Anneka Gupta: How to be strategic and lead in founder mode

1. 0:00 – 1:43

   Introduction to Anneka Gupta

   1. AGAnneka Gupta0:00

      When people say, "I want someone that's strategic," what they're really saying is, "I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product." So that's number one. And the second piece is, "I want someone that's going to champion and be a change agent to do things that may be hard, but actually best for the long-term interest of the product or company, even though those things are not gonna be easy to execute on." And I think if you have one without the other, ultimately people are not gonna see you as strategic.

   2. LRLenny Rachitsky0:38

      (instrumental music) Today my guest is Anika Gupta. Anika is chief product officer at Rubrik, a lecturer on product management at Stanford University's Graduate School of Business, and on the board of Tinuiti. Previously, she was president, GM, and head of product at LiveRamp, where she spent 11 years and joined as one of their earliest employees. A bunch of former guests recommended Anika come on this podcast, and you will soon see why. In our conversation, Anika shares a ton of powerful advice on navigating difficult personalities, giving and hearing hard feedback, bringing humor and gratitude to every situation, managing your energy versus managing your time, super tactical tips for how to become more strategic and how to make better decisions, and also how to break into product management for people that are trying to become product managers. There's something in this episode for everyone and I am excited for you to learn from Anika. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It's the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Anika Gupta.

2. 1:43 – 5:30

   Key mindsets for success

   1. LRLenny Rachitsky1:45

      Anika, thank you so much for being here and welcome to the podcast.

   2. AGAnneka Gupta1:51

      Thanks for having me.

   3. LRLenny Rachitsky1:52

      So I'm gonna start with a question that I've started to ask guests that come on the podcast that have had extraordinarily successful careers and also just consistently successful careers. So here's the question. What do you believe are one or two skills or mindsets or habits that you think most contributed to your success that you think might be helpful for other people to learn and build to help them have more successful careers?

   4. AGAnneka Gupta2:18

      So it's funny. Before we kicked this off, you talked about the Post-it that you have on your computer that says-

   5. LRLenny Rachitsky2:23

      Yeah.

   6. AGAnneka Gupta2:24

      ... have fun.

   7. LRLenny Rachitsky2:25

      Mm-hmm.

   8. AGAnneka Gupta2:25

      And my one mindset, uh, that I really have leaned into after someone actually gave me advice on this is to figure out how to have fun in my job even in the most difficult of times. And the reason why I say that is because when you're hit with really hard times, it's easy to operate from a mindset of scarcity and to look at everything as an unachievable hurdle to overcome. And when I was able to switch my mindset and say, "Well, I'm actually gonna figure out a way to have fun with this," it actually changed my entire approach for how to deal with super difficult situations. And this advice specifically came up to me when I had a scenario where I had to essentially change out all of my direct reports in very short order. And I figured that out. It was a super daunting situation. I didn't know how I was gonna manage and at first I felt so scared by what was ahead of me and how much change I was gonna have to go through in a very short period of time. But when I got this advice, I started to try to reframe my thinking and it actually really made it so that I was able to get through that hard time and opened my mind up to so many more opportunities. So now I try to embody that in every situation that I come up, come across where I'm faced with something super, super challenging.

   9. LRLenny Rachitsky3:45

      I love this advice. It's something that I've recently seen also in public speaking. If you can just frame, reframe your thinking from, "I'm scared of this," to, um, "This is gonna be fun. I'm gonna have so much fun doing this. It's gonna be, like this energy and anxiety I'm feeling is me feeling like it's gonna be a lot of fun." So spending a little more time here, how, how do you actually do this? So in this case you shared an example of you're, basically you have to fire a bunch of people, not something, uh, one can, uh, quickly think about how to have fun with that. How do you, how did you do this? Is it just in your mind, you're like, "I'm gonna have fun with this," or is there something tactically people can do to make something fun?

   10. AGAnneka Gupta4:18

       I think there are a couple of things that I did, and, and I've continued to do. One is figure out and really look at the situation and ask myself, what can I learn from this situation? What can I get out of this that's a positive outcome even though it is incredibly challenging to be facing it right now? So that's one thing that I've done. The second thing I think that has been really helpful is in going into meetings or other si- situations where I was bringing... I was trying to figure out how to collectively solve s- some big challenge, figuring out how to bring humor into the meeting and just starting it on a light note. And that elevated my own, uh, mood and way I was approaching the meeting, but also adds a level of levity to the situation for other people as well, which I think as a leader is super important because it's not just about your own mindset, but how are you transferring that mindset to the people that you're working with and the people that are working for you?

   11. LRLenny Rachitsky5:12

       Got it. So part of it is just like how do I add a little humor? Part of it is just thinking, how do I make this fun? Is part of this just like this is not as important as, as, as, thing, people make it out to be and w- that we could just have a little fun with this thing, it doesn't have to be like we're not, you know, curing cancer-

   12. AGAnneka Gupta5:28

       Yeah. Yeah.

   13. LRLenny Rachitsky5:28

       ... as they say?

   14. AGAnneka Gupta5:29

       Definitely

3. 5:30 – 9:05

   Managing energy for optimal performance

   1. AGAnneka Gupta5:30

      I think that helps. Reflecting a- on this too, I feel like a lot of it comes down to the amount of emotional and mental energy I can bring to solving a problem. And there's always so much going on in life, like personal life as well as, uh, professional life, trying to figure out how can I architect my day and time to maximize my energy and be able to bring my full self to work and to these difficult situations so that I can have that mindset to look at things more broadly versus operating from a place of scarcity. And that may come down to like simple things like making sure that I have lunch.... (laughs) sometimes when things get so busy, you're like, "Oh, I'm just gonna grab a protein bar and I'm gonna skip lunch," but I found that that really decreases my energy. Or trying to do things that are really difficult late in the day. 5:00 to 6:00 PM is my worst time of day, and I know that about myself. So I'm not gonna schedule in my d- most difficult meeting or, you know, writing up a strategy deck or something for that period of time, because I know that that's not gonna be my best and it's actually going to make it more difficult for me to get the work done. And that has... Being able to kind of manage my, my energy levels and figuring out how to schedule my time for my energy has really allowed me also to figure out how to have that abundant mindset in all situations.

   2. LRLenny Rachitsky6:48

      Hmm. This episode is brought to you by the Enterprise Ready Conference, a one-day event in San Francisco bringing together product and engineering leaders shaping the future of enterprise SaaS. The event features a curated list of speakers with direct experience building for the enterprise, including leaders from OpenAI, Vanta, Checkr, Dropbox, and Canva. Topics include advanced identity management, compliance, encryption, and logging, essentially at complex features that most enterprise customers require. If you're a founder, exec, product manager, or engineer tasked with the enterprise roadmap, this conference is for you. You'll get detailed insights from industry leaders that have years of experience navigating the same challenges that you face today. And best of all, it's completely free since it's hosted by WorkOS. Spots are filling up quickly. Make sure to request an invite at enterpriseready.com. That's enterpriseready.com. Today's episode is brought to you by Command.ai. If you're like me and most users that have built product for, you're probably used to chatbots at the bottom right of websites, where you ask a question and it says something like, "Check out these three helpful articles. Did that answer your question?" And then you click away, and then a few seconds later, you get bombarded with some other useless pop-ups. For those of us who work on software, no one wants their product to feel like this. Command.ai is an AI power toolkit for support, product, growth, and marketing teams that embeds in your company's product. The AI support agent can deflect upwards of 80% of support questions, providing actually useful answers, and it can magically co-browse with your users to show them around your interface. They do pop-ups too, but their nudges are based on in-product behaviors like confusion or intent classification, which makes them much less annoying and much more impactful. Command.ai works with web apps, mobile apps, and websites. And they work with industry leading companies like Gusto, Freshworks, HashiCorp, LaunchDarkly, and over 25 million end users interact with Command.ai interfaces. To try out Command.ai, you can sign up at command.ai/lenny and experience a custom demo of how it works in your app. That's command.ai/lenny.

