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

[00:00] 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. [00:30] and playing one against the other, like, that doesn't work. [00:32] Thank you. [00:36] Today my guest is Tamar Yehoshua. Tamar is currently President of Product and Technology at Glean, [00:43] One of the most successful enterprise AI companies out there right now [00:46] 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 the revenue, went through IPO, and then got bought by Salesforce. [00:57] Tamar also led product and engineering teams at Google, where for many years she was responsible for the Google search experience. [01:04] 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, Sneak, 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 Stuart Butterfield and Mark Benioff,

[01:34] 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. [01:45] 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. [02:12] Tamara, thank you so much for being here and welcome to the podcast. Thank you so much for having me. [02:17] I've had so many people recommend you coming on this podcast. I'm really happy that we're finally doing this. [02:23] I want to start with a question that I've started to ask people who have had extraordinarily successful careers, which you've had. [02:30] So let me ask you, [02:31] What are one or two specific skills or mindsets or habits? [02:37] that you think most contributed to your success during the course of your career that you think might be helpful to people who are [02:43] trying to figure out how to accelerate their career or just be more successful in their career. [02:47] One of the things that I think is [02:49] overlooked, [02:51] 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 going to get the next job unless you do really well.

[03:07] at the job that you're in, like knock it out of the park, however simple, however easy it may be to you. [03:14] do a great job. And 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 [03:36] Those are a given. You need to do that. [03:39] 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. [04:09] solution designed entirely with your user in mind. Getting started is easy. Xplow 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 Xplow's AI features for their own report and dashboard generation, eliminating customer data requests for your support team.

[04:39] white-labeled analytics experience in days. Try it for free at xplo.co slash Lenny. That's E-X-P-L-O dot C-O slash Lenny. [04:51] 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. [05:21] 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 [05:51] That's S-P-R-I-G dot com slash Lenny. [05:55] So now the question is, [05:57] the difference in leadership and executive roles and like when you're getting there. So how do you start transitioning? [06:04] So after you've done a great job at everything and you understand the [06:09] the core skills that you need and

[06:12] Another thing you really need to know is understanding [06:17] people. [06:18] and motivations. [06:20] 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? [06:38] So you need to understand motivations and 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? [06:49] Why do they want to work hard? What are they trying to accomplish? What's the goal for their career? [06:54] 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. [07:07] And when I was growing up, we would have family occasions, go to the fence, whatever. And afterwards, [07:13] in the car ride back, he would always give his perspective of analyzing what happened at the event. [07:21] what this person was thinking. Why did they say this? What? What? And then he would, he would like, [07:27] 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. So I think when you want to build for people and lead organizations, it is about the people and understanding them and motivating them.

[07:57] I love this advice. And there's I feel like we could do a whole podcast on just this topic. [08:02] So on this last point about understanding [08:04] People, [08:06] 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? [08:17] One of the things that I caution product managers about is that you don't want to be too overly reliant on metrics. [08:25] 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. [08:45] Don't assume you know. [08:47] Go in. Mark Benioff would always say have a beginner's mind. [08:52] Go in assuming that you know nothing. [08:56] 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 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. [09:13] Well, no, you got to earn that right. [09:15] 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.

[09:32] 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, [09:43] They are, and there's other reasons that are being promoted. [09:46] Is there an example from your career or a story you could tell I'd just like to [09:51] clarify what doing a great job looked like, where it's not just like I hit my goals, [09:56] It's like, here's what it looks like. Here's how you actually get ahead. [10:00] Are you helping the business move forward? [10:04] So it's not about I achieved what I was asked to do. [10:09] 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? [10:20] And that is different. It's a different mindset. [10:23] Did you enable the entire organization to be more productive? [10:28] despite you. So 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, across, across different programs. And I went back to my, I took a vacation, I came back and I said, you know, [10:45] I don't think this team should exist. [10:48] 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. [10:58] It's not going to be productive. And my manager was so stunned.

