women in Silicon Valley

(1:00:08) Eating your vegetables—why you need to power through things you find challenging

(1:05:07) Why you should write to crystallize knowledge, rather than for likes

(1:06:54) How to successfully build a company with your spouse

(1:11:07) Lightning round


• SurveyMonkey: https://www.surveymonkey.com/

• Values exercise: https://www.adachen.com/build-your-inner-scorecard-a-10-minute-exercise-for-better-decisions/

• Clay: https://www.clay.com/

The Dip: A Little Book That Teaches You When to Quit (and When to Stick): https://www.amazon.com/Dip-Little-Book-Teaches-Stick/dp/1591841666/

• Research on the coaching industry: https://www.adachen.com/an-in-depth-guide-to-executive-coaching-everything-you-need-to-know-part-1/

• The inner scorecard: https://fs.blog/the-inner-scorecard/

• How to find a coach: https://www.adachen.com/a-practical-guide-how-to-find-an-executive-coach-part-3/

Radical Candor: https://www.amazon.com/Radical-Candor-Revised-Kim-Scott/dp/1250258405/

• Kim Malone Scott: https://kimmalonescott.com/

Influence: The Psychology of Persuasion: https://a.co/d/6JycbJo

Designing Your Life: https://a.co/d/cS2IqG0

Ted Lasso on AppleTV+: https://tv.apple.com/us/show/ted-lasso/

Star Trek: Strange New Worlds on Paramount+: https://www.paramountplus.com/shows/star-trek-strange-new-worlds/

• Notejoy: https://notejoy.com/

• Captio: https://captio.co/

• Note to Self: https://notetoselfapp.com/

• Arc: https://arc.net/

Make Time: How to Focus on What Matters Every Day: https://www.amazon.com/Make-Time-Focus-Matters-Every/dp/0525572422

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Get full access to Lenny's Newsletter at www.lennysnewsletter.com/subscribe


Ada Chen Rekhi (00:00:00):

It's a terrible outcome to wake up one day and be late career and feel trapped because you have a certain lifestyle or a certain expectations of 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 navigate our career paths and find the thing that's most optimal for us. Which is usually a mix of career success, but also meaningfulness and alignment in the work that we're doing with our values.

Lenny (00:00:36):

Welcome to Lenny's Podcast, where I interview world-class product leaders and growth experts to learn from their hard [inaudible 00:00:42] 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, it 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 practically 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.


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 let's 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.


As of today's, Sprig is making that even easier with the 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 ask me to create a template around product sense.


One of the questions they get most is how to develop your product sense. 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. Ada, welcome to the podcast.

Ada Chen Rekhi (00:03:20):

Thanks. I'm excited to be here.

Lenny (00:03:22):

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 event diagram of maybe an ideal guest for the podcast. You've done growth. You've done products. You've started a company. You're also an executive coach to founders. So there's a variety of topics I'm excited to begin too. So thanks again for being here.

Ada Chen Rekhi (00:03:22):

Yeah, I'm excited to be here.

Lenny (00:03:45):

An interesting thing that I'll start with is that when we were chatting about what to focus on in our conversation, where you're 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. 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?

Ada Chen Rekhi (00:04:08):

A curiosity loop is essentially 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, 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. I don't normally do this, but I actually showed you some of the anonymized feedback from people really just talking about what resonated and what didn't. So I came out of it just so much smarter, and curiosity loops are my method of doing so.

Lenny (00:04:42):

Often, people ask friends for advice on just like, "Hey, what should I do here? What can I maybe talk about on this podcast?" Your approach had a lot of structure to it. So maybe two questions just like, what is the actual structure to this concept? And then two, just people... You can often ask friends for advice, but you also don't want to over bug them with questions. How do you think about just not over asking everyone questions all the time, but all decisions you want to make? So I guess the question is, when do you use this versus just not?

Ada Chen Rekhi (00:05:12):

I think that there are heavyweight and lightweight ways to use this. So the heavyweight way was 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 make it your ongoing theme of what you're curious about as you interact with people. So maybe it's this thing where every single day as you talk to people, if you have 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? 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.


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? A lot of it 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 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.


So in this case, a question's good if it's specific, if it solicits rationale, and it's not biased. You don't want to start a question with, here's what I think because people have this tendency to want to please you or to agree with you. 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? 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 the output that you're going to get from it is probably going to be similarly bad. 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 webdev thing. So my plan is to quit my job, do a webdev bootcamp and then go find a job elsewhere. Do you think that's a good idea?"


There's just so much rich data to actually explore with that. First, are you suited to being a developer? Are webdev boot camps effective? What's the state of the economy in the hiring market right now for junior web developers? And 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 the first piece. The next piece is really around how do you curate who you ask? 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 webdev themselves, for my example question. Another one, and this dimension I think is really important, is someone who knows you really well and can provide insight on how well does that work for you. And then after that, you really want to ask the question. And this touches on 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. 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?" Some people went above and beyond and scrolled through and gave me feedback on every single topic. 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 the list that I chose for this curiosity loop, you would be able to sit down on your couch at the end of the night, read this interesting email and tap out a quick reply and 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 close the loop, I think a big piece of it is processing that information and then thanking them for it. 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. 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. Maybe it's not at that level, 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.