4. 9:05 – 18:26

   Founder mode

   1. LRLenny Rachitsky9:05

      I'm gonna go in a totally different direction. We were, before we were recording, we were also chatting about founder mode, and this is recently... This episode we're recording shortly after Paul Graham put out his now classic, instant classic founder mo- mode post. And, uh, he had some really interesting takes on, uh, ways to think about founder mode, both from product leader perspective, from a founder perspective. So, there's kind of two questions I want to ask, but just broadly, what's your take on founder mode?

   2. AGAnneka Gupta9:33

      Well, first of all, I think Paul Graham did an amazing thing by putting a name to something so many of us have seen in practice. And while he didn't in his article say this is exactly what this is, I think many, many people that I talk to were like, "Oh, yeah, I recognize this." I recognize people that I've worked for that have done founder, CEOs that have done founder mode great, founders that have done founder mode poorly. And it opened up a level of discussion that I think is really valuable for everyone to be having, whether you're a founder or you're someone that works for a founder.

   3. LRLenny Rachitsky10:04

      Okay, so I'm gonna ask two questions around this. One is from the perspective of working for a founder in founder mode, the other is being a product leader in founder mode. So first of all, I imagine you've worked with a few founders that operate in founder mode. As a CPO, as the head of product, that's often a difficult place to be between the founder and the team that are building the thing. Uh, what have you learned about how to effectively work as a product leader, uh, with a founder in founder mode?

   4. AGAnneka Gupta10:30

      So I think when a founder's in founder mode, what they are doing, and if they're doing it well, what they're doing is really deeply understanding the business and then figuring out when to use their power as a founder to either tweak things and send something in a slightly different direction or fundamentally innovate and completely change directions or completely innovate in a, in a totally new area. Now, I think the way to use that effectively as a, a head of product is to recognize that they have that power, to figure out how to use that power to get the things done that you know are best for the company. So, I always think about, like, I have all the people around me, whether they're people on my team, my peers, or my CEO. These are different resources I have to go get a initiative done or get work done in the company. And as a... Having a founder that can effectively operate in founder mode means that I can go and have a conversation with the CEO and say, "Hey, look, like, we have this huge opportunity and this is, these are the things that aren't working and I need your help to help figure out how we can move the needle more substantially in the direction that we need to go." And so activating that founder, that CEO to really be able to push the initiative that I think is best by making them an ally in doing so. So I think that's one aspect. The second aspect is, which often happens, it's very difficult for many people and, and have had this happen to me many times, is when founder's like, "Well, I have this idea," and then you may or may not agree that that's the best direction to go in, and how do you navigate that, that kind of situation? So one is actually taking a step back and objectively saying, "Well, why are they pushing this?" Maybe it's the wrong...... mechanism to go actually get done a strategy that's quite important for the company, so having a really deep understanding about why are they asking this? What are they ultimately trying to get at? And what is the objective that they're trying to get at? And is this the right way to get at it? And if the answer is no to that, then you can go have a conversation. If you know what the objective is, you can go have a conversation with that founder and say, "Hey look, I know this is what you're trying to do. But maybe instead of looking at option A here of how we go about tackling this, we should explore these three other options instead." And that can help you, can help navigate that conversation. Now, sometimes, it's difficult to even get to that kind of understanding of the objective because someone might be just super set in their ways of, "Hey, I'm gonna go. I really wanna go after this opportunity. It's my pet project." Then you have to decide as a head of product, do I really wanna fight this or do I just, you know, get, give in on this, let it go, and, you know, also make sure that we get the stuff done that's most important to the company? You have to make that, that judgment call as a head of product and decide, you know, what is really gonna make or break the company? What's the hill that I'm gonna die on and is this something that I can shift or is this something that is, is not worth shifting? Of course it comes down to the personality. I've been very fortunate that I've actually had very few of those situations-

   5. LRLenny Rachitsky13:35

      Mm-hmm.

   6. AGAnneka Gupta13:35

      ... where I've, uh, where the founder has been like, "Hey, I really wanna go in this direction," and I haven't agreed at least with what we're trying to go after regardless of, like, the mechanism behind it.

   7. LRLenny Rachitsky13:47

      I really love the point you made especially about how the founder could be this lever to get things done when you identify something needs to change, the best way to change that is just con- have the founder go in there, tell everyone, "Hey, we're gonna do this thing differently." That's such a, like a, a positive spin on how to leverage founder mode where a founder actually has a lot of power to change that other people in the company don't. Okay. So let's go from the other side. So, uh, I was talking to Nikhyl Singhal who runs The Skip which is a community you're part of about you and he said that you are, you're a leader who excels in founder mode, that you operate in founder mode a lot. And so as a product leader, what have you learned about just how to think in founder mode, operate in founder mode, leverage that approach to leading teams, leading product teams?

   8. AGAnneka Gupta14:32

      Yeah. I think it's e- often, um, easy as a leader to say I'm not gonna roll up my sleeves and get into the details of the business or ask a lot of detailed questions about the business because you want to empower people and make them successful. And what I've found is that understanding the details of the business and asking questions and understanding to the utmost extent you can what's working, what's not, what are the financial goals of the business, are we on track to get there, how are we making decisions, getting into that level of depth is super important and then you can decide as a leader what do you wanna do with that information. So there's a lot of information that I collect about what's happening in the organization, the decisions that we're making, that I don't do anything with at a point in time. That's my choice to make. But I want the information because in understanding the depth and what is happening, I can decide where I actually think I need to go in deep and make a, a either very significant course correction or a, a small course correction. And then the way that I think about how do I bring my team along for that so they don't feel like I'm coming in and stomping all over (laughs) the work that they're doing or trying to readjudicate a decision is one, is like how do I get in there early? So how do I ask w- one, one of the tactics I use is I ask people to present their strategies for things that I think we may need to do a course correction on and I have them come in and then I ask them questions and then I make suggestions and I'm able to do that in a forum where it doesn't feel like I'm coming in and rewriting the entire strategy but I'm giving them their an opportunity to present their best thinking and then trying to figure out how do I take that and make that better and make them feel like I'm making it better versus stomping all over and, and dismissing the work that they've done. Uh, and I pick a strategic set of areas so I think about, like, what is most important for the business? What's gonna kill the business if we don't get right and what are the biggest opportunities for the business that we need to go after regardless of how difficult it is for us to actually execute on them? And by doing that, then at least I have clarity in my mind and I can provide clarity to the team about what is most important and rally the troops around making that stuff happen if that is what is essentially right. And I'll have all the context because I've asked all the questions of, like, why this is right for the business. Why is this gonna help us with increased margins or get better growth or get into a new persona if that's what we're trying to do as an overall organization?

   9. LRLenny Rachitsky17:04

      So in that, in that example, and, and I love this tactic, you have your team come in. You ask them, "Tell me which, what the strategy is for this thing that you're working on." Y- the, what you've seen work is instead of, like, no, this is broken, this is wrong, this isn't gonna work, your approach is ask questions and hope that they see the flaws or gaps. Is that, is that really what you're saying?

   10. AGAnneka Gupta17:24

       Or, yeah, it's ask questions but it's not always, you can't always lead someone somewhere with asking questions.

   11. LRLenny Rachitsky17:29

       Mm-hmm.

   12. AGAnneka Gupta17:29

       It's also sharing a hypothesis. So I might have a particular hypothesis about the business where I might say something like, "Well, I was talking to security leaders in our customer advisory board recently and I heard this piece of feedback and this is what it made me think about our strategy. What do you think about that?" And then let them say, like, "Okay, yeah, actually I see this," or maybe, "I have some follow-up questions," and it actually opens a whole discussion where I'm still able to point my, to, uh, provide my perspective and point of view but not completely shut down the discussion because what I always worry about as a leader is I'm gonna come in and say something and because I'm one of the more senior people in the room, no one is going to, gonna say if they have a concern and the reality is, is I'm not always right. Far from it. But I wanna be able to seed, seed an assumption and then have a discussion based on that and then figure out what the right outcome is about what we should do next based on that

5. 18:26 – 27:54

   Becoming more strategic

   1. AGAnneka Gupta18:26

      discussion.

