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Anneka Gupta is the Chief Product Officer at Rubrik, a leading B2B cybersecurity company. She previously spent 11 years at LiveRamp, where she was the President and Head of Product and Platforms leading product development and go-to-market operations and strategy. Anneka also sits on the board of directors for Tinuiti and teaches product management at Stanford University. In our conversation, we discuss: • Navigating “founder mode” dynamics in organizations • Navigating difficult personalities and aligning teams • The PM skill of summarization • Giving and receiving hard feedback effectively • The value of a positive mindset • Tips for breaking into product management • Much more — Brought to you by: • The Enterprise Ready Conference — For B2B leaders building enterprise SaaS: https://www.enterprise-ready.com/ • Command AI — AI-powered user assistance for modern products and impatient users: https://www.command.ai/lenny • Eppo — Run reliable, impactful experiments: https://www.geteppo.com/ Find the transcript at: https://www.lennysnewsletter.com/p/becoming-more-strategic-anneka-gupta Where to find Anneka Gupta: • X: https://x.com/annekagupta • LinkedIn: https://www.linkedin.com/in/annekagupta Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Introduction to Anneka Gupta (01:43) Key mindsets for success (05:30) Managing energy for optimal performance (09:05) Founder mode (18:26) Becoming more strategic (27:54) The importance of decision-making (37:18) Navigating difficult personalities (41:38) Techniques for giving and receiving feedback (51:01) Transitioning into product management (54:56) Advice for aspiring product managers (59:39) Leveraging AI tools in product management (01:01:27) The power of a positive mindset (01:04:30) Lightning round Referenced: • Founder Mode: https://paulgraham.com/foundermode.html • Building a long and meaningful career | Nikhyl Singhal (Meta, Google): https://www.lennysnewsletter.com/p/building-a-long-and-meaningful-career • The Skip community: https://www.linkedin.com/company/skip-community/ • Rubrik: https://www.rubrik.com/ • 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): https://www.lennysnewsletter.com/p/the-ultimate-guide-to-strategy-roger-martin • Playing to Win: How Strategy Really Works: https://www.amazon.com/Playing-Win-Strategy-Really-Works/dp/142218739X • Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske: https://www.lennysnewsletter.com/p/unconventional-product-advice-alex-komoroske • Acquired podcast interviews Zuckerberg in San Francisco: https://transistor.fm/acquired-live/ • Hema Mohan on LinkedIn: https://www.linkedin.com/in/hemamohan/ • Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity: https://www.amazon.com/Radical-Candor-Kick-Ass-Without-Humanity/dp/1250103509 • Radical Candor: From theory to practice with author Kim Scott: https://www.lennysnewsletter.com/p/radical-candor-from-theory-to-practice • LiveRamp: https://liveramp.com/ • Product Management class at Stanford: https://www.gsb.stanford.edu/experience/learning/experiential-learning/action-learning-program/product-management • Figma: https://www.figma.com/ • Dovetail: https://try.dovetail.com/ • The Remarkable Advantage of Abundant Thinking: https://review.firstround.com/the-remarkable-advantage-of-abundant-thinking/ • The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers: https://www.amazon.com/Hard-Thing-About-Things-Building/dp/0062273205 • Brandon Sanderson’s books: https://www.amazon.com/stores/Brandon-Sanderson/author/B001IGFHW6 • Fallout on Prime Video: https://www.amazon.com/dp/B0CN4HV16N • Thunderbolt 4 ( 3-meter cable): https://www.apple.com/shop/product/MW5H3AM/A/thunderbolt-4-usb%E2%80%91c-pro-cable-3-m • Isaac Asimov: https://en.wikipedia.org/wiki/Isaac_Asimov • The complete Foundation series: https://www.amazon.com/Complete-Asimovs-Foundation-Foundations-Prelude/dp/B01EFDEMS8 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed.
Anneka Gupta discusses what it truly means to be strategic in a business context. She emphasizes the importance of articulating a compelling rationale behind decisions and championing necessary changes for long-term success, even when they are difficult to implement. This segment sets the stage for understanding the mindset required for effective leadership.