Lenny (00:10:21):

So to summarize, I wrote these pieces down. The concept broadly is if you want 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 part two is actually pick the right friends. But one is just, come up with a question that's specific. As in just like, what should I do with my life? But more, should I take the specific role at the specific company? Figure out the people that know you well and maybe have some context on this decision. How many people do you usually email for this sort of thing? What's a number?

Ada Chen Rekhi (00:10:55):

I would try to optimize for getting at least three or four responses. It just depends on the nature of the loop. And then you think about what is your response rate. So if you're emailing really busy people that you don't know very well, maybe you would assume that you only get half of people to respond. If you're emailing people really well and it's really lightweight like, yes or no, and here's why, then you might just send out a handful.

Lenny (00:11:22):

Okay, awesome. So it's five to 10 people, broadly sounds like. Oh yeah, you want to make it really quick and easy. So it's like, here's 10 things, which of these two do you think I should focus on? So it's a quick ask as something you recommend, and then just thank them for it after you finish. Is that broadly the approach?

Ada Chen Rekhi (00:11:39):

Yep, that's the approach. One thing I want to note is that it's actually really useful for personal things as well. So we framed it in this professional context of, I'm trying to change a job. But 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 forbids, something happened to both of us. How should she inherit the state? And my partner was basically saying, "18 years old, she gets everything fully unlocked." I was saying, "Oh, well 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.


One thing was really telling, no one out of everyone we asked said 18. So that really dragged my partner up. And then the other thing that was really interesting was that we learned a little bit about executive function and the research around it. So executive function, which is your ability to make decisions and plans and be thoughtful peaks at the age of 30, and it's all downhill from there. So bad news for people like me that are older.

Lenny (00:12:54):

And then I'm getting [inaudible 00:12:54] or game over.

Ada Chen Rekhi (00:12:55):

Yeah, exactly.

Lenny (00:12:55):

Just like I'm-

Ada Chen Rekhi (00:12:57):

But if you're thinking about 18, you are so far from your peak. So it 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 too much work to dig through papers or research or whatever else to try to come to a good decision on it.

Lenny (00:13:14):

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

Ada Chen Rekhi (00:13:31):

Yeah, definitely. One of the things that I always try to do is I try to explain to people in my ask, here's why I picked you. So for example, I picked you because I really trust you to be a sound source of truthful advice and give me some feedback. So I really value that. Do you mind spending a couple of minutes and just giving me some thoughts on this?

Lenny (00:13:53):

And how often are you pinging people? If you're a friend of Ada, are you getting curiosity looped every week, or how often? What's your rate limit?

Ada Chen Rekhi (00:14:02):

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

Lenny (00:14:12):

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

Ada Chen Rekhi (00:14:24):

Totally. Yep. I think this is really based off of the marketing concept of customer advisory councils. 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 giving us your quick thoughts and telling us why?" And then being able to as a marketer come back to the product conversation and say, here is the literal voice of the customer and four or five different verbatims on what people think about this really 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.

Lenny (00:15:07):

That's really interesting. It's basically user research for your life. User research, you're told don't do what people tell you to do. 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 own own life.

Ada Chen Rekhi (00:15:19):

Right. Right. Yes. That is the big caveat. Don't do what people tell you to do. Take it as an input and look for the hard feedback. Look for things that you strongly disagree with or are surprises to you. Because 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.

Lenny (00:15:43):

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

Ada Chen Rekhi (00:15:50):

So I think there were two topics on the list. The first one, it was just how do you onboard and hire and bring people onto the team? And the feedback I got there was like, "There's 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. I actually had someone write, and you probably read this, Lenny, "No. Stay far away from this. There's no winning on this topic."

Lenny (00:16:23):

Oh, my God. Okay, let's touch on that topic rather than, it's going to be great.

Ada Chen Rekhi (00:16:28):

Yeah. So let's ignore the advice?

Lenny (00:16:29):

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

Ada Chen Rekhi (00:16:51):

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. 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 a list. And the output on the end is basically three to five sentences that cover what are the values stack rank that are important to you right now in your personal and professional life? And what I really like is, it's 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 often we feel really pressured by. 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?

Lenny (00:17:53):

Sweet. 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 keep picking and then helps you whittle them down. I ended up with six. I feel like that's one too many. Actually, I added a bonus one because it's just one that I really like. But should I read through what I came up with?

Ada Chen Rekhi (00:18:18):

Yeah, that sounds great.

Lenny (00:18:19):

So here's what my values, I guess. Choose adventure, stay optimistic, treat others 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.

Ada Chen Rekhi (00:18:44):

I love it. What a great list of values and what stands out to me from that list too, Lenny, is this idea of achievement or status or success. A lot of the things that we talk about publicly, 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.

Lenny (00:19:04):

Yes, I hope so.

Ada Chen Rekhi (00:19:08):

Let me ask you this. Let's try to apply some of the values in real time as an experiment.

Lenny (00:19:14):

Oh, boy.

Ada Chen Rekhi (00:19:15):

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 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.

