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

Introduction to Anneka Gupta (0s)

• When people say they want someone who is strategic, they mean someone who can articulate a compelling and simple reason behind decisions and direction, and also champion and be a change agent to make tough decisions that are in the best long-term interest of the product or company, even if they are hard to execute (13s).
• Anneka Gupta is the Chief Product Officer at Rubric, a lecturer on product management at Stanford University's Graduate School of Business, and on the board of Tenuity (42s).
• Previously, Anneka was President, GM, and head of product at LiveRamp, where she spent 11 years and joined as one of the earliest employees (51s).
• Anneka shares advice on navigating difficult personalities, giving and hearing hard feedback, bringing humor and gratitude to every situation, managing energy versus managing time, and becoming more strategic (1m3s).
• She also provides tactical tips for making better decisions and breaking into product management for those trying to become product managers (1m22s).
• This conversation covers a range of topics, including powerful advice, strategic decision-making, and career development, making it relevant to a wide range of listeners (1m27s).

Key mindsets for success (1m43s)

• A key mindset for success is to figure out how to have fun in one's job, even in difficult times, as it can change one's approach to dealing with challenging situations (2m24s).
• Having fun in one's job can help shift the mindset from scarcity to a more positive approach, making it easier to overcome hurdles (2m36s).
• This mindset was helpful in a situation where Anneka Gupta had to replace all her direct reports in a short period, a daunting task that initially caused fear and anxiety (3m5s).
• To embody this mindset, one can reframe their thinking by asking what can be learned from a challenging situation and what positive outcome can be achieved (4m21s).
• Bringing humor into meetings and starting on a light note can also help elevate one's mood and approach to challenging situations, as well as transfer a positive mindset to others (4m46s).
• Adding humor and making a situation more enjoyable can help reduce stress and make it more manageable, even in difficult circumstances (5m12s).
• Reframing one's thinking to focus on the positive aspects of a situation and not making it more important than it needs to be can also help make it more enjoyable (5m17s).

Managing energy for optimal performance (5m30s)

• Managing energy levels is crucial for optimal performance, as it affects the ability to bring a full self to work and tackle difficult situations with a mindset that looks at things more broadly, rather than operating from a place of scarcity (5m31s).
• Simple things like having lunch and avoiding skipping meals can significantly impact energy levels, as going without lunch can decrease energy and make it harder to get work done (6m5s).
• Identifying and avoiding scheduling difficult tasks during low-energy periods, such as 5-6 pm, can help manage energy levels and make it easier to complete tasks (6m16s).
• Scheduling time according to energy levels allows for a more abundant mindset in all situations, enabling better performance and problem-solving (6m42s).
• The Enterprise Ready conference is a one-day event in San Francisco that brings together product and engineering leaders to discuss topics like advanced identity management, compliance, encryption, and logging (6m51s).
• The conference features speakers with direct experience building for the Enterprise, including leaders from Open AI, Vanta, Checker, Dropbox, and Canva, and is free to attend (6m54s).
• Command AI is an AI-powered toolkit for support, product growth, and marketing teams that embeds in a company's product, providing useful answers to support questions and allowing for co-browsing with users (8m10s).
• Command AI works with web apps, mobile apps, and websites, and is used by industry-leading companies like Gusto, Freshworks, HashiCorp, LaunchDarkly, and over 25 million end users (8m41s).