"when people say I want someone that's strategic what they're really saying is I want someone that can come up with an articulate a compelling and simple why behind the decisions and the direction of t..."
Anneka shares her personal approach to maintaining a positive mindset at work, even during tough times. She highlights the significance of reframing challenges as opportunities for fun and learning, which can transform one's perspective and enhance problem-solving capabilities. This mindset shift is crucial for navigating difficult situations effectively.
"Gupta anuka thank you so much for being here and welcome to the podcast thanks for having me so I want to start with a question that I've started to ask guests that come on the podcast that have had e..."
In this segment, Anneka elaborates on practical strategies for managing challenging situations at work. She discusses the importance of humor and lightness in meetings to elevate the mood and foster a collaborative environment. This approach not only benefits her but also positively influences her team, showcasing the leader's role in shaping workplace dynamics.
"deal with super difficult situations and this advice specifically came up to me when I had a scenario where I had to essentially change out all of my direct reports in very short order and I figured t..."
Anneka emphasizes the critical role of energy management in achieving peak performance. She shares insights on scheduling tasks according to personal energy levels and the importance of self-care, such as taking breaks and eating properly. This segment highlights how managing one's energy can lead to a more abundant mindset and better decision-making.
"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 uh mood and way I was approaching the meetin..."
Anneka discusses the concept of 'founder mode' and its implications for product leaders. She explains how understanding a founder's perspective can help product leaders effectively collaborate and drive initiatives forward. This segment provides valuable insights into leveraging the founder's influence to achieve strategic goals within an organization.
"situations this episode is brought to you by the Enterprise ready conference a one-day Event in San Francisco bringing together product and Engineering leaders shaping the future of enterprise s the e..."
Anneka Gupta discusses the importance of understanding the objectives behind a founder's requests and how to navigate conversations when there are disagreements. She emphasizes the need to assess whether the proposed strategies align with the company's goals and how to approach discussions with founders effectively.
"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 r..."
In this segment, Anneka explains how founders can be powerful levers for change within an organization. She shares insights on how to utilize a founder's authority to implement necessary changes while maintaining a positive atmosphere and ensuring team alignment.
"decide as a head of product do I really want to fight this or do I just you know get give in on this Let It Go and you know also make sure that we get the stuff done that's most important to the compa..."
Anneka emphasizes the significance of understanding the intricate details of the business as a leader. She discusses how asking detailed questions and gathering information can help in making informed decisions and guiding the team effectively.
"people in the company don't okay so let's go from the other side so uh I was talking in Nel singal who runs the skip which is a community are part of about you and he said that you're you're a leader ..."
In this segment, Anneka shares her approach to engaging her team in strategic discussions. She highlights the importance of allowing team members to present their strategies and how to provide constructive feedback without undermining their efforts.
"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 ..."
Anneka discusses the dual aspects of being strategic: articulating a compelling 'why' behind decisions and championing significant changes. She reflects on the balance between these elements and how they contribute to being perceived as a strategic leader.
"better versus stomping all over and and dismissing the work that they've done uh and I pick a strategic set of areas so I think about like what is most important for the business what's going to kill ..."
Anneka shares her tactic of summarization during meetings as a way to synthesize diverse viewpoints. She explains how summarizing discussions can help clarify direction and foster strategic thinking among team members.
"overall organization so in that in that example and I love this tactic you have your team come in you ask them tell me which what the strategy is for this thing that you're working on the what you've ..."
In this segment, Anneka reflects on feedback she received regarding her strategic thinking. She discusses her journey to improve in this area and the key elements that define strategic leadership.
"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 ..."
Anneka elaborates on the importance of articulating the rationale behind decisions in a clear and compelling manner. She explains how this clarity can drive alignment and support for strategic initiatives.
"when I reflected back I think it actually all came back to the same themes which was think when people say I want someone that's strategic what they're really saying is I want someone that can come up..."
