You Don’t Have to Be a Well-Run Company to Win: Surprising Lessons in Product Leadership and AI Strategy

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Tamar Joshua 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 grew, including 10x revenue growth, a public offering, and an acquisition by Salesforce. She also led product and engineering teams at Google, where she worked on search, identity, and privacy, and A9.com, an Amazon company. Tamar has served on the boards of RetailMeNot, ServiceNow, Snyk, and Yext. In our conversation, we discuss:

• Why You Don’t Have 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 to Stay Ahead in a Rapidly Changing Technology Landscape

• Much more

The transcript can be found here: https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua

Some conclusions:

1. The best way to move up is to crush it in the role you have. Don’t get too caught up in the next job title or level: focus on making a meaningful impact where you are now. This means delivering excellent results, mastering your core tasks, and solving real problems. If you don’t excel in your current role, you won’t be noticed when the next opportunity comes along.

2. Whether you build products or manage teams, success depends on understanding people. Dig into what drives your users or team members. What interests them? What frustrates them? Learn to read body language and motivations. This insight is crucial to creating products that resonate and to leading teams effectively.

3. Operational excellence does not guarantee success. Companies with strong product-market fit can thrive despite internal chaos, while well-run companies can get into trouble if they fail to meet a real customer need.

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

5. Don’t worry about a five-year plan. Instead, focus on where talented people you respect work. Your career will benefit from environments with strong talent and leadership, even if the company isn’t perfect.

6. Lessons from technology leaders:

   1. Jeff Bezos

      1. Maintain core principles: Define a set of core principles for your team or organization and apply them consistently to every decision. This creates clarity and alignment in your activities.

      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 making final decisions.

   2. Stewart Butterfield

      1. Prototyping is essential: Invest time in prototyping before you start full development. This will allow you 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. Stay focused on your vision while remaining adaptable to change.

   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 discuss:

(00:00) Tamar’s background

(02:09) Important advice for a successful career

(06:54) Understanding people and motivations

(09:33) The importance of impact

(11:20) Navigating the chaos of the company

(18:40) Career planning: a different perspective

(26:22) Lessons from Industry Leaders

(37:59) Build stronger cross-functional relationships

(42:00) Streamline OKR reviews with asynchronous methods

(45:26) Why you don’t have to worry so much about dissatisfying users

(47:50) The power of listening in leadership

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

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

Referred to:

• Collect: https://glean.co/

• Snyk: https://snyk.io/

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

• MySpace – what went wrong: ‘The site was a huge spaghetti 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 Way 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/ethaanismann/

• 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/

• Dream power: 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 Tackle Your Everyday Parenting Challenges: https://www.amazon.com/Listen-Simple-Everyday-Parenting-Challenges/dp/0997459301

• How to Talk So Kids Listen and Listen So Kids 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 Strike: https://www.gong.io/

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

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

• Bend the Universe to 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-BERT: https://en.wikipedia.org/wiki/BERT_(language_model)

• Ben’s snacks: 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 Go Viral Consistently: Nikita Bier’s Guide to Consumer App Success (TBH Co-Founder, Gas, Advisor, Investor): https://www.lennysnewsletter.com/p/how-to-consistently-go-viral-nikita-bier

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

Production and marketing by https://penname.co/For questions about sponsoring the podcast, email [email protected].

Lenny may be an investor in the companies discussed.