[11:03] He was like, wait, you're saying no. I'm like, yeah, because here's how you should organize it. [11:09] And then he's like, you know, you're right. [11:12] And I'll find you something else. And he did. [11:15] If I were to put this into one word, it's impact. [11:17] drive impact. [11:18] Yeah. [11:19] Amazing. OK, going in a different direction, [11:22] We were chatting before we started recording this, and something that you shared with me [11:26] and some people may be really surprised to hear this, but I completely agree with this take, is that [11:31] you don't need to be a well-run business [11:34] to win. [11:35] Okay. [11:36] I've seen this myself. [11:38] I'd love to hear your insights here, and especially where you noticed this. What parts of your career noticed this to be true? [11:44] 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. [11:58] But what I've seen is... [12:00] When a company isn't well-run, like... [12:02] IT isn't working, marketing is broken, there are not enough people in HR, there's a lot of turnover, all of these things. [12:11] I've seen that they're not correlated to the company being successful. [12:15] So I can think of a couple 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 reorgs all the time. People I talk to are super unhappy, but the numbers are amazing.

[12:35] Like they're growing like crazy. [12:38] And the opposite of Sid is also true. I can think of one company I know really well, amazing CEO, well run, well oiled machine, everything, hired good executives, [12:49] and they flatlined. [12:50] So you just see it. You see it over and over again. And people get very upset about these things that aren't working. [12:58] And one of the things I try and do is give a perspective of what matters and what doesn't. [13:04] And it might even be to the sales team because you get like all these requests for features all the time. [13:09] If you did every single one, it would be impossible. But even if you did, [13:14] 80, 90 percent of them all matter for the success of the company. But then there are some that really matter. [13:21] 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, [13:30] people want to use your product, right? That they're clamoring for it. So you've built something that people value, [13:37] and that people value and that solves a problem for them. [13:42] But that's also not good enough. [13:44] You need to build a great product, but you also have to have distribution, and you need to have a sales team that works. [13:50] And those are probably and you have to have enough money in the bank to get there. [13:54] 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 it clearly didn't have an impact.

[14:10] 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. [14:20] 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. Every startup has so many things that are broken. [14:29] 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, [14:35] We don't know what we're doing. I don't know how this thing is running. [14:38] I don't know how this will continue to be successful. [14:41] Your experience is 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. Until they get to a certain scale. [14:54] Now, once you reach a certain scale and you've already conquered the market, then you kind of need to be well run. 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 5000 people or 10,000 people. Like you got to have things that I mean, then you're like a growth engine. So different. You have to know what phase you're in. [15:17] and what's important at that phase. So it isn't that [15:22] at every phase chaos is okay and also some chaos is okay and some chaos [15:27] is not okay if you're changing your strategy all the time. [15:30] And you're changing your direction and you're changing like you're changing projects on people all the time so that they can't actually achieve anything. So there's this is again, so you can't simplify it, that some chaos is OK and some isn't. And also some chaos is right for you as a person.

[15:49] Like there are some well run. There's some really great companies I would never work at. [15:53] Because they don't fit me. [15:55] They're not... [15:56] 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, [16:06] If the chaos is chaos and something that's going to make you upset and unhappy, don't work there. Is there a correlation there just like? [16:13] Companies that have strong product market fit. [16:15] Things are just breaking as they're going through hypergrowth. [16:19] Just thoughts on why this is the case. 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 in 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 percent of the company has been there less than six months. [16:44] But you have to grow really fast because once you hit product market fit, if you don't, [16:49] then [16:50] your growth will stop. [16:52] So if you're suddenly growing, especially if you're an enterprise company, you have to have salespeople. If you're a consumer company, your systems have to keep running as you scale. And, you know, 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. And so I do think a lot of it is it's very hard to grow that fast. [17:15] And so things really do start breaking. But then once you get