Lenny (00:19:37):

So an ongoing decision I have is I have all these opportunities of things I can be doing. Additional things I can be doing. The podcast, this actually was a good example of I never wanted to do a podcast because I really wanted to... Life is good. I was writing this newsletters, doing great, making a living, doing one great email a week. And I was like, "Why would I do anything more? This is good." So I've constantly resisted, I resisted the podcast for two to three years, and then eventually succumbed. And it was a great decision in the end. But now, I have other things that I'm trying to not do, but they're always pushing into my mind space like, a book for example. Of 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?


I'm looking at my values a little bit, and one of them is choose adventure, which you would think would be just do stuff, just try stuff out. But I feel like maybe it's just a missing bullet point here of, I just want to do less. I'm trying to take on less and do less and cut out and-

Ada Chen Rekhi (00:20:44):

That's really interesting.

Lenny (00:20:44):

... simplify. Yeah. Because there's just endless things I could be doing, and I want to spend time with my wife. And now, my new child is coming in a couple of months, if all goes well. So that's where my mind goes when you ask that.

Ada Chen Rekhi (00:20:57):

Yeah. Yeah. And then maybe if you were to decompose adventure, what adventure actually means to you 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.

Lenny (00:21:13):

Right. That's so true. The beginning of it is an adventure. And then that's such a good point because yeah, once you start a thing... Something I always say about this content creation life is like, it's easy to start. It's hard to keep it going, and it becomes just 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 the treadmill. Not that I'm complaining, but that's just a reality of this path. So that is such a good point that it becomes not adventurous very quickly. So that's really interesting.

Ada Chen Rekhi (00:21:13):

I love it.

Lenny (00:21:42):

I guess the other thing is just, what's a cutoff? What am I... I do a bunch of angel investing and so I'm thinking about just stopping that for a while just so I get up more time with my new child and just carve out things that maybe aren't as essential.

Ada Chen Rekhi (00:21:55):

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. I think that there are some points in our lives where writing a book, it just seems really obvious. It's good for your career. It's the next level in terms of where you go from the community, the newsletter, the podcast and getting to that next level. But where I think there is value is these lists of values can help ground us from those obvious decisions. So in my life, to share a mini example of this, there have been a lot of cases where the next obvious step for me might be to go an executive at a big company and to go chase the dream and continue on the latter climb of my career.


As I've examined my own personal values, a big piece of it has really been around prioritizing relationships 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. 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. Even though it might be objectively better, depending on what scorecard you actually use, I would actually be less happy with some of those outcomes. So I think values are this really nice useful tool to think about how do you make better decisions again to maximize for your own alignment with life.

Lenny (00:23:23):

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

Ada Chen Rekhi (00:24:00):

Yeah, and it's really self-aware of you too. I think too. Cut it off because you start realizing that you're doing this course, and it's not giving you energy or it's not quite the right thing. It's really hard to say no to things.

Lenny (00:24:12):

It is. It is.

Ada Chen Rekhi (00:24:12):

And I don't think we focus on that enough.

Lenny (00:24:14):

Yeah, I've learned how to do that better. I have all these auto templates of ways to say no in different ways. Actually, ChatGPT, somebody's tweeted this that it has all kinds of good suggestions. If you could ask it, how do I say no to my manager who wants me to prioritize a feature? And has all kinds of clever words to [inaudible 00:24:30].

Ada Chen Rekhi (00:24:30):

Oh. Yeah, that's a great use for it.

Lenny (00:24:32):

The other thing that I realized as we were going through this exercise that I imagine you find also is when you come up with an initial set of values, I was realizing I maybe another value of just keeping things simple, simplifying. And I imagine that's part of the process of narrowing in on what's important to you is you take this first pass and then you try to use it in making a decision and then you realize, oh, there's this other thing that's really important to me and that updates your values.

Ada Chen Rekhi (00:24:57):

Yeah, I think you could definitely use that process to force yourself to make a stack ring and to be really clear, and also change it. Change it. It's yours. So change it over time as it suits you.

Lenny (00:25:08):

All right. It feels like there should be a curiosity loop AI bot with your values that you email, what should I do with this decision? And then it's like, oh, you think simplicity is great? You should not do this.

Ada Chen Rekhi (00:25:20):

The next big idea.

Lenny (00:25:22):

There we go. Somebody build that. Okay, so it's funny we went into reverse interview, and then I have to asking questions again. So let's do this. You talked about your career and how you 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 early career advice. You coach a lot of founders. You had a really in incredible career doing all kinds of interesting things. What have you learned about what works best for optimizing in your early career?

Ada Chen Rekhi (00:25:55):

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 adCenter to SVP of marketing at SurveyMonkey, leading a global team. And when I reflect back on what works across my early career, it really comes down in a nutshell to this career concept of explore and exploit, which actually sounds dark now that I'm saying it out loud, but-

Lenny (00:26:27):

Yeah, sounds great. I love it.

Ada Chen Rekhi (00:26:29):

Explore and exploit, if you're familiar with it from growth background, is really just around what mode you're in. You're either in a mode of explorer 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 with that growth mindset where you have a hypothesis. So coming out of school, my first job was at Microsoft. I was at adCenter. The big thing I learned from the 367 days that I was there was that 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 want to try something smaller, but I also wanted to try marketing. So I moved to this series a startup where I had to sample 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. What I learned from that experience was then I love marketing, games was pretty fun and being in a smaller team was really dynamic. It was this choice on, do I exploit and 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. My big thesis was, let me try being a founder. So then I founded Connected, and Connected was this personal CRM that's a little bit like 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-

Lenny (00:28:20):

Yeah. It's a beautiful product.