   2. LRLenny Rachitsky18:27

      Speaking of strategy, you shared with me that when you... At one point in your career, you got this feedback that you just weren't strategic enough, and that that comment led you to research and dig into, what does it mean to be strategic, and also just to level up your strategic mindset in the way you think about strategy. What did you end up with recognizing is being strategic? What is that in your work, in your research, and then how did you actually get better at this... at this work of being strategic?

   3. AGAnneka Gupta18:57

      I ha- got this feedback once in a performance review, and then I actually got it as well a few years ago when I was interviewing for head of product roles, and I thought I had made a lot of progress on it. But when I reflected back, I think it actually all came back to the same themes, which was, I think when people say, "I want someone that's strategic," what they're really saying is, "I want someone that can come up with and articulate a compelling and simple why behind the decisions, and the direction of the company and product." So that's number one. And the second piece is, "I want someone that's going to champion and be a change agent to do things that may be hard, but actually best for the long-term interest of the product or company, even though those things are not gonna be easy to- to execute on." And I think if you have one without the other, ultimately people are not gonna see you as strategic. If you're really good at- at articulating the why, but you're only bringing small ideas to the table, then that's not strategic. If you're championing big ideas, but you can't articulate the why behind them in a compelling and simple way, then you're not gonna be seen as strategic either. So that's the formula that- that I've come up with that this is what it means. And so I focused a lot on, how do I make sure I do both of these things? How do I champion a few things that are really big ideas that are going to help change the direction of the company? And then how do I articulate that in a simple and compelling why?

   4. LRLenny Rachitsky20:26

      That's such a cool, simple way of thinking about this. Is there an example from your work that might illustrate some of this from- from a project you worked on or a product you- you built?

   5. AGAnneka Gupta20:35

      I could take some recent examples. We've been doing a lot of strategic planning for where do we wanna be as a company over the next three years, and Rubrik operates in the cybersecurity space. It's a very fast-moving landscape. There's a lot of places that we could go as a bu- business, and one of the ways that, um, you know, I've exhibited this and- and this is what I recommend to other people too, is sometimes it's really hard to come up with the compelling and simple why behind something, and sometimes it's also really hard to come up with, like, a really big idea out of thin air. So these things can be very challenging. The first step that I found is very useful, and I use this tactic every single day in meetings, is just summarization. So hearing, bringing people together, lots of different voices into a room and hearing what they have to say, and at various times in the conversation summarizing what people are saying, and summarizing what that means in terms of the direction that we could go in. And then that's a checkpoint of saying, "Okay, this is how I've synthesized what- what is happening. Is this correct or do we actually need to do another turn because we don't all agree with where- where we're landing here?" And that summarization, even though I may not be adding a new idea into that, I found people actually view that as strategy. They view the summarization, the effective summarization as strategy. So I think that's one element, and then what I've also found is that when I summarize what other people are saying, and especially multiple different stakeholders, then I can think about offline, and not in the context of, like, right in the meeting, sometimes during the meeting too, I guess, is how do I make this idea one click better? And it's not about how do you do something radically, radically different, but taking ideas and then making it slightly better, slightly better. And there are ways... And wh- when you think about that, especially from an outside-in perspective of what are the customer problems we're trying to solve, and how are we gonna take this to market, and don't worry about how difficult the technical implementation is going to be, then you start to get to these big ideas that can really be the- the change agent ideas. So I've started doing this more and more, and I think especially in the past three to six months, and I'm seeing a material difference in terms of the number of big ideas that we're going and pursuing overall as a company, and also the quality of the strategic thinking that I can bring to the table, and it's been really exciting and rewarding.

   6. LRLenny Rachitsky23:02

      There's so much you're sharing that resonates with other podcast episodes. For example, this idea of just going one click better. I had, uh, Roger Martin on the podcast, who wrote this book Playing to Win, which is one of the more popular strategy books, and he has this concept of betterment as a way to work on strategy. A lot of people go, like, huge with a big strategy and vision. His advice is just find the thing that is the biggest constraint and bottleneck to your business right now and just make it better, and that's your next step, and then just keep doing that and you'll- you'll end up in a much better place over time, even though it feels like you're just doing one little thing. And so I love this idea of just going... Picking one thing and making it one click better. There's gonna be an episode that comes out right before this with, uh, Alex Komorowski, and he has this concept of the adjacent possible, and it's just like, find the next thing that's possible and focus on that versus some big lofty thing. So I'm just sharing a bunch of stuff. It's not a question. (laughs) And then-

   7. AGAnneka Gupta23:57

      That totally resonates though.

   8. LRLenny Rachitsky23:58

      Okay. Okay. Okay. Great. Uh, and then the summarization idea, I love it. It's so tactical. Basically any PM can do this just in a meeting, just like, "Okay, let me just summarize it to make sure everyone's on the same page." Funny enough, this is the feedback I get on this podcast, and I haven't been doing this in our conversation yet, but I often try to summarize the person's point and everyone's like, "Oh, I love that you do that. That's so helpful." And so, uh, so I totally see the power of that in my experience. (laughs)

   9. AGAnneka Gupta24:22

      It also makes people feel heard, and especially when you have a lot of diverse voices in the room that may not agree on all things, but have valid viewpoints...... it helps bring people together, and ultimately the diverse perspectives are going to yield better insights and better decisions for the organizations. You want that, but some people shy away from that because it's scary, because you have to deal with a lot of conflict. And it's a way to kind of move beyond the conflict and get to the heart of an issue, which in my mind, that's what the PM job is all about, is getting to the very, very heart of a problem.

   10. LRLenny Rachitsky24:56

       If someone wants to work on the skill of summarizing as kind of a tactic, can you give just like, like an example of how you would do that? Are there like phrases you use? Are there words or an example you could give of just like, here's how it would look in a meeting?

   11. AGAnneka Gupta25:10

       Yeah. Um, so often if there's a lot of discussion going on, sometimes it can be a little hard to insert yourself. I still may insert myself and say, "Hey, let me pause here for a second and try to capture what has been said." This is what I've heard. I've heard that we have, you know, our customers are having these kinds of challenges. We feel like this is the way that we wanna solve these challenges. We have a right to win in this way, and therefore we're gonna take this action. Is everyone in agreement with that or, um, or is there some dissent about whether, you know, that- that's an accurate portrayal of where we've landed with this conversation? And that's the way I'll- I'll fr- frame it up. And again, ending it on a question so that you're not coming in and just being like, "Hey, this is what, where we- we're at." But then inviting people to discuss and say, "Yes," or, "No, I agree with eight- 90% of that, but 10%, we're 10% off," and that helps move the conversation forward because sometimes you'll get stuck in these circular discussions that aren't moving forward and you need to figure out a way to move it forward.

   12. LRLenny Rachitsky26:11

       And then your experiences just doing that makes you look more strategic and-

   13. AGAnneka Gupta26:16

       Yes. Yes.

   14. LRLenny Rachitsky26:16

       ... gives people the impression you're thinking strategically.

   15. AGAnneka Gupta26:18

       Yeah.

   16. LRLenny Rachitsky26:19

       Awesome.

   17. AGAnneka Gupta26:19

       The other way you could do it is if you're in a room with someone and you have a whiteboard is actually summarize on the whiteboard while people are talking, and then show your summarized framework or whatever on that. So that's kind of a good way to do it too if you're having a hard time interrupting the flow of discussion, or you don't feel as comfortable thinking on your feet and interrupting and then framing your- your point of view. Um, you can do that. In Zoom, you can also use the chat. I've done that very effectively and said, "I'm not gonna interrupt the flow of conversation, but I'm just gonna summarize in Zoom chat, this is what I've heard, um, and this is what I think, you know, we're saying in this conversation." And then sometimes that'll get invited back into the broader conversation, um, that's happening live on the Zoom itself.

