Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua (Product at Glean, ex-Google and Slack)
Tamar Yehoshua, President of Product & Technology at Glean, shares career advice, including excelling in your current role and following top talent. She also discusses leveraging AI for productivity and strategic thinking, emphasizing its transformative impact on product and engineering jobs.
Deep Dive Analysis
13 Topic Outline
Introduction and Career Overview
Core Skills for Career Success
The Importance of Understanding People and Motivations
Driving Impact in Your Role
Why Well-Run Companies Don't Always Win
Why You Don't Need a Career Plan
Lessons from Jeff Bezos and Stewart Butterfield
Building Strong Cross-Functional Relationships
Streamlining OKR Reviews with Asynchronous Methods
Don't Over-Index on Unhappy Users
The Power of Authentic Listening
Leveraging AI to Stay Ahead in Your Career
Adapting to Rapid Tech Changes and Lightning Round
5 Key Concepts
Product Market Fit
This refers to a state where people genuinely want to use your product and are clamoring for it. Without it, a company struggles significantly, as building something people aren't excited about makes it very hard to succeed, even with strong distribution.
Beginner's Mind
This mental model, advocated by Mark Benioff, involves approaching situations, especially when interacting with customers, with the assumption that you know nothing. It encourages deep listening and learning without preconceived notions, allowing for a fresh perspective on user needs.
Gravitational Pull (of companies)
This describes certain companies that attract and accumulate the best talent in the industry. These companies become a nexus for highly skilled individuals, and joining them can significantly accelerate one's career through learning and networking, even if the company's ultimate financial success is uncertain.
Making a Decision Right
This philosophy suggests that there are no inherently 'right' decisions in life or career; instead, you commit to a decision and actively work to make it successful. It emphasizes taking ownership of your choices and moving forward without regret, focusing on how you approach the path you've chosen.
Non-Deterministic Systems (LLMs)
This refers to Large Language Models (LLMs) that do not always produce the same output for the same input, and can sometimes generate illogical or 'dumb' responses. Integrating these systems into enterprise software requires educating users about their unpredictable nature and building guardrails to guide effective usage.
7 Questions Answered
One of the most overlooked skills is doing an exceptionally good job at your current role, beyond just hitting goals, by driving impact and helping the business move forward. Another crucial skill is understanding people and their motivations, both for product users and team members.
Not necessarily. Many highly successful companies, especially during hyper-growth phases, can be chaotic internally with broken processes, high turnover, and frequent reorgs, yet still achieve amazing numbers due to strong product-market fit and effective distribution.
No, it's not always necessary. Many successful individuals, including Tamar, never had a five-year career plan. A good strategy is to follow great people who are the best at what they do, as you will learn the most from them and build valuable connections, regardless of the company's ultimate success.
The most important thing is to ensure strong alignment and mutual respect with your engineering partner, clearly defining roles and responsibilities to avoid conflicting directions. Spend a lot of time together, document decisions, and be direct and transparent in communication.
Product managers should focus on designing for the larger number of future users rather than getting caught in the trap of a vocal minority who may be unhappy with changes. When making changes, be respectful, transparent, and authentic in explaining the 'why,' and listen to feedback without being dismissive.
AI will blur the lines between product managers, engineers, and designers by enabling PMs to build prototypes and designs faster, and automating routine tasks. To prepare, people must actively use AI products like ChatGPT, Claude, and Glean to understand their capabilities and integrate them into their workflows, leveraging them to work faster and better.
Product teams need to build guardrails and provide suggestions to help users understand what questions will work and what won't, as chat interfaces are still new for many. It's also crucial to ensure the product's core differentiator is not solely based on compensating for current LLM limitations, as LLMs will rapidly improve, making such work obsolete.
57 Actionable Insights
1. Excel in Your Current Role
Focus on performing exceptionally well in your current job, “knocking it out of the park,” as this is foundational for advancing to the next career level.
2. Drive Measurable Impact
Consistently strive to drive measurable impact that moves the business forward, rather than simply completing tasks or launching features.
3. Prioritize Skill Acquisition
Focus on acquiring valuable skills throughout your career, as skills are permanent assets that remain with you even if companies fail, unlike financial returns or company success.
4. Follow Top Talent for Career Growth
Instead of rigid career planning, prioritize following and working with people who are the best at what they do in their respective fields, as this is where you will learn the most valuable skills.
5. Prioritize Product-Market Fit & Distribution
Focus on building a product people truly value and clamor for (product-market fit), ensuring you also have effective distribution, a functional sales team, and sufficient funding.
6. Understand User & Team Motivations
Develop a deep understanding of people’s motivations, both for product users (what delights/frustrates them) and for team members (what drives their work and career goals).
7. Cultivate a Beginner’s Mind
Approach problems with a “beginner’s mind,” assuming you know nothing, and actively ask many questions and listen to customers and people to gain genuine understanding.
8. Develop Product Intuition
Balance reliance on metrics with developing strong product intuition, making decisions based on a deep, intuitive understanding of your customers and product when it “feels right.”
