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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 — Brought to you by: • Explo—Embed customer-facing analytics in your product: https://explo.co/lenny • Sprig—Build products for people, not data points: https://sprig.com/getstarted?utm_source=lenny&utm_medium=podcast • Sidebar—Accelerate your career by surrounding yourself with extraordinary peers: https://www.sidebar.com/lenny?utm_source=lennys&utm_medium=newsletter&utm_campaign=waitlist&utm_content=2 Find the transcript at: https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua Where to find Tamar Yehoshua: • X: https://x.com/TYehoshua • LinkedIn: https://www.linkedin.com/in/tamar-yehoshua-886217/ • Newsletter: https://tamaryehoshua.substack.com/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ 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/ ...References continued at: https://www.lennysnewsletter.com/p/you-dont-need-to-be-a-well-run-company-to-win-tamar-yehoshua 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.
Tamar Yehoshua emphasizes the critical role of having a strong engineering partner when pursuing product ideas. She discusses the necessity of aligning roles and responsibilities to avoid confusion within teams, highlighting the importance of collaboration in achieving success.
"make sure you go somewhere where you have a good engineering partner because if you have great ideas of what to build but you can't get them built then you go nowhere so that has to be part of your ev..."
In this segment, Tamar shares essential skills and mindsets that have contributed to her successful career. She stresses the importance of excelling in your current role and understanding the technical aspects of your job, particularly for product managers.
"yahoshua Tamar thank you so much for being here and welcome to the podcast thank you so much for having me I've had so many people recommend you coming on this podcast I'm really happy that we're fina..."
Tamar discusses the significance of understanding people and their motivations in product management. She shares insights from her upbringing, emphasizing the need to read social cues and understand user needs to build effective products and teams.
"in in tech jobs there's like table Stakes there's table Stakes of you need to be technical you need to know the latest technology you need to understand your product the product you're working on no m..."
Tamar cautions against over-reliance on metrics in product management. She advocates for intuition and understanding customer needs, sharing how to balance data with instinct to make informed product decisions.
"free at expo. Lenny that's ex. Lenny this episode is brought to you by sprig what if product teams knew exactly what to build to reach their goals from increasing conversion to boosting engagement the..."
In this segment, Tamar reflects on what it means to do a great job in your current position. She emphasizes the importance of creating real impact and contributing to the organization’s productivity rather than just meeting goals.
"so how do you start transitioning so after you've done a great job at everything and you understand the the core skills that you need another thing you really need to know is understanding people and ..."
Tamar shares her perspective on the chaotic nature of many successful companies. She discusses how internal disorganization does not necessarily correlate with a company's success and highlights the importance of focusing on what truly matters.
"motivating them I I love this advice and I feel like we could do a whole podcast on just this topic so on this last point about understanding people is there an example of this in either a product you..."
Tamar challenges the notion that a well-run company is essential for success. She provides examples from her career, illustrating how some chaotic environments can still thrive while others with strong leadership may struggle.
"your users are actually trying to achieve going back to your first point about doing a great job at the job you have I imagine some people hear this and the devices do a great job at the job you're al..."
In this segment, Tamar discusses the importance of identifying key factors that contribute to a company's success. She emphasizes the need for product-market fit, effective distribution, and a capable sales team as critical components.
"impact yeah amazing okay going in a different direction we were chatting before we started recording this and something that you shared with me and some people may be really surprised to hear this but..."
Tamar elaborates on the balance between chaos and structure in organizations. She explains that while some chaos can be beneficial, excessive disorganization can hinder productivity and progress.
"working and one of the things I try and do is give a perspective of what matters and what doesn't and it might even be to the sales team because you get like all these requests for features all the ti..."
Tamar concludes by discussing the importance of finding a company culture that aligns with personal values and work style. She reflects on her preferences for chaotic versus well-structured environments and how they impact job satisfaction.
"professional managers and things are about the cost and executing and getting all the like once you get to like over 5,000 people or 10,000 people like you gotta have things that I mean then you're li..."
Tamar emphasizes that achieving strong product-market fit is essential for a company's survival and growth. She discusses how companies that fail to maintain their product's performance during rapid growth often struggle, using Myspace as an example of a company that couldn't keep up with user demands.
"case a lot of it is that because if you are in hypergrowth you've got customers coming at a really fast pace you're growing your company really quickly and the number of employees and it's just really..."
Reflecting on her time at Airbnb, Tamar shares insights about the chaotic environment typical of hypergrowth companies. She stresses that while chaos is common, it should not be an excuse for poor organization and that maintaining a functional workplace is crucial for employee satisfaction and productivity.
"problems strong product Market fit well no product Market fit is a desence let say it more like that like you can't like if you built a product that people aren't really excited to use then you don't ..."
Tamar shares her contrarian view on career planning, stating that she never had a fixed five-year plan. She encourages individuals to follow their interests and the people they admire, rather than stressing over a rigid career path, highlighting the value of learning from others in the industry.
"great okay another maybe contrarian opinion that you hold uh along the career track is that you don't need to plan your career I also 100% agree with this I had no plan for my career I never knew wher..."
