Becoming more strategic, navigating difficult colleagues, harnessing founder mode, and more | Anneka Gupta (Chief Product Officer at Rubrik)

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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

Some takeaways:

1. Don’t just manage your time—manage your energy. Identify your peak performance times throughout the day and schedule your most challenging tasks accordingly. If you know you’re at your best in the morning, tackle difficult meetings or strategic planning during that window.

2. Rather than pursuing big changes right away, focus on making things “one click better.” Identify the most significant constraints in your strategy and work on refining those elements. Over time, these small adjustments can lead to substantial improvements in outcomes.

3. In meetings, practice summarizing discussions to ensure everyone is aligned. Try saying something like, “Let me pause and summarize what I’ve heard: Our customers are facing X challenges, and we believe Y is the solution. Is that an accurate reflection?” This approach fosters clarity, makes participants feel heard, and can break up circular conversations.

4. Be clear on your “why”: When pitching ideas or initiatives, ensure you articulate the reasoning behind them. Transparency about your motivations helps others understand your vision and aligns them with your goals, making them more likely to support your initiatives.

5. When dealing with challenging colleagues, approach them with curiosity rather than frustration. Take the time to figure out what drives the other person. Ask yourself: What do they truly care about? Is it their career advancement, their reputation, or the success of the company? Once you understand their motivations, you can align your goals with theirs, making it easier to collaborate.

6. To give effective feedback:

   1. Explicitly communicate that you care about the person’s success

   2. Be direct and specific about the issue and its impact

   3. Offer concrete examples and suggestions for improvement

   4. Frame feedback in terms of perception when appropriate

Where to find Anneka Gupta:

• X: https://x.com/annekagupta

• LinkedIn: https://www.linkedin.com/in/annekagupta

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

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Lenny may be an investor in the companies discussed.