Becoming more strategic, navigating difficult colleagues, founder mode, more | Anneka Gupta

Anneka Gupta: 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 going to be easy to execute on.” And I think if you have one without the other, ultimately people are not going to see you as strategic.

Critical Mindset for Success

Lenny Rachitsky: Today my guest is Anneka Gupta. Anneka 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 Anneka Come on this podcast and you’ll soon see why.

In our conversation, Anneka 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 Anneka. 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 feature episodes and it helps the podcast tremendously. With that, I bring you Anneka Gupta. Anneka, thank you so much for being here and welcome to the podcast.

Manage Energy, Not Time

Anneka Gupta: Thanks for having me.

Operating in Founder Mode

Lenny Rachitsky: So, I want to 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?

Anneka Gupta: So it’s funny, before we kicked this off, you talked about the post-it that you have on your computer that says have fun. My one mindset 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. 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 going to figure out a way to have fun with this,” it actually changed my entire for how to deal with super difficult situations.

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 going to manage and at first I felt so scared by what was ahead of me and how much change I was going to 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 across where I’m faced with something super, super challenging.

Founder Mode as a Product Leader

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

Anneka Gupta: I think there were a couple of things that I did 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 situations where I was trying to figure out how to collectively solve some big challenge, figuring out how to bring humor into the meeting. Just starting it on a light note and that elevated my own 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.

Replacing Negation with Questions

Lenny Rachitsky: 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 people make it out to be and we could just have a little fun with this thing. It doesn’t have to be like we’re not curing cancer.

Anneka Gupta: Yeah, definitely I think that helps. Reflecting 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 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 so that I can have that mindset to look at things more broadly versus operating from a place of scarcity. That may come down to simple things like making sure that I have lunch. Sometimes when things get so busy you’re like, “Oh, I’m just going to grab a protein bar and I’m going to skip lunch.” But I found that that really decreases my energy.

Or, trying to do things that are really difficult late in the day. Five to 6:00 PM is my worst time of day and I know that about myself, so I’m not going to schedule in my most difficult meeting or writing up a strategy deck or something for that period of time because I know that that’s not going to be my best and it’s actually going to make it more difficult for me to get the work done. Being able to manage 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.

What It Means to Be Strategic

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I’m going to go in a totally different direction. 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 mode post. And he had some really interesting takes on 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?

Anneka Gupta: 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 talked to were like, “Oh yeah, I recognize this.” I recognize people that I’ve worked for, 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.

The Wisdom of “A Little Better”

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

Anneka Gupta: So, I think when a founder’s in founder mode 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 totally new area. Now I think the way to use that effectively as 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 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 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, we have this huge opportunity and 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. I think one aspect. The second aspect is, which often happens, it’s very difficult for many people and I’ve had this happen to me many times, is when a founder is 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 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? 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 have explored these three other options instead.” And that can help you and 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 really want to go after this opportunity. It’s my pet project.” Then you have to decide as a head of product, do I really want to fight this or do I just give in on this, let it go? And also make sure that we get the stuff done that’s most important to the company. You have to make that judgment call as a head of product and decide what is really going to make or break the company. What’s the hill that I’m going to die on and is this something that I can shift or is this something that 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 where the founder has been like, “Hey, I really want to go in this direction and I haven’t agreed, at least with what we’re trying to go after, regardless of the mechanism behind it.”

Practical Approaches to Synthesizing

Lenny Rachitsky: 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 have the founder go in there, tell everyone, “Hey, we’re going to do this thing differently.” It’s such like 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, 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’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?

Anneka Gupta: Yeah, I think it’s often easy as a leader to say, “I’m not going to 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.” 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 want to 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 either very significant course correction or a small course correction. 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 the work that they’re doing or trying to re-adjudicate a decision, one, is how do I get in there early?

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 suggestion. 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 there 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 dismissing the work that they’ve done.

I pick a strategic set of areas. So I think about what is most important for the business? What’s going to 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 that? 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 why this is right for the business, why is this going to 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.

