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

24:44And I imagine that's part of the process of like narrowing in on what's important to you is you kind of 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 that updates your rallies. Yeah, I think you could definitely use that process to force yourself to make a stack ring and to be really clear. And, you know, also change it. Change it. It's yours, right? So change it over time as it suits you. All right. I feel like there should be a curiosity loop, AI bot with your values that you email.

25:14What should I do with this decision? And then it's like, oh, you think simplicity is great. You should not do this. The next big idea. Yeah. There we go. Somebody build that. Okay. So it's kind of funny. We went since like reverse interview and then I have to just like asking questions again. So let's do this. 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 of questions there. One is just like early career advice. You coach a lot of founders. You had a really incredible career doing all kinds of interesting things.

25:48what if you learned about what works best for optimizing your early career? 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 works across my early career, it really kind of comes down in a nutshell to this career concept of explore and exploit Which actually sound kind of dark now that I'm singing out loud, but Explore and exploit if you're familiar with it from you know growth background is really just around what What mode you're in?

26:36You'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.

27:06I was at AdCenter. The big thing I learned from the 367 days that I was there was the head 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. And so I moved to this series, they start up 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.

27:42And, 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 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?

28:20Yeah, and... And the product. Yeah, it's a beautiful product. much more beautiful than what we built at the time. And Tita 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 really liked small teams. They're pros and cons to sort of this corporate life where maybe things are really slow pace, but the scale is really important. And so that was really what carried me through a lot of my early career.

28:54And after connected was acquired by LinkedIn, I kind of moved into this white mode. So is that LinkedIn for a period of time? Well, 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.

29:31I didn't understand growth. I was, you know, fair to middleing at pricing. I really didn't understand how to build a subscription's 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 gross 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 worked together from a financial planning and analysis stage to all of the optimizations that they did.

30:23And 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 had subs experience and I was a product marketer That was actually the winning combination that caused SurveyMonkey to send me a LinkedIn in mill 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 We have plenty of that.

31:08We're happy to teach that to you I really like this framework. I've never heard of this. I have explored an 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 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 Like with something that maybe doesn't feel good, but may lead to something, like someone maybe in a job right now or just like, 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.

31:48And I don't want to 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 recording and get out? That's a great question. And it's a really tough one that is kind of contextual on the person that you are. So one of the things that I like to share is sort of this idea of 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 if you take a frog and you throw an apod a boiling water, it'll jump out.

32:25But if you take a frog and you put it in a pot 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 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 kind of 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 kind of getting to that next step.

33:01But 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. 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.

33:41But 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? You don't agree with the direction of the company that you're in. and 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 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 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?

34:17How 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 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 project So in my case, it was really growth and subscriptions, right? That experience that I really wanted or to even let's say you hit a black Blink wall there even take it as a gift of time Which is great.

35:00I'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 or Learning something new on your own time that you can leverage in another way I like that. Make the most of the time, even if it's not like the best opportunity for you. Also, love the frog -boiling metaphor. Little gory. 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 going to keep an eye on your environment and which way is the trending?

35:34Yeah, temperature and thermostat in your office. The other thing that 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 is going to look so great. You 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 like you're, you're tired and you die. Like life is that resume, right? Like that is your life, you're living and there's not going to be a point at which like, like, you have to realize, okay, I've done all the things to make my resume awesome.

36:09Like, what do I actually want to do? Am I like 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 have just like over optimizing to make an awesome series of roles and logos and then forgetting? Like, do I actually enjoy this? What am I doing? I have experienced that personally a lot. I think that it may be sort of a generational thing or it just may be my background, but having grown up with sort of 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.

36:52And 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 plot line, how well does that optimize for those values? Like 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.

37:44And 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 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 and the work that we're doing with our values.

38:25I 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 template library, which you can find at Sprig .com slash 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.

39:01One 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 Jeweled Walter, who are the whole guest post on how to develop your product sense, which inform this template that you'll find. Just go to sprig .com slash templates to find this playbook and 85 more that is sprig .com slash templates. SPRIG .com slash templates. What triggered your re -evaluation of that path? Was there just like a oh man?