Anneka discusses the strategic planning process at Rubrik, focusing on the fast-paced cybersecurity landscape. She shares her approach to identifying opportunities and aligning the team around a clear vision for the future.
"what it means and so I focused a lot on how do I make sure I do both of these things how do I Champion a few things that are really big ideas that are going to help change the direction of the company..."
In this segment, Anneka emphasizes the effectiveness of summarization in meetings. She shares how this practice not only clarifies discussions but also fosters a collaborative environment where diverse perspectives can thrive.
"compelling and simple why behind something and sometimes 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 ..."
Anneka discusses the concept of making incremental improvements in strategy. She highlights the importance of focusing on small, actionable changes that can lead to significant advancements over time.
"can think about offline and not in the context of like write in the meeting sometimes write in the meeting too I guess is how do I make this idea one click better and it's not about how do you do some..."
Anneka shares her insights on fostering a collaborative environment in product management. She discusses the value of diverse voices and how to navigate conflicts to reach effective solutions.
"much you're sharing that resonates with other podcast episodes for example this idea of just going one click better I had uh Roger Martin on the podcast wrote this book playing to win which is one of ..."
In this final segment, Anneka provides practical examples of how to summarize discussions in meetings. She shares phrases and strategies to ensure clarity and alignment among team members.
"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..."
In this segment, Anneka Gupta provides practical techniques for summarizing discussions in meetings. She suggests pausing to capture key points and framing them as questions to invite further discussion. Gupta also mentions using tools like whiteboards or Zoom chat to summarize points without interrupting the flow of conversation, making it easier for PMs to contribute effectively.
"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 gettin..."
Anneka Gupta shares insights on how to be perceived as more strategic in a PM role. She emphasizes the importance of clarity in the rationale behind ideas and the necessity of being the driving force behind initiatives. Gupta advises PMs to not only present ideas but also ensure they are executed, reinforcing the connection between strategic thinking and action.
"you're not coming in and just being like hey this is what where we we're at but then inviting people to discuss and say yes or no I agree with 90% of that but 10% 10% off and that helps move the conve..."
Gupta discusses her experience as a 'historian' in product management, emphasizing the value of understanding past decisions within an organization. She explains how analyzing previous successes and failures can inform better decision-making in the future. This historical perspective helps PMs navigate challenges and avoid repeating mistakes.
"conversation um that's happening live on the zoom itself that's a much lower Stakes way of doing it and I I'm picturing all the PMS listening to this are going to start doing this and there's going to..."
In this segment, Anneka Gupta highlights the significance of making timely decisions in product management. She warns against analysis paralysis and stresses that committing to a decision, even with incomplete information, can lead to valuable insights and learning opportunities. Gupta encourages PMs to embrace decision-making as a dynamic process that allows for iteration and improvement.
"relation to being kind of a historian which I love this concept talk about that Insight yeah um so I was at my previous company for 11 years so I kind of ended up becoming the historian and when I joi..."
Anneka Gupta shares strategies for fostering a culture where team members feel safe making decisions with limited information. She emphasizes the importance of establishing clear hypotheses and rewarding learning over outcomes. Gupta believes that encouraging a mindset focused on learning from both successes and failures can empower teams to take calculated risks.
"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 why like what happened with it how did we decide to do this and just really lea..."
Gupta discusses the iterative nature of product management decisions, emphasizing that making a decision is just the beginning. She explains how committing to a decision allows teams to gather real-world data and insights, which can lead to adjustments and improvements. This segment reinforces the idea that learning from the decision-making process is crucial for long-term success.
"your parting advice when she left to join a different company was it's not about making the right decision it's about making the decision and that's like the thing she remembered about you most that p..."
In this segment, Anneka Gupta reflects on her experiences in product development, sharing lessons learned from past projects. She discusses the importance of understanding customer needs and the challenges of selling new products within an organization. Gupta emphasizes that even setbacks can provide valuable insights that inform future strategies.
"at all because you won't get any new information if you don't make any decision at all as a PM might be listening to this feeling like okay yeah that sounds great but then I make a bad decision and th..."
