Lessons in product leadership and AI strategy from Glean, Google, Amazon, and Slack | Tamar Yehoshua

Foundational Skills and Career Growth

Tamar Yehoshua: 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 evaluation criteria that you meet and value your engineering partner before you join. And then I think what’s really important is that you’re aligned. You understand your roles and responsibilities and where you’re going to divide and conquer and where you’re going to be aligned. You don’t want any of this … Like people in the organization, they ask mom, they asked dad and they got different opinions and playing one against the other. That doesn’t work.

Lenny Rachitsky: Today, my guest is Tamar Yehoshua. Tamar is currently president of product and technology at Glean, one of the most successful enterprise AI companies out there right now. Prior to joining Glean, Tamar was chief product officer at Slack for four years where she led product design and research as the company scaled 10Xed their revenue, went through IPO and then got bought by Salesforce. Tamar also led product and engineering teams at Google, where for many years she was responsible for the Google search experience. She also spent five years at Amazon as director of engineering and vice president at A9.com. She was also a venture partner at IVP and has been on board of directors for ServiceNow, Snyk, RetailMeNot, and Yext. In our conversation, we get into all kinds of juicy advice, including why companies don’t have to be run well to win, why you don’t need a career plan, the two habits she credits most for helping her succeed throughout her career, what she learned from Jeff Bezos and Stewart Butterfield and Marc Benioff, how to build stronger cross-functional relationships and a bunch of advice on AI including how it will likely change your jobs, examples of how she and her colleagues are already using AI to be more productive in their work and what she’s learned about building AI-based products that are non-deterministic and can be very unpredictable.

This episode is for anyone looking to level up as a leader and get a better sense of how AI will change your job. If you enjoy this podcast, don’t forget to subscribe and follow it in your favorite podcasting app or YouTube. It’s the best way to avoid missing future episodes and it helps the podcast tremendously. With that, I bring you Tamar Yehoshua.

Tamar, thank you so much for being here and welcome to the podcast.

Understanding Human and Product Motivations

Tamar Yehoshua: Thank you so much for having me.

Winning Without Perfect Management

Lenny Rachitsky: I’ve had so many people recommend you coming on this podcast. I’m really happy that we’re finally doing this. I want to start with a question that I’ve started to ask people who have had extraordinarily successful careers, which you’ve had. So let me ask you, what are one or two specific skills or mindsets or habits that you think most contributed to your success during the course of your career that you think might be helpful to people who are trying to figure out how to accelerate their career or just be more successful in their career?

Tamar Yehoshua: One of the things that I think is overlooked is do a really good job at whatever your job is at that point. People have a tendency … Especially product managers are very ambitious and they want to get to the next level and they’re always eyeing the next job, but you’re not going to get the next job unless you do really well at the job that you’re in. Knock it out of the park. However simple, however easy it may be to you, do a great job. And in tech jobs, there’s 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 matter what your role is. You have to understand it deeply. You need to understand metrics. So especially product managers have a wide breadth of things that they need to understand. So those are a given. You need to do that.

Unplanned Career Development

Lenny Rachitsky:

Tamar Yehoshua: So now the question is the difference in leadership and executive roles and when you’re getting there. So how do you start transitioning? So after you’ve done a great job at everything and you understand the core skills that you need, another thing you really need to know is understanding people and motivations. And when you’re building products, you have to understand why does somebody want to use your product? What problem are they solving? Why do they want to click on that button? What’s going to make them feel good when they click on it? What’s going to give them delight and what’s also going to make them feel bad and frustrated and what do they not want to do? So you need to understand motivations in people for building products and for building teams and organizations. So just like why does somebody want to click on a button, why does somebody want to join your team? Why do they want to work hard? What are they trying to accomplish? What’s the goal for their career?

So you have to be able to read people, ask lots of questions to understand them. And I’ll say one thing that really helped me, this is a strange segue, but my father was a psychiatrist and when I was growing up, we would have family occasions, go to events, whatever, and afterwards in the car ride back, he would always give his perspective of analyzing what happened at the event. What this person was thinking. Why did they say this? And then he would quiz me of, “Why do you think they did that?” And it was really interesting because it taught me to see the whole room. To see how people react. Like Lenny, if you say something and somebody else is there, look at the other person. What’s their face saying? You can understand so much if you’re paying attention. So I think when you want to build for people and lead organizations, it is about the people and understanding them and motivating them.

Advice for Top Company Rejections

Lenny Rachitsky: I love this advice. 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 built of just like, “Oh, here’s something I noticed about someone using Slack or Google or Amazon that changed the way I think about building this specific feature.”?

Lessons from Jeff Bezos

Tamar Yehoshua: One of the things that I caution product managers about is that you don’t want to be too overly reliant on metrics and you want to also have an intuition. You want product managers who understand intuitively their customers and their product and sometimes you’ll make decisions because you just know it’s the right thing to do because it feels right and it usually is right if you understand your product well enough. How do you get good at it? Ask a lot of questions. Don’t assume you know. Marc Benioff would always say, “Have a beginner’s mind. Go in assuming that you know nothing and listen to your customers, listen to the people.” Because I also see this as you’re building a feature and you think it’s the best thing. Because of course everyone’s going to want it because you worked on it and you’re going to put it front and center in the interface where everybody’s going to see it. Well, no, you got to earn that right. And that is another thing that people do is they want the thing they worked on to be right there, but it might not be the most important thing that a person needs at that point. So have perspective. Have perspective of what your users are actually trying to achieve.

Engineering Infra for Prototyping

Lenny Rachitsky: Going back to your first point about doing a great job at the job you have, I imagine some people hear this and the advice is do a great job at the job you’re already doing, and they may feel like they are, and there’s other reasons they aren’t being promoted. Is there an example from your career or a story you could tell of just like to clarify what doing a great job look like where it’s not just like I hit my goals. It’s like, here’s what it looks like. Here’s how you actually get ahead.

Marc Benioff’s Marketing Skills

Tamar Yehoshua: Are you helping the business move forward? So it’s not about I achieve what I was asked to do, but did you build something that people actually used? It’s not about just launching something and did you do the right thing for the company? And that is different. It’s a different mindset. Did you enable the entire organization to be more productive despite you? I remember very early in my career I was working as an engineer and I was offered a job to manage a team that was across different programs. I took a vacation, I came back and I said, “I don’t think this team should exist.” It was my first management job and I wanted to be a manager. And I said, “Here’s why I don’t think that this team should exist. It’s not the right thing for the company. It’s not going to be productive.” And my manager was so stunned. He was like, “Wait. You’re saying no?” I’m like, “Yeah, because here’s how you should organize it.” And then he’s like, “You’re right, and I’ll find you something else,” and he did.

Specific Ways to Build Cross-Functional Alignment

Lenny Rachitsky: If I were to put this into one word, it’s impact. Drive impact.

Don’t Overly Fear Upsetting Users

Tamar Yehoshua: Yeah.

Lenny Rachitsky: 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 I completely agree with this take, is that you don’t need to be a well-run business to win. I’ve seen this myself. I’d love to hear your insights here and especially where you notice this. What parts of your career noticed this to be true?