Ada Chen Rekhi (00:28:22):

Yeah, it's a beautiful product, much more beautiful than what we built at the time. It was such a great learning experience to discover what it was like to be a founder of a company and an entrepreneur. My personal learning out of all of those things was really just that I was continuously optimizing that I loved marketing. I loved being a founder. I really like small teams. There are pros and cons to this corporate life, where maybe things are really slow paced, but the scale is really important. So that was really what carried me through a lot of my early career. After Connected was acquired by LinkedIn, I 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 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 fair to middling at pricing. I really didn't understand how to build a subscriptions business and how to price it. 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.


So I managed to get into this great role leading gross marketing for LinkedIn, working with their growth team from a hundred 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 saw how all of those pieces and worked together from a financial planning and analysis stage to all of the optimizations that they did. 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. 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 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.

Lenny (00:31:10):

I really like this framework. I've never heard it described this way. Explore and exploit connects a lot with what I always recommend which, early on, is to optimize for a variety of experience so that you can figure out where you actually have a good time and what you're interested in versus getting stuck on the first thing something. I don't know if you'll have 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, or just like, "I really don't like this job, but I feel like it'll lead to something great. And I don't want to give up too quickly." So I guess the question is, what are heuristics that tell you to stick it out and stick with something that you think will lead to something great versus hold the recording and get out?

Ada Chen Rekhi (00:32:01):

That's a great question, and it's a really tough one that is contextual on the person that you are. So one of the things that I like to share is this idea of, it's a little gory, don't be the frog. So if you are familiar with the story of the frog, it's this idea of boiling the frog. So if you take a frog, and you throw in a pot of boiling water, it'll jump out. But if you take a frog and you put in a pot and you increase the temperature degree by degree by degree, the frog doesn't notice and before it knows, it's boiled alive. And how I apply this to your question 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 we sit with them or we think, "Gosh, it'll get better. The next manager will get better. I'm always one conversation or one promotion away from 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 temperature of the water trending. That's what makes the advice really contextual. I really 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 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're 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. 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. I think that happens a lot, where you providing a lot of value and doing a good job at a company, but you might not be learning things that stretch you and grow you to achieve your ultimate goal. When you are aware of that learning, I think that's the point at which you have to say, "How do I change that? How do I 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 go do something else, take a course or sign up for something new. It might actually mean a proactive conversation with your manager 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 projects. So in my case, it was really growth and subscriptions, that experience that I really wanted. Let's say, you hit 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 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 or learning something new on your own time that you can leverage in another way.

Lenny (00:35:17):

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

Ada Chen Rekhi (00:35:23):

Little gory.

Lenny (00:35:24):

No, it's great. So I guess the lesson there is think about are you that frog being boiled right now and think ahead, is this going to be the end of the-

Ada Chen Rekhi (00:35:24):

Right. Keep an eye on your environment and which way is it trending?

Lenny (00:35:35):

Yeah, the temperature on the thermostat in your office. The other thing this makes me think about is, it's 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 going to look so great." And this other logo and this cool title and role. I find that just like, you do that long enough in your life, you end up... You retire, and then you die. Life is that resume. Right? That is your life, you're living, and there's not going to be a point at which you have to realize, okay, I've done all the things to make my resume. Also, I'm like, "What do I actually want to do? Am I enjoying this?" Because it'll never end. You're never going to end trying to make a better resume and a more awesome background for yourself. Do you experience that with yourself or other people you work with of just over optimizing to make an awesome series of roles and logos and then forgetting, do I actually enjoy any of this? What am I doing?

Ada Chen Rekhi (00:36:31):

I have experienced that personally a lot. I think that it may be a generational thing or it just may be my background, but having grown up with the Asian tiger parenting, it's very focused on logos or certain accomplishments or certain achievements like, going to an Ivy League school, working in a company that someone's heard of, being able to have a certain title. At a certain point, I bailed out a bit and I really started to think about who am I trying to please and optimize for? 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. I looked at those values and I said, "Well, if I draw a straight line from where I am right now and just extend it forward and play the rest of the movie as it plays out, given the current plot line, how well does that optimize for those values?"


That's great. 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. So getting very intentional about that and being clear about who your audience is as you navigate your career. I think it's a terrible outcome to wake up one day and be late career and feel trapped because you have a certain lifestyle or a certain expectations of 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 navigate our career paths and find the thing that's most optimal for us, which is usually a mix of career success, but also meaningfulness and alignment in the work that we're doing with our values.

Lenny (00:38:25):

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. 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/plates.


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.

Ada Chen Rekhi (00:39:40):

Really just a career opportunity. And it was this step where I could do something that was, at the time, really high profile and really exciting and felt great, but also involved demanding travel and grueling hours. And wasn't in a space that I was excited about, but it looked 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." What I realized at the time, after I did it, was that my top three values, the things that I cared about this job would categorically just fail at because I would be gone all the time, in pursuit of glory that I didn't really care about. Instead, 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.