   18. LRLenny Rachitsky27:05

       That's a much lower stakes way of doing it, and I- I'm picturing all the PMs listening to this are gonna start doing this and there's gonna be all these summaries now in Zoom chats and everyone will be like, "Oh my God, why is everyone sharing summaries?"

   19. AGAnneka Gupta27:13

       And then A- then Zoom AI will start just doing it all for you. (laughs)

   20. LRLenny Rachitsky27:16

       (laughs) Yeah.

   21. AGAnneka Gupta27:16

       It doesn't have to think again.

   22. LRLenny Rachitsky27:18

       And then PMs are over and AI has replaced us all.

   23. AGAnneka Gupta27:21

       Yeah. (laughs)

   24. LRLenny Rachitsky27:21

       Um, okay. So then just to close the loop on becoming more strategic, your advice is when someone's like, "Hey, you're not strategic enough, you need to be more strategic," your insights is the two things to work on is, one, be clear on the whys behind the ideas that you're working on, and be very clister- crystal clear. People may not be understanding why you're working on the things you want to work on, the things you're pitching. And then two is actually be the person that makes these things happen, not just put a doc out there. If you're not actually achieving them, people are gonna think you're not strategic.

   25. AGAnneka Gupta27:52

       Yep.

   26. LRLenny Rachitsky27:53

       Awesome. Okay.

6. 27:54 – 37:18

   The importance of decision-making

   1. LRLenny Rachitsky27:54

      I want to talk about decision-making. You have a really interesting perspective on how to become a better decision-maker in relation to being kind of a historian, which I love this concept. Talk about that insight.

   2. AGAnneka Gupta28:07

      Yeah. Um, so I was at my previous company for 11 years, so I kind of ended up becoming the historian. And when I joined Rubrik about three years ago, I came into an organization that had a lot of history that I just didn't know about. So one of the things that I decided to do when I joined the company was to really understand what happened in the past, like what were the products that we launched that weren't successful? Why weren't they successful? What was the perspective on the history of how we've decided to develop the things that we've ha- we did, and why? What was the perception of different people in the organization? And I tried to construct this, like, past knowledge of what had happened and what were the decisions that were made and why were those decisions made, whether they were good or bad, didn't matter, so that I could better understand how to make decisions going forward and to learn from the mistakes that I didn't personally live through. And I think that's the part that's really important about being a historian. You can always be a historian. It doesn't have to be just when you join a company. But even today, I'll hear about projects from many years ago that people bring up and I'll be like, "Tell me about this project. Why... Like, what happened with it? How did we decide to do this?" And just really learn and be curious about it because that gives me more context into, well, what is it that we did poorly and how can we do that better? And also, what is the baggage that people have around trying to do something similar again? Because people always come with their baggage of, "Oh, this hasn't worked before, so why is it gonna work now?" And as a product leader, you're obviously putting in place a lot of thoughts and ideas around, this is what I want to go achieve and these are the initiatives, and some people are gonna come and say, "Well, we've tried that before," especially if you've been at an organization that's been around for a while.

   3. LRLenny Rachitsky29:56

      I've been that guy. We've done this so many times. Why are we... This, it didn't work.

   4. AGAnneka Gupta30:01

      Yes.

   5. LRLenny Rachitsky30:01

      Why are we thinking about this again? So, okay, so the advice is here if you're new to a company especially, go through a bunch of, just like study the past decisions that were made and share them out if, as a part of that. And then as a side effect, it'll help you make better decisions 'cause you'll have this history about what the company has done. I love that. Along the same lines of decision-making, I asked, uh, your former colleague, Rachel Wolon, what to ask you, and she said that your parting advice when she left to join a different company was, it's not about making the right decision, it's about making the decision.And, uh, that's like the thing she remembered about you most, that parting advice. Talk about why that is so important and your insight there.

   6. AGAnneka Gupta30:42

      Y- it's very easy to get into analysis paralysis before making a decision and say, "Well, if I just had this one more data point. If I just knew this, then I could make a decision." But the reality is, is that you are always operating off of imprecise information as a product leader, and what I've found is that once you commit to a decision, you actually learn more post committing to that decision about what's gonna work and not gonna work. And you get ou- move out of the hypothetical. And as long as your decision is like 70% right, you can iterate on that 20, 30% in either direction. Uh, but if you don't commit then you don't actually get any new information that is high fidelity and high quality. So I'm big t- uh, a believer in- in making decisions. You, I know you've had a few guests talk about speed is super important in organizations. Well, I think making decisions quickly and then being able to iterate on them is a- is a form of that. Uh, just make a decision. Don't make it uninformed but have a strong hypothesis. And then just keep testing whether that hypothesis is accurate or not, and you'll shift here and there. You might build something that you have to throw away 20% of the work on, but that's okay. It's better than making no decision at all, because you won't get any new information if you don't make any decision at all.

   7. LRLenny Rachitsky31:56

      As a PM that might be listening to this, feeling like, okay, yeah, that sounds great, but then I make a bad decision and then my, and then Anika's gonna be like, "You messed up here. You got the wrong, you've shipped the wrong thing here. It didn't work." How do you, how do you create a culture where people don't feel that and aren't as afraid of making bad decisions and making decisions with 70% of the information?

   8. AGAnneka Gupta32:20

      I think part of it comes down to making sure there's a strong hypothesis that everyone understands when you're making the decision. Or it might not just be one hypothesis. It might be a serie of hy- series of hypotheses, of, and assumptions that we're making that are informing the- the decision. So it might be a hypothesis that, you know, some- this segment of customers is gonna be willing to pay for this product because it's solving an urgent and important enough need for them that they're gonna go do it, and this is the evidence we have to find it. But this is also the stuff we don't know. And then along the way, we learn whether that hypothesis is true or not. And so at the end of the day if something didn't work out, we can go back to the original hypothesis and say, "Well, this is what we learned in this process, that we are, um, our hypothesis was actually not true, and we learned all of this after the fact." And I think the way to make a culture of risk-taking and w- people willing to make these bets and go out on a limb is to reward the learning versus the outcome. And that's what I try to focus on is if we're constantly learning, it is okay if we make bad decisions, but we learn from them and we get better for next time. And even in making this bad decision, we learned something about our customers or our business that we otherwise wouldn't have learned that we can use in some- in- in other contexts.

   9. LRLenny Rachitsky33:40

      I love, first of all, I love that this comes back to your strategic lesson of just if you have a strong why behind something, that's incredibly powerful and people will be confident that you're thinking strategically. Uh, two, I was just at an, uh, talk with Zuck. When he was giving, he was being interviewed at the Chase Center, the Acquired podcast had this whole event, and his main thing that he talked about that Facebook, that he values most in the culture of Facebook is learning faster than anyone else. Shipping stuff that isn't perfect but just so that you can get one more turn and learn something faster than someone else. So that super resonates. That's Facebook's culture. Um, is there an example of something you worked on where you, where that, you, where you did that where you kind of shipped something that you weren't fully confident in and you learned faster?

   10. AGAnneka Gupta34:26

       Yeah, I mean, I- I think there's a lot (laughs) because anytime you're shipping products, there's so many different things that could go right and wrong. You know, there's a situation where we created a really amazing high value product, and we decided not to monetize it. And then we realized after the fact, wait, we should've monetized it. So we're trying to figure out how to package some new capabilities to monetize this thing that we know has a lot of value without taking away what we've already given to existing customers. So that was something we learned along the way that we originally didn't think, oh, we should monetize this, but then we realized oh, there's actually an avenue to do that after the fact. There's been other things where we've developed a set of capabilities thinking that it will solve for this new persona's problems, but then we misunderstood how easy it was going to be to go sell to that new persona within our own organization. I've made that mistake many times actually. (laughs)

   11. LRLenny Rachitsky35:26

       Mm-hmm.

