You don’t need to be a well-run company to win: Surprising lessons in product leadership and AI strategy | Tamar Yehoshua (President at Glean, ex-CPO at Slack, VP at Google, VP at Amazon)

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• Explo—Embed customer-facing analytics in your product
• Sprig⁠⁠—Build products for people, not data points
• Sidebar—Accelerate your career by surrounding yourself with extraordinary peers

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Tamar Yehoshua is the president of product and technology at Glean. Prior to joining Glean, Tamar was chief product officer at Slack, where she led product, design, and research as the company scaled, including a 10x increase in revenue, its public listing, and an acquisition by Salesforce. She also led product and engineering teams at Google, working on search, identity, and privacy, and at A9.com, an Amazon company. Tamar has served on the board of directors for RetailMeNot, ServiceNow, Snyk, and Yext. In our conversation, we discuss:

• Why you don’t need to be a well-run company to win

• The impact of AI on product management and the future of work

• How to build strong cross-functional relationships, especially with engineers

• Lessons learned from working with leaders like Jeff Bezos and Stewart Butterfield

• Strategies for staying ahead in a rapidly evolving tech landscape

• Much more

Some takeaways:

1. The best way to move up is to crush it in the role you’re in. Don’t get too caught up in the next job title or level—focus on making a significant impact where you are now. This means delivering excellent results, mastering your core responsibilities, and solving real problems. If you’re not excelling in your current position, you won’t get noticed for the next opportunity.

2. Whether you’re building products or managing teams, success hinges on understanding people. Dive into what drives your users or team members. What do they care about? What frustrates them? Learn to read body language and motivations. This insight is crucial for creating products that resonate and for leading teams effectively.

3. Operational excellence doesn’t guarantee success. Companies with strong product-market fit can thrive despite internal chaos, while well-run companies may struggle if they don’t solve a real customer need.

4. Choose a company or role that aligns with your strengths and working style. Just because a company is successful doesn’t mean it’s the right fit for you. Ensure that the work environment and culture match your preferences and career goals.

5. Don’t stress over having a five-year plan. Instead, focus on where talented people you respect are working. Your career will benefit from being in environments with strong talent and leadership, even if the company isn’t perfect.

6. Lessons from tech leaders:

   1. Jeff Bezos

      1. Uphold core principles: Define a set of core principles for your team or organization and apply them consistently in every decision. This ensures clarity and alignment across your operations.

      2. Prioritize team input: Bezos always listens to his team before sharing his own perspective. Foster a culture where team members’ insights are prioritized and considered before final decisions are made.

   2. Stewart Butterfield

      1. Prototyping is key: Before full-scale development, invest time in creating prototypes to validate concepts and gather feedback.

      2. Cultivate a long-term vision: Develop a strategic plan with clear long-term goals, as demonstrated by Butterfield’s master plan for Slack. Maintain a focus on your vision while remaining adaptable to changes.

   3. Marc Benioff

      1. Harness the power of marketing: Treat your marketing efforts with the same strategic rigor as product development. Be bold, creative, and strategic in how you present and position your brand to maximize its impact.

Where to find Tamar Yehoshua:

• X: https://x.com/TYehoshua

• LinkedIn: https://www.linkedin.com/in/tamar-yehoshua-886217/

• Newsletter: https://tamaryehoshua.substack.com/

In this episode, we cover:

(00:00) Tamar’s background

(02:09) Key advice for career success

(06:54) Understanding people and motivations

(09:33) The importance of impact

(11:20) Navigating company chaos

(18:40) Career planning: a different perspective

(26:22) Lessons from industry leaders

(37:59) Building stronger cross-functional relationships 

(42:00) Streamlining OKR reviews with async methods

(45:26) Why you shouldn’t worry so much about making users unhappy

(47:50) The power of listening in leadership

(52:34) How to leverage AI so you don’t fall behind

(01:06:39) Closing thoughts and lightning round

Referenced:

• Glean: https://www.glean.com/

• Snyk: https://snyk.io/

• The Magic Loop: https://www.lennysnewsletter.com/p/the-magic-loop

•  MySpace—what went wrong: ‘The site was a massive spaghetti-ball mess’: https://www.theguardian.com/technology/2015/mar/06/myspace-what-went-wrong-sean-percival-spotify

• The PayPal Mafia: https://en.wikipedia.org/wiki/PayPal_Mafia

• Jeff Bezos on X: https://x.com/jeffbezos

• Stewart Butterfield on X: https://x.com/stewart

• Working Backwards: Insights, Stories, and Secrets from Inside Amazon: https://www.amazon.com/Working-Backwards-Insights-Stories-Secrets/dp/1250267595

• The Everything Store: Jeff Bezos and the Age of Amazon: https://www.amazon.com/Everything-Store-Jeff-Bezos-Amazon/dp/0316219282/

• Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Backwards): https://www.lennysnewsletter.com/p/unpacking-amazons-unique-ways-of

• Ethan Eismann on LinkedIn: https://www.linkedin.com/in/ethaneismann/

• Ricky Robinett’s X post about his daughter using Cursor AI to build an app: https://x.com/rickyrobinett/status/1825581674870055189

• Cursor: https://www.cursor.com/

• Marc Benioff on LinkedIn: https://www.linkedin.com/in/marcbenioff/

• Dreamforce: https://www.salesforce.com/dreamforce/

• Behind the Cloud: The Untold Story of How Salesforce.com Went from Idea to Billion-Dollar Company—and Revolutionized an Industry: https://www.amazon.com/Behind-Cloud-Salesforce-com-Billion-Dollar-Company/dp/0470521163

• Fuzzy Khosrowshahi joins Notion as CTO: https://www.notion.so/blog/notion-new-cto

• Cal Henderson on LinkedIn: https://www.linkedin.com/in/iamcal/

• Rachel Whetstone on LinkedIn: https://www.linkedin.com/in/rachel-whetstone-497890127/

• Listen: Five Simple Tools to Meet Your Everyday Parenting Challenges: https://www.amazon.com/Listen-Simple-Everyday-Parenting-Challenges/dp/0997459301

• How to Talk So Kids Will Listen & Listen So Kids Will Talk: https://www.amazon.com/How-Talk-Kids-Will-Listen/dp/1451663889

• Figma AI: https://www.figma.com/ai/

• ChatGPT: https://chatgpt.com/

• Claude: https://claude.ai/

• Gemini: https://gemini.google.com/app

• Gong: https://www.gong.io/

• Investing in AI for AI’s Sake: My Conversation with LaunchDarkly CPO Claire Vo: https://tamaryehoshua.substack.com/p/investing-in-ai-for-ais-sake

• Claire Vo on LinkedIn: https://www.linkedin.com/in/clairevo/

• Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD): https://www.lennysnewsletter.com/p/bending-the-universe-in-your-favor

• Jira: https://www.atlassian.com/software/jira

• BERT: https://en.wikipedia.org/wiki/BERT_(language_model)

• Ben’s Bites: https://bensbites.beehiiv.com/

• The Neuron: https://www.theneurondaily.com/

• No Priors podcast: https://www.youtube.com/@NoPriorsPodcast

• The Cognitive Revolution: https://www.cognitiverevolution.ai/

• Kevin Weil on LinkedIn: https://www.linkedin.com/in/kevinweil/

• Mike Krieger on LinkedIn: https://www.linkedin.com/in/mikekrieger/

• Switch: How to Change Things when Change Is Hard: https://www.amazon.com/Switch-Change-Things-When-Hard/dp/0385528752/r

• Team of Rivals: The Political Genius of Abraham Lincoln: https://www.amazon.com/Team-Rivals-Political-Abraham-Lincoln/dp/0743270754

• Magpie Murders on Prime Video: https://www.amazon.com/Magpie-Murders-Season-1/dp/B0B7C9CWVY

• Bisou Chocolate: https://www.bisouchocolate.com/

• How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier

• Healthy Sleep Habits, Happy Child: A New Step-by-Step Guide for a Good Night’s Sleep: https://www.amazon.com/Healthy-Sleep-Habits-Happy-Child/dp/0593158547

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.