YouSaid · the spoken record

Anneka Gupta

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69
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2024-10-17
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2024-10-17
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  1. “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 Rubric 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 like a really big idea out of thin air. So these things can be very challenging. The first step that I found is very useful. And I use this tactic every single day in meetings is just summarization. So hearing, bringing people together, lots of different voices into a room and hearing what they have to say and at various times in the conversation summarizing what people are saying and”

    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. “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've focused a lot on how do I make sure I do both of these things? How do I champion a few things that are really big ideas that are going to help change the direction of the company? And then how do I articulate that in a simple and compelling way?”

    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 got this feedback once in a performance review, and then I actually got it as well a few years ago when I was interviewing for head of product roles. And I thought I had made a lot of progress on it. But when I reflected back, I think it actually all came back to the same themes, which was, I think when people say I want someone that's strategic, what they're really saying is I want someone that can come up with and articulate a compelling and simple why behind the decisions and the direction of the company and product. So that's number one. And the second piece is I want someone that's going to champion and be a change agent to do things that may be hard, but actually best for the long-term interest of the product or company, even though those things are not 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...”

    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. “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.”

    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. “Yeah, it's ask questions, but it's not always. 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 say something like, well, I was talking to security leaders in our customer advisory board recently and I heard this piece of feedback. And this is what it made me think about our strategy. What do you think about that? And then let them say like, okay, yeah, actually I see this or maybe I have some follow-up questions. And it actually opens a whole discussion where I'm still able to point, provide my perspective and point of view, but not completely shut down the discussion. Because what I always worry about as a leader is I'm 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 in a”

    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. “Where I actually think I need to go in. Rallied the troops around making that stuff happen, if that is what is essentially right. And I'll have all the context because I've asked all the questions of like why this is right for the business. Why is this 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”

    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. “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. And what I've found is that understanding the details of the business and asking questions and understanding to the utmost extent you can what's working, what's not, what are the financial goals of the business? Are we on track to get there? How are we making decisions, getting into that level of depth is super important? And then you can decide as a leader what do you want to do with that information? So there's a lot of information that I collect about what's happening in the organization, 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 an understanding the depth and what is happening, I can decide.”

    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. “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 like the mechanism behind 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

  9. “Important to the company. You have to make that 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. Those situations where”

    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. “Strategy that's quite important for the company. So having a really deep understanding about why they are asking this? What are they ultimately trying to get at? And what is the objective that they're trying to get at? And is this the right way to get at it? And if the answer is no to that, then you can go have a conversation. If you know what the objective is, you can go have a conversation with that founder and say, hey, look, I know this is what you're trying to do, but maybe instead of looking at option A here of how we go about tackling this, we should have explored these three other options instead. And that can help you can help navigate that conversation. Now sometimes it's difficult to even get to that kind of understanding of the objective because someone might be just super set in their ways of, hey, I'm going to go. 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, you know, give in on this, let it go, and also make sure that we get the stuff done that's most.”

    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. “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. So I think that's one aspect. The second aspect, which often happens at very difficult for many people and have had this happen to me many times, is when founders 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.”

    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. “So, I think when a founders and founder mode, what they are doing, and if they're doing it well, what they're doing is really deeply understanding the business and then figuring out when to use their power as a founder to either tweak things and send something in a slightly different direction or fundamentally innovate and completely change directions or completely innovate in a 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 an initiative done or get work done in the company. And as having a founder that can effectively”

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

    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. “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. That has been able to kind of 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.”

    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. “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 situations so that I can have that mindset to look at things more broadly versus operating from a place of scarcity. And that may come down to like simple things like making sure that I have lunch. 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, 5 to 6 p.m. is my worst time of day. And I know that about myself. So I'm not going 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

  16. “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 bringing, I was trying to figure out how to collectively solve some big challenge, figuring out how to bring humor into the meeting and just starting it on a light note. And that elevated my own 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?”

    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. “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 open my mind up to so many more opportunities. So now I try to embody that in every situation that I come up across where I'm faced with something super, super challenging.”

    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. “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. And 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. And the reason why I say that is because when you're hit with really hard times, it's easy to operate from a mindset of scarcity and to look at everything as an unachievable hurdle to overcome. And when I was able to switch my mindset and say, well, I'm actually going to figure out a way to have fun with this. It actually changed my entire approach for how to deal with super difficult situations. And this advice specifically came up to me when I had a scenario where I had to essentially change out all of my direct reports in very short order. And I've 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.”

    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. “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.”

    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