39:36I need to really rethink where I'm going and then I have a follow -up question. Really just 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 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 value's exercise to say like, Ada, go through and fill out this value's exercise and apply it to this job. And 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.

40:21In 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. 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 are 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 friends just kind of learn to just like, okay, that's the ego monster pulling at me.

41:01I don't have to listen to that. It doesn't mean I'm going to be happy if I listen to this. to this guy and that's been really helpful to my friend to kind of dissociate that part of the brain. Yeah, the the ego monster is a great way to put it. I use Something that Warren Buffett has talked about which is inner scorecard versus outer scorecard 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.

41:40You know, 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 kind of helps you sort of trade off against some of that external pressure and the ego monster. This might be a good segue to chat about coaching. I imagine a lot of people listening to their select, yes, I want to do that.

42:17I 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? 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.

42:54And 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? 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 have spent your valuable time and you know, often pricey fees to achieve the same goal, but maybe in a better way.

43:32And 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 hit their wheelhouse of things that they know about, then to go ask one person, what do you think I should do in the 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 a reforch 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.

44:20Likewise, if you're just feeling like you're 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 kind of thing that lasts you for years and years. 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 -cell, 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.

44:59And then when do you find that it's actually actually important and valuable and something someone should try to get? I wouldn't be a coach if I didn't think that it wasn't important in volleyball. 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 kind of 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 kind of in this unique state where everything is chaos. They have no structure.

45:35They 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 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 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 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 is really rational to help guide you through them with potentially some frameworks and extra advice.

46:29So I had a couple of coaches in my career and would made me feel like I should pursue that is when you think about a sports athlete or an athlete, like no one 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 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 really, I should probably get a coach helping out with stuff.

47:09Even though there was anything super specific, I'm like, I need to fix this problem is just like, wow, it was just intellectually makes sense. And so it was actually really important and transformative for me. 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 you know, 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. And 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.

47:49I talk including coaches, including founders, including executives. And there's this sort of shocking data point in there where half of people that found their coach literally went with the first coach that they talked to. It's that your buddy said, I work with a 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, you know, kind of this reflection of how do you learn best, right?

48:29When 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. What's one thing that people may not think about or just like something that you find really important that maybe is this, is that expected when you're looking for a coach?

49:00I 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 interview 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 had explored with them, and how well they got you and sort of remembered the pieces of the conversation and help you put it together.

49:36Way 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 now push 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 is working with you, maybe like an offensive coach or a defensive coach or working on a particular swing.

50:14It 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. And you shouldn't think about it as sort of 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. Does anyone ever get multiple executive coaches? I like how we went from you don't need to coach them. Maybe you need a month to prepare your experience for them.

50:48I 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 to get into fundraising. Got it. Right. Right. Very niche things because they're about to enter a process or someone who's trying to get into a writing coach. Right. In addition to some of their executive and leadership work that they might be doing. Okay. That makes sense. I love it. I'm going to get four coaches. One for every, everything I do. A podcast coach.

51:25A newsletter coach. is like a writing coach. And then a parent coach, don't forget that. Parent coach, a job board, a job board coach. And then just a life coach. Okay, I want it. Okay, so let's touch on the thing that your friend said we shouldn't touch on, which is being a woman in leadership in Silicon Valley. And 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 kind of find a somewhere path?

52:03This 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 sort of 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 show this in a coaching context and sort of back out.

52:41So I was working with a seed stage founder and she's so smart. She is 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. And we've 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.

53:31So, you know, old t -shirt, hair back in a claw, bra straps were showing and, you know, she She was just incredibly casual in terms of 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 this 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 meeting that we had together, you know, there was kind of like this disparity on how I would have 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.

54:26And 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 tire 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.

55:10And 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?

55:49What'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. Because 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 not even about being female.

56:30It'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. 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.

57:12But 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 want to play at that level. I'm nervous for you giving her that sort of feedback. I was so nervous. I actually almost didn't do it and then took a deep breath and then decided, you know, what the heck, I think she's great.

57:46I 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? I think it was a company culture where they talk about how you're being selfish, not giving having someone heart feedback because you don't want to 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.

