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Tamar Yehoshua: Why chaotic companies can still win big

Tamar Yehoshua chased great people over plans at Google and Amazon; her time at Slack and Glean shows chaos and hypergrowth can still win on distribution.

Tamar YehoshuaguestLenny Rachitskyhost
Sep 26, 20241h 17mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 2:09

    Tamar’s background

    1. TY

      (instrumental music) 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'll 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 asked mom, they asked dad, and they got different opinions, and playing one against the other, like that doesn't work.

    2. LR

      (instrumental music) 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, 10X'd the 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 the 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 our 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 on 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.

  2. 2:09 – 6:54

    Key advice for career success

    1. LR

    2. TY

      (instrumental music)

    3. LR

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

    4. TY

      Thank you so much for having me.

    5. LR

      I've had so many people recommend you coming on this podcast. I'm really happy that we're finally doing this. I'm going 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?

    6. TY

      One of the things that I think is overlooked is: do a really good job at whatever your job is at that point. So 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 gonna get the next job unless you do really well at the job that you're in. Like knock it out of the park, however simple, however easy it may be to you, do a great job. And 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 matter what your role is, you have to understand it deeply. You need to understand metrics. So especially product managers have kind of a wide berth of things that they need to understand. So those, those are a given. You need to do that.

    7. LR

      (instrumental music) This episode is brought to you by Explo, a game changer for customer-facing analytics and data reporting. Are your users craving more dashboards, reports, and analytics within your product? Are you tired of trying to build it yourself? As a product leader, you probably have these requests in your roadmap, but the struggle to prioritize them is real. Building analytics from scratch can be time-consuming, expensive, and a really challenging process. Enter Explo. Explo is a fully white-labeled, embedded analytics solution, designed entirely with your user in mind. Getting started is easy. Explo connects to any relational database or warehouse, and with its low-code functionality, you can build and style dashboards in minutes. Once you're ready, simply embed the dashboard or report into your application with a tiny code snippet. The best part? Your end users can use Explo's AI features for their own report and dashboard generation, eliminating customer data requests for your support team. Build and embed a fully white-labeled analytics experience in days. Try it for free at explo.co/lenny. That's E-X-P-L-O.co/lenny. (instrumental music) 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, these challenges require a deep understanding of your users, something that you can't get from product analytics alone. Meet Sprig, a product experience platform that generates AI-powered opportunities to continuously improve your product at scale. First, Sprig captures your product experience in real time through heat maps, replays, surveys, and feedback studies. Then Sprig's industry-leading AI instantly analyzes all of your product experience data to generate real-time insights. Sprig AI goes even further, with actionable product recommendations to drive revenue, retention, and user satisfaction. Join product teams at Figma and at Notion by uncovering AI-powered product opportunities at scale. Visit sprig.com/lenny to book a demo and get a $75 gift card. That's S-P-R-I-G.com/lenny.

    8. TY

      So now the question is the difference in leadership and executive roles, and like 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...... 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? Wha- what's gonna 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 wanna work hard? What are they trying to accomplish? What's the goal for their career?

  3. 6:54 – 9:33

    Understanding people and motivations

    1. TY

      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, you know, 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? What, wha- and then he would, he would like quiz me of like, "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.

    2. LR

      Mm-hmm.

    3. TY

      So, I think when you want to build for people and lead organizations, it is about the people and understanding them and motivating them.

    4. LR

      I l- I love this advice, and there's, 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?

    5. TY

      One of the things that I, 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, 'cause 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. Go in, uh, 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 like you're building a feature and you think it's the best thing, 'cause of course everyone's gonna want it, 'cause you worked on it, and you're gonna put it front and center in the interface where everybody's gonna see it. Well, no, you gotta 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 per- thing that a person needs at that point. So, have perspective. Have perspective of what your users are actually trying to achieve.

  4. 9:33 – 11:20

    The importance of impact

    1. TY

    2. LR

      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, or and there's other reasons they aren't being promoted. Is there an example from your career or a story you could tell just like to clarify like what doing a great job looked like, where it's not just like, "I, I hit my goals." It's like here's what it looks like. Here's how you actually get ahead.

    3. TY

      Are you helping the business move forward? So it's not about I achieved 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 pro- more productive despite you? So, uh, there, 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, uh, across a, it was, uh, ac- across different programs. And I went back to my... I took a vacation, I came back, and I said, "You know, I don't think this team should exist." It was my first management job. And they were like... 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 gonna 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 know, you're right. And I'll find you something else." And he did.

    4. LR

      If I were to put this into one word, it's impact, drive impact.

    5. TY

      Yeah.

    6. LR

      Amazing.