   12. AGAnneka Gupta35:26

       And so now I- I think back and now what I've taken from that is really know how you're gonna sell something and who's gonna do the selling before you actually go build out the product, because if you don't have that right focus, you may build out the best product and yet it's gonna get zero adoption because no one in your organization is ready to sell it. Uh, so there's tons of stuff like that where it's like been, okay, yeah we can, we've learned something from this and it's not all throwaway. It just means that we've gotta do something differently for this product, and we need to do something differently for our organization going forward.

   13. LRLenny Rachitsky36:01

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7. 37:18 – 41:38

   Navigating difficult personalities

   1. LRLenny Rachitsky37:20

      I wanna come back to something Rachel also shared with me when I asked her what questions to ask you. And by the way, first of all, she spent, like, a lot of time raving about how amazing you are first. That was the first (laughs) set of conversations, and then she came up with a bunch of questions to ask you. And so her other question was about how good you are at navigating very difficult personalities. She shared this quote that she constantly saw you interact with and bring together several leaders who had much higher egos and very disparate points of view who are not informed or thoughtful or as gracious as you were. And she also said you have a very low ego. And so she wanted me just to ask you for h- what you've learned about how to navigate very difficult personalities and help people align when that is not innately wh- what they want to do.

   2. AGAnneka Gupta38:07

      I try to embody the mindset of feeling like and believing that I can work with anyone. And I think what I do when I hit a difficult personality, and difficult personalities come in all shapes and sizes and forms, is I really try to understand what drives that person. What really I... What is it that they really care about? Hopefully it's they care about something deeply about the company and making the company successful. Sometimes it's s- they care about their own personal career, how they're showing up, what people view of them. That's fine. I just need to understand what it is that they really care about. And then if I need something from them, what is it that I can do to motivate them to find what I, what I need from them important, and trying to make that match of, like, they have this desire. It's kind of like building a product. They have this desire, and how am I gonna get them to care about the thing that I'm gonna care, that I wanna care about? The other thing I do is, like, instead of feeling, like, anger or frustration with the person, uh, and instead trying to shift that to a mindset of feeling gratitude and s- a positive emotion about them, is I look at them and I ask myself, "What can I learn?" And maybe I don't want to adopt their personality or (laughs) their d- to, uh, operate the way that they are operating. But everyone has something that they can teach you, uh, whether it's their communication style, or the way they're able to marshal people together, the way they come up with visionary ideas. Whatever it may be, trying to study that person and be curious about them, learn from them and then thank them for that and feel the generosity genuinely about what I got from this situation. It's easier to do sometimes than others. But I think it comes back to that abundant mindset. If you could approach it with an abundant mindset, then you can really consciously do this. And when you actually learn something, you will feel the gratitude, when you recognize that you are able to get something from that.

   3. LRLenny Rachitsky40:13

      I love that this connects with your other original piece of advice of just turning something into, "This is gonna be fun. Let's make this fun." And in this case, it's like make it great. H- "What can I learn from this person even though they're really annoying me and it's frustrating, and they don't want anything done?" And then your other point of understanding what they want and y- kind of using that as a way to pull them in your direction, how do you figure out what they want? Do you have any tricks for just like, "Here's how I learn what this person's motivations are and goals are?"

   4. AGAnneka Gupta40:42

      Talk to other people that have worked with them before and have done so successfully. So that might be people that work for them, because if you work for a person like that, you have to figure out... Uh, and, and, and, or, if you're successfully, w- successful working for that person, you probably understand what makes them tick. Um, so that's one. Or work, w- talk to people that are peers. Anything like that to try to understand and build this view of this person that helps me empathize with them and also helps me understand what they may be wanting to get out of a situation and why.

   5. LRLenny Rachitsky41:16

      I love that. That's... And yeah, they don't have to be involved in that. You just ask other people, "What is this person's motivations?" And then the idea is, uh, connect what they want with the thing you're trying to achieve. Beautiful. Uh, I really love this idea of, (laughs) when you're frustrated by someone, just, like, reframing it to, like, "I'm grateful I'm gonna learn something from this person in our interaction, even though, uh, they're making life hard for me." I really love that.

8. 41:38 – 51:01

   Techniques for giving and receiving feedback

   1. LRLenny Rachitsky41:39

      Another skill I hear you're really strong at, and this comes from another one of your colleagues, uh, Hema Mohan, uh, shared that you're world class at giving feedback, giving hard feedback, and receiving hard feedback. And so I wanna just ask you, what have you learned about how to do this? It's very hard to give hard feedback. That's why it's called hard feedback. So either, from either direction, what have you learned about receiving hard feedback or giving hard feedback where someone actually hears you and doesn't get, you know, defensive?

   2. AGAnneka Gupta42:07

      The answer is so much. (laughs) I've learned so much from it. So maybe I'll t- I'll start with receiving feedback. Um, so on the receiving feedback side, I think it's very natural to feel upset, defensive, all the negative emotions, when you first see a piece of negative feedback, whether it's you're reading it in a employee survey or you're receiving it in a one-on-one from a direct report, or from a manager, or from a peer. And I try to let myself just feel the things that I'm gonna feel. And sometimes that's an emotional feeling, sometimes that means I wanna step out of the room, or it depends on who I'm talking to. But let myself feel the things that I'm gonna feel and then-... once that's passed, whether that's a few hours or a few days, don't react. Don't try to say, "Oh, I don't believe this." Listen, and then ask myself, like, "Okay, well, where is this feedback coming from?" Like, "Why, why am I getting this feedback?" And is, uh, and try to be super curious about it. And that might be going back to the person that gave me the feedback and asking, and maybe asking someone that's a peer, um, in, you know, or somewhere in the organization that might have more context and, and flavor to what the feedback really is. Just trying to learn. And then I can decide, do I think this is valid or not? Is this something I should do something about or not? Actually, all feedback I think is valid. People's feelings are valid. But it doesn't mean that you need to do something about all of those things. And so that has, you know, going through that process and, like, letting myself ride the emotional wave, uh, and not judging myself for that, but then not reacting, um, and letting myself then figure out and come back curious. And I think when you come back curious, people then want to give you more feedback because they know that you're listening and that you're, you're hearing what they say.

   3. LRLenny Rachitsky43:55

      So the advice is feel it. Like, don't block it off and be like, "No, no, no, no, no, this isn't real." So fully let your body go through the roller coaster of feeling the negative feedback. Sometimes the feedback is just like, "No, this isn't actually a thing." Do you have any just, like, heuristic of, like, I should actually pay attention to this deeply, or just like let me wait for more data points?

   4. AGAnneka Gupta44:15

      Yeah. I think in product you receive feedback all the time for your organization or for yourself, and you can't make everyone happy. Like, everyone wants a different thing from product. So I think this comes up quite often, uh, where there's a lot of feedback for the organization or for you as a leader, and you have to decide what to focus on and what not to focus on. I always try to anchor on, well, what is best for the company, and what does the company need from me and from my team at this point in time?

   5. LRLenny Rachitsky44:45

      Mm-hmm.

   6. AGAnneka Gupta44:45

      And there's stuff that is a must-have on that list, and there's stuff that's nice to have. And sometimes, you know, there's just too many must-haves to go deal with the nice-to-haves, and you have to just be like, "Well, you know, I know this is a problem," or, "I know we could be do- 10% better in this," but it actually doesn't matter as much as fixing these things that are really, really important, and are really what's gonna help my organization deliver what it needs to for the company and for the business overall.

   7. LRLenny Rachitsky45:13

      In terms of receiving hard feedback, so you shared one example, or I shared an example where someone said you weren't strategic enough. Is there another example of receiving hard feedback that you got where you're like, "Ugh, that sucks"? Either earlier in your career or more recently. Anything else come to mind?