How AI Will Change Work

Tamar Yehoshua: I love working at well-run companies. It’s more fun, your people are happier. I like running a well-run team, so I aspire to have a very well run team and to work at a well run company. But what I’ve seen is when a company isn’t well run like IT isn’t working, marketing is broken, there are not enough people in HR, there’s a lot of turnover. All of these things I’ve seen that they’re not correlated to the company being successful. So I can think of a couple examples right now of companies I know … Not Glean, where I’m working today. Where there’s high executive turnover. Where people get yelled at. There are lots of people fired. There’s reorgs all the time. People I talk to are super unhappy, but the numbers are amazing. They’re growing like crazy. And the opposite sit is also true. I can think of one company I know really well, amazing, CEO, well run, well oiled machine, everything. Hired good executives and they flat lined.

So you just see it. You see it over and over again and people get very upset about these things that aren’t working. And one of the things that 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 all these requests for features all the time. If you did every single one, it would be impossible. Even if you did, 80, 90% of them won’t matter for the success of the company. But then there are some that really matter. So what are the things that really matter? We always talk about product market fit. Nobody really knows what product market fit is. Everybody has a different explanation, but it means people want to use your product. That they’re clamoring for it. So you’ve built something that people value and that people value and that solves a problem for them, but that’s also not good enough. You need to build a great product, but you also have to have distribution and you need to have a sales team that works. And you have to have enough money in the bank to get there. So those are probably the things that are the most important. I might be missing something.

And then within each of those, there’s the things that really mattered and there’s so many features that we built at Slack that were the most important features ever that failed and nobody used so it clearly didn’t have an impact. And you can see that in retrospect, but I think after being at multiple different big companies and small companies, I have that perspective of let’s just make sure that we do the right things and don’t get too worked up about all the things that are broken because every startup has so many things that are broken.

Real-World AI Use Cases

Lenny Rachitsky: So I think a really interesting insight here is that if you’re working at a company that is just chaotic and it feels like we don’t know what we’re doing, I don’t know how this thing is running, I don’t know how this will continue to be successful, your experience is it … Is it that most of the successful companies you’ve been at are just chaotic internally and aren’t incredibly run and that’s normal, that’s very typical?

Tamar Yehoshua: Until they get to a certain scale. Now, once you reach a certain scale and you’ve already conquered the market, then you need to be well run. Then you bring in professional managers and things are about the cost and executing and getting all the … Once you get to over 5,000 people or 10,000 people, you got to have things that … Then you’re a growth engine. You have to know what phase you’re in and what’s important at that phase. So it isn’t that at every phase, chaos is okay, and also some chaos is okay and some chaos is not okay. If you’re changing your strategy all the time and you’re changing your direction and you’re changing projects on people all the time so that they can’t actually achieve anything … So this is again, so you can’t simplify it that some chaos is okay and some isn’t. And also some chaos is right for you as a person. There are some really great companies I would never work at because they don’t fit me. They’re not a company I would enjoy going to work in the morning or they’re not aligned with what I’m good at. So just because a company is doing well, if the chaos is chaos and something that’s going to make you upset and unhappy don’t work there.

PM’s Unique Edge in the AI Era

Lenny Rachitsky: Is there a correlation there? Just like companies that have strong product market fit, things are just breaking as they’re going through hyper growth? Just thoughts on why this is the case.

Tamar Yehoshua: A lot of it is that because if you are in hyper growth, 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 hard to keep up. Because things in the infrastructure break, things in the communication breakdown. You’ve got at any given point 50% of the company has been there less than six months. But you have to grow really fast because once you hit product market fit, if you don’t, then your growth will stop. So if you’re suddenly growing, especially if you’re an enterprise company, you have to have salespeople, if you’re a consumer company or systems have to keep running as you scale. And look at companies like MySpace, well, they died because their product got too slow. And so some companies have initial product market fit and then they don’t keep up. So I do think a lot of it is it’s very hard to grow that fast. And so things really do start breaking, but then once you get all the right leadership in place, processes in place, then it starts to get better. So it goes through ups and downs in level of chaos.

Challenges of Building Non-Deterministic AI Products

Lenny Rachitsky: There’s one takeaway here that product market fit solves a lot of problems. Strong product market fit.

Tamar Yehoshua: Well, no product market fit is a death sentence. I would say it more like that. If you built a product that people aren’t really excited to use, then you don’t have a company because it’s very hard to do that unless you have distribution machine and then you catch up over time. But we will not name companies like that. So there are other ways of doing it, but yeah, that is the most important thing.

Closing and Where to Connect

Lenny Rachitsky: Yeah. I will say during my experience at Airbnb, I absolutely saw this. It was just nonstop chaos. And I always felt like, well, how is this continuing to operate and succeed? Things are just out of control. Everything’s changing every six months. I don’t know what’s happening here. And I think a lesson here is just that’s normal for a hyper growth business that has strong product market fit. But again, not a good excuse to just allow chaos. And it’s not like chaos means success, right?

Recommended Books and Leadership

Tamar Yehoshua: And it’s not a good excuse to not have an organization that’s functioning. You should still strive to have an organization that’s functioning and keep people happy and motivated and all that.

Lenny Rachitsky: Great. Okay. Another maybe contrarian opinion that you hold 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 where the hell I was going to go. I never had this vision of here’s what I want to do. I just followed things that were pulling me and things that seemed interesting. I love that you also tell people this. I’d love to hear your insights here. Especially for someone that’s either struggling with their career or just stressed. They don’t have a plan or their plan’s not working the way they wanted it to.

Media and Product Recommendations

Tamar Yehoshua: Really recently I was talking to somebody in their twenties who was asking me for career advice. Should I be a product manager, et cetera. And I’m trying to put together my five-year plan and I said, “I never had a five-year plan.” So to be clear, some people need that. That’s the kind of people they are. They want the planning. I said, “It’s great if you want that, but I never had it.” And the person I was talking to just relaxed and they’re like, “Oh my God, that’s so great to hear because I have no idea what I want to do in five years.” I’m like, “I still have no idea what I want to do in five years. I’ve never had an idea what I want to do in five years.” Early in your career you have a lot more angst about it because the forks in the road are more significant because they can go, do 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 meet a lot of kids in their … I shouldn’t call them kids. My kids are my kids’ friends. But a lot of people who are younger in their career who are struggling with this a little bit. So what I believe, and I’ve always believed is that you follow people. You learn the most from people. I don’t look for domains. Some people have a domain, like I’m super interested in climate or whatever and they really want to work in that area and that’s fine so maybe within that area. But you follow people who are the best at what they do. So it’s not good enough to follow somebody who you like. You want to follow somebody who’s either the best product thinker or the best engineer or the best salesperson. And so that you will learn the skill of how to be the best at that.

So you follow people where you’re going to learn the most. And a way to do that also is you look at where the great people are going. So you want to go to companies where there’s also a nexus of great people because they together will do great things. And even if the company fails or succeeds, but not as much as you’d like, you still have those connections. Everybody talks about the PayPal Mafia and how they’ve gone on to do things. I was super lucky to be at Google for so many years and I spent a lot of time with Googlers that I met and that are all working in different companies now because you build those relationships by working together. So if you follow people and where you’re going to learn the most and you go step by step, I think that’s a great way of progressing in your career.