Founder mode (9m5s)

• Paul Graham's post on "founder mode" has sparked a valuable discussion about the concept, allowing people to recognize and understand the behavior of founders who operate in this mode, whether they do it well or poorly (9m31s).
• Founder mode is characterized by a founder deeply understanding the business and using their power to tweak or fundamentally change directions, and product leaders can effectively work with a founder in this mode by recognizing their power and using it to get things done that are best for the company (10m28s).
• To work effectively with a founder in founder mode, product leaders should consider the founder as a resource to get initiatives done, and have conversations with them to activate their support and make them an ally in pushing initiatives forward (11m27s).
• When a founder has an idea that a product leader may not agree with, it's essential to take a step back, understand why the founder is pushing for that idea, and determine if it's the right mechanism to achieve the company's strategy and objectives (12m9s).
• Product leaders should have a deep understanding of the founder's objectives and be able to navigate situations where they may not agree on the direction, by having open and objective conversations to find the best way forward (12m32s).
• To navigate difficult conversations with founders, it's essential to understand the objective they're trying to achieve, and then explore alternative options to tackle the issue, which can help in navigating the conversation effectively (12m34s).
• As a head of product, it's crucial to decide whether to fight for a particular project or let it go, ensuring that the most important tasks for the company are accomplished, and making judgment calls on what will make or break the company (13m3s).
• Founders can be a powerful lever to get things done, and identifying something that needs to change can be achieved by having the founder communicate the change to the team with a positive spin, leveraging their power to drive change (13m48s).
• Operating in "founder mode" as a product leader involves understanding the details of the business, asking detailed questions, and getting into the depth of the organization to make informed decisions (14m18s).
• To think in "founder mode," it's essential to understand the financial goals of the business, what's working, and what's not, and then decide how to use that information to make significant or small course corrections (14m30s).
• Collecting information about the organization and its decisions allows leaders to decide where to intervene and make corrections, and it's crucial to bring the team along by getting involved early and asking questions to avoid disrupting their work (15m11s).
• One tactic used to get involved early is to ask team members to present their strategies, which helps in understanding their thought process and making informed decisions (15m50s).
• To navigate difficult colleagues and provide strategic guidance, it's essential to create a forum where they feel comfortable presenting their ideas and receiving feedback, rather than feeling like their work is being dismissed or rewritten (15m55s).
• When providing feedback, it's crucial to ask questions and make suggestions in a way that makes the team feel like their ideas are being improved upon, rather than stomped on (16m1s).
• To prioritize strategic areas, consider what's most important for the business, what could kill the business if not done correctly, and what opportunities need to be pursued, regardless of difficulty (16m23s).
• By focusing on these key areas, clarity can be provided to the team, and everyone can rally around making the most important things happen (16m39s).
• When discussing strategy with the team, instead of immediately pointing out flaws, ask questions and share hypotheses to encourage discussion and exploration of ideas (17m5s).
• Sharing a hypothesis can be an effective way to provide perspective and point of view without shutting down the discussion, and it allows for a more collaborative approach to finding the right outcome (17m31s).
• As a leader, it's essential to create an environment where team members feel comfortable sharing their concerns and ideas, even if they disagree with the leader's perspective (18m5s).
• By seeding an assumption and having a discussion based on that, leaders can encourage collaboration and find the best solution for the business (18m17s).

Becoming more strategic (18m26s)