9. Embrace AI for Productivity
Recognize that AI will profoundly change work; actively learn to leverage it to work faster and better, as those who do will gain a significant advantage.
10. Actively Experiment with AI Tools
Consistently try out and experiment with new AI products like ChatGPT, Glean, or Claude to understand their capabilities and integrate them into your workflow, just as you would with any new technology.
11. Focus on Strategic & Creative PM Work
To thrive in an AI-driven world, product managers should focus on strategic thinking, creativity, and problem-solving, as AI excels at routine tasks but not at generating truly differentiated solutions.
12. Make Decisions Right
Commit to your decisions and actively work to “make them right” through your efforts and attitude, rather than dwelling on regret or hypothetical alternative paths.
13. Establish Clear Roles & Alignment
Ensure clear understanding of roles, responsibilities, and alignment with cross-functional partners to avoid conflicting directions and promote effective collaboration.
14. Communicate Directly & Transparently
Spend significant time with partners, document decisions, and speak up directly if you disagree with priorities, avoiding passive-aggressive communication or undermining decisions.
15. Build Trust and Respect
Foster strong cross-functional relationships by building mutual respect and trust, ensuring partners follow through on commitments.
16. Prioritize a Strong Engineering Partner
Before joining a company, assess and value your potential engineering partner to ensure your product ideas can be effectively built and executed.
17. Embrace Long-Term Product Vision
Adopt a long-term perspective for product development, understanding that building great products is a multi-year endeavor and viewing resource constraints as a potential advantage.
18. Leverage Prototyping for Product Thinking
Embrace extensive prototyping to “feel” and test product ideas, moving beyond mock-ups to truly understand user experience and inform deep product thinking before committing to development.
19. Build a Prototyping-Friendly Infrastructure
Cultivate an engineering infrastructure and mindset that prioritizes rapid prototyping, allowing teams to quickly build and discard code to test ideas efficiently before committing to production-ready development.
20. Design for Future Users
When making product changes, prioritize designing for the larger number of future users rather than over-indexing on the vocal minority of existing users who might be unhappy with changes.
21. Communicate Changes Respectfully
When making product changes, communicate transparently, authentically, and respectfully, explaining the real reasons behind decisions and listening to user feedback, rather than being dismissive.
22. Automate Routine PM Tasks
Leverage AI to automate routine product management tasks like updating Jira or creating launch plans, freeing up time for more creative and strategic work.
23. Automate Insights from Sales Calls
Automate the extraction of insights from sales call transcripts (e.g., using Glean with Gong) to identify top requested features, understanding that initial prompts may require iteration to achieve desired accuracy.
24. Analyze Large Data with AI
Leverage AI tools with large context windows (e.g., Gemini) to analyze extensive qualitative data like Discord transcripts, extracting insights on product sentiment, requested features, and user dissatisfaction.
25. Use AI for Feature Status Confidence
Create custom AI prompts to aggregate information from various sources (e.g., LaunchCal, Jira, Slack, beta feedback) to assess the true status and confidence level of feature launch dates.
26. Use Role-Based AI Prompts
Enhance AI output by giving it a specific role (e.g., “You are a product manager at Glean”) in your prompts, which helps tailor the response to a relevant perspective.
27. Automate Incident Management Research
Leverage AI to automate parts of incident management, such as quickly identifying similar past incidents to aid in faster resolution.
28. Stay Informed on AI Trends
Actively consume AI-focused newsletters and podcasts (e.g., Ben’s Bites, The Neuron, No Priors) to stay updated on the latest developments and leverage AI tools like ChatGPT’s voice mode for information consumption.
29. Adapt to Rapid Tech Change
Actively change your working methods and “get in the thick of it” by trying out new tools to keep pace with the rapidly evolving tech environment, especially with AI, to seize new opportunities.
30. Avoid Dismissing New AI Tools
Do not quickly dismiss new AI tools after a brief trial; persist in experimenting and adapting your workflow to leverage them, as clinging to old methods is a “dangerous spot.”
31. Build Sustainable AI Differentiators
When building AI products, ensure your core differentiator is sustainable and not merely compensating for current LLM limitations, as LLMs will rapidly improve and render such compensatory work obsolete.
32. Observe & Analyze Human Behavior
Practice observing people’s reactions and body language in social settings to better understand their thoughts and motivations, enhancing your ability to read a room.
33. Prioritize User Needs Over Features
Maintain perspective on what users are truly trying to achieve, avoiding the urge to prominently display features you personally worked on if they aren’t the most important for the user at that moment.
34. Focus on Business Impact
Measure success by the impact you drive for the business, ensuring you build products people actually use and enable the entire organization to be more productive, rather than just hitting assigned goals.
35. Adapt to Company Phase
Understand the current growth phase of your company and adapt your priorities and strategies to what is most important for that specific stage.
36. Prioritize Personal Fit Over Success
Do not work at a company, even a successful one, if its internal chaos or culture will make you upset and unhappy, as personal fit is crucial.