Creating a Fault-Tolerant Culture

Lenny Rachitsky: So in that example, and I love this tactic, you have your team come in, you ask them, “Tell me what the strategy is for this thing that you’re working on.” What you’ve seen work is instead of like, “No, this is broken, this is wrong, this isn’t going to work.” Your approach is ask questions and hope that they see the flaws or gaps. Is that how-

Anneka Gupta: Yeah, it’s ask questions, but you can’t always lead someone somewhere with asking questions. It’s also sharing a hypothesis. So I might have a particular hypothesis about the business where I might see 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.”

It actually opens a whole discussion where I’m still able to provide my perspective and point of view but not completely shut down the discussion. Because what I always worry about is a leader is I’m going to come in and say something, and because I’m one of the more senior people in the room, no one is going to say if they have a concern. And the reality is I’m not always right far from it, but I want to be able to 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 discussion.

Navigating Difficult Colleagues

Lenny Rachitsky: Speaking of strategy, you shared with me that 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 and the way you think about strategy. What did you end up with recognizing as being strategic? What is that in your work and in your research? And then how did you actually get better at this work of being strategic?

Anneka Gupta: I 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. 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 going to be easy to execute on.”

And I think if you have one without the other, ultimately people are not going to see you as strategic. If you’re really good 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 going to be seen as strategic either. So, that’s the formula that I’ve come up with. 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 a 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?

Giving and Receiving Candid Feedback

Lenny Rachitsky: 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 a project you worked on or a product you built?

Anneka Gupta: I can take some recent examples. We’ve been doing a lot of strategic planning for where do we want to 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 business, and one of the ways that I’ve exhibited this, 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 a really big idea out of thin air. So these things can be very challenging. The first step that I found as very useful, and I use this tactic every single day in meetings, is just summarization. So, 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 is happening. Is this correct or do we actually need to do another turn because we don’t all agree with where we’re landing here?” 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 effective summarization as strategy. So I think that’s one element. 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 right in the meeting, sometimes in the meeting too I guess, is how do I make this idea one click better? It’s not about how do you do something radically, radically different, but taking ideas and then making it slightly better, slightly better.

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 going to 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 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.

Real Examples of Receiving Difficult Feedback

Lenny Rachitsky: 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 Roger Martin on the podcast where 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 huge with a big strategy and vision, and 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 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 picking one thing and making it one click better. There’s going to be an episode that comes out right before this with Alex Komoroske, and he has this concept of the adjacent possible and it’s just 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, that’s not a question.

Anneka Gupta: That totally resonates though.

How to Deliver Difficult Feedback

Lenny Rachitsky: Okay, okay. Okay, great. And then the summarization idea, I love it. So tactical, basically any PM can do this just in a meeting just like, “Okay, let me just summarize 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.” So I totally see the power of that in my experience.

Anneka Gupta: 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.

Transitioning from Engineering to Product Management

Lenny Rachitsky: If someone wants to work on this skill of summarizing as kind of a tactic, can you give just an example of how you would do that? Is there like a phrase to use? Is there words or an example you could give of just like here’s how it would look in a meeting?

Anneka Gupta: Yeah. 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 our customers are having these kinds of challenges. We feel like this is the way that we want to solve these challenges. We have a right to win in this way and therefore we’re going to take this action.

Is everyone in agreement with that or is there some dissent about whether that’s an accurate portrayal of where we’ve landed with this conversation? That’s the way I’ll frame it up and again, ending it on a question so that you’re not coming in and just being like, “Hey, this is where we’re at.” But then inviting people to discuss and say “Yes,” or “No, I agree with 90% of that or 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.

Common Misconceptions for New PMs

Lenny Rachitsky: And then you experience is just doing that makes you look more strategic and gives people the impression you’re thinking strategically?

Key Insights Gained from Teaching

Anneka Gupta: Yes. Yeah.

Lenny Rachitsky: Awesome.

How to Actually Break into PM

Anneka Gupta: The other way you can 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 point of view, you can do that. In Zoom you can also use a chat. I’ve done that very effectively and said, “I’m not going to interrupt the flow conversation. I’m just going to summarize in Zoom chat this is what I’ve heard, and this is what I think we’re saying in this conversation.” And then sometimes that’ll get invited back into the broader conversation that’s happening live on the Zoom itself.