In this segment, Tamar discusses the importance of surrounding oneself with talented individuals. She advises listeners to seek opportunities where they can learn from the best in their field, emphasizing that the relationships built in these environments can significantly impact career growth.
"I go get an MBA or do I go work for somebody do I be a product manager or an engineer and those really take you in very different paths and I I meet a lot of kids in their shouldn't call them kids um ..."
Tamar warns against prioritizing financial returns when choosing career paths. She argues that while financial success is unpredictable, the skills gained from working with talented people are invaluable and can lead to long-term career benefits, regardless of a company's success.
"as much as you'd like you still have the those connections I mean everybody talks about the PayPal Mafia and how they've gone on to do things like I was super lucky to be at Google for so many years a..."
Tamar advises job seekers to focus on companies where they can learn and grow, rather than just aiming for top brands. She reflects on her own career, acknowledging that not every job change led to success, but the learning experiences were crucial for her development.
"thought uh yeah and it's it's really bad when you don't have the gravitational pull it's it's it's super hard I would say that one thing that if you're a manager I always advise managers go somewhere ..."
Tamar emphasizes the importance of networking with talented individuals. She suggests that aspiring professionals should identify and pursue opportunities at companies where respected leaders work, as this can enhance their career trajectory and provide valuable connections.
"the hardest to predict you know who's good you know who you want to work with you can predict where you're going to learn because even if a company fails you learn a lot but predicting financial succe..."
Tamar shares insights from her experiences with industry leaders like Jeff Bezos and Stewart Butterfield. She highlights the importance of listening and collaboration in leadership, as well as the value of understanding the principles that guide successful companies.
"that didn't do well and so then people will assume that every time I made a job change it was to a company that did well no that was not the case so if you if you focus on that learning bit you will g..."
Tamar Yehoshua shares her insights from working with Jeff Bezos at Amazon, highlighting his unique approach to meetings and decision-making. She emphasizes the importance of his six-pager format over PowerPoint, his practice of listening to his team before speaking, and his deep understanding of various domains. Yehoshua reflects on how Bezos's consistent principles, such as customer-driven focus, shaped the operational culture at Amazon.
"Amazon was known in the valley and and that this is another example I went there because I went to work for udy manbar who started A9 and he was talking to me one night trying to recruit me and he spe..."
In this segment, Tamar discusses the significance of prototyping in product development, drawing from her experiences with Stewart Butterfield at Slack. She explains how Butterfield's long-term vision and attention to detail influenced product strategy, and how he encouraged teams to create prototypes to truly understand user experience rather than relying solely on mockups.
"enables you to operate a large organization more effectively and then there's one other thing that I I really remember was a very one of the few really small meetings I was in with him and we were pre..."
Tamar emphasizes the critical role of cross-functional relationships in product leadership. She shares her experiences with engineering partners, particularly Cal Henderson at Slack, and discusses the importance of mutual respect, clear roles, and open communication to ensure successful collaboration between product, engineering, and design teams.
"always part of his vision so he saw forward in the vision but he also was very much into the details and I think the thing that I learned from him the most was the power of prototyping and that even t..."
Tamar discusses the mindset shift required for effective prototyping in product development. She highlights the need for an engineering infrastructure that supports rapid prototyping and the importance of having engineers who embrace a prototyping mindset. Yehoshua also mentions how AI tools are making it easier to build prototypes, unlocking new opportunities for product innovation.
"catalyze your career 93% of members say sidebar helped them achieve a significant positive change in their career check them out at sidebar. c/ Lenny as a product leader how do you think about just th..."
In this segment, Tamar shares strategies for aligning product and engineering teams to drive successful outcomes. She stresses the importance of spending time together, documenting discussions, and being direct about priorities. Yehoshua reflects on her experiences with her engineering partner, emphasizing the need for trust and respect to ensure that projects move forward efficiently.
"working faster but you need the engineering team to have the same mindset the product and Engineering have to work together and design because design is just in it in it as much and sometimes you can ..."
Tamar Yehoshua discusses the importance of trust and respect in cross-functional teams, highlighting how effective collaboration with engineers and product managers can lead to successful outcomes. She shares her experiences working with leaders who exemplified these values, emphasizing the need for ownership and accountability in team dynamics.
"unclear we would talk and we would say okay who's going to who's going to take this one and would do all our reviews together and so all of the okr reviews all of the we had weekly exec reviews um we ..."
In this segment, Tamar explains the tactics used to create alignment between product and engineering teams. She emphasizes the necessity of spending time together, documenting discussions, and being direct about priorities to ensure everyone is on the same page. The use of OKRs and structured meetings is highlighted as a method for maintaining focus and accountability.
"you talked about being a which I love and I fully have seen that power of that of you and your engine manager design manager being aligned on and you tell me if I'm wrong but specifically on what goal..."
Tamar shares innovative strategies for conducting OKR reviews asynchronously to improve efficiency. She describes how her team transitioned to using Slack channels for updates and video presentations, allowing for more streamlined communication and reducing the time spent in meetings. This approach fosters better engagement and allows for deeper dives into high-priority projects.