  5. 11:20 – 18:40

    Navigating company chaos

    1. LR

      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, where you notice this. What parts of your career notice this to be true?

    2. TY

      I love working at well-run companies. It's more fun. It, 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, 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 of examples right now of companies I know, not Glean, where I'm working today, where there's like high executive turnover, where people get yelled at. There are lots of people fired. There's re-orgs all the time. People I talk to are super unhappy, but the numbers are amazing. Like, they're growing like crazy. And the opposite 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 I try and do is give a perspective of what matters and what doesn't. And it might even be to the sales team 'cause you get like all these requests for features all the time. If you did every single one, it would be impossible, but 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 like, people want to use your product, right? (laughs) That they're like clamoring for it. So you've built something that people value and that they're, 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 those are probably ... 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, 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 they 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, 'cause every startup has so many things that are broken.

    3. LR

      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, uh, I don't know how this will continue to be successful, your experience is that most ... Is it that most of the successful companies you've been at are just like chaotic internally and aren't like incredibly ru- run and that's normal, that's very typical?

    4. TY

      Until they get to a certain scale.

    5. LR

      Mm-hmm.

    6. TY

      Now once you reach a certain scale and you've already conquered the market, then you kind of need to be well-run. (laughs)

    7. LR

      (laughs)

    8. TY

      Then you bring in 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 got to have things that, that ... I mean, then you're like a growth engine. So different ... 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, like, you're changing projects and people all the time so that they can't, like, actually achieve anything. So there's, this is again, so it's y- 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. Like, there are some well-run ... 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 gonna make you upset and unhappy, don't work there.

    9. LR

      Is there a correlation there of just like companies that have strong product-market fit, things are just breaking as they hypergrow, hyper- going through hypergrowth? Just thoughts on why this is the case.

    10. TY

      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 hard to keep up, because things in the infrastructure break, things in the communication break down. You've got, at any given point, 50% of the company has been there less than six months. So, 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 b- have salespeople. If you're a consumer company, your systems have to keep running as, as you scale, and you know, we've had 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 and ... 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 and level of chaos.

    11. LR

      Is one takeaway here that product-market fit solves a lot of problems, strong product-market fit?

    12. TY

      Well, no product-market fit is a death sentence. (laughs) I would 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 have a company, um, 'cause it's very hard to, to do that unless you have a distribution machine and then you catch up over time, but we will not name companies like that. Uh, so you, there are other ways, uh, of doing it, but yeah, that is the, the most important thing.

    13. LR

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

    14. TY

      Right. And it's not a good excuse to, like, not have an organization that's functioning.

    15. LR

      Not care. Yeah.

    16. TY

      You should still strive to have an organization that's functioning and keep people happy and motivated and all that.

    17. LR

      Great.

  6. 18:40 – 26:22

    Career planning: a different perspective

    1. LR

      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 where the hell it was gonna go. I never had this, like, vision of, here's what I want to do. I just kind of 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.

    2. TY

      I, really recently, I was talking to somebody in their 20s who was asking me for career advice and, you know, should I be a product manager, et cetera. And, um, like, I'm trying to put together my five-year plan. And I said, "I never had a five-year plan." Like, 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." So, and w- and when, you know, early in your career you have a lot more angst about it, because the forks in the road are more significant, 'cause they can go like, "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 f- I meet a lot of kids in their... I shouldn't call them kids. Um, my kids or my kids' friends. But (laughs) I meet a lot of, uh, people who are younger in their career who, uh, 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 or... I mean, some people have a domain, like I'm super interested in, like, you know, 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 gonna 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 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, and I know... I spent a lot of time with ex-Googlers that I met and that are all working in different companies now, 'cause you build those relationships by working together. So if you follow people and where you're gonna l- learn the most, and you go step by step, I think that's a great way of pr- uh, progressing in your career.

    3. LR

      That's such tactical advice, and I've seen this succee- this work for a lot of people that just go where their favorite former employees work, and... And not favorite, to your point, but, like, the people that they most respect and have been most impressed by. And, uh, I think it's such an... It's such an easy thing to do. It's like, it's a really easy heuristic for understanding where to go. There's something Marc Andreessen once shared that I re- I'm reminded of when you say this, is that there's this, like... There's like a term for this, I forget the actual term, but there's like... Certain companies have this gravitational pull where they are acquiring all the best talent. They're currently, like, 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. Um, I guess, any thoughts on that thought?