Lenny Rachitsky: That’s a much lower stakes way of doing it, and I’m picturing all the PMs listening to this, they’re going to start doing this and there’s going to be all these summaries now in Zoom chats and everyone will be like, “Oh my God, why is everyone sharing?”

AI Corner: Using AI Tools at Work

Anneka Gupta: And then Zoom AI will start just doing it all for you. Then we’ll have to think again.

Lenny Rachitsky: And then PMs are over and AI replaced us all.

Mindset and Personal Growth

Anneka Gupta: Yes.

Lightning Q&A Session

Lenny Rachitsky: 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 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 going to think you’re not strategic.

Anneka Gupta: Yep.

Lenny Rachitsky: Awesome. Okay. 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.

Anneka Gupta: Yeah, 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. 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 did and why? What was the perception of different people in the organization? I tried to construct this 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 it 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.

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 will bring up and I’ll be like, “Tell me about this project. 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 going to 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 going to come and say, “Well, we’ve tried that before.” Especially you’ve been at an organization that’s been around for a while.

Lenny Rachitsky: I’ve been that guy. We’ve done this so many times. It didn’t work. Why are we thinking about this again? Okay, so the advice is if you’re new to a company especially, just study the past decisions that were made and share them out as a part of that and then as a side effect, it’ll help you make better decisions because you’ll have this history about what the company has done. I love that. Along the same lines of decision-making, I asked your former colleague Rachel Wolan 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. That’s like the things she remembered about you most, that parting advice. Talk about why that is so important and your insight there.

Anneka Gupta: 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 that you were always operating off of imprecise information as a product leader. What I’ve found is that once you commit to a decision, you actually learn more post committing to that decision about what’s going to work and not going to work, and you 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, 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 a big believer in making decisions…

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 form of that. 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.

Lenny Rachitsky: 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 Anneka is going to be like, “You messed up here. You’ve shipped the wrong thing here. It didn’t work.” 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?

Anneka Gupta: 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 series of hypotheses and assumptions that we’re making that are informing the decision. So it might be a hypothesis that this segment of customers is going to be willing to pay for this product because it’s solving an urgent and important enough need for them that they’re going to go do it and this is the evidence we have to find it, but this is also the stuff we don’t know.

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 our hypothesis was actually not true, and we learned all of this after the fact.” I think the way to make a culture of risk taking and people willing to make these bets and go out on a limb is to reward the learning versus the outcome. 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. Even in making this bad decision, we learn something about our customers or our business that we otherwise wouldn’t have learned that we can use in another context.

Lenny Rachitsky: 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. Two, I was just at a talk with Zuck. He’s being interviewed at the Chase Center, the Acquired Podcast at this whole event, and his main thing that he talked about 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. Is there an example of something you worked on where you did that, where you kind of ship something that you weren’t fully confident in and you learn faster?

Anneka Gupta: Yeah, I mean, I think there’s a lot because anytime you’re shipping products, there’s so many different things that could go right and wrong. 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 have 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 that 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.

And so now I think now what I’ve taken from that is really know how you’re going to sell something and who’s going to 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 going to get zero adoption because no one in your organization is ready to sell it. So there’s tons of stuff like that where it’s like been okay, yeah, we’ve learned something from this, and it’s not all throwaway, it just means that we’ve got to do something differently for this product and we need to do something differently for our organization going forward.

Lenny Rachitsky:

I want to come back to something Rachel also shared with me when asked her what questions to ask you. By the way, first of all, she spent a lot of time raving about how amazing you are first. That was the first 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 showed 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 very low ego. She wanted me just to ask you for what you’ve learned about how to navigate very difficult personalities and help people align when it’s not neatly what they want to do.

Anneka Gupta: I try to embody the mindset of feeling like and believing that I can work with anyone. 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 is it that they really care about? Hopefully they care about something deeply about the company and making the company successful. Sometimes 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 need from them important? And trying to make that match of they have this desire kind of like building a product, they have this desire and how am I going to get them to care about the thing that I want to care about?