"sometimes there would be there'd be like five to 10 teams that we would then have a follow-up meeting with we would say there's things that we that this is like a really high priority project or there..."
Tamar discusses the common pitfall of product managers focusing too much on the vocal minority of users who may be unhappy with changes. She advises that while it's important to listen to feedback, product decisions should prioritize the broader user base. She shares insights on how to communicate changes effectively and maintain transparency with users.
"and so then were like we have to do something drastic and that's when we moved them to async it was also right after slack Clips launched I got it that's the video feature very cool and then I don't k..."
In this segment, Tamar recounts a leadership lesson learned from a colleague at Google who exemplified the power of listening. She emphasizes that authentic communication and understanding employee concerns can significantly impact morale and acceptance of changes within an organization. This principle applies not only in product management but also in parenting and personal relationships.
"then do it and deal with the people who are unhappy but the trick is you have to be respectful and you have to be transparent and you have to explain you have to go to people and say this is why we ma..."
Tamar shares her insights on how AI is set to transform product management roles. Drawing from her background in AI, she discusses the evolving landscape and the necessity for product managers to adapt. She encourages professionals to actively use AI tools to enhance their workflows and stay competitive, highlighting innovative use cases that demonstrate the potential of AI in streamlining processes.
"you just act you're authentic you listen to people and you're transparent it's so funny this reminds me of a book I'm reading a parenting book I'm reading right now that a former guest recommended cal..."
Tamar shares her experience of creating a prompt in Glean to track the status of product features. By integrating various data sources, she can quickly assess launch readiness and identify potential issues, demonstrating how AI can streamline project management tasks.
"think about like for the argument oh I'm too busy well if you use these products you're actually not gonna you're it's going to be leverage on your time so you get a lot of Articles sent to you summar..."
Tamar highlights how engineers at Glean are using AI to automate parts of incident management. This application of AI not only saves time but also enhances the team's ability to respond to issues effectively, showcasing the practical benefits of AI in tech operations.
"and keep trying because the models that we have today can do a lot already yeah I love your example of the PM and what they did with the Discord Channel is there anything else along those lines that e..."
Tamar discusses the utility of AI in summarizing industry news for product managers. By leveraging AI tools, PMs can stay informed about relevant developments without being overwhelmed by information overload, allowing them to focus on strategic decision-making.
"weeks ago because we're advancing our prompting capabilities and so I was testing it out and I was like oh I could do this so that's like uh and that's another example and uh Engineers are using it fo..."
Tamar argues that while AI can assist with data analysis, the creative aspect of product management remains crucial. She believes that PMs who can think strategically and creatively will thrive in an AI-driven environment, as AI lacks the ability to innovate.
"yeah I think that just I think that beginning of the prompt is something a lot of people don't know is the power of just giving it a role like you are a product manager at glean from that perspective ..."
Tamar reflects on how AI will reshape the role of product managers. She suggests that while some traditional PM tasks may be automated, the demand for strategic and creative PMs will increase, leading to a more dynamic and impactful role in tech.
"statue shared is she's making six figures off this product that she builds on the weekends Chad PRD so cool incredible but it also shows what you can build with ey right it's just her I think she just..."
Tamar explains the challenges of integrating AI into products, emphasizing the need for guardrails and user education. She discusses how Glean uses AI to enhance enterprise search and the importance of ensuring that AI tools remain relevant as technology evolves.
"more creative and I think designers and PMs are kind of going to blend because the best designers I've worked with are product thinkers and a lot of really good PMs can also design depends on the what..."
In closing, Tamar shares her excitement and concerns about the fast-paced changes in technology. She encourages listeners to embrace new tools and adapt their workflows to stay competitive, highlighting the opportunities that lie ahead in the evolving tech landscape.
"obviously an example which integrates llms which innately are non-deterministic and hard to know if they're going to provide anything good sometimes something really dumb comes out do you have any adv..."
In a rapid-fire lightning round, Tamar shares her favorite books, shows, and products. She highlights 'Switch' by Chip and Dan Heath for organizational leadership and 'Team of Rivals' for insights into leadership during challenging times. Tamar also discusses her favorite dark chocolate and the transformative impact of Glean on her work processes.
"it like a person you look to like hey what's new there are definitely like AI newsletters that I look at there's AI podcast that I listen to I now have a commute so in some ways that's good because I ..."
Tamar reflects on a life motto shared by her father about making decisions and committing to them. She emphasizes the importance of moving forward without regrets. Additionally, she offers parenting advice on ensuring children get adequate sleep and sharing personal experiences to foster open communication with them.
"summit.com awesome with that tomorrow we've reached our very exciting lightning round are you ready I am ready okay let's do this first question what are two three books that you have recommended most..."
Tamar discusses how listeners can connect with her through LinkedIn and her Substack, 'Practical Intelligence.' She invites feedback from Glean users to improve the product. This segment wraps up the conversation, encouraging engagement and continued learning in the AI and tech space.
"so that's on the kind of organizational leadership and one book I really liked was uh Team of Rivals uh it's a it's a book about Lincoln and putting together his cabinet in during the Civil War one I ..."