Lenny (00:40:36):

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... To do the thing that's impressive and take on the really cool role, and just get an awesome title, and do something really impressive, that's just like yelling at them from the corner. And my friend's just 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 going to be happy if I listen to this guy." And that's been really helpful to my friend just to disassociate that part of the brain.

Ada Chen Rekhi (00:41:10):

Yeah. The ego monster is a great way to put it. I use something that Warren Buffet has talked about, which is inner scorecard versus outer scorecard.

Lenny (00:41:19):

Tell me more.

Ada Chen Rekhi (00:41:20):

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 things that people really care about. And then your inner scorecard is things that actually matter to you, how you spent your day, how good of a person you are. Did you have an adventure today, Lenny? Were you kind? 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 helps you trade off against some of that external pressure and the ego monster.

Lenny (00:42:11):

This might be a good segue to chat about coaching. I imagine a lot of people listening to this like, "Yes, I want to do that. I want to measure myself according to my values and check in on this. And am I doing the wrong path?" It's hard to do just on your own, I find. And I think that's one of the benefits of an executive coach. 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.

Ada Chen Rekhi (00:42:42):

I'll have a hot take on this, 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.

Lenny (00:42:52):


Ada Chen Rekhi (00:42:54):

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? Roll it forward six months, what have you gotten done in your coaching experience. 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 have spent your valuable time and often pricey fees to achieve the same goal, but maybe in a better way." 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 this one person's opinion. It's actually way better to run a curiosity loop, for example, and get the benefit a couple different minds on a specific topic and 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 want to learn about growth, maybe you should take are Reforge course and get access to all of the resources and the insights of the EIRs and the growth advisors that Reforge and get an overview and survey of the landscape instead of one person's experience and the handful of companies that they might have worked with. Likewise, if you're just feeling like you're a little emotionally overcome, I think coaches are this great resource around that, but it's actually better to 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 thing that lasts you for years and years.


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?" 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.

Lenny (00:44:59):

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

Ada Chen Rekhi (00:45:06):

I wouldn't be a coach if I didn't think that it wasn't important and valuable. I think that in certain contexts it can be super helpful. So when you have situations where you're in a state of hyper growth, and you need very accelerated learning, and you need someone 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 in this unique state where everything is chaos. They have no structure. They don't know what their jobs are. 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. There's really intense highs and lows. 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.


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. So there are a lot of things that we want to be coached on where either it takes a lot of time for us to work through and progress because it's a long-term project, for example, or it's something very sensitive. 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.

Lenny (00:46:30):

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 athlete or, I don't know, athlete. No one does not have a coach, 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. It just makes you realize that other people in their profession that have a coach helping them out are just going to 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 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 was just like, wow, this just intellectually make sense. So it was actually really important and transformative for me.

Ada Chen Rekhi (00:47:21):

If you go to my site, I actually have this guide that I've written over time on both my take on how do you find a coach, and the TLDR 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. It's surprising because I did this piece of research, which I also wrote about, and we could link to, but I talked to over 80 people about their experiences with a coach. I talked including coaches, including founders, including executives and there's this shocking data point in there where half of people that founder their coach literally went with the first coach that they talked to. It's that your buddy said, "I work with this great coach." And then you go and you hire 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 this reflection of how do you learn best? 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 frameworks? Coaches come in all of those different flavors. So I think it's really worth it to explore before you get into such a deep relationship with someone, just so that both people can feel really sure about it.

Lenny (00:48:51):

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

Ada Chen Rekhi (00:49:00):

I thought that credentials and 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, how safe you felt with them, how deeply you would explore with them, and how well they got you, and 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 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 talk to a couple different people.


And then the other thing which comes back to the sports coaching analogy is that there are different coaches that are really good at different things. So just like how, if you're a star tennis player, you might actually have multiple coaches working with you, maybe 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 work on your speaking or help you with getting into your groove on writing or help you achieve a specific goal. You shouldn't think about it as this long-term commitment to stay with one person, but instead more choosing off of a menu and thinking about what goal are you trying to achieve right now?

Lenny (00:50:39):

Does anyone ever get multiple executive coaches that... I like how we went from, you don't need a coach to maybe need a month [inaudible 00:50:46] hamstrings.

Ada Chen Rekhi (00:50:48):

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. 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.

Lenny (00:51:04):

Got it. Right. Niche skills.

Ada Chen Rekhi (00:51:05):

Right. For niche things because they're about to enter a process or someone who's trying to get into a writing coach-

Lenny (00:51:11):

Got it. Yeah.

Ada Chen Rekhi (00:51:13):

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

Lenny (00:51:17):

Okay. That makes sense. I love it. I'm going to get four coaches. One for everything I do

Ada Chen Rekhi (00:51:23):

A podcast coach.

Lenny (00:51:23):

Podcast coach.

Ada Chen Rekhi (00:51:25):

A newsletter coach.

Lenny (00:51:26):

A writing coach, and a-

Ada Chen Rekhi (00:51:30):

Yes. And then a parent coach. Don't forget that.