    4. TY

      Uh, yeah. And it's- it's really bad when you don't have the gravitational pull. (laughs) 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 where you can recruit. And one... 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 gonna make their careers." S- oh, I was like, "Whoa." 'Cause I was getting offers for, like, some kind of turnaround jobs. And, you know, if you think you can turn around, great, but you want... If you're gonna hire the best people, you want to make sure that it's gonna be a good place for them and that they're gonna learn and they're gonna 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 looking, putting too much emphasis on, where will I get a big financial return? And I 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 gonna learn, 'cause even if a company fails, you learn a lot. But predicting financial success is so hard because you don't know what's gonna happen with the market, with the world, with, like, crypto and then AI. And people who do that and say, like... 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 you- when, when people do that. But I think that, that it's just a, it's a dangerous thing to do.

    5. LR

      I imagine some people hearing this advice are gonna feel like, "I'm not gonna get a job at OpenAI or Glean in this..." Or other awesome companies that everyone wants to go work at. Any advice to those folks?

    6. TY

      There's lots of good companies and there's lots of smart people.

    7. LR

      Mm-hmm.

    8. TY

      You don't have to be at the top brand. And if you go somewhere where you're gonna learn and it's gonna get you there... I mean, I made mistakes. I made, 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. Like careers you don't make every step is to the right place. You, you remember in what you cited, all the companies I went to that did well, you left out all the ones 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 (laughs) , that was not the case. So if you, if you focus on that learning bit, you will get there. And there are lots of paths. There isn't just the, you know, OpenAI or Glean or Anthropic.

    9. LR

      Awesome. And again, I love how tactical this is. Like 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-

    10. TY

      Yeah.

    11. LR

      ... it's, 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?

    12. TY

      Uh, skills can't be taken away. A company can fail, but if you learn a skill, you will always have that skill.

    13. LR

      Mm-hmm. I love that. And I've totally seen this to work, so I, I really love that you're focusing on this advice.

  7. 26:22 – 37:59

    Lessons from industry leaders

    1. LR

      You've mentioned places you've worked and folks you've worked with, 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?

    2. TY

      Probably can't narrow down to one.

    3. LR

      (laughs)

    4. TY

      But from, uh, I'll talk about Bezos first. So I was very lucky to join Amazon early when I still, like I had quarterly meetings with Jeff Bezos.

    5. LR

      Oh, wow.

    6. TY

      And this was before AWS launched, so it was before Amazon was known in the Valley. And, and that ki- this is another example. I went there because I went to work for Udi Manber 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 like there were any books on it. And that really convinced me to go there. So there's a lot written on Bezos. Read his shareholder li- letters, read the books about him, read Colin Bryar's Working Backwards, The Everything Box I think it's called, or The Everything Store.

    7. LR

      The Everything Store, yeah.

    8. TY

      And, uh, there, I mean, 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 things. One, you know, uh, a lot of people have written about these six-pagers. So you af- you can't, he doesn't believe in PowerPoint. You write a six-pager about... I mean, it's like, you know, studying for the final exam is writing these six pages. So you go into the meeting and there's people around the table, his, 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 thinks (laughs) , I just wanna hear what Bezos thinks." But he wants to, 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 (laughs) in that, uh, I've worked with a lot of smart people, but his ability to go deep in any domain and nail the, the core issue and remember... Like we would have quarterly meetings and from quarter to quarter, he would like remember things that he had talked about before. And then he would go into like the architecture of search and why are you doing it this way or that way and, and you're just like blown away that he knows that. But the thing that, for me, the biggest takeaway from those meetings was his consistency. Which is he had principles that you, 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. The (laughs) that was just the thing. You had to like write what they were because people couldn't figure out what they are, so anytime you showed an icon, he would get annoyed. But there were like... So, but you would go in and after a couple of meetings you're like, "Okay, I know what he's gonna ask about. I know how he's thinking and I know what his principles are." And I think those, that consistency enables you to operate a large organization more effectively.

    9. LR

      Mm-hmm.

    10. TY

      And then there was one other thing that I, I really remember was a very s- one of the few really small meetings I was in with him, and we were presenting working on an, a new product and I was like, "You know, our competitors have like 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. It's gonna... You have to be in it for the long term. And I... You can be sure I never went in and said, "I need a lot more resources." (laughs) So that was Bezos.

    11. LR

      Awesome.

    12. TY

      Uh, Stewart, again, I went to Slack because I wanted to work with Stewart B- Butterfield. I think he is the best product thinker in the Valley, or he's not, not c- 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, um, that's Slack Connect. Build a platform that makes all of your other SaaS products more valuable, the Slack platform, and then do some magic AI stuff. Ma- magic AI stuff took a lot longer (laughs) , uh, but-

    13. LR

      That was part of his plan early on, is magic AI stuff?