Mottos and Parenting Advice

Lenny Rachitsky: That’s such tactical advice. And I’ve seen this work for a lot of people that just go where their favorite former employees work. And not favorite to your point, but the people that they most respect and have been most impressed by. And I think it’s such an easy thing to do. It’s a really easy heuristic for understanding where to go. There’s something Marc Andreessen once shared that I’m reminded of when you say this. There’s a term for this, I forget the actual term, but there’s certain companies have this gravitational pull where they are acquiring all the best talent. They’re currently the gravity in the space and everyone awesome is going there. And you have to, as a company, know you’re one of those companies or you’re the opposite. You’re losing all the people and they’re all going to this other company. I guess any thoughts on that?

Tamar Yehoshua: Yeah. And it’s really bad when you don’t have a gravitational pull. It’s super hard. I would say that one thing that if you’re a manager, I always advise managers, go somewhere where you can recruit. I got a piece of advice from a friend that I thought was amazing advice as a leader. She said to me, “Take a job where if you hire people, it’s going to make their careers.” I was like, “Whoa.” Because I was getting offers for some turnaround jobs. And if you think you can turn around, great. But if you’re going to hire the best people, you want to make sure that it’s going to be a good place for them and that they’re going to learn and they’re going to grow. And so you want to do right by them. And you really earnestly want to say you can make your career by coming here.

And I thought that gave such a higher bar for every job I was looking at as a leader that I thought it was just amazing advice. And then on the flip side, on the negative side, some people are putting too much emphasis on where will I get a big financial return? And I’ve found that financial returns are 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 success is so hard because you don’t know what’s going to happen with the market, with the world, with crypto, and Meta AI. And people who do that and say … I had one person say, “I took this job because I’m a mercenary. They just paid me a ton.” Did not work out for him. And I feel really bad when people do that, but I think that it’s a dangerous thing to do.

Podcast Closing Remarks

Lenny Rachitsky: I imagine some people hearing this advice are going to feel like, “I’m not going to get a job at OpenAI or Glean or other awesome companies that everyone wants to go work at.” Any advice to those folks?

Tamar Yehoshua: There’s lots of good companies and there’s lots of smart people. You don’t have to be at the top brand. And if you go somewhere where you’re going to learn and it’s going to get you there. I made mistakes. I went to some companies, multiple companies that failed or stopped growing and didn’t do well or didn’t have all the right people. Careers you don’t make every step is to the right place. You remember in what you cited, all the companies I went to that did well, you left out all the ones that I went to 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 focus on that learning bit, you will get there. And there are lots of paths. There isn’t just the OpenAI or Glean or Anthropic.

Lenny Rachitsky: Awesome. And again, I love how tactical this is. If someone is trying to figure out where to go work if they’re unhappy in their current job or don’t have a job right now is just make a list of the people you most respect that are the best at the thing they do, see where they work and there’s your list of companies to potentially go after. There’s a lot of benefits to this as you shared. It’s not just helping you pick the place to work, it’s the network. It’ll level you up. Is there anything else along those lines that is helpful for people to think about why this is a really good strategy?

Tamar Yehoshua: Skills can’t be taken away. A company can fail, but if you learn a skill, you will always have that skill.

Lenny Rachitsky: I love that. And I’ve totally seen this to work, so I really love that you’re focusing on this advice. You’ve mentioned places you’ve worked and folks you’ve worked with. You worked with folks like Jeff Bezos, Stewart Butterfield, some of the top product thinkers, leaders in the world. So let me just ask, what’s one thing you learned from Jeff Bezos and Stewart Butterfield?

Tamar Yehoshua: Probably can’t narrow it down to one, but I’ll talk about Bezos first. I was very lucky to join Amazon early when I still … I had quarterly meetings with Jeff Bezos. And this was before AWS launched, so it was before Amazon was known in the Valley. This is another example. I went there because I went to work for Udi Manbe who started A9 and he was talking to me one night trying to recruit me and he spent two hours on the phone with me telling me how amazing Jeff Bezos was. And this was before there were any books on him. And that really convinced me to go there. So there’s a lot written on Bezos. Read his shareholder letters, read the books about him, read Colin Bryar’s Working Backwards. The Everything Box I think it’s called or The Everything Store.

Lenny Rachitsky: The Everything Store. Yeah.

Tamar Yehoshua: There’s so many good books and there’s so much to learn about how he works. So I won’t try and cover those things. The things that stood out to me from the meetings I had with him were a couple of things. One, a lot of people have written about these six pagers, so he doesn’t believe in PowerPoint. You write a six pager about … It’s like studying for the final exam is writing these six pagers. So you go into the meeting and there’s the people around the table, his executive team and him. First he does not speak until everybody around the table speaks. So he goes around to all his leads and said, “What do you think? What do you think? What do you think?” And I’m sitting there like, “I don’t care what anyone think. I just want to hear what Bezos thinks.” But he wants to make sure that it’s a team effort and that he’s listening to what everybody in his organization thinks.

And he always spoke last. He is by far the smartest person I’ve ever met in my life. I’ve worked with a lot of smart people. But his ability to go deep in any domain and nail the core issue, and remember. We would’ve quarterly meetings and from quarter to quarter he would remember things that he had talked about before and then he would go into the architecture of search and why are you doing it this way or that way? And you’re just blown away that he knows that. For me, the biggest takeaway from those meetings was his consistency, which is he had principles that it made it easier for you to operate in his company because you knew what he cared about because he always had these principles. Everything had to be customer driven, everything had to be relevant for the customer.

He hated icons. That was just the thing. You had to write what they were because people couldn’t figure out what they are. So anytime you showed an icon, he would get annoyed. But you would go in and after a couple of meetings you’re like, “Okay. I know what he’s going to ask about. I know how he’s thinking and I know what his principles are.” And I think that consistency enables you to operate a large organization more effectively. And then there’s one other thing that I really remember was one of the few really small meetings I was in with him and we were presenting working on a new product, and I was like, “Our competitors have 10 times as many people as we do on this.” And he looks at me and he said, “That is your advantage.” And then he goes into his talk about how it’s a hill and it takes seven years to build a product. You can’t look at it in the near term. You have to be in it for the long term. You can be sure I never went in and said, “I need a lot more resources.” So that was Bezos.

Lenny Rachitsky: Awesome.

Tamar Yehoshua: Stewart. Again, I went to Slack because I wanted to work with Stewart Butterfield. I think he is the best product thinker in the Valley. He’s not working in product right now. He’s taking time off. But he’s got this combination of long-term thinking and in the details. So in 2014, he wrote a master plan for Slack, which was build a product people love, build a network. That’s Slack Connect. Build a platform that makes all of your other SaaS products more valuable. That’s Slack Platform. And then do some magic AI stuff. Magic AI stuff took a lot longer, but-

Lenny Rachitsky: That was part of his plan early on is magic AI stuff.

Tamar Yehoshua: It literally was. There was a grid with four boxes in 2014 and it never changed. That was his master plan and what we worked on each year changed. But somebody recently asked me, “You guys did Slack Connect much later?” I’m like, “Yeah, but it was always part of the plan.” It was 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 though he was such a great product thinker, he would always say, “I can’t tell you if this is going to work. I have to feel it. I have to try it. And a mock-up doesn’t tell you what it’s going to feel like.” And he would push people to do prototypes, not incremental of just to get a feature out, but really to think. Very soon after I started, we launched … I hired a design lead, Ethan Eismannn, and he led a redesign of the new information architecture for Slack.