Lenny (00:51:30):

Parent coach. A job board coach, and then just a life coach. Okay. I'm on it. Okay. So let's touch on the thing that your friends said we shouldn't touch on, which is being a woman in leadership in Silicon Valley. I guess I'll just frame it simply. Imagine there's many young women listening to this podcast, and many may dream of a career like yours, all the things you've shared. What advice do you have for young women just starting out in their career hoping to find a similar path?

Ada Chen Rekhi (00:52:03):

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 want to have respect for the inherent challenges of being a non stereotypically great fit for leadership roles or certain career success roles in Silicon Valley and acknowledge that. And also try to push for some of the agency of the things that you can do. So I'm going to start with just this quick story about someone that I worked with who's given me permission to share this, in a coaching context and then back out. So I was working with a 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 going to make a huge dent in the universe.


We've been working together on Zoom for a couple of months, and I'd built this great respect for her competence as an operator, and 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. I feel almost nervous talking about this here. The disparity between 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 dressed as if she was hanging out on the weekend. So old T-shirt, hair back and in a claw, bra straps were showing. She was just incredibly casual in terms of her physical appearance. It took me almost like a little bit of a step back to reevaluate and think, "Oh, this is the same person, but she actually just presents so differently.


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. I shared a lot of my impressions with her and I told her, "I respect you so much as an operator. I want to tell you that in the physical meeting that we had together, there was this disparity on how I would've potentially perceived you when I first met you in person versus what I've come to know about you from the months that we spent together."


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. No one's actually said it to me before, and I'm about to go into fundraising. 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 a seasoned operator that I am." 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.


So this is, 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 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 what are the rules on how to get intros or give intros. What's the right way to follow up? What are the impressions that people have about you? 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 because there's no winning, which is similar to the feedback that I got.


SO where I lean in is to say, we're not powerless and there's something that all of us can do if we're in a position where we feel like not even about being female, it's about being perceived as too young or too old, too tall, too short, not the right race. Whatever reason that you feel people may be disqualifying you or not seeing you. We're not powerless, even though this game is rigged. 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. In this case, for the founder in this example, she really turned to her friends and did a mini makeover and 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 a ton of people noticing that something was really different about her in a positive way simply because 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 adapt ourselves to play that game if you want to play at that level.

Lenny (00:57:33):

How nervous were you giving her that feedback?

Ada Chen Rekhi (00:57:37):

I was so nervous. I actually almost didn't do it, and then took a deep breath and then decided, what the heck? I think she's great. I think she would really benefit from doing it and I gave it. 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?

Lenny (00:58:03):

I think there was a company culture where they talk about how you're being selfish, not giving someone hard feedback because you don't want to be stressed or risk causing damage to your own reputation. But you're not helping them. So it's a really interesting insight of just like, don't be selfish. Do something that's hard when you think it's going to help someone else.

Ada Chen Rekhi (00:58:26):

Right. But I think on the topic of being female or on the topic of physical appearance or maybe even some of the topics around being an immigrant, if you're in a position where you can give that feedback, I think the struggle is often will it be well received? And that's where the feedback comes from 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. But there's just so many downsides to giving advice or giving someone input like that the default course is just to avoid. But then that person never learns the rules of the game.

Lenny (00:59:05):

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

Ada Chen Rekhi (00:59:14):

Yeah, Kim Malone Scott, I think.

Lenny (00:59:16):

Yeah. And Sheryl Sandberg had a similar story where she... I think Sheryl Sandberg gave her a really hard feedback and she didn't take it that well, actually. I think you did a better job, or your friend actually took the feedback and did something with it. I think the whole book was just like, "Hey, I actually do this where people actually listen." I think the framework is, you got to communicate that you care deeply about that person, but you want to challenge them directly also at the same time.

Ada Chen Rekhi (00:59:40):

Yeah, 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 me sound stupid." And she didn't take that well, but at the same time, later on in retrospect, 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.

Lenny (01:00:09):

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

Ada Chen Rekhi (01:00:13):

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. So I have all these branded terms for things, but-

Lenny (01:00:13):

That's great.

Ada Chen Rekhi (01:00:30):

... 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. So the researchers say, "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." So when I think about career strategy and when I think about improving yourself and I think about 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 genuine dislike where you've done it and you really don't like it. So 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.


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 going to be good. So my mini example of that was early on in my career, I was really awkward and not very good at networking. 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 of months, go to an external event, and I would count out 10 business cards. And the rule was, I had to hand out all 10 of those business cards by introducing myself to people that were new, and touch the back wall of the venue of that event and then I could leave.


I did that a couple of weeks in a row, and it was horrible. It was really awful, but it got a lot better. 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 understanding how this intro and networking thing worked in terms of meeting people and moving through a crowd. Some of those relationships now from that first job and those first couple months are pretty much foundational to the network and the people that I know today. So it really paid off for me because I really focused on eating my vegetables and powering through that initial discomfort.


So to 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 be very deliberate and intentional about practicing it to get to the point where you have some faculty at it because it's just really important in some cases to be good at certain skills.