   8. AGAnneka Gupta45:26

      I mean, all the time. (laughs) Yeah, so there's always hard stuff. Um, you know, it's like there, we'll, people will give feedback of, "Oh, um, I feel like we're not moving fast enough on our roadmap and priorities. We need to be doing more. Why aren't we moving fast?" Uh, or-

   9. LRLenny Rachitsky45:46

      Never, never heard that one before.

   10. AGAnneka Gupta45:47

       Never heard that one before, right? Um, or, um, disparaging the direction that we're taking a certain product because they don't agree with it because a competitor is doing something else, but we've decided for our reasons that we're not gonna go follow that path. Like, there's always something that, that people have negative feedback about, and sometimes I'm like, "Okay, this is an eye roll." Like, I understand where they're coming from. I understand why they're giving me this feedback. But I also don't agree that we should change directions because of it. Uh, so, I don't know. Uh, like some of the things cut d- cut deeper than others, but I think people are making, like personal statements about my team or they're feeling like, "Hey, the product team isn't listening to feedback," or, "The product team has a bad culture," or like, "Anika isn't listening." Things like that cut deep and are a lot more... They, they, m- I know like physically or physiologically they make me kind of seize up a little bit. But again, then I try to feel the things they gonna feel, and try to understand why are they saying that? Why do they really feel that? And what does that mean behaviorally that I have to do differently or my team has to do differently? Or maybe just two people on my team need to do differently and someone is extrapolating this out to be a much bigger problem than what it actually is.

   11. LRLenny Rachitsky46:59

       Awesome. Okay. And then I, we were gonna shift to what you've learned about giving hard feedback so that someone actually listens and doesn't just put up a shield and like-

   12. AGAnneka Gupta47:08

       Yeah.

   13. LRLenny Rachitsky47:08

       ... "Sh- yeah, it's not real."

   14. AGAnneka Gupta47:10

       So I think in giving feedback, you can never fully control how someone else is going to respond to that feedback. All you can control is what you do, your body language, and what you say. And what I have found is that if I can convey, and I will say this very directly to people, I care so much about you and I'm giving you this feedback because I want you to be successful and I want you to be able to reach the pinnacle of what I know you can accomplish, and you do all of that setup and you don't just hope that they understand that, you actually explicitly say that and you show that in your body language, then it makes the other person much more receptive to hearing whatever you have to say. And then I think the other piece is that you should not... You've gotta be direct. Like the worst feedback is the kind of passive-aggressive feedback versus saying directly, "This is what you are doing or this is how you are being perceived in the organization, and here are the three things that you can do to make it, to change the way you're being perceived or to change, ch- change the outcomes of, of what you're driving or become more strategic," or whatever it is that I'm trying to give feedback on. And I try, I do a lot of prep before I give someone a lot of feedback. I really think about like how can I frame this in a way that's gonna resonate with them that doesn't come across as attacking them, but helps them understand why what they're doing isn't working or is being perceived poorly? And try to give them examples and even examples that I've personally had to go through myself of how I've approached those situations. Uh, and let them ask questions and brainstorm with them, be part of the solution versus saying like, "Here's all this feedback. Now you go figure out what to do with it."

   15. LRLenny Rachitsky48:56

       This reminds me of, um, radical candor. Basically, make people feel like... Care deeply about them, but cha- be very direct about what they can be doing better. Are there, like, phrases or ways you kind of set up the conversation? You ta- you mentioned a few of just, like, "I want to help you become the best version of who you could be and what you're capable of." Is there any phrases you find helpful that you've come back to often of just, like, a way to start the conversation?

   16. AGAnneka Gupta49:19

       Yeah. I- I- I think kind of what I started with is like, "I care a lot about you."

   17. LRLenny Rachitsky49:23

       Mm-hmm.

   18. AGAnneka Gupta49:23

       "You have a lot of potential. I can see you doing these kinds of things. I can see you getting to where you wanna go in your career." Sometimes I even start the conversation by asking them, "What do you wanna do? Where do you wanna get- go in your career?" And that will help me frame up which of these things are important because honestly, you know, if someone wants to be eventually, like, a CPO, the feedback I'm gonna give to them is very different than if they're like, "Hey, you know, like, I don't really wanna manage people ever. I just want to be the best IC I can ever be." I'm not gonna give them the same feedback. And so having that conversation up front also allows them even before I jump into the feedback to give them their perspective of what they want, and then I can tailor the conversation more to what they're looking for. And I think that has really helped as well, make sure that I focus on the things that are gonna really matter. During the feedback conversations, I also try to frame things as, "This is how you're being perceived, then you are doing X." Because I think even though it's hard to hear, "Oh, hey, this person doesn't perceive you in the way that you may think," then we can talk about, "Well, how do... What are ways that we can change the perception?" I also think it's important because sometimes people are like, well, if you say, "Hey, like, I don't think you're X," and then they're like, "Well, yes, I am." And if you say, "Hey, well, this is how other people perceive you, including me, but maybe this is not what you are intending," and you actually say that, you're giving them the benefit of the doubt of, like, actually what they're be- what they want... What they're- how they're trying to show up is different than how people are perceiving them. And you can have a better conversation then around, "Well, what can you do to change that perception?"

9. 51:01 – 54:56

   Transitioning into product management

   1. AGAnneka Gupta51:01

   2. LRLenny Rachitsky51:01

      You mentioned, uh, IC product managers, and this is a good segue too. You're, you know, you're a big deal, fancy chief product officer person. A lot of people listening to this podcast are early career PMs or trying to get into product. Uh, I wanna ask a couple questions along these lines. One is about getting into products. So interestingly, you got into product the same way I got into product, which is you used to be an engineer and then you moved into product within a company, which is one of the... Maybe one of the simplest ways to get into product potentially. For people that are trying to break into product management, what advice do you often give them of how they could go about doing it? I know there's never the silver bullet, but what's your advice?

   3. AGAnneka Gupta51:41

      I definitely think doing it within the same company is a lot easier than trying to switch companies and switch jobs at the same time. Because when you're in... Within a company, you've already built credibility, hopefully. And if you haven't, then go crush it at your job so you build the credibility. Then you can start to raise your hand, interact with the product team, take on projects, and do things that allow you to get some experience and build a relationship with a leader on the product team who then may be willing to take a chance on you to put you into a product role, even if you don't have the experience. And especially when you're within the same company, you bring other things to the table. Let's say you're working in customer support. Well, you have a huge amount of knowledge about what are the big problems that people are calling up the support team or opening tickets on the support team for, and that is valuable knowledge for, uh, being a product manager. If you're coming from the sales side, you're coming with a knowledge of how to sell the product, what really resonates, how do you do the objection handling? And that can be a valuable, uh, perspective. If you come from the engineering side, well, you understand how the product is built and you understand the, you know, technical nuances of that. Well, that can also be a valuable way to enter into the product team. And that way, even though you don't have the direct product experience, you're still bringing something to the table where you are gonna have to get trained on core product management, but you're not gonna be... Have to be totally trained on the business or the technology.

   4. LRLenny Rachitsky53:06

      So is the advice basically get a job in any function, not necessarily any function, but join a company however you can essentially, and then push to try to get into the product team-

   5. AGAnneka Gupta53:19

      Yeah.

   6. LRLenny Rachitsky53:19

      ... in some form?

   7. AGAnneka Gupta53:20

      I think join a product-adjacent function-

   8. LRLenny Rachitsky53:22

      Mm-hmm. Mm-hmm.

   9. AGAnneka Gupta53:22

      ... which honestly, pretty much every function is product adjacent because what function does product not engage with, but as closely product adjacent as possible. And then, yeah, find your way, way into the product org from there.