Lenny Rachitsky: I worked with Ethan at Airbnb.

Tamar Yehoshua: Oh yeah.

Lenny Rachitsky: He was head of design for the search experience and the search team.

Tamar Yehoshua: Yeah. Ethan is awesome. And he came in and his first task was to work with Stewart on this redesign. And Stewart came in and said, “I want you to take everything in the interface and put it behind one button.” And everyone’s like, “That’s never going to work.” And he’s like, “Do it. Just do it.” And so we had our prototypers … We had also engineers, front-end engineers who were really good at prototyping, literally took everything in the interface and put it behind one button and he said, “This is how you’re going to see what you really need in the interface.” So we were never going to ship that, but it was the beginning of the redesign.

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As a product leader, how do you think about just the time it takes to create a prototype in something like this? As a pm I’m just like a lot of times we don’t have time to build this whole prototype. We got to ship stuff, we got to hit these calls, we got experiments to run, we’ll just build it and see how it goes. How do you think about making time for something like that?

Tamar Yehoshua: If you’re doing it right, it’ll be faster and you need to have an engineering infrastructure that enables prototyping. So some engineering infrastructures are too heavy and they don’t actually enable prototyping. We had a problem with our mobile apps that it was too hard to prototype and we actually redesigned our mobile apps until we got to the point where it was easier because our desktop app was pretty easy to prototype. But you have to have a layer of abstraction that enables you to do that, and you have to have engineers who have a prototyping mindset, and if you build multiple things and you have this mindset as I’m willing to throw it away, you write code that is never going to make it to production so you can just crank it out much faster and then you can see what works and then you build the production code. Until you actually get to your end goal of something 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. Sometimes you can get design engineers who are doing the prototyping. So your first prototypes are like Figma prototypes, and then you get prototypes on real data. When I was at Google, one of our teams, a front-end team, I remember we hired a bunch of prototypers and our head of front-end engineering said to me one day, this is my secret weapon. This is how we move faster. So I do think it’s a mindset shift and a tech stack shift.

Lenny Rachitsky: We’re going to talk about AI later, but it’s also getting easier to build prototypes with AI. There’s this video recently that went around on Twitter where an eight-year-old girl was building an app and in like 45 minutes, she built a chatbot using this product called Cursor. So I think that’ll unlock a lot of great product on opportunities and just accelerate this sort of work. I asked about Jeff Bezos and Stewart Butterfield. I’m curious if there’s another leader you’ve worked with that maybe is less known that you also learned a ton from that might be worth talking about.

Tamar Yehoshua: I think that there are people who are really, really good at what they do. So Marc Benioff is an amazing marketeer. His marketing mind … After the acquisition, I got the opportunity to onstage with him at Dreamforce for … Because Slack was a new shiny thing so of course Slack was going to be in the keynote. And so I was in the Benioff’s keynote two years in a row. And so I watched how he approaches his keynote and the whole thing around Dreamforce. Dreamforce is incredible at the impact that it has on the ecosystem. And so I think that as a product, people don’t think of him as much, but as his marketing abilities are amazing what he’s done.

Lenny Rachitsky: I’ve written posts about how various companies got started in Salesforce history. Always comes to mind where they go to conferences where’s there’s no software mascot walking around. And I remember they did something around one of their competitors where they just created some real controversy around someone.

Tamar Yehoshua: Well, they went into their competitor’s conference and stood outside their competitor’s conference.

Lenny Rachitsky: Mm-hmm. Right. That’s what it was.

Tamar Yehoshua: This is in the Beyond Software. This is in his book that he wrote about the early phases of Salesforce. And it takes his guts. He pushes the envelope.

Lenny Rachitsky: I love that. It’s a really good point that people don’t think of Marc Benioff as a marketer. And that’s interesting that that’s maybe the main thing you took away from him is just the power of marketing and the skill.

Tamar Yehoshua: He approaches his marketing presentations like a product person approaches their building their product.

Lenny Rachitsky: Amazing. Okay. Speaking of former colleagues, I asked one of your former colleagues, his name is Fuzzy Khos. He’s now the CTO of Notion. You worked with him, I believe at Slack.

Tamar Yehoshua: And at Google.

Lenny Rachitsky: And at Google. Wow. Okay. So I asked him what to ask you, and he said that you’re amazing at building strong cross-functional relationships, especially with engineers. I know you used to be an engineer, so I get where that skill come from. What can you teach people about building stronger cross-functional relationships, especially PMs to build better relationships with their engineers, designers, other folks on their team?

Tamar Yehoshua: Probably the most important thing that a product leader does because if you have great ideas of what to build, but you can’t get them built, then you go nowhere. So one, make sure somewhere where you have a good engineering partner. So Henderson was the co-founder and CTO of Slack, and I couldn’t have asked for a better engineering partner. He’s just awesome. And that has to be part of your evaluation criteria that you meet and value your engineering partner before you join or you know that it’s not the right one and the organization is willing to make a change. So that can happen too. You can go in and understand that something has to change, but that is a very, very important thing of what you’re doing and what you’re assessing when you go in. And then I think what’s really important is that you’re aligned. You understand your roles and responsibilities and where you’re going to divide and conquer and where you’re going to be aligned.

You don’t want any of this … People in the organization, they asked Mom, they asked dad and they got different opinions and playing one against the other, that doesn’t work. So one, you have to know that you’re not going to do that. So if somebody would ask me something that it was in Cal’s domain, I’d be like, “Did you talk to Cal?” I would never try and go around him. So we were very clear on, you’re going to drive this, I’m going to drive this. And if it was unclear, we’d talk and we would say, “Okay. Who’s going to take this one?” And we would do all our reviews together. And so all of the OKR reviews, we had weekly exec reviews, we had the updates on our OKRs, so we did them all together, but I knew here’s the things that he was going to ask the questions on and dig deep. And then when I was, he would take a back seat, but of course we could ask questions in each other things, but I knew that he was taking ownership and he knew what I was taking ownership of.

But I think the bottom line was respect. Is that you have to respect and trust that they actually will follow up on what they say they will. In Cal and Fuzzy were amazing at that. I would go to Fuzzy and be like, “Hey, we need more mobile engineers because this one product is not going to ship.” And he’s like, “I’m on it. Got it.” And that was all I needed to do. And obviously if he couldn’t do it, he’d come back to me and, “Hey, there’s going to be a problem.” But it was like just things got done. That’s the best part of it.

Lenny Rachitsky: You talked about being aligned, 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 goals you’re trying to achieve, what success looks like, things like that. Are there any tactics you found to create that alignment? And also if there’s anything else you want to add to the point I just made about what it is you’re specifically aligned on, that’d be great.

Tamar Yehoshua: One, you got to spend a lot of time together. There isn’t a way around that. And you have to document things and make sure that you’ve talked it through. And if you don’t agree with something and you’re not sure it’s a priority, you have to speak up and you can’t just be like, “Okay, whatever.”, and then go to somebody in your team and be like, “Oh God, that that CTO, why did he make this decision?” That just doesn’t work. So I’m a very direct person. So if I don’t think that something is the right priority or is working, I will be very clear. We had different forms, so I’ll be very tactical here on the forms that Cal and I had together.