The other thing I do is instead of feeling like anger or frustration with the person and instead trying to shift that to a mindset of feeling gratitude and a positive emotion about them is I look at them and I ask myself what can I learn? Maybe I don’t want to adopt their personality or operate the way that they are operating, but everyone has something that they can teach you, 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 can 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.

Lenny Rachitsky: I love that this connects with your other original piece of advice of just turning something into this is going to be fun. Let’s make this fun. And in this case it’s like make it great. What can I learn from this person even though they’re really annoying me and it’s frustrating and don’t want anything done? Then your other point of understanding what they want and 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”?

Anneka Gupta: 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 and or you’re successful working for that person, you probably understand what makes them tick. So that’s one, or 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.

Lenny Rachitsky: I love that. 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 connect what they want with the thing you’re trying to achieve. Beautiful. I really love this idea of when you’re frustrated by someone just reframing it to like, “I’m grateful I’m going to learn something from this person in our interaction, even though they’re making life hard for me.” I really love that. Another skill I hear you’re really strong at, and this comes from another one of your colleagues, Hema Mohan shared that you’re world-class at giving feedback, giving hard feedback, and receiving hard feedback. And so I want to 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 from either direction, what have you learned about receiving hard feedback or giving hard feedback where someone actually hears Zoom doesn’t get defensive?

Anneka Gupta: The answer is so much, I’ve learned so much from it. So maybe I’ll start with receiving feedback. 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 going to feel. Sometimes that’s an emotional feeling, sometimes that means I want to step out of the room or it depends on who I’m talking to, but let myself feel the things that I’m going to feel. 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, okay, well where is this feedback coming from? Why am I getting this feedback?

And try to be super curious about it. And that might be going back to the person that gave me the feedback and maybe asking someone that’s a peer somewhere in the organization that might have more context and flavor to what the feedback really is, just trying to learn. 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. Going through that process and letting myself ride the emotional wave and not judging myself for that, but then not reacting and letting myself then figure out and come back curious. 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 hearing what they say.

Lenny Rachitsky: So the advice is feel it, 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 heuristic of like I should actually pay attention to this deeply or just like let me wait for more data points?

Anneka Gupta: Yeah, I think in product you receive feedback all the time for your organization or for yourself, and you can’t make everyone happy. Everyone wants a different thing from product. So I think this comes up quite often 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 for me and for my team at this point in time?” There’s stuff that is a must-have on that list, and there’s stuff that’s nice to have. Sometimes there’s just too many must-haves to go deal with the nice-to-haves and you have to just be like, well, I know this is a problem, or I know we could be 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 going to help my organization deliver what it needs to for the company and for the business overall.

Lenny Rachitsky: 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 that you’re like, “Ugh, that sucks”? Either earlier in your career or more recently, anything else come to mind?

Anneka Gupta: I mean all the time. So there’s always hard stuff. Well, people will give feedback of, “Oh, 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?” Or-

Lenny Rachitsky: Never heard that one before.

Anneka Gupta: Never heard that one before, right? Or 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 going to go follow that path. There’s always something that people have negative feedback about and sometimes I’m like, “Okay, this is an eye roll.” 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. I don’t know, some of the things cut deeper than others, but I think people are making 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. Anneka isn’t listening.” Things like that cut deep and are a lot more… I know like physiologically they make me kind of seize up a little bit, but again, then I try to feel the things I’m going to 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 actually is?

Lenny Rachitsky: Awesome. Okay, and then we were going to 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, “It’s not real.”

Anneka Gupta: 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. 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. Then I think the other piece is that you’ve got to be direct.

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 change the way you’re being perceived or to change the outcomes of what you’re driving or become more strategic or whatever it is that I’m trying to give feedback on. I do a lot of prep before I give someone a lot of feedback. I really think about how can I frame this in a way that’s going to 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. 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.”

Lenny Rachitsky: This reminds me of Radical Candor. Basically make people feel like you care deeply about them, but be very direct about what they can be doing better. Are there phrases or ways that you set up the conversation? 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 come back to often of just a way to start the conversation?