    14. TY

      It literally was. There was a, there was a grid with four boxes in 2014, and it never changed.

    15. LR

      Mm-hmm.

    16. TY

      That was his master plan. And what we worked on each year changed. But somebody recently asked me, "Well, did he always... Like, you know, you guys did Slack Connect much later." I'm like, "Yeah, that was always part of the plan." It was-

    17. LR

      Oh.

    18. TY

      ... 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 gonna work. I have to feel it. I have to try it. And a mockup doesn't tell you what it's gonna feel like." And he would push people to do prototypes, not incremental of just to get a feature out, but really to think. Uh, so very soon after I, I started, we launched, uh, hired a design lead, Ethan Nizman, and we, and he led a redesign of the new information architecture for Slack.

    19. LR

      Oh, yeah. I, uh, I worked with Ethan at Airbnb.

    20. TY

      Oh, yeah.

    21. LR

      Uh, he, uh, he was head of design for the search experience and the search team.

    22. TY

      Yeah. Ethan is awesome. And-

    23. LR

      Yeah. He's great.

    24. TY

      ... he came in, and his first task was to work with Stewart on, 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 gonna 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, like literally took everything in the interface and put it behind one button. And he said, "This is how you're gonna see what you really need in the interface." So we were never gonna ship that, but it was the beginning of the redesign.

    25. LR

      Let me tell you about a product called Sidebar. The most successful people that I know surround themselves with incredible peers. When you have a trusted group of peers, you can discuss challenges you're having, get career advice, and just gut check how you're thinking about your work, your career, and your life. This gives you more than a leg up. It gives you a leap forward. Having a group of trusted and amazing peers was key to my career growth, and this is the Sidebar ethos. But it's hard to build this trusted group of peers on your own. Sidebar is a platform for senior tech professionals, director to C level, to advance in their career. Members are matched into peer groups to lean on for unbiased opinions, diverse perspectives, and raw feedback. Guided by world-class programming and facilitation, all running on Sidebar's technology, Sidebar enables you to get focused, tactical feedback at every step of your career journey. If you's a listener of this podcast, you're already committed to growth. Sidebar is the missing piece to catalyze your career. 93% of members say Sidebar helped them achieve a significant positive change in their career. Check them out at sidebar.com/lenny. As a product leader, how do you think about just the time it takes to create a prototype in, in something like this? You know, as a PM, I'm just like, a lot of times, "We don't have time to build this whole prototype. We gotta ship stuff. We gotta 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?

    26. TY

      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. Like, we had a problem with our mobile apps, that it was too hard to prototype, and we actually redesigned our mobile apps till 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 you know is never gonna make it to production. So you can get, you can just crank it out much faster, and then you can see what works, and then you build the production code. And so you actually get to your end goal of something working faster.

    27. LR

      Mm-hmm.

    28. TY

      But you need the engineering team to have this same mindset. The product and engineering have to work together, and design, 'cause design is just in it, in it as much. 'Cause sometimes you can get design engineers who are doing the prototyping.

    29. LR

      Mm-hmm.

    30. TY

      So your first prototypes are like Figma prototypes, and then you get prototypes on real data. I, I had a, I, when I was at Google, one of our teams, a front end team, I remember we got, 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."

  8. 37:59 – 42:00

    Building stronger cross-functional relationships

    1. LR

      Okay. Speaking of former colleagues, uh, I asked one of your former colleagues. His name is Fuzzy Coase. He's now the CTO of Notion. You worked with him, I believe, at Slack?

    2. TY

      And at Google.

    3. LR

      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 comes from. What can you teach people about building stronger cross-functional relationships, especially PMs, to build better relationships with our engineers, designers, other folks on their team?

    4. TY

      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 ... Uh, so one, make sure you're somewhere where you have a good engineering partner. So Cal Henderson was the co-founder and CTO of Slack, and, like, I couldn't have asked for a better engineering partner. He's just awesome. And you, you need to ... That has to be part of your evaluation criteria, that you meet and value your engineering partner before you join, and ... Or you know that it's not the right one and the organization is willing to, to make a change. So that can happen, too. You can go in and understand that there ... that something has to change. But, 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 gonna divide and conquer and where you're gonna be aligned. You don't want any of this, like, people in the organization, they asked mom, they asked dad, and they got different opinions-

    5. LR

      (laughs)

    6. TY

      ... and playing one against the other. Like, that doesn't work. So, one, you have to know that you're not gonna do that. So if somebody would ask me something that 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 gonna drive this, I'm gonna drive this, and if it was unclear, we would talk, and we would say, "Okay, who's gonna, who's gonna take this one?" And we would do all our reviews together. And so all of the OKR reviews, all of the ... We had weekly exec reviews. Um, we had the updates on our, our OKRs. So we did them all together, but I knew, like, here's the things that he was gonna ask the questions on and dig deep. And then when I was, he would take a backseat. But of course we could ask questions on, in each other's 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 w- they will. And Cal and Fuzzy were, like, amazing at that. I would go to Fuzzy and be like, "Hey, we need more mobile engineers 'cause this one product is not gonna ship and we ..." And he's like, "I'm on it. Got it." And that was all I needed to do. And, like, obviously if he couldn't do it, he'd come back to me and like, "Hey, there's gonna be a problem." But it was like, just things got done.