Lenny (01:03:24):

I really like that. I also really like the physicality of that rule of touching the back wall. It just forces you to go through a room, and I just escape really quickly. Is there any other examples of things you've seen or recommend for doing things like, eating vegetables? That was a really good example of just forcing yourself to go to a networking event, touch the back wall. 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?

Ada Chen Rekhi (01:03:53):

Yeah. So there are actually a few of them. A lot of them around content creation because it's just so hard. So one of them that comes to mind is, I know a lot of people have talked about doing a LinkedIn 30. 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. I also think it's helpful to start thinking about things like getting into DMs. Right. It takes a lot of work to 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.

Lenny (01:04:34):


Ada Chen Rekhi (01:04:35):

But 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, and see what I get out of it?" Because that's really how you learn and how you grow.

Lenny (01:05:07):

The LinkedIn 30 idea, I like a lot. 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. Going to link post on LinkedIn. So cringey. I don't want to be this self-promotiony LinkedIn person." But what I find is if you reframe it to, "I just want to crystallize a thought that I have and just share something that is useful to me or an insight I've had, and not think of it from, I'm trying to get as many likes. I'm trying to go viral with this post, or I'm trying to just build some following." Just 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 it in a really simple way. That helps motivate. That, at least, works for me. It also ends up being useful for me. It's not like I'm trying to grow some following as a result of that.

Ada Chen Rekhi (01:05:59):

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. Imagine you're just talking to a friend or you're trying to talk to someone that's a trusted colleague, and just write for them. I think that's really helpful, and it helps us with the problem of getting in over your skis, really over fixating on the outcome of, 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.

Lenny (01:06:31):

Yeah, I love that. You could just even say, something I found useful day one and just approach it that way. That's the stuff that end up 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 the thing I've found useful. Enjoy it, if you can.

Ada Chen Rekhi (01:06:49):

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

Lenny (01:06:53):

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

Ada Chen Rekhi (01:07:10):

If you had asked me when I first started the company, it would've been an enthusiastic hell yes. I totally recommend. Now, I have a couple asterisks on top of it, and-

Lenny (01:07:10):

Go on.

Ada Chen Rekhi (01:07:23):

... 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. So what I've found is that it seems like it either goes really well or it goes really badly, and there's no in between. And asterisks are there because we've actually had a couple of friends try it, and it's been such a mixed bag of results. 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 active founding is such an active 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 played it out and said, "Well, okay, now we're going to walk around being obsessed about two completely different things. We may never see each other, and so why not try the same thing?" So our first experiment was actually trying it together, and we were nuts. I actually had a 30, 60 and 90 day plan where we would have check-ins. And some of the explicit questions in the check-in, is this affecting our relationship? Because I just wanted to make sure we were putting our relationship first. 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 and product and marketing together. So it's been phenomenal. The thing that I would say really helps us in terms of making it a successful relationship was 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 complimentary domains and skillsets, so we had really clear decision making rights. Sachin does product design and engineering. I focus on marketing, operations, finance, 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 who's driving and owning that project. So that was really helpful for us. And then the big part that I think is the murky Meyer 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? So if your partner comes to you and says that work was not good, that marketing plan or 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 take it as this personal offense. So the ability to be really truth seeking and 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 going to work with anyone. Much less your partner or a close friend on starting a company and what's really worked for us,

Lenny (01:10:37):

I am 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-

Ada Chen Rekhi (01:10:37):

That's self awareness.

Lenny (01:10:48):

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

Ada Chen Rekhi (01:10:57):

That's a good idea.

Lenny (01:10:58):

... [inaudible 01:10:58] for so long. Yeah, it could be its own little book. Is there anything else you wanted to share or touch on before we get to our very exciting lightning round?

Ada Chen Rekhi (01:11:06):

I think you covered most of it, Lenny.

Lenny (01:11:08):

With that then, we have reached our very exciting lightning round. I've got five questions for you. Are you ready?

Ada Chen Rekhi (01:11:15):

I am ready.

Lenny (01:11:17):

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

Ada Chen Rekhi (01:11:20):

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 is a breakdown of what are the different strategies to get people to say yes and help persuade them toward things. I think it really helps in terms of thinking through that and designing a product or a business around it.

Lenny (01:11:40):

I've got that in my bookshelf behind me.

Ada Chen Rekhi (01:11:43):

Oh, yeah. It's a great book. Yeah. The next book that I also recommend is a book called Designing Your Life, and it's out of the Stanford Design School. And it's by, let me look, Bill Burnett and Dave Evans. They're two Stanford D School professors, and what they're doing is they're applying design principles to life design. So how do you actually map that next level career that's both meaningful and fulfilling and also achieves maybe some of the success factors that you really care about, and brainstorm and be really creative about it. So when people are stuck or thinking about career strategy, that's actually one of the books that I always point out for them.

Lenny (01:12:23):

What's a favorite recent movie or TV show?

Ada Chen Rekhi (01:12:25):

So Ted Lasso is back, so I'm watching that, the newest season. I am also a Star Trek nerd, so I'm watching Star Trek: Strange New Worlds.

Lenny (01:12:25):

I didn't know there's a new Star Trek. That's good to know.