Anneka Gupta: Yeah, I think what I started with is like, “I care a lot about you. You have a lot of potential. I can see you doing these kinds of things. I can see you getting to where you want to go in your career.” Sometimes I even start the conversation by asking them, “What do you want to do? Where do you want to go in your career?” And that will help me frame up which of these things are important. Because honestly, if someone wants to be eventually like a CPO, the feedback I’m going to give to them is very different than if they’re like, “Hey, I don’t really want to manage people ever. I just want to be the best I see I can ever be.” I’m not going to 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.

I think that has really helped as well make sure that I focus on the things that are going to really matter. During the feedback conversations, I also try to frame things as this is how you’re being perceived than 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, what are ways that we can change the perception?” I also think it’s important because sometimes people are like if you say, “Hey, I don’t think you’re X,” and then they’re like, “Well, yes I am.” And if you’re saying, “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 actually how they’re trying to show up is different than how people are perceiving them. You can have a better conversation then around, “Well, what can you do to change that perception?”

Lenny Rachitsky: You mentioned I see product managers, and this is a good segue too. 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. I want to ask a couple of 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 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?

Anneka Gupta: 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 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. 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 being a product manager.

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 perspective. If you come from the engineering side, but you understand how the product is built and you understand that technical nuances of that well, that can also be a valuable way to enter into the product team. That way, even though you don’t have the direct product experience, you’re still bringing something to the table where you are going to have to get trained on core product management, but you’re not going to have to be totally trained on the business or the technology.

Lenny Rachitsky: 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 in some form?

Anneka Gupta: Yeah, I think join a product adjacent function, 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 into the product world from there.

Lenny Rachitsky: Ideally there’s something within the company, there’s 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 there you’re just like should you talk about this in your interview just like, “Hey, I would 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?

Anneka Gupta: Well, I think it depends. For instance, when I joined LiveRamp, which was my previous company as a software engineer, I actually did say in the interview process I want to 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 5000-person company, you’re hiring manager is probably not going to receive it well if you’re like, “Hey, I’m interviewing for product marketing, but really what I want to do is go into product.” So, it just kind of depends on the company and the stage. 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. Really taking initiative to do that so that you can find an inroad into product management.

Lenny Rachitsky: 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, then 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?

Anneka Gupta: 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 going to have to use?” What was surprising 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. 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 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 want to go and thinking that they need to learn some tools or process versus the mindset and the skills required to clarify ambiguity.

Lenny Rachitsky: 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 like here’s something that’s really helped me understand about this function and the skill as you were putting together the class?

Anneka Gupta: Yeah, I know anytime 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. I don’t know if there’s 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 how to answer this question. I can provide an example for it.” That was super interesting to me because I didn’t expect that coming out of the conversation. Yes, there’s frameworks we developed to talk about ideation and product discovery and all of that, but I think those are fairly flexible frameworks.

What was most enlightening was being able to crystallize the answers to some of these questions, whether it was about how do you interact as a PM effectively with engineering or what happens if the data shows you that it doesn’t matter which direction you pick, like there’s merits to both ways. How do you actually go about making those decisions? 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 that actually go back to my own team and share the same answer that I came up with in class, I was like, “Oh, this is actually a valuable thing to share with my team back at my company.”

Lenny Rachitsky: 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 that he had in his head and then he writes them down as soon as he says something that’s really clever in any way. He’s like, “Okay, I’m going to remember that now.” Coming back to how to become a PM, so you see all these people getting and taking this class want to become product managers. I know they’re like Stanford students and people more likely hire Stanford people. But I guess in terms of how they end up becoming PMs, if you were to look at the pie chart of the people that end up getting a PM job, what’s 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? How are people actually getting into the PM role in that class?

Anneka Gupta: Yeah, I think very few are directly going 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 in product management, but it’s a super small company. So I think those have been the two most successful paths to get into product.

Lenny Rachitsky: 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. 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 useful in some AI tool in how you work? Like something you found that helps you work more productively, more efficiently, either you or people on your team?

Anneka Gupta: 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 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 call. So we’re starting to use that more and more. It’s very powerful capability. I definitely think that that kind of summarization of information for PMs is a big unlock 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.

Lenny Rachitsky: Is there a specific tool that you love to help you with that that you may want to give a shout-out to or is it something you guys built?