• Being strategic in one's work involves two key components: coming up with an articulate, compelling, and simple "why" behind decisions and direction, and championing and being a change agent for ideas that may be hard to execute but are best for the long-term interest of the product or company (19m13s).
• Having one component without the other is not enough to be seen as strategic; one must be able to both articulate the "why" and champion big ideas (19m49s).
• To become more strategic, one can focus on developing these two components, such as by identifying a few big ideas that can help change the direction of the company and articulating a simple and compelling "why" behind them (20m10s).
• Strategic planning involves considering where a company wants to be in the next few years and identifying the best direction to take; this can be challenging, especially in fast-moving landscapes like the cyber security space (20m38s).
• A useful tactic for strategic planning is summarization, which involves bringing people together, hearing their ideas, and summarizing what they say to identify potential directions and ensure everyone is on the same page (21m10s).
• Summarization can be viewed as a strategic activity, even if it doesn't involve adding new ideas, as it helps to synthesize information and ensure everyone is aligned (21m50s).
• Summarization is a key strategy for improving ideas, and it involves taking others' ideas and making them slightly better, rather than trying to come up with something radically different (21m54s).
• This approach can be applied by thinking about customer problems and how to take an idea to market, without worrying about the technical implementation, and it can lead to big, change-agent ideas (22m27s).
• Going "one click better" is a concept that involves finding the biggest constraint or bottleneck in a business and making it better, rather than trying to come up with a huge strategy and vision (23m6s).
• This approach is similar to the concept of "betterment" discussed by Roger Martin in his book "Playing to Win", which involves finding the biggest constraint and making it better, and then repeating the process (23m9s).
• Another related concept is the "adjacent possible", discussed by Alex Kosi, which involves finding the next possible thing and focusing on that, rather than trying to achieve a big, lofty goal (23m43s).
• Summarization can be a tactical tool for product managers, and it involves summarizing others' ideas to ensure everyone is on the same page, which can help bring people together and yield better insights and decisions (23m59s).
• Summarization can also make people feel heard, especially in diverse groups, and it can help move beyond conflict and get to the heart of an issue (24m21s).
• To develop the skill of summarization, one can practice summarizing others' ideas in meetings, using phrases such as "just to make sure I understand" or "so what I hear you saying is" (25m1s).
• To become more strategic, it's essential to be clear on the "why" behind the ideas being worked on and ensure that others understand this reasoning, as people may not comprehend the motivation behind the projects or initiatives being pitched (27m32s).
• Being the person who makes things happen, rather than just presenting ideas, is crucial in being perceived as strategic, as people will view someone as non-strategic if they're not achieving their goals (27m49s).
• In meetings, inserting oneself to summarize the discussion and capture the key points can help move the conversation forward and give the impression of thinking strategically (25m18s).
• Summarizing the discussion on a whiteboard or in a Zoom chat can be an effective way to contribute to the conversation without interrupting the flow of discussion (26m22s).
• Using a Zoom chat to summarize the conversation can be a lower-stakes way of contributing and can sometimes lead to being invited back into the broader conversation (26m50s).
• When navigating difficult colleagues, being able to summarize the discussion and capture the key points can help to move the conversation forward and avoid getting stuck in circular discussions (26m5s).

The importance of decision-making (27m54s)