37. Achieve Product-Market Fit
Recognize that achieving strong product-market fit is critical for survival and growth, as its absence is a “death sentence” for a company.
38. Seek Companies with Top Talent
Identify companies that attract and retain a “nexus of great people,” as working alongside them fosters learning, builds valuable connections, and leads to greater collective achievements.
39. As a Leader, Choose Impactful Roles
As a leader, select roles where you can genuinely tell potential hires that joining will significantly advance their careers, ensuring it’s a place where they can learn and grow.
40. Don’t Over-Prioritize Financial Return
Avoid over-emphasizing potential financial returns when choosing a job, as financial success is highly unpredictable and focusing solely on it can lead to negative outcomes.
41. Study Bezos’s Principles
Learn from Jeff Bezos by reading his shareholder letters and books like “Working Backwards” or “The Everything Store” to understand his operating principles and leadership style.
42. Use Six-Pagers for Deep Thinking
Adopt the practice of writing detailed “six-pager” documents instead of PowerPoints to encourage deeper thinking, analysis, and comprehensive communication.
43. Lead with Consistent Principles
Lead with consistent, clearly articulated principles (e.g., customer-driven, customer-relevant) to make it easier for your team to understand priorities and operate effectively.
44. Encourage Team Input First
As a leader, ensure everyone at the table speaks and shares their thoughts before you, fostering a team effort and demonstrating that you value diverse perspectives.
45. Develop a Consistent Master Plan
Create a long-term “master plan” with a consistent vision for your product, allowing annual work to adapt while remaining anchored to the overarching strategic goals.
46. Value Strong Marketing
Recognize the significant impact of strong marketing and learn from leaders like Mark Benioff, who approaches marketing with a product-like mindset to build powerful ecosystems and influence.
47. Respect Partner’s Domain
Clearly define and respect your cross-functional partner’s domain, avoiding going around them and collaboratively deciding ownership for unclear responsibilities.
48. Streamline OKR Reviews with Async Video
For large organizations, streamline OKR reviews by having teams post short video summaries and documents in dedicated channels, allowing leaders to review asynchronously and provide feedback.
49. Iterate on Internal Processes
Regularly review and iterate on internal processes, such as OKR planning, on a quarterly basis, just as you would with product development, to continuously improve efficiency.
50. Practice Authentic Leadership
Lead authentically by listening to people, being transparent, and taking direct action to address concerns, even if it means personally engaging with individual team members.
51. Use AI for Information Summarization
Overcome time constraints by using AI tools to summarize long articles, transcripts, or other information, leveraging AI to gain insights more efficiently than manual review.
52. Apply Creativity & Patience with AI
Use your creative problem-solving skills as a PM to identify unique ways AI can assist you, and have the patience to iterate and refine your approach until the tools effectively meet your needs.
53. Read “Switch” for Organizational Change
Read “Switch: How to Change Things When Change Is Hard” by Chip and Dan Heath to learn effective strategies for motivating people and setting a clear path to drive organizational change.
54. Read “Team of Rivals” for Leadership
Read “Team of Rivals” to gain insights into leadership, particularly how Abraham Lincoln managed to unite diverse and often opposing figures in his cabinet during the Civil War.
55. Prioritize Children’s Sleep
Ensure children develop healthy sleep habits, as good sleep is fundamental for their well-being and happiness, and can be achieved through methods like sleep training.
56. Share Your Life with Kids
To encourage your children to open up, proactively share details about your own day and experiences with them, fostering a reciprocal environment for communication.
57. Master Core Tech Skills
For tech roles, deeply understand the latest technology, your specific product, and relevant metrics as these are fundamental “table stakes” for success.
6 Key Quotes
You're not going to get the next job unless you do really well at the job that you're in. Like, knock it out of the park.
Tamar Yehoshua
If I were to put this into one word, it's impact. Drive impact.
Tamar Yehoshua
Skills can't be taken away. A company can fail. But if you learn a skill, you will always have that skill.
Tamar Yehoshua
There are no right decisions. You make a decision right.
Tamar Yehoshua
AI, the one thing it's not good at is being creative.
Tamar Yehoshua
You don't want any of this like people in the organization, they ask mom, they ask dad, and they got different opinions and claim one against the other like that doesn't work.
Tamar Yehoshua
1 Protocols
Streamlining OKR Reviews (Slack)
Tamar Yehoshua- Teams post a document and a Slack video (with a time limit) summarizing their OKRs and major points in a dedicated Slack channel.
- Product and Engineering leadership (Tamar and CTO Cal Henderson) watch all videos together.
- Leadership posts follow-up questions in the channel.
- For high-priority projects or many questions, a follow-up meeting is scheduled with the team.
- A weekly Monday meeting reviews progress on top OKRs (red, yellow, green status), focusing only on red ones and their issues, with both product and engineering leadership present.
- A weekly meeting with product and engineering leadership (and their chiefs of staff) discusses any organizational issues.
- The OKR planning process is iterated on quarterly, just like a product, to adjust and improve efficiency.