Lenny Rachitsky: Perfect.

Tamar Yehoshua: We used OKRs to drive our processes and we would have the teams present OKRs to us. When the team got too large, it got to be too much time to go through every team’s OKR review so we had a Slack channel for each team, their OKRs, a planning channel for each one. And people would post a doc and then a Slack video of going through the major points. And we had a time limit of how long they were allowed to be. And they would say, “Here’s our OKRs, here’s the things that you would pay attention to.” And then Cal and I would do a marathon and we would watch them all together. And-

Lenny Rachitsky: In a room sitting there watching them together?

Tamar Yehoshua: Correct. And then we would say, “Do we have any follow-up questions?” And we put in channel our follow-up questions to the team. And sometimes there’d be five to 10 teams that we would then have a follow-up meeting with. We would say that this is a really high priority project or there are a lot of questions that we have, and then we would do a meeting but we were always doing those meetings together. So that was the OKR reviews of getting the alignment. And by asking the questions, we could then … By it just being us, we could dig into the team. And we each had a chief of staff, so it was the two of us plus our two chiefs of staff, and which they also did a divide and conquer and they worked really well together. They were both long time Slack employees. So for years they had … One had been an engineering director and one had been a TPM. And then every Monday we had a Monday meeting where we reviewed the progress on the top OKRs and red, yellow, green and don’t talk through the green ones, only talk through the red ones and what are the issues. And again, both there. And then we had a weekly meeting with the four of us where we would just go through any issues in the organization, what’s going on, what’s not.

Lenny Rachitsky: And the four of us is you, the CTO, the chiefs of staff.

Tamar Yehoshua: Yep. And sometimes we would invite people. Like there’s an issue with QA, so we’d have the QA leader come in and present to us. But we tried to limit the number of meetings with teams. So it’d be like the Monday meeting was the big meeting that you had to be there and you had to be able to talk to your project and that was it.

Lenny Rachitsky: There’s so much awesomeness here. I love the idea of this Async share your plan in a video instead of meetings with everyone in real time. And you could just do a lot of the stuff Async.

Tamar Yehoshua: We iterated every quarter, just like you iterate on a product. So every quarter we would say did the OKR planning work or not, and then we would adjust. So we got to the point where at one point we added up all the hours of OKR reviews and all the people in them and it was some insane number, like 300 and something and we’re like, “This has gotten out of hand.” So then we’re like, “We have to do something drastic.” And that’s when we moved them to Async. It was also right after Slack Clips launched.

Lenny Rachitsky: Got it. That’s the video feature. Very cool. Then I know you launched huddles, right? Slack Huddles? Did you use that as a part of this or eventually you just get people into a little huddle asynchronously and talk-

Tamar Yehoshua: Sometimes. Absolutely. We would be in the reviews and we would huddle with somebody to ask a quick question. We use Huddled all the time. I still do. I love Huddles.

Lenny Rachitsky: I love it. One crazy thing about Slack is people in Slack don’t actually use email internally. It’s like all in Slack. It’s like the actual vision of Slack working within Slack.

Tamar Yehoshua: No email unless you’re dealing with somebody external. And no, it’s mostly Slack Connect anyway.

Lenny Rachitsky: Anyway. Wow, that’s amazing. Okay. I have one more question around product stuff and then I want to talk about AI. So I was reading your newsletter on Substack, which we’ll link to and you share this really interesting insight that I’ve experienced myself that I’ll quote you here. One of the mistakes that I see a lot of product managers make is they over index on people who are going to be unhappy with the products they’re launching. And basically your advice is not to worry so much about making users unhappy, which I think is counterintuitive to some people. Can you just talk about this lesson and I’d love to hear what product you launched that made people unhappy that you realized, oh, maybe we don’t need to worry about this as much.

Tamar Yehoshua: I saw it more when you unlaunch things, you take things away there’s always some set of users that are using a feature that nobody else does, and then you take it away and they’re super unhappy, but there are more people you’re going to make happy. So a product manager gets caught in this trap of the vocal minority and the number of people using your product … Depends on what phase. Are you a Google? Are you Slack? Are you a Glean? But the number of people using your product today is usually unless you’re a Google far smaller than the number of people who are going to be using your product tomorrow. So design it for the bigger number of people who are going to be using it tomorrow. If you have to redo the UI and the Who Moved My Cheese, people will be unhappy, but all the new people are going to be like, “This is so much easier.” 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 made this change.” And you have to be authentic. You can’t be dismissive and you can’t have marketing speak. You have to really say, “Here’s for real why.” And you have to listen to your audience. You don’t want to alienate your early users because most people … If you made a good decision on why you moved this or why we stopped using Slack calls and moved to Huddles and you have to do it over time and give people choice and then give them enough time to move. So you have to do it in the right way. But if people feel heard, it makes a difference.

I have an example that’s not a product example, but I think is a really good one. It’s a leadership example. So when I was at Google, there was always a controversy about something, but there was a controversy about … It was Blogger or something. I can’t even remember what it was. It was like we made a change. We were like 50,000 people at the time. There was an engineer in my team, an IT engineer that was super unhappy about the change. And I knew Rachel Whetstone, she was in charge of all of PR and global policy at Google. So huge job. And I emailed Rachel and I’m like, “Hey, do you have an FAQ or something that can help me? Because I don’t know why you made this change and that I can help explain to the engineer in my team.”

She did not respond to my email. She picked up the phone and she called him. I had no idea she did this. She just called this IT engineer and she listened to him and she heard why he was upset and she explained her reasoning. He was so blown away that she called him that he completely changed his opinion and then he told everyone else in the org. And so it had this effect. And I learned a lot from watching her do that. She never even told me she did it later. She just did it. You just act. You’re authentic. You listen to people and you’re transparent.

Lenny Rachitsky: It’s so funny. This reminds me of a parenting book I’m reading right now that a former guest recommended called Listen. And the core thesis of the book is when your kids are acting up or they’re getting off track, so much of what they need is a sense that you’re connected to them, a connection which is rooted in you listening to them. And so all-

Tamar Yehoshua: My favorite parenting book … I don’t know if this is the same one or a different one, it’s How to Talk so Your Kids Will Listen & How to Listen so Your Kids Will Talk. Maybe it’s the new name of that book, but it’s so good and it’s so true in everything and also in products. So whether you’re in a forum and explaining to customers, whether you’re enterprise customers, you’re explaining, you’re hearing them out, people want to understand.

Lenny Rachitsky: Amazing. There’s so many applications of just the power of listening. Okay. Well, not quite a segue, but let’s talk about AI. You’re at the epicenter of AI now with Glean. How do you anticipate AI will change our jobs and product? What do you think people may be aren’t recognizing it, realizing it? What have you seen?