[17:19] 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. [17:28] There's one takeaway here that product market fit solves a lot of problems. [17:32] Strong product market fit? Well, no product market fit is a death sentence. I'd say more like that. Like you can't, like if you built a product that people aren't, [17:42] really excited to use, then you don't have a company because it's very hard to do that unless you have a 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. [17:58] the most important thing. [18:00] Yeah, I will say, during my experience at Airbnb, I absolutely saw this. It was just [18:05] nonstop chaos and 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. [18:23] But again, not a good excuse to just allow chaos and it's not like chaos means success. Right. 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. [18:40] Okay, another... [18:42] maybe contrarian opinion that you hold? [18:44] along the career track is that you don't need to plan your career. [18:49] I also 100% agree with this. I had no plan for my career. I never knew where the hell it was going to go. I never had this like vision of here's what I want to do. I just kind of followed.

[18:59] things that were pulling me and things that seemed interesting. I love that you also [19:02] 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. [19:12] I really recently I was talking to somebody in their 20s who was asking me for career advice and should I be a product manager, et cetera. And like I'm trying to put together my five year plan. And I said I never had a five year plan. [19:25] Like, so to be clear, some people need that. [19:28] 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 I'm not. [19:37] The person I was talking to just relaxed. [19:40] 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, wow. [19:46] 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. [19:52] So when, you know, 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 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 meet a lot of kids in there. I shouldn't call them kids because they're my kids friends. But a lot of people who are younger in their career who are struggling with this a little bit. [20:22] So what I believe is, [20:24] and I've always believed, is that you follow people. [20:27] You learn the most from people. I don't look for domains. 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.

[20:46] 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. [21:00] 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 are. [21:15] will do great things. And even if the company fails or succeeds, but not as much as you'd like, [21:22] you still have those connections. I mean, 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 know [21:33] I spent a lot of time with ex 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. [21:47] and you go step by step, I think that's a great way of progressing in your career. That's such tactical advice. [21:55] And I've seen this work for a lot of people that just go where their favorite [21:59] former employees work and not favorite to your point, but like the people that they most respect. [22:05] and have been most impressed by. [22:07] And... [22:08] I think it's such an easy thing to do. It's a really easy heuristic. [22:13] for understanding where to go. [22:15] There's something Mark Andreessen once shared that I'm reminded of when you say this, is that there's a term for this. I forget the actual term.

[22:22] There's like certain companies have this gravitational pull. [22:25] where they are acquiring all the best talent. They're currently like the gravity team. [22:29] in the space and everyone awesome is going there. [22:32] 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. [22:39] I guess any thoughts on that? [22:41] I thought... [22:42] Yeah, and it's really bad when you don't have the gravitational pull. It's super hard. I would say that one thing that if you're a manager, I always advise managers is, [22:53] Go somewhere where you can recruit. [22:55] Thank you. [22:56] And one, I got a piece of advice from a friend that I thought was amazing advice as a leader. [23:03] She said to me, [23:05] Take a job where if you hire people, it's going to make their careers. [23:13] I was like, whoa, because I was getting offers for like some kind of turnaround jobs. [23:18] And, you know, if you think you can turn around, great, but you want... [23:22] If you're going to hire the best people, [23:25] you want to make sure that it's going to be a good place for them. [23:27] and that they're going to learn and they're going to grow. [23:30] And so you want to do right by them and you really... [23:33] earnestly want to say you can make your career by coming here and I thought I [23:37] that gave such a higher bar for every job I was looking at. [23:42] as a leader. [23:44] that I thought was just amazing advice. [23:47] And then on the flip side, on the negative side, some people are looking.

[23:52] putting too much emphasis on where will I get a big financial return? [23:57] And I found that financial returns are the hardest to predict. [24:02] You know who's good. You know who you want to work with. You can predict where you're going to learn. [24:08] Because even if a company fails, you learn a lot. [24:10] but predicting financial success is [24:13] is so hard because you don't know what's going to happen with the market, with the world, with like crypto and AI. And people who do that and say like I had one person say I took this job because I'm a mercenary. [24:28] They just paid me a ton. [24:30] did not work out for him. [24:31] Thank you. [24:32] And I feel really bad when you when when people do that. But I think that that it's just it's a dangerous thing to do. [24:39] Thank you. [24:40] I imagine some people hearing this advice are going to feel like, [24:43] I'm not going to get a job at OpenAI or Glean or... [24:48] other awesome companies that everyone wants to go work at. [24:51] Any advice to those folks? 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 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. [25:21] 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.

