Navigating Difficult Conversations

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

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• The Enterprise Ready Conference — For B2B leaders building enterprise SaaS

• Command AI — AI-powered user assistance for modern products and impatient users

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Find the transcript at: https://www.lennysnewsletter.com/p/becoming-more-strategic-anneka-gupta

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Where to find Anneka Gupta:

• X: https://x.com/annekagupta

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

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

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

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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

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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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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

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