Anneka Gupta: Yeah, we use Dovetail and it’s been fantastic. Connects into all of the Zoom calls and everything, it does a great job with summarization, with search, everything.

Lenny Rachitsky: Awesome. I love it when someone recommends a very awesome sponsor of the podcast. Dovetail is ongoing and excellent sponsor, so I’m really happy to hear that. Amazing. Anneka, is there anything else that you thought you wanted to share or that you want to leave listeners with that you think might be helpful before we get to a very exciting lightning round?

Anneka Gupta: 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 the positive mindset, you can do more than you could ever possibly hope to achieve.

Lenny Rachitsky: I’m going to pull on this thread because 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 how to build that mindset? Like 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 they might teach me? Is there just anything you’ve done that has helped you build this mindset?

Anneka Gupta: 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, writing them on my phone and trying to explore why am I feeling this way? Why am I getting triggered? What is it about the 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 let me let this go.” I realize that this isn’t rational 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 talk to someone about and say, “Hey, I need you to do this differently to be able to make myself feel better and make the situation better.”

Lenny Rachitsky: 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 dive into it and explore it and give it a 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. It’s not what you would expect because 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 share that.

Anneka Gupta: It’s like doing cognitive behavioral therapy on yourself. 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 asking myself the same questions that I think are asked in those settings.

Lenny Rachitsky: Love that. All right, Anneka, is there anything else that you wanted to share or leave listeners with?

Anneka Gupta: I think that’s all I can think of.

Lenny Rachitsky: Well, with that, we’ve reached our very exciting lightning round. Are you ready?

Anneka Gupta: I’m ready.

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

Anneka Gupta: The Hard Thing About Hard Things by Ben Horowitz, such a great book, great again about mindset of how to approach hard things. Second is I’m a huge fantasy sci-fi fan, so I love Brandon Sanderson’s books. I highly recommend those to people as well.

Lenny Rachitsky: All I know about him is I saw videos of him after COVID where he just said, “I wrote five new books during COVIID.” I was like, “what is going on?”

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

Lenny Rachitsky: And he writes fantasy books, is that right?

Anneka Gupta: He writes fantasy, yep.

Lenny Rachitsky: Okay, cool. It 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’ve really enjoyed?

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

Lenny Rachitsky: Yeah, it’s just very quirky and fun.

Anneka Gupta: Yes.

Lenny Rachitsky: And unexpected. Awesome. Do you have a favorite product that you’ve recently discovered that you really love?

Anneka Gupta: My eight-foot iPhone charger. So I have a cord that’s very long that allows me to move around the house and do stuff while my phone is charging because my phone is always running out of batteries. So, highly recommend getting a super long charging cord.

Lenny Rachitsky: 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 during life?

Anneka Gupta: 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. I think that helps not only 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.

Lenny Rachitsky: Final question. I heard that you’re a big fan of Isaac Asimov. Do you have a favorite Asimov book, one that you’d think if someone were to explore his canon, they might want to start with?

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

Lenny Rachitsky: And I’ll build on that and say, “Don’t watch the show because the show is so different from the book series.” I don’t know if you’ve seen it and-

Anneka Gupta: Yes, I have.

Lenny Rachitsky: … not nearly as good.

Anneka Gupta: Okay.

Lenny Rachitsky: I was just like, what is going on? This is not the story.

Anneka Gupta: Yeah, very different.

Lenny Rachitsky: What are they doing? Amazing. Anneka, this has been amazing. We covered so much ground. I feel like this is going to help a lot of people. Two final questions, where can folks find you online if they want to follow up on things, maybe ask you questions or just check out the stuff you’re up to and how can listeners be useful to you?

Anneka Gupta: You can find me on LinkedIn, follow me, DM me. I would love to connect. The way you can help me is we’re actually redesigning our Stanford class right now for PMs, and I would love to hear from you if you 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.

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

Anneka Gupta: Yes.

Lenny Rachitsky: Easy. Amazing. Anneka, thank you so much for being here.

Anneka Gupta: Thanks for having me.

Lenny Rachitsky: Absolutely. My pleasure. Bye everyone.

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