[25:37] There isn't just the... [25:39] you know, OpenAI or Lean or Anthropoc. [25:42] Awesome. [25:42] And again, I love how tactical this is. Like if someone is trying to figure out where to go work, [25:47] 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. [25:53] see where they work, and there's your list of companies to potentially go after. [25:57] 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. [26:02] 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? [26:09] So skills can't be taken away. A company can fail. But if you learn a skill, you will always have that skill. [26:16] Love that. [26:17] And I've totally seen this to work, so I really love that you're focusing on this advice. [26:22] You mentioned [26:23] places you've worked and folks you've worked with [26:25] Worked with folks like Jeff Bezos, Stuart Butterfield, some of the top [26:29] product thinkers, leaders in the world. [26:32] So let me just ask, what's one thing you learned from Jeff Bezos and Stuart Butterfield? [26:36] Probably can't narrow down to one, but I'll talk about Bezos first. I was very lucky to join Amazon early when I still had quarterly meetings with Jeff Bezos. Oh, wow. And this was before AWS launched. So it was before Amazon was known in the Valley. [26:52] And this is another example. I went there because I went to work for Udi Manbar, who started day nine, 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. [27:05] And this was before like there were any books on it. And that really convinced me to go there.

[27:12] So, [27:13] There's a lot written on Bezos. Read his shareholder letters, read the books about him, read Colin Breyer's Working Backwards, the Everything Box, I think it's called, or the Everything Store. Everything Store, yeah. And 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. [27:33] 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 you can't, he doesn't believe in PowerPoint. You write a six pager about, I mean, it's like, you know, studying for a final exam. It's writing these six pages. So you go into the meeting. [27:50] And there's people around the table, his executive team and him. [27:55] First, he does not speak until everybody around the table speaks. [27:59] 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. 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. [28:19] He is [28:21] by far the smartest person I've ever met in my life in that I've worked with a lot of smart people, but his ability to go deep, [28:31] in any domain and nail 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 you're just like blown away that he knows that. But the thing that for me, the biggest takeaway from this meetings was his consistency.

[28:57] 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. [29:05] because he always had these principles everything had to be customer driven everything had to be relevant for the customer [29:12] I hated icons. [29:13] 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 they were like, so, but you would go in and after a couple of meetings, you're like, okay, I know what he's going to ask about. [29:27] 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. [29:37] And then there was one other thing that I really remember was a very small, 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, you know, our competitors have like 10 times as many people as we do on this. And he looks at me and he said, [29:54] That is your advantage. [29:56] Thank you. [29:56] 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 going to you have to be in it for the long term. And I. [30:07] You can be sure I never went in and said I need a lot more resources. [30:12] Thank you. [30:13] So that was Bezos. [30:15] Awesome. [30:16] Stuart, again, I went to Slack because I wanted to work with Stuart Butterfield. I think he is the best product thinker in the Valley, or he's not working in product right now. He's taking time off, but he's got this combination of long-term thinking in the details. So in 2014, he wrote a master plan for Slack, which was build a product people love.