58:23Like do something that's hard when you think it's going to help someone else. 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? If you're in a position where you can give that feedback, I think the struggle is going 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 that the default course is just to avoid.

59:01But then that person never learns the roles of the game. Yeah, absolutely. Make me think also a little bit about radical candor. Like basically, I don't know if you read that book, but yeah, Kim Malone Scott, I think. Yeah. And Cheryl Sanberg had a similar story where she, I think Cheryl Sanberg gave her a really hard feedback and she didn't take it that well, actually. I think you did a better job. Your friend actually took the feedback and did something with it. I think the whole book was just like, how do you actually do this where people actually And I think the framework is you got to communicate the care deeply about the person, but you want to challenge them directly also at the same time.

59:40Yeah, it's it's a great story. I think Cheryl Sandberg took her side after one of her meetings and basically told her that if you say it makes you sound stupid. And she didn't take that well, but at the same time, later on in retrospect, you know, she reflected that it was so brave and so helpful of someone like Cheryl to go give that feedback because there's a real cost to it. There's real risk to it. Any other thoughts or advice on these lines that you want to leave people with? The biggest piece of advice that I have that comes to mind is really around trying to be be really thoughtful on something I call eating your vegetables.

1:00:26So, I have all these brand of terms for things. But eating your vegetables is really this idea around how little kids don't really develop an appreciation for vegetables until their 10 or 12 exposures in. And so the researchers say, you know, it's both 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 genuine dislike where you've done it and you really don't like it.

1:01:13And 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. And 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. And so, my many 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.

1:01:49Totally 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 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 touched the back wall of the venue of that event and then I could leave. 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.

1:02:23One 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 in those first couple months are 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.

1:02:59And 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 have some faculty at it, because it's just really important in some cases to be good at certain skills. I really like that. I also really like the physicality of that a rule of touching the back wall, it kind of just forces you to go through a room and I just like escape really quickly.

1:03:34Is there any other examples of things you've seen or recommend for doing things like getting vegetables? Like that was a really good example, just forcing yourself to go to networking event and 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? 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. 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.

1:04:13And 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? 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. 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 extraversion in that case to start meeting up with people and having conversations with them.

1:04:47So forcing yourself in some way to really think about well instead of having one outreach and then feeling 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. The LinkedIn 30 idea I like a lot and something that I'll share as a tip is when you hear that embed a lot of people are just like oh my I got a link post on LinkedIn so cringey. I don't want to be this like self -promotion -y LinkedIn person. But what I find is if you reframe it to, I just want to crystallize a thought that I have and just like share something that is useful to me and we're 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.

1:05:40Just 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 it 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. I find that really helpful as well. One piece of advice that's similar to that that I've heard is right for an audience of one. Like imagine you're just talking to a friend or or you're trying to talk to someone that's a trusted colleague and just write for them.

1:06:11I think that's really helpful and it kind of helps us with the problem of getting in over your skis, right? Really overfixating 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. Yeah, I love that. But you could just even say something I found useful day one and just approach it that way. And that's the stuff that ends 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 been useful and joy if you can.

1:06:49Yeah, yeah. People can really tell when you're being genuine and authentic online. Absolutely. More and more. Maybe a last question. You started a company with your partner. your both co -founders, you and your husband. And I'm curious, what's your take on that approach to starting a company? Would you recommend for other folks or not? If you would ask 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. I think. Go on. 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.

1:07:38And 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 asterisk is 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, Satchin 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 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.

1:08:28And we were kind of 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, is this affecting our relationship? Because 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 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?

1:09:08We had a very, very good set of complimentary 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 murky mire for couples. And maybe even for close friends working together is how do you engage in constructive conflict?

1:09:46How 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 fence So the ability to be really true 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.

1:10:27I 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 work for us. 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 wear it. That self -awareness. Yeah. No, 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 insights on how it's worked.

