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Anneka Gupta

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2024-10-17
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2024-10-17
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  1. So, 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 redesigning our Stanford class right now for PMs. And I would love to hear from you if you haven't done any, 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  2. I really like the foundation series. So, starting with that 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  3. 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 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  4. 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

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  5. 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. Very entertaining.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  6. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  7. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  8. 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 like asking myself the same questions that I think are asked in those settings.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  9. 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 it within my control? And what is it maybe 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  10. 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 cringed to go back and 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, why am I feeling this way? 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 let me let this go. I realize that this is an irrational.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  11. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  12. Something you guys built. Yeah, we use Dovetail and it's been fantastic. Connection to all of the Zoom calls and everything does a great job with summarization, with search, everything.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  13. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  14. 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

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  15. How do you like what happened if the data shows you that 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 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  16. 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 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 how to answer this question. I can provide an example for it. And that was super interesting to me because I didn't expect that coming out of the conversation. Yes, like 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 like, how do you interact as a PM effectively with engineering or how do you

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  17. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  18. 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? 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. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  19. Projects for sure that our 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

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  20. Well, I think it depends. So, 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 5,000 person company, your 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. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  21. Yeah, I think join a product adjacent function, which honestly pretty much every function is product adjacent because what function does product non-engage with? But as closely product adjacent as possible, and then find your way into the product word from there.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  22. 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, will you understand how the product is built and you understand the 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 going to have

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  23. 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. 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 being a product manager. You're coming from the sales side, you're coming with a knowledge.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  24. 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 person? I also think it's important because sometimes people are like, well, if you say, hey, like, I don't think you're ex. 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 what they want to 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

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  25. Yeah, I think what I started with is like, I care a lot about 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, you know, if someone wants to be eventually a CPO, the feedback I'm going to give to them is very different than if they're like, hey, you know, like, 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. And 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, then you are doing

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  26. 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 the outcomes of what you're driving or become more strategic or whatever it is that I'm trying to give feedback on. And 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 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

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  27. 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 got to 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  28. But again, then I try to feel the things I'm going to feel and try to understand why they are 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  29. 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 reason that we're not going to go follow that path. Like 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. So I don't know. Some of the things cut deeper than others, but I think people are making personal statements about my team or their feeling like, hey, the pride team isn't listening to feedback or the pride team has a bad culture, like Annika isn't listening, things like that, cut deep and are a lot more. I know like physically or physiologically they make me kind of seize up a little.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  30. 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 from my team at this point in time? 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 can 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  31. So that has going through that process and like 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. 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 hearing what they say.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  32. And 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. 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 try to be super curious about it. And that might be going back to the person I gave me the feedback and asking and maybe asking someone that's a peer or somewhere in the organization that might have more context 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  33. And there is so much. I 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 reading it in a employee survey or you're receiving it in a one-on-one from a direct report or from a manager, from a peer. I try to let myself just feel the things that I'm going to feel.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  34. 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 you're successfully successful working for that person, you probably understand what makes them tick. So that's one or work, but 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  35. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  36. 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? And 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,

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  37. 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, a difficult personalities come in all shapes and sizes and forms is I really try to understand what drives that person, what really, 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 like 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'm going to care about?

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  38. Within our own organization. I've made that mistake many times, actually. And so 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 can, 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  39. 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. 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 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 always should monetize this, but then we realized 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 personas problem, but then we misunderstood how easy it was going to be to go sell to that new persona.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  40. Of risk taking and 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 learn something about our customers or our business that we otherwise wouldn't have learned that we can use in another context.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  41. 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 of an 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. 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 hypothesis was actually not true. And we learned all of this after the fact. And I think the way to make a culture

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  42. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  43. 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 are always operating off of imprecise information as a product leader. And what I 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 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  44. 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. 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 an organization that's been around for a while.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  45. Yeah, so I was at my previous company for 11 years, so I kind of ended up becoming the historian. And when I joined rubric 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 had, we did, and why, what was the perception of different people in the organization. And 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, didn't matter, so that I could better understand how to make decisions going forward.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  46. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  47. 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 we have, you know, 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? And 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 what we're at, but then inviting people to discuss and say yes or no, I agree with 90% of that, but 10% or 10% off. And that helps move the conversation forward because sometimes.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  48. 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.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  49. And 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 were going and pursuing overall as a company and also the quality of the strategic thinking that I can bring to the table.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source

  50. 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? 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 I in the meeting too, I guess, is how do I make this idea one click better? And it's not about how you do something radically, radically different, but taking ideas and then making it slightly better, slightly better. And there are ways.

    2024-10-17 · Lenny's Podcast · Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik) · IDENTIFIED FROM THE TRANSCRIPT · source