[30:41] Build a network. [30:43] 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. Magic AI stuff took a lot longer. [30:54] That was part of his plan early on, his magic AI stuff. It literally was. There was a grid with four boxes in 2014, and it never changed. [31:02] That was his master plan and what we worked on each year changed. [31:07] But somebody recently asked me, well, did he always like, you know, you guys did Slack Connect much later. I'm like, yeah, it was always part of the plan. [31:14] It was always part of his vision. So he saw... [31:17] forward, [31:18] 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. [31:25] 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. [31:38] 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, [31:50] I started, we launched, I hired a design lead, Ethan Eisman, and he led a redesign of the new information architecture for Slack. I worked with Ethan at Airbnb. [32:00] Oh, yeah. He was head of design for the search experience in the search team. [32:04] Yeah, Eden is awesome. And he came in and his first task was to work with Stuart on on this redesign. And Stuart came in and said, "I want you to take

[32:13] everything in the interface and put it behind one button. [32:18] And everyone's like, that's never going to work. And he's like, do it. Just do it. [32:23] 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. [32:30] and put it behind one button. And he said, this is how you're going to see what you really need in the interface. [32:36] So we were never going to ship that. But it was the beginning of the redesign. [32:41] 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. [33:11] 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're a listener of this podcast, you're already committed

[33:41] 93% of members say Sidebar helped them achieve a significant positive change in their career. Check them out at Sidebar.com slash Lenny. [33:52] As a product leader, how do you think about just the time it takes to create a prototype in something like this? You know, as a PM, I'm just like... [33:59] A lot of times, we don't have time to build this whole prototype. We've got to ship stuff. We've got to hit these calls. We've got experiments to run. [34:04] Let's just build it and see how it goes. How do you think about it? [34:06] Making time for something like that. [34:08] If you're doing it right, it'll be faster. [34:11] And you need to have an engineering infrastructure that enables prototyping. [34:16] So some engineering infrastructures are too heavy and they don't actually enable prototyping. Like we had a problem with our mobile apps. [34:24] that it was too hard to prototype and we actually redesigned our mobile apps. [34:28] 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 [34:35] that enables you to do that. And you have to have engineers who have a prototyping mindset. [34:40] And if you build multiple things and you have this mindset as I'm willing to throw it away, [34:46] You write code that you know is never going to make it to production. [34:50] 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 type. [34:57] And so you actually get to your end goal of something working. [35:00] 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 as much as sometimes you can get design engineers who are doing the prototyping.

[35:15] So your first prototypes are like Figma prototypes, and then you get prototypes on real data. I had a, when I was at Google, one of our teams, the 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. [35:31] This is how we move faster. So I do think it's a mindset shift and a tech stack shift. [35:39] We're going to talk about AI later, but it's also getting easier to build prototypes with AI. [35:44] There was this video recently that went around on Twitter where an 8-year-old girl was building an app and [35:48] In 45 minutes, you build a chatbot using this protocol cursor. So I think that'll unlock a lot of great product... [35:56] opportunities and just accelerate this sort of work. [36:01] I asked about Jeff Bezos and Stuart Butterfield. I'm curious if there's another leader you've worked with that maybe is less known. [36:07] that you also learned a ton from that might be worth [36:10] talking about [36:11] I think that there are people who are really, really good at what they do. So Mark Benioff is an amazing marketeer. [36:22] He's [36:23] So I like his marketing mind. So after the acquisition, I got the opportunity to be on stage with him at Dreamforce or because, you know, Slack was a new shiny thing. So of course, Slack was going to be in the keynote. [36:37] And so I was in the Benioff keynote two years in a row. And so I watched how he approaches his keynote and the whole thing around Dreamforce. I mean, Dreamforce is...

[36:50] Incredible. [36:52] at the impact that it has on the ecosystem. And so I think that as a [36:57] Product people don't think of him as much, but as his marketing abilities are amazing what he's done. [37:06] I've written posts about how various companies got started in Salesforce's story. [37:10] Always comes to mind where they go to conferences with no software, mascot walking around. [37:16] And I remember they did something around one of the competitors where they just like created some real controversy around someone. Well, they went in to their competitors conference and stood outside. Right. That's what it was. It was this is in the beyond software. So this is in his book that he wrote about the early phases of Salesforce. And it takes guts. He pushes the envelope. [37:39] Mm. [37:40] I love that. It's a really good point that people don't think of Mark Benioff as a marketer. [37:44] And that's interesting that that's one of the maybe the main thing you took away from him is just the power of marketing and the skill. [37:49] He approaches his marketing presentations like a product person approaches their building their product. Amazing. Okay, speaking of former colleagues, I asked one of your former colleagues, his name is Fuzzy Kos. He's now the CTO of Notion. You worked with him, I believe, at Slack? [38:09] And at Google. And at Google. Wow. Okay. So I asked them what to ask you. [38:13] And he said that you're amazing at... [38:15] Building strong cross-functional relationships, especially with engineers. I know you used to be an engineer, so I get where that skill comes from.