• To become a better decision maker, it's essential to understand the past decisions made by the organization, including what worked and what didn't, and why certain decisions were made, which can be achieved by studying the company's history and learning from past mistakes (27m54s).
• When joining a new company, it's crucial to learn about the organization's past, including successful and unsuccessful products, and the perspectives of different people within the organization to gain context and make better decisions going forward (28m6s).
• Being a historian within an organization can be done at any time, not just when joining a new company, and involves being curious about past projects and decisions to learn from them and understand the baggage people may have when trying to implement similar ideas (29m7s).
• As a product leader, it's common for people to bring up past failed projects and express skepticism about new ideas, but understanding the past can help address these concerns and improve decision making (29m37s).
• When new to a company, studying past decisions and sharing them with others can help make better decisions and provide valuable context (30m4s).
• It's essential to avoid analysis paralysis and make decisions even with imperfect information, as committing to a decision allows for learning and iteration, and a decision that's 70% right can be improved upon (30m32s).
• Rachel Wan, a former colleague, remembered the parting advice to "make the decision" rather than waiting for perfect information, highlighting the importance of taking action and iterating rather than getting stuck in analysis (30m28s).
• Making decisions quickly and iterating on them is crucial in organizations, as it allows for the gathering of high-fidelity and high-quality information, and it's better than making no decision at all, which yields no new information (31m27s).
• To create a culture where people don't feel afraid of making bad decisions, it's essential to have a strong hypothesis that everyone understands, and to reward learning rather than the outcome (32m19s).
• Having a strong "why" behind a decision is incredibly powerful and helps people feel confident that the decision-maker is thinking strategically (33m42s).
• Facebook's culture values learning faster than anyone else, shipping imperfect products to get one more turn and learn something faster than others, which resonates with the idea of making decisions quickly and iterating on them (34m1s).
• Shipping products that aren't fully confident in can be beneficial, as it allows for faster learning and improvement, and there are many examples of this in product development, where many things can go right or wrong (34m26s).
• Creating a culture of risk-taking and learning involves focusing on the process and the learning that comes from it, rather than just the outcome, and being open to adjusting hypotheses and assumptions based on new information (33m12s).
• Making decisions with 70% of the information and being willing to iterate and adjust is a key part of being strategic and making progress in organizations (32m15s).
• Having a clear understanding of the hypotheses and assumptions behind a decision can help to mitigate the fear of making bad decisions and promote a culture of risk-taking and learning (32m21s).
• A company developed a product without initially planning to monetize it, but later realized its value and is now trying to figure out how to package new capabilities to monetize it without taking away from existing customers (34m41s).
• The company has learned from past mistakes, such as developing capabilities for a new persona without understanding how easy it would be to sell to that persona within their own organization (35m7s).
• It's essential to know how to sell a product and who will be doing the selling before building it out, as a lack of focus in this area can lead to zero adoption despite having a great product (35m26s).
• The company has learned that it's not always a matter of throwing away a product, but rather doing something differently for that product and the organization going forward (35m49s).
• Experimentation is increasingly essential for driving growth and understanding the performance of new features, and companies like Twitch, Muro, Clickup, and DraftKings rely on EPO for this purpose (36m9s).
• EPO is a Next Generation AB testing and feature management platform built by alums of Airbnb and Snowflake, which helps increase experimentation velocity and unlock rigorous deep analysis (36m2s).
• EPO offers advanced statistical methods, an accessible UI, and out-of-the-box reporting, making it easy to share experiment insights with teams and spark new ideas for the AV testing flywheel (36m41s).
• EPO powers experimentation across various use cases, including product growth, machine learning, monetization, and email marketing (36m59s).

Navigating difficult personalities (37m18s)

• Navigating difficult personalities involves understanding what drives the person, what they care about, and what motivates them, whether it's the company's success or their personal career, and using that information to find common ground and achieve a desired outcome (37m59s).
• Approaching difficult personalities with an abundant mindset and a willingness to learn from them can help shift feelings of anger or frustration to gratitude and positive emotions (39m15s).
• To understand what someone wants, it can be helpful to talk to other people who have worked with them successfully, such as their team members or peers, to build a view of the person and empathize with them (40m41s).
• Reframing interactions with difficult personalities as opportunities to learn something can make it easier to navigate challenging situations and find ways to align with their goals (41m32s).
• Understanding what drives someone and what they care about can help in finding ways to motivate them and align their goals with the desired outcome (38m47s).
• Everyone has something to teach, and approaching difficult personalities with curiosity and a willingness to learn can help in finding ways to work with them effectively (39m30s).
• Shifting the mindset from feeling anger or frustration to feeling gratitude and positive emotions can help in navigating difficult personalities and finding ways to align with their goals (39m19s).
• Building a product or finding a solution that meets the needs of a difficult personality can be achieved by understanding what they care about and finding ways to match their desires with the desired outcome (38m58s).

Techniques for giving and receiving feedback (41m38s)