Ada Chen Rekhi (01:12:41):

Oh, It's so good. I think the thing I love about Star Trek is just that, unlike some of the classic storylines that you see right now on TV coming out now, sometimes the episodes are just happy. They explore a planet. Nothing bad happens. They see something really wondrous. They all leave happy, and they pat themselves on the back for having explored something. It's something that's missing in the genre of TV that they still have, this happiness factor where sometimes life is good and sometimes life is bad.

Lenny (01:13:09):

I like the sound of that. Although, I've learned about storytelling for a story to be interesting. There needs to be some conflict or problem. So I imagine there's something going wrong somewhere in the middle.

Ada Chen Rekhi (01:13:20):

But it's not wrong. It's something interesting happens.

Lenny (01:13:23):


Ada Chen Rekhi (01:13:23):

And then it's resolved, and it's happy. Right. But it just doesn't always need to be, something tries to kill you.

Lenny (01:13:28):

I got to watch that. That sounds great. I was a huge Star Trek fan back in the day. Didn't know they were still making new ones. What's a favorite interview question you like to ask when you're interviewing people?

Ada Chen Rekhi (01:13:37):

What's a common misconception people have about you? I usually like to throw that in toward the end of the interview, and the reason why I think it's really useful is it's a way for me to reset my bias. I may have had a certain impression about them, and this is their opportunity to speak up and say, "Hey, a lot of people think this about me, but it's not true." It's also this reflection of their self-awareness.

Lenny (01:14:01):

Great. What are some products that you've recently discovered or use regularly, SaaS products or even consumer fun random products that you want to share?

Ada Chen Rekhi (01:14:14):

Yeah. I can't go through this podcast without giving a shout-out to Notejoy. So Notejoy is a fast and focused notes app for individuals and teams. So that's the company that I work on. So I use it for everything from Noora product roadmaps to my coaching notes, to even prepping for something like this podcast. I use Notejoy all the time. Another one that I really use a lot is Captio. It's been around for a while, but it's a little iOS app. I don't know if it's on Android, but basically it's a blank notepad. You can dump your brain into it, and there's one button, and it emails it to you. So when I find that I'm really distracted, or I just want to remember something, I use Captio all the time just to quickly capture my ideas. And then I process it later in my inbox.


And then something that I just downloaded this week is Arc, the new browser. I'm actually really excited about its vision. I'm not sure if I'm going to work it into my workflow yet or how it fits in, but it's really beautiful and it's really cool to see someone iterating on the cluster that is browser tabs.

Lenny (01:15:11):

Yep. Love Arc. Went deep on Arc in the previous episode and I used Captio, however you call it. And I found another app, actually, the similar thing that I found even more simple. It's called Note to Self, just sits on my doc. Anytime I want to email myself a thought, I open it up and this type of thing. Somehow, it ends up being even easier. So that's another one to check out, Note to Self. Final question. You're really big on productivity. What's one tip that you found that has been really helpful for you in your day-to-day life, being more productive?

Ada Chen Rekhi (01:15:43):

Figure out, maybe the night before, the one thing that you want to get done in your day, and then at the earliest opportunity, just try to give yourself five minutes on it. Just five minutes. And the reason why I say five minutes is that there is this challenge that I experience and maybe other people experience as well, which is really just 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 need to get done simply because I'm avoiding that one thing. And then before you know it's the end of the day and I'm like, "I still have to go do that thing." By really focusing on what's the number one thing and then just getting started on it a little bit. It just makes it really lightweight. And usually, what I find is that five minutes turns into a solid hour just knocking that thing out early in my day, and I feel really accomplished. But it's a mental hurdle that I really struggle with.

Lenny (01:16:37):

I really like the approach of the five minutes because that's such a trick to get you to like, "All right, I'll just do five minutes. I got to get this done."

Ada Chen Rekhi (01:16:44):

Right. It's quick.

Lenny (01:16:44):

I need to bring it. Yeah. There's a book that many people on this podcast have recommended called Make Time, and there's a framework within that called The Highlight, where you pick the highlight of your day, and that's the thing you got to do first and make... That's like, if you do nothing else, do your highlight and-

Ada Chen Rekhi (01:16:59):

Yeah, really similar then.

Lenny (01:17:01):

Yeah, and they don't do the five-minute thing, so I think that's a clever element of it. Ada, this was amazing. This chat was full of feelings, and frogs, and vegetables, and frameworks and insights. Thank you again so much for being here. Two final questions. Where can folks find you online if they want to learn more, reach out and how can listeners be useful to you?

Ada Chen Rekhi (01:17:21):

You can find me online. On Twitter and LinkedIn, I'm Ada Chen, A-D-A-C-H-E-N. I have a website, adachen.com, and you can always just shoot me an email, adachen@gmail.com. In terms of how listeners can be useful to me, any feedback and riffs on some of the ideas and topics that we've shared. I'm always eager to learn from other people. So feel free to drop a note and say hello. And if you're a founder and you're interested in learning more about coaching, I'm always happy to talk.

Lenny (01:17:51):

Awesome. And then Notejoy, how do they check that out?

Ada Chen Rekhi (01:17:54):


Lenny (01:17:56):

So easy. Great domain. Ada, thank you again.

Ada Chen Rekhi (01:18:00):

Thank you.

Lenny (01:18:01):

Bye everyone. Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.