   10. LRLenny Rachitsky53:34

       Ideally, there's something within the company, there's like some program I imagine that does this sort of thing. Some companies have something structured, some are just kind of ad hoc. Is there anything in there you just like, like should you talk about this in your interview? Just like, "Hey, I'd really love to become product manager someday. Do you have anything along those lines that would help me get into that or not?" Or should you not talk about that?

   11. AGAnneka Gupta53:52

       Well, I- I think it depends. So for instance, when I, um, joined LiveRamp, which was my previous company as a software engineer, I actually did say in the interview process, "I wanna become a product manager, I think." At that point I was still early in my career, I didn't know for sure, but I said that. Now that was a 20-person startup. So it was worth saying it because they didn't really have a product team and I wanted to put it out there that that was something I was interested in growing into. If you're joining a 5,000-person company, your hiring manager is probably not going to receive it well if you're like, "Hey, I'm (laughs) interviewing for product marketing, but really what I wanna do is go into product." So it just kind of depends on the company and the stage. You have to play that, um... You have to play that wisely. But I think once you're in a company, then finding a way to make a relationship with the product leader or if you're in a startup that is really small and they don't have product management, well, then you have the opportunity to take on projects for sure that are product management related because no one is doing that work. Um, really taking initiative to do that so that you can find an inroad

10. 54:56 – 59:39

    Advice for aspiring product managers

    1. AGAnneka Gupta54:56

       into product management.

    2. LRLenny Rachitsky54:57

       Kind of along these lines, you have a really unique perspective on new PMs because you teach product management at Stanford. You've been doing that for a while.I just want to ask, you work with a lot of people that are new to product, thinking about getting into product and get into product. What do you find are the things that new PMs or people getting into product most misunderstand about the role of PM or are most surprised by when they become product managers?

    3. AGAnneka Gupta55:23

       When we interviewed students, as we were designing the class, about what they wanted to learn, what was most surprising to me was that students would say, "Well, can you teach me how to use Figma? Can you teach me the tools that product managers are gonna have to use?" And what was surprising to me about that was I don't think it's the tools that you need to learn to be successful. I think what you need to learn to be successful is how to take very ambiguous situations and consistently drive more and more clarity over time. Eh, and so it was interesting to see this mismatch between what people said they wanted to learn and what I felt they actually needed to learn. Now, having taught this class for a few years now, I think talking to students who have then left and become product managers, they've seen a lot of, of this in practice now and I think they understand that. But there is this mismatch of people who haven't been in product management saying they wanna go and thinking that they need to learn some, like, tools or process versus the mindset and the skills required to clarify ambiguity.

    4. LRLenny Rachitsky56:29

       Along those lines, I actually saw you somewhere in a talk or maybe something you wrote talk about how creating this class and creating the curriculum helped you crystallize your own thinking on product and helped you crystallize the mental models of becoming a product manager. Is there anything that you recall from that time of just like, "Here's something that's really helped me understand about this function and this skill," as you were putting together the class?

    5. AGAnneka Gupta56:51

       Yeah. I know any time you're teaching something, you have to figure out a way to synthesize it for another audience. And so many of us have learned product management just figuring it out on the job. Um, I don't know if there's, like, a particular framework that I would say came out of that. But what I found very interesting was seeing the questions that people asked in the class and then feeling like, "Oh, I understand the an- like, I understand how to answer this question. I can provide an example for it." And that was v- that was super interesting to me because, like, I didn't expect that coming out of the conversation. Yes, like there's frameworks we, we developed to talk about ideation and product discovery and all of that, but I think those are fairly flexible frameworks. Uh, what was, was most enlightening was being able to crystallize the answers to some of these questions, whether it was about, like, how do you interact as a PM effectively with engineering? Or how do you, um, how do you... Or like, what happens if the data shows you that, you know, it doesn't matter which direction you put, pick? Like, there's merits to both ways, how do you actually go about making those decisions? It, it was very interesting being able to then have those conversations with students and bring in the real life examples. And I found in some situations, I'd actually go back to my own team and share (laughs) the same answer-

    6. LRLenny Rachitsky58:08

       Mm-hmm.

    7. AGAnneka Gupta58:08

       ... that I, I came up with in class. I was like, "Oh, this is actually a valuable thing to share, share with my team back at-

    8. LRLenny Rachitsky58:13

       Mm-hmm.

    9. AGAnneka Gupta58:14

       ... uh, my company."

    10. LRLenny Rachitsky58:15

        It reminds me of the recent chat I had with this guy, Alex Komoroske, where he talked about how oftentimes talking with people helps them uncover new insights-

    11. AGAnneka Gupta58:23

        Yes.

    12. LRLenny Rachitsky58:23

        ... that he had in his head and then he writes them down. As soon as he says something that's really clever-

    13. AGAnneka Gupta58:27

        Yeah.

    14. LRLenny Rachitsky58:27

        ... in a new way, he's like, "Okay, I'm gonna remember that now." (laughs) Well, coming back to how to become a PM, so you see all these people getting in, taking this class, want to become product managers. I know they're like Stanford students and, you know, they have... People will more likely hire Stanford people. But I guess in terms of how they end up becoming PMs, what's, if you were to, like, look at the pie chart of the people that end up getting a PM job, what's, like, the biggest chunk? Is it they join at some other function and then move into product? Do they just join as a junior PM somewhere? Like, how are people actually getting into the PM role through, in that class?

    15. AGAnneka Gupta59:00

        Yeah. I think very few are directly going-

    16. LRLenny Rachitsky59:03

        Mm-hmm.

    17. AGAnneka Gupta59:03

        ... to an established company and becoming a PM directly. So, I would say a big chunk of them... Some of them are, but many of those then had PM experience to begin with or had engineering experience and then went to a technical company into a PM role. The vast majority of them are joining product adjacent roles or they're going to small startups where they might be doing product management, might be the first product manager or they might be doing product management plus plus, chief of staff, something like that where they get to put their hands on product management, uh, but it's a super small company. So I think those have been the two most successful paths to get into product.

11. 59:39 – 1:01:27

    Leveraging AI tools in product management

    1. AGAnneka Gupta59:39

    2. LRLenny Rachitsky59:40

       Awesome. That's a really interesting lens into how people actually get into this role. Potentially final question, but we'll see where it goes. Uh, I have this recurring segment on this podcast called AI Corner where I try to get a sense of just how people are finding AI tools useful in their work, in their life. So let me just ask you, is there anything you've found, uh, useful in some AI tool in how you work, like something you've found that helps you work more productively, more efficiently? Either you or people on your team.

    3. AGAnneka Gupta1:00:08

       One way that we're using AI today is summarizing our user research calls. So that has been really valuable because we're doing all these calls all the time. We're getting a ton of rich insights. Some of those rich insights are related to the specific project that we were doing this call for and some of them aren't. And now, we have that summarized and tagged in a way where we can look up, you can look up any sort of thing that you want around the calls that we've done, and it'll find you the call, it'll find you the context, it'll find you the transcript, and summarize exactly what we've learned from that, that call. So we're starting to use that more and more. It's a very powerful capability. I definitely think that that kind of summarization of information for PMs is a big unlock for, for organizations. And I think we're still in the very, very early days of AI making a meaningful difference to the way that PMs do their work.

    4. LRLenny Rachitsky1:01:01

       Is there a specific tool that you love to help you with that, that you may wanna-... give a shout-out to-

    5. AGAnneka Gupta1:01:06

       Sure.

    6. LRLenny Rachitsky1:01:06

       ... or is it something you guys built?

    7. AGAnneka Gupta1:01:08

       Yeah. Uh, we use Dovetail and it's been f- fantastic. Connects into all of the Zoom calls and everything, does a great job with, uh, summarization, with search, everything.

    8. LRLenny Rachitsky1:01:18

       Awesome. Uh, I love it when someone recommends a very awesome sponsor of the podcast. Dovetail is a, a ongoing and excellent sponsor, so I'm really happy to hear that.