    7. LR

      Mm-hmm.

    8. TY

      That's, that's the best part of it.

    9. LR

      You talked about being aligned, which, uh, I love and I fully have seen that power of that, of you and your eng 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 I ... 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.

    10. TY

      One, you gotta spend a lot of time together. I mean, there isn't kind of 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, like, why did he make this decision?" Like, 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, that Cal and I had together.

    11. LR

      Perfect.

    12. TY

      Uh, so we had, um ...

  9. 42:00 – 45:26

    Streamlining OKR reviews with async methods

    1. TY

      We used OKRs to, 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 them ... We had a Slack channel for each team. Their OKRs, a, a planning channel for each one. And people would pres- uh, 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, here's the, our OKRs. Here's the things that you pay attention to." And then Cal and I would do a marathon and we would watch them all together. And-

    2. LR

      Like, in a room sitting there watching them together?

    3. TY

      Correct.

    4. LR

      Mm-hmm.

    5. TY

      And, uh, and then we would, like, say, "Are we ... Do we have any follow-up questions?" And we put in channel our follow-up questions.... and to the team. And 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 are, this is like 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, was getting the alignment. And by asking the questions, we could then, by it just being us, we could kind of dig into the team. And, oh, we had, 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. Uh, they were both longtime Slack employees. So for years they, they had... One had been an engineering director and one had been a TPM. Uh, and then we r- every Monday we had a Monday meeting where we reviewed the progress on the top OKRs.

    6. LR

      Yeah.

    7. TY

      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, uh, meeting with the four of us, uh, where we would just go through any issues in the organization, what's going on, what's not.

    8. LR

      And the four of us is you, the CTO, the chiefs of staff?

    9. TY

      Yeah. And sometimes we would invite people, like there was 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, like teams. So it'd be like the OKR, 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.

    10. LR

      There's so much awesomeness here. I love the idea of this async share your plan and a video instead of meetings with everyone in real time, and you could just do a lot of this stuff async.

    11. TY

      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.

    12. LR

      Mm-hmm.

    13. TY

      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 like some insane number, like 300 and something. And we're like, "This has gotten out of hand."

    14. LR

      (laughs)

    15. TY

      And so then we're like, "We have to do something drastic." And that's when we moved them to async.

    16. LR

      Mm-hmm.

    17. TY

      It was also right after Slack Clips launched.

    18. LR

      I got it. That's the video feature. Very cool. And then I don't know if you're, uh, you launched huddles, right? Slack huddles? You're-

    19. TY

      Yeah.

    20. LR

      Uh, did you use that as a part of this, where eventually you just get people into a little huddle asynchronously and talk through stuff?

    21. TY

      Sometimes, absolutely. We would be in the reviews-

    22. LR

      ... That's cool.

    23. TY

      ... and we would huddle with somebody to ask a quick question. We used huddles all the time. I still do. I love huddles.

    24. LR

      I love it, I love it. Uh, one crazy thing about Slack is people in Slack don't actually use email internally, right? It's like all in Slack. It's like the actual vision of Slack, working within Slack.

    25. TY

      No email, unless you're dealing with somebody external-

    26. LR

      External, yeah.

    27. TY

      ... and now it's mostly Slack Connect anyway.

    28. LR

      Wow. That's amazing.

  10. 45:26 – 47:50

    Why you shouldn’t worry so much about making users unhappy

    1. LR

      Okay, uh, 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 shared this really interesting insight that I've experienced myself that, uh, I'll quote you here, one of the mistakes that I see a lot of product, product managers make is they overindex on people who are gonna be unhappy with the products they're launching. And you basically, your advice is not to worry so much about making users unhappy, which I think is counterintuitive, 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."