Anneka Gupta emphasizes the importance of understanding the sales strategy and target audience before developing a product. She shares her experiences of building products that lacked adoption due to insufficient focus on who would sell them, highlighting the need for alignment within the organization to ensure successful product launches.
"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 I think now what I've taken from that is really know how you're going to sell s..."
In this segment, Anneka discusses her approach to working with difficult personalities in the workplace. She shares insights on understanding what drives these individuals, fostering a mindset of gratitude, and learning from challenging interactions. By focusing on empathy and curiosity, she aims to align goals and motivations with those who may initially seem uncooperative.
"forward this episode is brought to you by EPO EPO is a Next Generation AB testing and feature management platform built by alums of Airbnb and snowflake for modern growth teams companies like twitch M..."
Anneka Gupta explains how empathy plays a crucial role in navigating challenging workplace dynamics. She suggests that understanding the motivations of difficult colleagues can lead to better collaboration. By approaching interactions with a mindset of learning and gratitude, she believes one can transform frustrations into opportunities for growth.
"Lenny and 10x your experiment velocity that's get.com Lenny I want to come back to something Rachel also shared with me when I asked her what questions to ask you and by the way first of all she spent..."
In this segment, Anneka shares her strategy for learning from difficult interactions with colleagues. She emphasizes the importance of curiosity and understanding the underlying motivations of others. By reframing frustrations into learning experiences, she encourages a positive mindset that can lead to better team dynamics.
"and help people align when that is notely what they want to do 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 person..."
Anneka discusses the emotional challenges of receiving hard feedback and how to process it effectively. She advocates for allowing oneself to feel the initial emotional response before reflecting on the feedback's validity. By approaching feedback with curiosity and openness, she believes individuals can foster a culture of continuous improvement.
"they have this desire and how am I going to get them to care about the thing that I'm going to care that I want to care about the other thing I do is like instead of feeling like anger or frustration ..."
In this segment, Anneka shares her insights on how to navigate feedback in product management. She emphasizes the importance of distinguishing between valid feedback and personal opinions, focusing on what truly benefits the organization. By prioritizing the company's needs, she guides listeners on how to handle diverse feedback effectively.
"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..."
Anneka Gupta provides valuable tips on how to give hard feedback in a constructive manner. She stresses the importance of being direct while also conveying care and support for the recipient. By preparing thoughtfully and framing feedback positively, she aims to create an environment where individuals feel empowered to improve.
"just ask other people what is this person's motivations and then ideas uh connect what they want with the thing you're trying to achieve beautiful uh I really love this idea of when you're frustrated ..."
In this segment, Anneka discusses the significance of fostering a feedback culture within teams. She highlights the need for open communication and the importance of being receptive to feedback. By encouraging curiosity and understanding, she believes teams can enhance collaboration and drive better outcomes.
"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 h..."
Anneka shares her approach to balancing feedback in product management. She explains how to prioritize feedback based on its relevance to the company's goals. By focusing on what truly matters, she guides listeners on how to navigate the complexities of feedback while maintaining a clear vision for product success.
"your body go through the roller coaster of feeling the negative feedback sometimes the feedback is just like no this isn't actually a thing do you have any just like heris of like I should actually pa..."
Anneka Gupta emphasizes the importance of delivering direct feedback in a caring manner. She discusses how to frame feedback to ensure the recipient feels supported and understood, which increases receptiveness. Gupta highlights the need for clarity and directness in feedback, avoiding passive-aggressive comments, and providing actionable steps for improvement.
"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..."
In this segment, Anneka Gupta shares her approach to initiating feedback conversations. She stresses the importance of expressing care and understanding the recipient's career goals to tailor the feedback effectively. By aligning feedback with the individual's aspirations, she believes it fosters a more constructive dialogue.
"I try I do a lot of prep before I give someone a lot of feedback I really think about like how can I frame this in a way that's going to resonate with them that doesn't come across as attacking them b..."