[38:23] Thank you. [38:23] What can you... [38:24] teach people about building stronger cross-functional relationships, especially PMs. [38:30] to build better relationships with our engineers, designers, other folks on their team. [38:34] 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 so one, make sure you somewhere where you have a good engineering partner. So Cal Henderson was a 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. [39:02] 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. [39:24] 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 ask dad, and they got different opinions and playing one against the other like that doesn't work. [39:38] So when you have to know that you're not going to 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 it. So we were very clear on you're going to drive this. [39:50] I'm going to drive this. And if it was unclear, we would talk. And we would say, okay, who's going to take this one? And we would do all our reviews together.

[40:00] And so all of the OKR reviews, all of the we had weekly exec reviews, we had the updates on our OKRs. So we did them all together. But I knew, like, here's the things that he was going to ask the questions on and dig deep. [40:15] And then when I was, he would take a backseat. But of course, we could ask questions 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. [40:28] is that you have to respect and trust [40:31] that they actually will follow up on what they say they will in Cal and Fuzzy. We're like, amazing 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 we and he's like, I'm on it, got it. That was all I needed to do. And like, obviously, he couldn't do it, he come back to me and like, hey, there's gonna be a problem. [40:50] But it was like just things got done. [40:53] That's the best part of it. [40:56] You talked about being aligned, which I love and I fully have seen that power of that, of you and your engine manager, your design manager being aligned on [41:04] 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. One, you got to 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.

[41:34] And you can't just be like, OK, 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 Cal and I had. Perfect. [41:57] So we had... [42:00] 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 them get a Slack channel for each team. [42:13] There are 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 here's the 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. [42:35] In a room sitting there watching them together. [42:38] Correct. [42:39] And and then we would like say, do we have any follow up questions? And we put in channel our follow up questions. [42:45] to the team. And sometimes there would be, there'd be like [42:49] five to ten teams that we would then have a follow-up meeting with. We would say there's things that we, this is like a really high priority project or there's 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, our views of 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 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

[43:19] So for years, they they had one had been an engineering director and one had been a TPM. [43:25] And then we, 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? [43:39] And again, both there. [43:40] And then we had a weekly meeting with the four of us where we would just go through [43:47] any issues in the organization, what's going on, what's not. [43:51] And the four of us is you, the CTO, the chiefs of staff. Yeah. [43:55] 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. [44:01] 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. [44:08] that you had to be there and you had to be able to talk to your project. [44:12] And that was it. 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. [44:22] 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 like some insane number, like 300 and something. And we're like, this has gotten out of hand. And so 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.

[44:50] I got it. That's the video feature. Very cool. And then I don't know if you're-- you launched huddles, right? Slack huddles? [44:56] uh, [44:57] Did you use that as a part of this where eventually you just get people into a little huddle asynchronously and talk? Sometimes, absolutely. We would be in the reviews and we would huddle with somebody to ask a quick question. We used huddles all the time. I still do. I love huddles. [45:09] I love it. [45:10] 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. No email, unless you're dealing with somebody external, and now it's mostly Slack Connect anyway. Wow. [45:24] That's amazing. [45:26] Okay, I have one more question around product stuff, and then I want to talk about AI. [45:30] Thank you. [45:31] So I was reading your newsletter and, [45:33] on Substack, which will link to you. [45:35] You share this really interesting insight that I've experienced myself that [45:39] 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. [45:45] with the products they're launching. [45:48] And... [45:49] Basically, your advice is not to worry so much about making users unhappy, which I think is counterintuitive to some people. 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. [46:03] Okay. [46:03] 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. [46:15] And then you take it away and they're super unhappy, but there are more people you're going to make happy. So you get a product manager gets caught in this trap of, you know,