• Receiving hard feedback can evoke natural feelings of being upset and defensive, but it's essential to allow oneself to feel these emotions and then move past them to process the feedback objectively (42m13s).
• When receiving feedback, it's crucial to listen, be curious, and try to understand the context and reasoning behind the feedback, which may involve asking questions to the person who provided the feedback or seeking additional context from others (42m56s).
• All feedback is valid in the sense that people's feelings are valid, but it doesn't necessarily mean that action needs to be taken on every piece of feedback (43m28s).
• When giving feedback, it's essential to be strategic and focus on what is best for the company, prioritizing must-haves over nice-to-haves, and being willing to let go of less important issues (44m34s).
• In product development, it's common to receive feedback from various stakeholders, and it's impossible to make everyone happy, so it's crucial to anchor on what is best for the company and prioritize accordingly (44m14s).
• Being open to feedback and willing to listen can encourage others to provide more feedback, as they know their input will be heard and considered (43m47s).
• When deciding whether to act on feedback, it's helpful to consider whether the issue is a must-have or nice-to-have and whether it aligns with the company's current needs and priorities (44m44s).
• It's also important to recognize that sometimes, it's necessary to acknowledge a problem or area for improvement but prioritize more critical issues (44m54s).
• Receiving hard feedback is crucial for an organization's growth, and it's essential to be open to constructive criticism, even if it's difficult to hear, to help the organization deliver its goals and meet business needs (45m4s).
• Hard feedback can come in various forms, such as criticism about not moving fast enough on the roadmap and priorities, or disagreement with the direction of a certain product, and it's essential to understand where the feedback is coming from and why it's being given (45m31s).
• Some feedback can be more personal and cut deeper, such as comments about one's team or leadership style, and it's essential to acknowledge these feelings and try to understand the underlying reasons for the feedback (46m19s).
• When giving hard feedback, it's essential to convey that the feedback is coming from a place of care and a desire for the person's success, and to be direct and explicit about the issues and the desired changes (47m25s).
• Being direct and explicit in feedback is crucial, as passive-aggressive feedback can be unhelpful, and it's essential to provide specific examples and actionable steps for improvement (47m55s).
• Preparing thoroughly before giving feedback is vital, thinking about how to frame the feedback in a way that will resonate with the person and avoid coming across as attacking them (48m22s).
• Approaching difficult conversations with colleagues involves understanding why their actions may not be working or are being perceived poorly, and providing examples of how to improve, rather than simply giving feedback and expecting them to figure it out. (48m31s)
• Radical candor is a helpful approach, which involves being direct about areas for improvement while also showing that you care deeply about the person. (48m53s)
• Starting conversations by expressing that you care about the person and want to help them become the best version of themselves can be an effective way to frame the discussion. (49m20s)
• Asking colleagues about their career goals and aspirations can help tailor the conversation and provide more relevant feedback. (49m30s)
• Focusing on how the person is being perceived, rather than making assumptions about their intentions, can be a more productive way to have the conversation. (50m11s)
• Framing the conversation in this way allows for a discussion about how to change the perception, rather than simply debating whether or not the perception is accurate. (50m25s)
• Giving the person the benefit of the doubt and assuming that their intentions may be different from how they are being perceived can help to have a more constructive conversation. (50m43s)

Transitioning into product management (51m1s)

• Transitioning into product management can be done by moving into a product role within the same company, which is often easier than switching companies and jobs at the same time, as it allows individuals to leverage their existing credibility and relationships within the organization (51m25s).
• To make this transition, individuals should focus on building credibility in their current role, then start interacting with the product team, taking on projects, and building a relationship with a product leader who can help them get into a product role (51m50s).
• When transitioning from a different function, such as customer support, sales, or engineering, individuals can bring valuable knowledge and perspectives to the product team, making them a more attractive candidate for a product role (52m16s).
• The advice is to join a product-adjacent function within a company and then find a way to transition into the product team, as most functions are closely related to product management (53m21s).
• When interviewing for a role, it may be beneficial to express interest in becoming a product manager, but this depends on the company size and stage, and should be done wisely (53m43s).
• Once in a company, finding a relationship with a product leader and taking initiative to work on product management-related projects can help individuals find an inroad into product management (54m34s).