    2. TY

      I saw it more when, yeah, you unlaunch things. (laughs) 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 gonna make happy. So you get, 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 a Slack, are you a Glean? But number of people using your product today is usually, unless you're a Google, far smaller than the number of people who are gonna be using your product tomorrow. So design it for the people, the bigger number of people who are gonna be using it tomorrow. Like if you have to redo the UI and, you know, they're like, "Who moved my cheese?" people will be unhappy, but all the new people are gonna 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, here's for real why." And you have to listen to your, listen to your audience. You don't want to alienate your early, uh, users. Because most people, like if you made a good decision on why you moved this or why we, like stopped using Slack calls and moved to huddles, and like you have to do it over time and give people choice and then, uh, 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.

  11. 47:50 – 52:34

    The power of listening in leadership

    1. TY

      And I have a, I have an example that's not a product example, but I think-

    2. LR

      Mm-hmm.

    3. TY

      ... is a really good one. It's a leadership example. So it was, when I was at Google, there was always a controversy about something, but there was a controversy about, it was like Blogger or something. I can't even remember what it was. It was like we made a change and, uh, there was an engineer in my, in my, or th- we were like 50,000 people at this time. There was an engineer in my team, an IC engineer who was like super unhappy about the change. And I knew Rachel Redstone, she was in charge of all of PR and global policy at Google. So huge job. And, uh, I emailed Rachel and I'm like, "Hey, do you have like an FAQ or something that I, can help me, 'cause I don't know why you made this change, and that I can help explain to the engineer on my team?" She did not respond to my email. She picked up the phone and she called him. I had no idea she was, she did this. She just called this IC 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. Like, she never even told me she did it, like, later. She just, she just did it. You just act, you're authentic, you listen to people, and you're transparent.

    4. LR

      It's so funny. This reminds me of a book I'm reading, a, 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 there's, they're getting off track, so much of what they need is, is a sense that you're connected to them, a connection which is rooted in you listening to them. And so all the-

    5. TY

      My, my favorite parenting book-

    6. LR

      Oh, yeah.

    7. TY

      ... I don't know if this is-

    8. LR

      Yeah.

    9. TY

      ... is the same one or a different one. It's How to Talk So Your Kids Will Listen and How to Listen So Your Kids Will Talk.

    10. LR

      Mm-hmm. Mm-hmm.

    11. TY

      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.

    12. LR

      Uh, amazing. There's so many applications of just the power of listening. Okay. Well, uh, not quite a segue, but let's talk about AI. You're kind of at the epicenter of AI now with Glean. How do you anticipate AI will change our jobs and products? What do you think people maybe aren't recognizing yet, realizing yet? What have you seen?

    13. TY

      I'm gonna give you a little bit of my history with AI to get to that point.

    14. LR

      Perfect.

    15. TY

      So I actually... (laughs) This is... When AI was a completely different technology stack, I have a master's in AI. So I started, like, working in AI when it, it's evolved so much, and then of course at Google using it for autocomplete and search and, and there, it's, it's transformed so many times. But then with this last transformation of gen AI, and that's what brought me to, to Glean of seeing this, like meeting lots of AI companies, I'm like, "Wow, this is really gonna transform how we work." And it's just fascinating seeing these products. I, I was kind of one of those people, like, "Oh, yeah, it's gonna be so far away," until, like, I saw GPT-3. And I think A- AI, it's... We are underestimating how much it's gonna change how we work. It's not gonna be sudden from today to tomorrow, because people haven't figured it out yet. They kind of haven't figured out how exactly to leverage it. But the people who have are gonna be so far ahead. They're gonna be far ahead of everyone else, because they're gonna be working faster, they're gonna be working better. And in five to 10 years, I think the lines between product managers and engineers and designers are gonna blur, because AI will enable product managers to build prototypes, to build designs, designers to, to build, uh, to build uh 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 copilots. So they're not quite there. There's... 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 gonna keep getting better. So, I think, um, people have to be careful about not getting left behind. But their jobs aren't gonna go away. They're just gonna change, and we're gonna... I'm, I'm of the believer that we're just gonna allow more software. But I talk 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, that's a dangerous spot to be in, I think.

  12. 52:34 – 1:06:39

    How to leverage AI so you don’t fall behind

    1. LR

      For people that get anxiety hearing this, where they're feeling go- that they're gonna 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 how some- what's something someone can do to s- not fall behind?

    2. TY

      Use the products. Like, 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 w- what isn't. And the same goes even more for AI. Use ChatGPT. If your organization has Glean, use Glean. Use Claude. Try 'em all. Like, try them and see what they do. Um, 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, like, blew me away. So he said... And this was, like, a couple 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 tran- channel, which was huge, right? 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, uh, feature? What are the things people are unhappy with?" Like, this never would have occurred to me. I was like, "That is so smart." And he's like, "It was like a gold mine," 'cause do you know how long it would have taken him to read?