Tamar Yehoshua: I’m going to give you a little bit of my history with AI to get to that point. When AI was a completely different technology stack … I have a master’s in AI. So I started working in AI when … It’s evolved so much. And then of course at Google using it for auto complete and search. It’s transformed so many times. But then with this last transformation of GenAI … And that’s what brought me to Glean of seeing this, meeting lots of AI companies and like, “Wow. This is really going to transform how we work.” And it’s just fascinating seeing these products. I was one of those people like, “Oh yeah, it’s going to be so far away.” Until I saw GPT3. And I think AI, we are underestimating how much it’s going to change how we work. It’s not going to be sudden from today to tomorrow because people haven’t figured it out yet. They haven’t figured out how exactly to leverage it. But the people who have are going to be so far ahead. They’re going to be far ahead of everyone else because they’re going to be working faster, they’re going to be working better.

And in five to 10 years, I think the lines between product managers and engineers and designers are going to blur because AI will enable product managers to build prototypes, to build designs. Designers to build a pro like Figma already has their Figma AI. You can press a button and you can get your initial prototype working. You’ve got all the co-pilots. So they’re not quite there. You still, like with Copilot or with Cursor, you need to be an experienced engineer to know when it’s getting it wrong, but they’re going to keep getting better. I think people have to be careful about not getting left behind, but their jobs aren’t going to go away. They’re just going to change. I’m of the believer that we’re just going to have a lot more software. But I talked to engineers and to PMs saying, “Yeah, I tried that. It doesn’t really work.” And then go back to how I worked before. And that’s a dangerous spot to be in I think.

Lenny Rachitsky: For people that get anxiety hearing this where they’re feeling they’re going to be left behind and like, “Oh my God, I don’t know enough time to do this or I don’t know what I’m doing here.” Do you have any advice for what’s something someone can do to not fall behind?

Tamar Yehoshua: Use the products. This is what good PMs should do period. Always be using new products. It’s not a unique thing for AI. When mobile came out, PMs needed to be using mobile apps all the time to try them out, see what the UIs are, see what’s working and what isn’t. And the same goes even more for AI. Use ChatGPT. If your organization has Glean, use Glean. Use Claude. Try them all. Try them and see what they do. I was talking to a product manager I know who is more forward-thinking and loves playing with new products and he had this use case that blew me away. So he said … And this was a couple of months ago, so before … It was right when Gemini had expanded the context window. So his product had a Discord channel and he took the transcript from the Discord channel, which was huge. And he fed it into Gemini the entire channel and then used it to ask questions. Like what is the sentiment of my product? What is the most requested feature? What are the things people are unhappy with? This never would’ve occurred to me. It’s like, that is so smart. And he’s like, “It was like a goldmine.” Do you know how long it would’ve taken him to read? And he just wouldn’t have done it.

So think about for the argument, oh, I’m too busy. Well, if you use these products it’s going to be a leverage on your time. So you get a lot of articles sent to you, summarize them, use AI to summarize the articles. We use Gong at Glean to record all our sales calls. We have a Glean app that will read all the Gong transcripts, put them in a spreadsheet in a certain format of who the AE is, etc. And then summarize all the top requested features from all the Gong calls. And it took a while to get it right. At first the summarization, the prompt wasn’t good enough and would give us features that our salespeople would recommend and didn’t distinguish that this was actually the customer. So you have to tweak it. It’s not going to work out of the box. But then we got it to the point where it worked and these things really save time and you have to use your creative juices as a PM to figure out how it can help you and have patience to iterate and keep trying because the models that we have today can do a lot already.

Lenny Rachitsky: Yeah. I love your example of the PM and what they did with the Discord channel. Is there anything else along those lines that either you’ve done to leverage some AI tool to be more productive or folks in your team have done to be more productive youth, either your product leaders or other folks?

Tamar Yehoshua: So many examples. So one that I did really recently is I wrote a prompt in Glean to help me get the status of features. And we have a Launch Cal, and you can look at Launch Cal it’ll say a date. But then is it really the date? What are the outstanding issues? So it will look at our Launch Cal and it will see if there are any open year tickets, what the Slack conversations are and the customers who are beta testing it, bring all these together to tell me, okay, launch date is this according to Launch Cal, but here are all the open issues and here are the open conversations that people are talking about. So then it can give me the confidence level of the future looking. So I can run the prompt, just put in the name of the feature. So I don’t have to read all of these channels.

So this is a prompt that I built two weeks ago because we’re advancing our prompting capabilities. And so I was testing it out and I was like, “Ooh, I could do this.” So that’s another example and engineers are using it for automating part of the incident management of I got an incident, how do I see were their previous incidents that were similar to it, where they’re not. And so these are the type of things you can look at to help you. But the simplest, simplest is there’s so much news. Let me just paste in all of these things and summarize them. As a product manager at Gleam, here are all the latest news. What do I have to care about? What’s impacting me and potentially competitive to any of the products that I have?

Lenny Rachitsky: And putting that into say Claude or ChatGPT you’re saying.

Tamar Yehoshua: Yeah.

Lenny Rachitsky: Yeah. 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 Gleam. From that perspective, give me this summary versus just summarize this and that ends up being really powerful right.

Tamar Yehoshua: A hundred percent. And you can compare what is Claude’s PR saying that … They just launched Claude Enterprise. How is Claude Enterprise different from OpenAI Enterprise? Again, you can do it yourself, but these micro improvements in your productivity help. For my newsletter, I interviewed Claire Vo who came out with ChatPRD. And so product managers are using is. We’re just starting to evaluate it internally, so I haven’t personally used it yet, but it’s super cool and you can use ChatGPT to do a PRD. And ChatPRD, it’s more templatized and more frameworks of how to do that. And again, these things are going to keep getting better.

Lenny Rachitsky: Claire’s been on the podcast, she’s going to be speaking at the Lenny and Friends Summit coming up October 24th.

Tamar Yehoshua: Oh, cool.

Lenny Rachitsky: Yeah. A crazy stat she shared. She’s making six figures off this product that she builds on the weekends ChatPRD.

Tamar Yehoshua: So cool.

Lenny Rachitsky: Incredible.

Tamar Yehoshua: But it also shows what you can build with AI.

Lenny Rachitsky: Right. It’s just her. I think she just recently hired some engineers to help because she has three kids CTO at LaunchDarkly and just is building this on the side making a hundred thousand plus dollars. Incredible. I want to add a couple of things here. So one is for folks looking for ideas for how to use AI tooling for their PM job. There’s a couple of posts I’ve written that I’ll link to in the show notes just to put that out there of just a bunch of PM sharing, here’s what I’ve done with these various tools. Another thought I’d love to get your take on. There’s a lot of fear that the PM job be replaced by AI. And I’ve recently realized that it’s the opposite. I think the PM role is the best positioned to thrive in the world of AI because if you just think about you have a tool that can just build a thing for you, just like you’re staring at this blank thing that can build anything for you, which function would you think would have the best chance of asking it of what to build and how to articulate what to build best?

To me, it’s clearly Product People. They’re best at figuring out what to build, what matters most, where the impact’s going to be what customers need. Not to say other functions don’t also have the skills, but I feel like of all functions, PMs have the most of that specific skill. I’d love to get your take on that.