1:10:56That's a great idea. It's so long. Yeah. It could be it's a little book. Is there anything else you wanted to share or touch on before we get to You are very exciting Lightning Round. I think you covered most of it, Lightning. With that, then, we have reached our very exciting Lightning Round. I've got five questions for you. Are you ready? I am ready. What are two or three books that you've recommended most to other people? Persuasion by Robert Chaldeanie. I think it's a great book. If you're a marketer, it's a great book. If you're a founder or a product person, but it really kind of is a breakdown of what the different strategies to get people to say yes and help persuade them toward things.

1:11:35And I think it really helps in terms of thinking through that and designing a product or business around it. I've got that in my bookshelf behind me. Yeah, it's a great book. 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, we look, Bill Burnett and Dave Evans. And there are two Stanford D -School professors, and what they're doing is they're applying design principles to life design. And so how do you actually map that next level career that's both meaningful and fulfilling and also, you know, achieves maybe some of the success factors that you really care about?

1:12:15And brainstorm and be really creative about it. And so when people are stuck or thinking about career strategy, that's actually one of the books that I always point out for them. What's a favorite recent movie or TV show? So Ted Lasso is back. So I'm watching that the new season and I am also a Star Trek nerd. So I'm watching Star Trek, Strange New Worlds. And in the other's a new Star Trek. That's good to know. It's so good. I mean, I think that's being I love about Star Trek is just that unlike some of the classic storylines that you see right now and TV coming out now, sometimes the episodes are just happy.

1:12:52Like they explore a planet, And nothing bad happens. They see something really wondrous. They all leave happy. And you know, they pat themselves on the back for having explored something. And it's something that's sort of missing in the genre of TV that they still have. This sort of happiness factor where sometimes life is good and sometimes life is bad. I like the sound of that. Although I find, like I've learned about storytelling for a story to be interesting. There needs to be some kind of conflict or problem. And so I imagine there's something going wrong somewhere in the middle. But it's not wrong.

1:13:21It's something interesting happens. And then it's resolved and it's happy, right? But it just doesn't always need to be something tries to kill you. I got to watch that. That sounds great. I was a huge start track 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? What's a common misconception people have about you? And I usually like to throw that in toward the end of the interview. And the reason why I think it's really useful is it's a way for me to kind of reset my bias. I may have had a certain impression about them, and this is sort of their opportunity to speak up and say, hey, a lot of people think this about me, but it's not true.

1:13:58And it's also kind of this reflection of their self -awareness. Great. What are some products that you've recently discovered or use regularly SaaS products or even consumer -fund random products that you want to share? Yeah, I can't go through this podcast without giving a shout out to Notejoy. So Notejoy is a fast and focused NoteSapp for individuals and teams. And so that's the company that I work on. So I use it for everything from Nora 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 CappDio.

1:14:35It'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. And 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. And 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.

1:15:10Yeah, love arc. When deep on arc in a previous episode and a cappedio, I used cappedio, cappedio, 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 dock. Anytime I want to email myself a thought, I open it up and there's 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. 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.

1:15:54And the reason why I say five minutes is that there is sort of this challenge that I experience and maybe other people experience as well, which is really just like 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, 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.

1:16:26And 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. I really like the approach of the five minutes because that's such a trick to get you to like, and I don't just do five minutes, I gotta get this done. Right, great. Yeah, there's a book that many people on this podcast have recommended called Make Time, and there's a framework within that they call the highlight where you pick the highlight of your day, and that's the thing you gotta do first, and make that's like if you do nothing else to your highlight.

1:16:58and yeah, really similar then. Yeah, and they don't do the five minute things. 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 working folks find you online. If they want to learn more reach out and how can listeners be useful to you? You can find me online on Twitter and LinkedIn. I'm Ada Chen, ADACHEN. I have a website, AdaCen .com. and you can always just shoot me an email, aided .chat at gmail .com. In terms of how listeners can be useful to me, any feedback and sort of, you know, riffs on some of the ideas and, you know, topics that we've shared, I'm always eager to learn from other people, so, you know, don't feel free to drop a note and say hello.

1:17:46And if you're a founder and you're interested in learning more about coaching, I'm always happy to talk. Awesome, and then, no joy, how do they check that out? No joy .com. So easy. Great domain. Ada, thank you again. Thank you. 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 a leaving review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at Lenny's Podcast .com. See you in the next episode!