    3. LR

      Mm-hmm.

    4. TY

      And he just wouldn't have done it, right? So you're... Think about, like, for the argument, "Oh, I'm too busy." Well, if you use these products, you're actually not gonna... You're gonna... It's gonna be leveraging your time. So you get a lot of articles sent to you. Summarize them. You ai- use AI to summarize the articles. Uh, we use Gong at Glean to record our all sales, all our sales calls. We have a Glean app that will read all the Gong transcripts, put them in a spreadsheet in, um, in a certain format of who the AE is, et cetera, and then summarize all the top-requested features from all the Gong re- Gong calls. And we had... It took a while to get it right. Like, at first, it would... The, the summarization, the prompt wasn't good enough and would give us features that, like, our salespeople would recommend (laughs) and didn't distinguish that this was actually the customer. So you have to tweak it. It's not gonna work out of the box. But then we got it to the point where it worked, and, like, 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.

    5. LR

      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 on your team have done to be more productive if they're product leaders or other folks?

    6. TY

      So many examples. Um, so one that I did really recently is, I wrote, uh, I wrote a prompt in, in Glean to help me get the status of features. And like, we have a launch cal, and you can look at launch cal and it'll say a date. But then, like, is it really the date? What are the outstanding issues? So it will look at our launch cal, and it will look at, see if there are any open Jira tickets, what the Slack conversations are, to see, and the customers who are beta testing it, and like bring all this 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 te- give me the confidence level of the feature I'm looking at. So I can run the prompt, just put in the name of the feature, and get, like... So I don't have to read all of these channels. So this is a prompt that I built, like, two weeks ago, because we're advancing our prompting capabilities, and so I, I was testing it out. And I was like, "Ooh, I could do this." So that's like, uh, an- that's another example. And, uh, engineers are using it for automating part of the incident management, of like, oh, I got an incident, how do I see all of, were there previous incidents that were similar to it? Were there not? And so these are the type of things you can look at to say, uh, to, to help you. Uh, but, like, the simplest, simplest is, there's so much news, let me just, like, paste in all of these things and, and, and summarize them. Like, as a product manager at Glean, here are all the latest news. What do I have to care about?

    7. LR

      Mm.

    8. TY

      What's, what's impacting me and potentially competitive to any of the products that I have?

    9. LR

      And putting that into, say, Claude or ChatGPT, you're saying?

    10. TY

      Yeah.

    11. LR

      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, a role. Like, you are a product manager at Glean. From that perspective, give me this summary, versus just, summarize this. And that ends up being really powerful, right?

    12. TY

      100%. And you can compare, like, what is Claude, you know, PR saying that S- They, they just, uh, launched, uh, Claude Enterprise. How is Claude Enterprise different from OpenAI Enterprise? And what are... Like, 'cause it, these things, it, they- Again, you can do it yourself, but these micro improvements in your productivity, um, help. There's a, I, for my newsletter I interviewed Claire Vo, who came out with ChatPRD. And so p- product managers are using it. We're just starting to evaluate it internally in Glean. So, I haven't personally used it yet, but it's super cool. And you can use ChatBRD- ChatGPT to, to do a PRD. And ChatPRD gives, it's more templatized and more frameworks of, of, of how to do that. And these, again, these things are gonna keep getting better.

    13. LR

      Claire's been on the podcast. She's gonna be speaking at the Lenny and Friends Summit coming up October 24th.

    14. TY

      Oh, cool.

    15. LR

      And, uh, yeah. And she, uh, a crazy stat she shared is she's making six figures off this product that she builds on the weekends, ChatPRD.

    16. TY

      So cool.

    17. LR

      Incredible.

    18. TY

      But it also shows what you can build with AI.

    19. LR

      Right. And it's just her. I think she just recently hired some engineers to help, 'cause she has, she has like three kids, a CTO at LaunchDarkly, and just is building this on the side making 100,000 plus dollars. Incredible. Uh, I wanna add one, a couple things here. So one is, uh, for folks looking for ideas for how to use AI tooling for their PM job, uh, there's a couple posts I've written that I'll link to you in the show notes, just to put that out there, of just a bunch of PMs sharing, "Here's what I've done with these various tools." Another thought I'd love you, get your take on. There's a lot of fear that the PM job will 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 a 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 of, that can build anything for you. Which function would you think would have the best chance of building some, of asking it what, 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 gonna be, what customers need. Not to say other functions don't also have these 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.

    20. TY

      I, I think that AI, the one thing it's not good at is being creative.

    21. LR

      Mm-hmm.