Advice for aspiring product managers (54m56s)

• New product managers often misunderstand the role of a product manager, focusing on learning tools such as Figma instead of developing the skills required to clarify ambiguity in complex situations (54m57s).
• When designing a class on product management, students expressed a desire to learn how to use specific tools, but the instructor believed that the key to success lies in learning how to drive clarity in ambiguous situations (55m21s).
• Teaching the class helped the instructor crystallize their own thinking on product management and develop mental models for becoming a product manager (56m32s).
• The process of teaching and synthesizing information for an audience helped the instructor develop frameworks for ideation, product discovery, and other aspects of product management (57m4s).
• The instructor found that answering questions from students and providing real-life examples helped them develop valuable insights that they could share with their own team (57m58s).
• The experience of teaching and discussing product management with students highlighted the importance of developing a mindset and skills that can clarify ambiguity, rather than just learning specific tools or processes (56m23s).
• Many people who become product managers (PMs) do not directly join an established company as a PM, but rather take alternative routes to get into the role (58m59s).
• A significant portion of PMs gain experience by joining product-adjacent roles or working at small startups where they may be the first product manager or handle multiple responsibilities, including product management (59m18s).
• Some individuals may have prior PM experience or an engineering background before transitioning into a PM role at a technical company (59m11s).
• A few people may directly join a company as a junior PM, but this is not the most common path (58m56s).
• The majority of PMs do not start their careers directly in product management, but rather transition into the role from other functions or gain experience in smaller companies (58m45s).

Leveraging AI tools in product management (59m39s)

• AI tools are being used to summarize user research calls, which helps in managing the large volume of insights gathered from these calls. This allows for easy lookup of specific information, providing context, transcripts, and summaries of what was learned. (1h0m8s)
• The summarization capability is seen as a powerful tool for product managers, offering significant potential benefits for organizations. However, it is noted that the use of AI in this area is still in its early stages. (1h0m42s)
• Dovetail is mentioned as a specific tool being used for summarization and search, integrating with Zoom calls to enhance productivity. (1h1m6s)

The power of a positive mindset (1h1m27s)

• The mindset one brings to their work is the most important factor in achieving success, and approaching situations with a positive mindset can lead to greater accomplishments than one might hope for (1h1m38s).
• Building a positive mindset can be achieved through practices such as journaling, which helps to process and understand thoughts and emotions (1h2m19s).
• Journaling involves writing down thoughts, especially negative ones, to explore why they are occurring and to break them down into manageable parts (1h2m40s).
• By putting thoughts down on paper, one can identify irrational thoughts and let them go, and also uncover what needs to be done differently to improve a situation (1h3m2s).
• This process is similar to cognitive behavioral therapy, where one asks themselves questions to understand and challenge their thoughts (1h4m6s).
• Listening to and exploring one's thoughts and emotions, rather than suppressing them, can actually reduce their power and create space for more positive thoughts and feelings (1h3m47s).
• This practice can help one to be more grateful and find the lessons in difficult situations, even when dealing with annoying people (1h2m8s).

Lightning round (1h4m30s)

• Recommended books include "The Hard Thing About Hard Things" by Ben Horowitz and Brandon Sanderson's fantasy and sci-fi books, which are admired for their unique writing style and the author's elite status in the craft (1h4m36s).
• A favorite recent movie or TV show is the dystopian series "Fallout," based on a post-apocalyptic world, which is entertaining, quirky, and fun (1h5m26s).
• A favorite product is an 8-foot iPhone charging cord, which allows for movement around the house while keeping the phone charged (1h5m46s).
• A favorite life motto is that everyone has something to teach and something to learn, which helps in interacting with people and combating imposter syndrome (1h6m12s).
• A favorite book by Isaac Asimov is the "Foundation" series, which is a good starting point for exploring his canon, but the book series is preferred over the show adaptation (1h6m50s).
• To connect with Anneka Gupta online, people can find her on LinkedIn, where they can follow her, send direct messages, and ask questions (1h7m27s).
• Listeners can be helpful by sharing their thoughts on what they wish a product management class could teach, especially if they have no prior PM experience, which can be shared via direct messages on LinkedIn or Twitter (1h7m33s).