Anneka Gupta discusses the critical distinction between how individuals perceive themselves and how others perceive them. She explains the importance of addressing these perceptions directly and collaboratively exploring ways to align them. This approach not only aids in personal development but also enhances team dynamics.
"about what they can be doing better are there like phrases or ways you kind of set up the conversation you talk you mentioned a few of just like I want to help you become the best version of who you c..."
In this segment, Anneka Gupta reflects on her journey into product management, emphasizing the value of starting in a related function within the same company. She advises aspiring product managers to leverage their existing knowledge and relationships to transition into product roles effectively.
"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 X because I think even though ..."
Anneka Gupta shares insights on how to build credibility when transitioning into product management. She highlights the importance of understanding customer pain points and collaborating with product teams to gain relevant experience. Gupta encourages individuals to take initiative and engage in product-related projects to facilitate their entry into the field.
"mentioned uh IC product managers and this is a good seg way too you're you know you're a big deal fancy Chief product officer person a lot of people listening to this podcast are early career PMS or t..."
Anneka Gupta discusses the various pathways to becoming a product manager, noting that many successful PMs come from adjacent roles or small startups. She emphasizes the importance of gaining hands-on experience and building relationships within product teams to enhance career prospects.
"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..."
In this segment, Anneka Gupta reflects on her experience teaching product management at Stanford. She shares how the process of designing the curriculum helped her crystallize her understanding of the role and the skills necessary for success in product management.
"some are just kind of at hoc is there anything there you just like like should you talk about this in your interview just like hey I really love to become product manager someday do you have anything ..."
Anneka Gupta addresses a common misconception among aspiring product managers regarding the importance of tools versus mindset. She emphasizes that the ability to navigate ambiguity and drive clarity is far more critical than mastering specific tools or processes.
"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 ..."
Anneka Gupta discusses how teaching product management has helped her clarify key concepts and frameworks. She shares insights gained from student interactions and how these experiences have informed her own practice as a Chief Product Officer.
"mindset and the skills required to clarify ambiguity along those lines actually saw you somewhere in a talk or maybe something you wrote talk about how creating this class and creating the curriculum ..."
In this segment, Anneka Gupta explores the use of AI tools in product management, particularly for summarizing user research calls. She highlights the benefits of AI in organizing insights and improving productivity, suggesting that AI is a significant unlock for product teams.
"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 I came up with in class I was..."
Anneka emphasizes the significance of maintaining a positive mindset in the workplace. She discusses how approaching situations with positivity can lead to greater achievements and personal growth. This segment explores practical strategies for cultivating a positive outlook, including journaling and self-reflection, which can help individuals navigate challenges and enhance their overall effectiveness.
"PMS do their work 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 yeah uh we use dovetail and it's been fantasti..."
In this insightful segment, Anneka shares her personal experience with journaling as a tool for self-reflection and emotional processing. She explains how writing down thoughts, especially negative ones, can help clarify feelings and identify irrational thought patterns. This practice not only aids in personal growth but also fosters a deeper understanding of one's reactions and triggers in various situations.
"learn to do it do you have any advice on just like how to build that mindset like you know connects to many of the things you said how can this be fun how can I be grateful to this person that's annoy..."
Anneka discusses the parallels between her self-reflective practices and cognitive behavioral therapy (CBT). She highlights the importance of exploring one's feelings and thoughts to reduce their power and create space for positive experiences. This segment provides listeners with valuable insights into how self-inquiry can lead to personal development and improved interactions with others.
"is an irrational way to think about this whereas other things I start to uncover well what is it about the situation and what is it that I need to do differently what's within my control and what is i..."
In this engaging lightning round, Anneka shares her favorite books, movies, and life mottos. She recommends 'The Hard Thing About Hard Things' by Ben Horowitz and the 'Foundation' series by Isaac Asimov, emphasizing the importance of mindset and learning from others. This segment offers a light-hearted yet insightful look into Anneka's personal preferences and philosophies that shape her approach to work and life.
"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 t..."