    22. TY

      So if you're a PM who's, who's doing the kind of route work, it's gonna 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 gonna differentiate, 'cause it's not gonna give you that leap. 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. 'Cause there's, are a significant number of PMs who are more like 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, we'll be able to automate, like updating Jira and like, you know, all these things that just take time, and creating even little, like, 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 kind of gonna blend, 'cause the best designers I've worked with-... are product thinkers, and a lot-

    23. LR

      Yeah.

    24. TY

      ... of really good PMs can also design. It depends on the- what- what kind of product you're PMing for. But, so I agree with-

    25. LR

      Mm-hmm.

    26. TY

      ... the caveat that it will become harder to be a great PM.

    27. LR

      Wait, say more about that. It'll be harder to be a great PM because, uh, this- many PMs are doing things that are mostly like project management, and that's the stuff that you-

    28. TY

      Well, yeah. Let me rephrase. It's not going to be harder-

    29. LR

      Yeah.

    30. TY

      ... to be a great PM, but to be a PM, the- the not so good PMs jobs will go away.

  13. 1:06:39 – 1:17:23

    Closing thoughts and lightning round

    1. LR

      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?

    2. TY

      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. I mean, 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 is gonna be- it's, it's gonna 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 much, how many products we can build.

    3. LR

      I love that. I, I can't help but drill in, uh, one level deeper. Is there anything you found to help you stay ahead and s- help you stay, you know, aware of what's happening? Are there like newsletters you find useful, ch- uh, podcasts that just like help you s- keep up to date on where things are going? Is it like a person you look to like, "Hey, what's new?"

    4. TY

      There are definitely like 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 (laughs) on the AI podcasts. So I just try and listen. I'm, I'm trying to build some prompts for myself to make it easier to say, like take in to, I haven't perfected this, but the ChatGPT voice mode where you can load it. Somebody who just, who I just hired at, 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.

    5. LR

      Mm-hmm.

    6. TY

      So I, I need to up my game there. Uh, but I definitely have a, a list of like Ben's Bites and The Neuron, and uh, I love, I like, those are good summaries. And like Eyal Gil and Sara Gove's podcast I listen to, Cognitive Revolution. There's, I, there is a, a kind of too many of 'em right now, but I, I pick and choose.

    7. LR

      Awesome. Okay. We'll link to those ones you just mentioned in, in the show notes. The Eyal Gil and Sara Gove podcast, it's called No Priors. I was actually just listening to it on the way here. Sara is gonna also be at Lenny's & Friends Summit. She's gonna be moderating a panel between, uh, Kevin Whale and, uh, Mikey Krieger, who are the CPOs of Anthropic and OpenAI. So there we go. Another quick plug for lennysandfriendssummit.com. No, I think it's lennysummit.com

    8. TY

      Awesome.

    9. LR

      (laughs) With that, Tamara, we've reached our very exciting lightning round. Are you ready?

    10. TY

      I am ready.

    11. LR

      Okay, (laughs) let's do this. First question. What are two or three books that you have recommended most to other people?

    12. TY

      So one book was recommended to me by Shishir, the CEO of Coda. Uh, when I started at Slack, he recommended the book Switch: How to Change Things When Change is Hard by, uh, Chip and Dan Heath. And it's such a good book, and it's about like how do you set a path for people to follow and 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 and we had an all hands about like there was, 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 Stuart and I'm like, "You did that all wrong." Like, "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 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 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's, uh, is fascinating.

    13. LR

      Don't think anyone's recommended either of these, so love 'em. Next question. Do you have a favorite recent movie or TV show you've really enjoyed?

    14. TY

      I don't know if you like British murder mysteries. (laughs)

    15. LR

      (laughs) I don't know either.

    16. TY

      It's kind of a ni- nish- niche thing.

    17. LR

      Yeah.

    18. TY

      But there's, there's a, uh, a guy named Anthony Horowitz and the latest series he did was called Magpie Murders, and it's just like kind of an intricate story. So I enjoyed it.

    19. LR

      Very niche but amazing.

    20. TY

      (laughs)

    21. LR

      Do you have a favorite product you've recently discovered that you really like?

    22. TY

      Well, I'm gonna give two. One is tech and one is non-tech. Um, so non-tech, I really like dark chocolate. (laughs) And I-

    23. LR

      Like actually just the, just cho- like a dark chocolate bar.

    24. TY

      A really good dark chocolate that's simple, like no frills-

    25. LR

      Oh, okay.

    26. TY

      ... none of this.

    27. LR

      Okay.

    28. TY

      Just dark chocolate.

    29. LR

      Is there like a-

    30. TY

      And I discovered this chocolate-

Episode duration: 1:17:23

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