Tamar Yehoshua: That. I think that AI, the one thing it’s not good at is being creative. So if you’re a PM who’s doing the grout work, it’s going to take your job away. But if you’re a PM who actually is strategic and can pull the pieces together and be creative and think how you do something that it’s going to differentiate. Because it’s not going to give you that leak. It’ll say, here’s what customers are asking for, here are the problems today, but you have to figure out how to solve it. So in some ways it might weed out the good from the bad PMs. Because there are a significant number of PMs who are more just execution. And I think that part of the job hopefully will be lowered because I hope a lot more of the execution will be able to automate updating Jira and all these things that just take time and creating even little Launch Cals, which PMs have to do manually now. So hopefully a lot of that work goes away and then people can be more creative. And I think designers and PMs are going to blend because the best designers I’ve worked with are product thinkers and a lot of really good PMs can also design. It depends on what kind of product you’re PMing for. So I agree with the caveat that it will become harder to be a great PM.

Lenny Rachitsky: Wait, say more about that. It’ll be harder to be a great PM because many PMs are doing things that are mostly project management and that’s the stuff that-

Tamar Yehoshua: Yeah. Let me rephrase. It’s not going to be harder to be a great PM, but to be a PM, the not so good PMs jobs will go away. The great PMs will still have great jobs.

Lenny Rachitsky: Yeah. I totally hear you. So in a sense there might be fewer. You might need fewer PMs, but I think that applies in theory to every function. Fewer engineers. Fewer designers.

Tamar Yehoshua: I don’t think you’ll need fewer. I think you’ll be able to do more things. Think about every company. Our head of sales came to me the other day, “You need to hire more engineers because we just have so many things we need to build.” I’m like, “When have you ever worked in a company where you thought that you didn’t need more engineers?” You always want people to build more stuff. So I don’t think you’re going to need fewer. I think you’re just going to get so much more done.

Lenny Rachitsky: A lot of people are building AI into their product. Glean is 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 advice on working with these very complicated systems that don’t necessarily … You can’t control and building them into your products? Anything you’ve learned that might be helpful?

Tamar Yehoshua: My first week at Glean was eye-opening in learning some of these things. But let me first just explain what Glean does for people who may not know. So Glean was started as enterprise search. Glean reads content of all your SaaS apps. So it reads the content from Microsoft, Google, Slack, Salesforce, Jira, like any SaaS tool that you use, it indexes it and enables you to search. So it started as just enterprise search and using AI. So it was an AI search using BERT models and using vector embeddings in 2019. Because the early engineers at Glean came from Google and Google created BERT to enhance search. And so it was obvious that they would be using ML techniques for search. Then GPT3 came along and added a natural language interface, a chat interface. You can ask the question in actual language and get an answer, and it basically is a knowledge graph of your organization. So you can ask any question. Think of ChatGPT for your enterprise. Ask any question about your enterprise.

So people understand search because they understand Google and you put in a query and then you refine it. But chat interfaces, people still don’t really know how to use. If you look at the stats from ChatGPT, from what I understand, the retention is fairly low. People use it, they play with it, and then they don’t get back to it because it’s not in their workflow and they have a hard time figuring out what they can and can’t do for it. When I got to Glean the first week I met with the assistant quality team and one of the biggest issues they have is people trying to use Glean for things that there’s no way it could know. Like what should my top priority be next week when we don’t even know what your priorities are. But then there’s golden cases that are just amazing.

The example of refining queries and searched years for people to understand how to do. And it took a lot of features of auto complete and refinements at the bottom of the page. So we need to build in those things, guardrails to help with the change. To help suggest, oh, Lenny, here’s what you could do. Here’s a prompt to find out the status of your feature that Tamar built. So how do you give people guardrails so that they understand what is going to work and what isn’t going to work? Because this whole, I don’t know what I can ask. And then on top of that, the non-deterministic. An enterprise CIO will go use ChatGPT on the weekends, but they come to work and they expect their software to be deterministic. So how do you help educate users about that?

And then the other thing I’ll say about using LLMs is the industry is transforming so rapidly that you need to make sure that your product gets better as the LLMs get better. And that too many people are building things to make up and compensate for the LLMs that all that work is going to go away. So it’s okay to do it to understand that it’s going to go away, but that can’t be your differentiator. You have to understand that your differentiator is something that will continue to be there as the LLMs get better and smarter.

Lenny Rachitsky: And as part of that, because the LLMs get so much smarter, everyone else will become awesome. And to keep up, you need something that is actually outside of the LLM that continues to differentiate you and is better than what other people are doing.

Tamar Yehoshua: Well, yeah. That your whole product gets better as the LLMs get better.

Lenny Rachitsky: That makes sense.

Tamar Yehoshua: It’s a frame of a of mind of how you approach the value add you’re having.

Lenny Rachitsky: Awesome. Tamar, to close out our conversation, is there anything else that we did not cover that you think is important to share or you think might be helpful to leave listeners with before we get to our very exciting lightning round?

Tamar Yehoshua: I in my decades of working in tech, have never been working in an environment that’s moving so quickly and it’s really exciting. It’s super energizing and it’s also scary. But you have to change how you’re working. You have to change how you’re working so that you can keep up because it’s going to be an interesting decade ahead with all these new tools that are coming out. And staying ahead will be hard, but it’s also, there’s so much I think richness and opportunity here. So I advise people to get in the thick of it and try it out because you’ll be surprised at how many products we can build.

Lenny Rachitsky: I love that. I can’t help but drill in one level deeper. Is there anything you found to help you stay ahead and help you stay aware of what’s happening? Are there newsletters you find useful? Chat, podcasts that just help you keep up to date on where things are going? Is it like a person you look to like, “Hey, what’s new?”

Tamar Yehoshua: There are definitely AI newsletters that I look at. There’s AI podcasts that I listen to. I now have a commute, so in some ways that’s good because I get to keep up on the AI podcasts. So I just try and listen. I’m trying to build some prompts for myself to make it easier to say … Take in … I haven’t perfected this, but the ChatGPT voice mode where you can load it. Somebody who I just hired it at Glean was saying he does this. He loads up stuff before his commute and then he’ll be like summarize these articles and then he can ask questions to it. So I need to up my game there. But I definitely have a list of Ben’s Bites and The Neuron. Those are good summaries and I like Gil and Sarah Guo’s podcast. I listen to Cognitive Revolution. There’s too many of them right now, but I pick and choose.

Lenny Rachitsky: Awesome. Okay. We’ll link to those ones you just mentioned in the show notes. We’ll have Gil and Sarah Guo’s podcast, it’s called No Priors. I was actually just listening to it on the way here. Sarah is going to also be at Lenny’s and Friends Summit. She’s going to be moderating a panel between Kevin Weil and Mikey Krieger who are the CPOs of Anthropic and Open AI. So there we go. Another quick plug for lennyandfriendssummit.com. I think it’s lennyssummit.com.

Tamar Yehoshua: Awesome.

Lenny Rachitsky: With that Tamar we’ve reached our very exciting lightning round. Are you ready?

Tamar Yehoshua: I am ready.

Lenny Rachitsky: Okay, let’s do this. First question, what are two or three books that you have recommended most to other people?