12. 1:01:27 – 1:04:30

    The power of a positive mindset

    1. LRLenny Rachitsky1:01:27

       Amazing. Uh, Anika, is there anything else that you thought, you wanted to share, or that you wanna leave listeners with that you think might be helpful before we get to our very exciting lightning round?

    2. AGAnneka Gupta1:01:38

       The mindset that you bring to your work is actually the most important thing over anything else that you can do, and if you are approaching every situation as much as possible with a positive mindset, you can do more than you could ever possibly hope to achieve.

    3. LRLenny Rachitsky1:01:56

       I'm gonna pull on this thread 'cause this is such a powerful point, and I think it's easy to just hear that. It's hard to learn to do it. Do you have any advice on just, like, how to build that mindset? Like, uh, you know, it connects to many of the things you said. How can this be fun? How can I be grateful to this person that's annoying me and the things that, uh, they might teach me? Is there just anything that you've done that has helped you build this mindset?

    4. AGAnneka Gupta1:02:20

       Journaling is very powerful. So actually growing up, I journaled every single day of my life from when I was 13 to when I was 23, and while I cringe to go back to read any of those, I think what it helped me do and build a practice around that I still do today is when I have a lot of thoughts going through my head, especially negative thoughts, just putting them all down on a piece of paper or writing them on my phone, and trying to explore why. Why am I feeling this way? What is... Why am I getting triggered? What is it about this situation that's making me feel so strongly? And when I put it down on paper, then it takes this thing that's abstract and things that I'm ruminating on and actually makes it possible for me to break it down and understand, well, okay, this is something I may feel, but the why behind it is a little irrational, so I... let me let this go. I realize that this is an irrational way to think about this. Whereas other things, I start to uncover, well, what is it about the situation and what is it that I need to do differently? What's within my control and what is it maybe that I need to go, uh, talk to someone about and say, "Hey, I need you to do this differently to be able to make the... make, make myself feel better and make the situation better?"

    5. LRLenny Rachitsky1:03:34

       It's interesting. This is another thread that's been coming up a bunch on the podcast recently, that when something is bothering you or something is hard, the more you actually listen to that part of yourself and, like, dive into it and explore it and give it a s- space to share and talk, the less power it gets and the more space is created for the stuff you actually want to take space. There's... It's like it's count-... It's, uh, not what you would expect 'cause usually it's like, "No. Shut up. Everything's fine." But the more you actually hear that out, the easier things get. So, I love that you shared that. In general-

    6. AGAnneka Gupta1:04:08

       It's like doing cognitive behavioral therapy on yourself.

    7. LRLenny Rachitsky1:04:12

       Hm. Interesting.

    8. AGAnneka Gupta1:04:13

       That's how I think of it. I've never actually done cognitive behavioral therapy, but I've read a lot about it, and sometimes when I go through this, I'm like, asking myself the same questions that I think are asked in those settings.

    9. LRLenny Rachitsky1:04:23

       I love that. All right. Anika, is there anything else that you wanted to share or leave listeners with?

    10. AGAnneka Gupta1:04:29

        I think that's, that's

13. 1:04:30 – 1:08:35

    Lightning round

    1. AGAnneka Gupta1:04:30

       all I could think of.

    2. LRLenny Rachitsky1:04:31

       Well, with that, we've reached our very exciting lightning round. Are you ready?

    3. AGAnneka Gupta1:04:35

       I'm ready.

    4. LRLenny Rachitsky1:04:36

       All right. First question, what are two or three books that you've recommended most to other people?

    5. AGAnneka Gupta1:04:41

       The Hard Thing About Hard Things, uh, by Ben Horowitz. Such a great book. Great, again, about mindset of how to approach hard things. Um, second is I'm a huge fantasy sci-fi fan, so I love Brandon Sanderson's books, so I highly recommend those to people as well.

    6. LRLenny Rachitsky1:04:57

       I, uh... All I know about him is I saw videos of him after COVID where he just said, "I wrote, like, five new books during COVID." I was like, "What is going on?"

    7. AGAnneka Gupta1:05:03

       He is someone that is at the top of his craft, and I admire people so much that are, like, truly the elite in what they do, and he is truly the elite in what he does, and he writes a lot about writing. He podcasts a lot about writing. It's pretty impressive.

    8. LRLenny Rachitsky1:05:17

       And he writes fantasy books? Is that right?

    9. AGAnneka Gupta1:05:18

       He writes fantasy, yep.

    10. LRLenny Rachitsky1:05:20

        Okay, cool. Feels like a lot of books to read though. I'm just like, "Oh my God. So many books." Okay, great. Next question. Do you have a favorite recent movie or TV show that you have really enjoyed?

    11. AGAnneka Gupta1:05:31

        Again, on the fantasy sci-fi track, I really like Fallout, which is a dystopian show based on a post-apocalyptic, post-nuclear war, uh, world. Yeah. It's very entertaining.

    12. LRLenny Rachitsky1:05:42

        Yeah. It's just, like, very, uh, quirky and fun and-

    13. AGAnneka Gupta1:05:45

        Yes.

    14. LRLenny Rachitsky1:05:46

        ... and un- unexpected. Awesome. Do you have a favorite product that you've recently discovered that you really love?

    15. AGAnneka Gupta1:05:53

        My eight-foot iPhone charger. So I have a cord that's very long (laughs) that allows me to move around the house and do stuff while my phone is charging 'cause my phone is always running out of batteries, so hap- like, highly recommend getting a super long charging cord.

    16. LRLenny Rachitsky1:06:10

        I've got one of those and I know exactly what you mean. Do you have a favorite life motto that you often come back to, find useful, and work here in life?

    17. AGAnneka Gupta1:06:18

        I think it comes back to dealing with lots of different types of people. I really try to remind myself that everyone has something to teach and everyone has something to learn, and I think that helps not only, like, like, think about how you interact with other people, but also combat imposter syndrome because you have something to bring to the table and teach as well as anyone else, no matter what your age is, no matter what your background, and leaning into that and realizing that people can learn from you and you can learn from others in every single situation.

    18. LRLenny Rachitsky1:06:51

        Final question. I heard that you're a big fan of Isaac Asimov. Uh, do you have a favorite Asimov book, one that you think if someone were to explore his, his, uh, canon they might wanna start with?

    19. AGAnneka Gupta1:07:01

        I really like the Foundation series, so starting with that is, is really good. It's a very different style of writing, so you kind of have to stick with it, but it's good. I promise.

    20. LRLenny Rachitsky1:07:11

        Uh, and I will build on that and say, don't watch the show 'cause the show is so different from the book series. I don't know if you've seen it and-

    21. AGAnneka Gupta1:07:16

        Yes, I have.

    22. LRLenny Rachitsky1:07:17

        ... not nearly as good.

    23. AGAnneka Gupta1:07:17

        Yeah.

    24. LRLenny Rachitsky1:07:18

        Okay. I was just like, "What is going on?"

    25. AGAnneka Gupta1:07:19

        Yeah. Very different.

    26. LRLenny Rachitsky1:07:20

        "This is not the story."

    27. AGAnneka Gupta1:07:21

        (laughs)

    28. LRLenny Rachitsky1:07:21

        "What are they doing?" Amazing. Anika, this has been amazing. We covered so much ground. I feel like this is gonna help a lot of people. Two final questions. Where can folks find you online if they wanna follow up on things, maybe ask you questions, or just check out the stuff you're up to, and, uh, how can listeners be useful to you?

    29. AGAnneka Gupta1:07:37

        Uh, so you, you can find me on LinkedIn. Follow me, DM me. Would love to connect, and the way you can help me is we're actually t- redesigning our Stanford class right now for PMs, and I would love to hear from you if you haven't done any P- you know, don't have any PM experience. What is it that you wish a class could teach you? And that would be super helpful for me as we're redesigning this class. Thanks.

    30. LRLenny Rachitsky1:07:59

        Amazing. And the way they could share that is DM you on LinkedIn or Twitter?

Episode duration: 1:08:36