Tamar Yehoshua: So one book was recommended to me by Shashir, the CEO of Cota. When I started at Slack, he recommended the book Switch: How to Change Things When Change Is Hard by Chip and Dan Heath. And it’s such a good book. And it’s about how do you set a path for people to follow. It’s the whole elephant and the rider. So setting the path but yet motivating people to go down the path. And I read it. We had an all hands about … I don’t even remember the topic. It was something that we were like all up in arms about that we had to do. And I had just read the book and after the all hands I went up to store it and I’m like, “You did that all wrong. You need to read this book. That is not how to get people motivated.” And he read the book and he’s like, “You’re right.” So it just changes how you think in organizations to affect change. So that’s on the organizational leadership. And one book I really liked was a Team of Rivals. It’s a book about Lincoln and putting together his cabinet during the Civil War. One, I just learned a lot about the Civil War that I didn’t really know. And it’s about, again, a book about leadership and it is fascinating.

Lenny Rachitsky: I don’t think anyone’s recommended either of these. So love them. Next question, do you have a favorite recent movie or TV show you really enjoyed?

Tamar Yehoshua: I don’t know if you like British murder mysteries.

Lenny Rachitsky: I don’t know either.

Tamar Yehoshua: It’s a niche thing, but there’s a guy named Anthony Horowitz and the latest series he did was called Magpie Murders. And it’s just an intricate story so I enjoyed it.

Lenny Rachitsky: Very niche but amazing. Do you have a favorite product you’ve recently discovered that you really like?

Tamar Yehoshua: Well, I’m going to give two. One is tech and one is non-tech. So non-tech I really like dark chocolate.

Lenny Rachitsky: Actually just like a dark chocolate bar.

Tamar Yehoshua: A really good dark chocolate that’s simple. Like no frills, none of this. Just dark chocolate. And I discovered this chocolate called Bisou chocolate. It’s a guy in Oakland who makes it himself. Super niche. He was selling at the farmer’s market. And it’s just like if you want like a simple play, no nuts, no anything just-

Lenny Rachitsky: No sea salt.

Tamar Yehoshua: Great pride in the beans he resources them from.

Lenny Rachitsky: Wow. It’s called Bisou with a B?

Tamar Yehoshua: Yeah. Bisou as in Kiss in French. And then on the tech side, the honest answer is Glean. I was listening to your podcast with Nikita who said that people over 22 don’t use new products except at work. And that stuck with me. The new products I usually use are at work and I use Glean 10, 15 times a day. I use it so much and it changed the way I onboarded. It changed the way I work. Even the simplest questions, you don’t bother people, you don’t interrupt people on Slack. You’re like, “What’s the latest status with this deal? What’s the last time we talked to them?” I meet somebody at a conference and I can quickly say, “Have we ever talked to this company before?” And I can just get an answer. Or without asking an engineer, “Where’s the latest design doc?” It has really transformed how I work. So I know it’s cheating in that it’s the product I work on, but it’s the actual honest answer.

Lenny Rachitsky: And for folks that haven’t heard of Glean, it’s one of the most successful B2B AI companies out there. It’s like a very large successful business and company that if you haven’t checked it out, you should definitely check it out.

Tamar Yehoshua: As our investors say, it’s one of the AI companies that’s actually making money.

Lenny Rachitsky: Very few of those. Awesome. Two more questions. Do you have a favorite life motto that you often come back to, repeat yourself, share with friends or family and work or in life?

Tamar Yehoshua: I have one that my father told me when I was being really indecisive about what college to go to. He was really bored of the conversation and he said, “There are no right decisions. You make a decision right.” And it is so true. Because you never know what’s going to happen in life. You just have to commit to whatever you’re doing and have no regrets about it. You can’t be like, “Oh,” 10 years later, “what if I had taken that job over there?” It’s like you make your success based on how you approach the decisions that you’ve made.

Lenny Rachitsky: So if you feel regret about something, this is a good one to pull out of just I will make this the best I can make it, and that’s all the best I can do.

Tamar Yehoshua: You can move forward.

Lenny Rachitsky: Move forward. I love that. Last question, I know you’re a parent. I’m a new parent. I have a 14-month old at this point. Is there a piece of parenting advice that you learned early on that you think might be helpful to me or folks that are new parents or something you’ve just learned yourself that you think might be helpful?

Tamar Yehoshua: 14 months. I think the best parenting book I read besides the How to Talk So Your Kids Will Listen & How to Listen so Your Kid Will Talk is, I think it’s called Healthy Sleep Habits, Happy Baby. We are much happier when we sleep well. We perform better at work when we sleep well. Children need to sleep. So making sure that they sleep well. And sometimes that’s like, I did the whole sleep training, cry until you fall asleep and my kids still speak to me. So it was okay. That is the basic things. Make sure that their basic needs are met and then as they grow up, share your life with them. So a piece of advice I was given was analogous to Talk so your Kids Will Listen is when they had come home from school. You can’t just say, “How was your day?” Say, “You know what? I did a podcast with this person and it was super interesting because they talked about this or that.” Or, “I’m massively screwed up and I should have asked them this or that.” And they’ll be like, “Oh my God, I was at school today and this is what happened.” If you share your life with them, they will share their life with you.

Lenny Rachitsky: Such good advice. I really appreciate it. Tamar, thank you so much for being here. You’re awesome. We got through so much great stuff. Everything I was hoping we get through. Two final questions. Where can folks find you if they want to read up on more stuff that you share and just follow you online and how can listeners be useful to you?

Tamar Yehoshua: Find me on LinkedIn and I have a subject called Practical Intelligence where I’ve been interviewing practitioners who are working with AI. It was my way of learning. I started when I was a VC. Trying to continue doing it. And how can I be helpful if you are a customer of Glean, I’d love to know what you think, what works and what does more.

Lenny Rachitsky: What’s the best way to share that with you? Is it like messaging on LinkedIn, subscribe to Substack?

Tamar Yehoshua: Message on LinkedIn, or comment on your-

Lenny Rachitsky: On [inaudible 01:16:50]. Yeah.

Tamar Yehoshua: Yeah. Those would probably be the two ways.

Lenny Rachitsky: Awesome. Tamar, thank you so much for being here.

Tamar Yehoshua: Thank you for having me.

Lenny Rachitsky: Bye, everyone.

Thank you so much for listening. If you found this valuable, you can subscribe to the show on Apple Podcasts, Spotify, or your favorite podcast app. Also, please consider giving us a rating or leaving a review as that really helps other listeners find the podcast. You can find all past episodes or learn more about the show at lennyspodcast.com. See you in the next episode.

Glossary

English	中文
Async	异步（Async）
Cal	Cal
chief of staff	幕僚长（chief of staff）
co-pilots	副驾驶（co-pilots）
engineering infrastructure	工程基础设施
Fuzzy Khos	Fuzzy Khos
GenAI	生成式 AI（GenAI）
Henderson	Henderson
Huddles	Huddles
Jeff Bezos	杰夫·贝佐斯
Lenny Rachitsky	Lenny Rachitsky
Marc Andreessen	Marc Andreessen
Marc Benioff	Marc Benioff
master plan	主计划
PayPal Mafia	PayPal Mafia
Practical Intelligence	Practical Intelligence
Rachel Whetstone	Rachel Whetstone
six pagers	六页纸
Slack Clips	Slack Clips
Stewart Butterfield	Stewart Butterfield
Tamar Yehoshua	Tamar Yehoshua
tech stack	技术栈

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