[46:27] the vocal minority. [46:29] 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 the number of people using your product today [46:37] is usually, unless you're Google, [46:40] far smaller than the number of people are going to be using your product tomorrow. [46:44] So design it for the people, the bigger number of people who are going to be using it tomorrow. Like if you have to redo the UI and, you know, they're like, with my cheese, people will be unhappy. But all the new people are going to be like, this is so much easier than that. [46:58] Do it and deal with the people who are unhappy. But the trick is you have to be respectful. [47:05] And you have to be transparent and you have to explain. [47:09] 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 listen to your audience. You don't want to alienate your early audience. [47:26] 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 [47:46] if people feel heard, [47:49] it makes a difference. And 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, I was, I was, I was,

[47:58] 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 there was an engineer in my in my or then we were like 50,000 people. There's an engineer in my team and I see engineers like super unhappy about the change. And I knew Rachel Whitstone. 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 like an FAQ or something that can help me? [48:28] I don't know why you made this change. And, [48:31] that I can help explain to the engineer in my team. [48:33] She did not respond to my email. [48:35] She picked up the phone and she called him. [48:38] I had no idea she did this. She just called this icy engineer and she listened to him. [48:43] And she heard why he was upset and she explained her reasoning. He was so blown away. [48:50] that she called him, that he completely changed his opinion, and then he told everyone else in the order. [48:56] And so it had this effect. And I learned a lot from watching her do that. [49:01] Like, [49:03] She never even told me she did it. Like later, she just did it. You just act. [49:08] You're authentic. [49:10] You listen to people and you're transparent. [49:12] It's so funny. This reminds me of a book I'm reading, a parenting book I'm reading right now that a former guest recommended called Listen. [49:18] And the core thesis of the book is when your kids are acting up or they're getting off track. [49:25] so much of [49:27] What they need is a sense that you're connected to them, a connection which is rooted in you listening to them.

[49:33] 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 and How to Listen So Your Kids Will Talk. Maybe it's the new name of that book. [49:45] 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. [49:58] Amazing. So many applications of just the power of listening. [50:02] Thank you. [50:03] Okay, well, not quite a segue, but let's talk about AI. [50:07] You're kind of at the epicenter of AI now with Glean. [50:11] How do you anticipate AI will change our jobs in product? What do you think people maybe aren't recognizing it, realizing it? What have you seen? [50:21] I'm going to give you a little bit of my history with AI to get to that point. So I actually, 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's evolved so much. And then, of course, at Google, using it for autocomplete and search. And it's transformed so many times. But then with this last transformation of Gen AI, and that's what brought me to Glean of seeing this, like meeting lots of AI companies. [50:51] this is really going to transform how we work. And it's just fascinating seeing these products. [50:57] I was kind of one of those people like, oh, yeah, it's going to be so far away until like I saw GPT-3.

[51:05] And, [51:07] I think it is 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 kind of haven't figured out how exactly to leverage it. [51:23] But the people who have are going to be so far ahead. [51:27] 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 to build to build a part like Sigma already has their fig may I can press a button and you can get your initial prototype working. You've got all the cold pilots. So they're not quite there. [51:57] there's you still like with copilot or with cursor, you need to be an experienced engineer to know when it's getting it on. [52:05] but they're going to keep getting better. [52:08] So I think people have to be careful about not getting left behind. [52:12] but their jobs aren't going to go away. [52:15] They're just going to change. [52:17] And we're going to I'm of the believer that we're just going to have a lot more software. But I talk to engineers and to PM saying, yeah, I tried that. It doesn't really work. And then go back to how I worked before. [52:28] And that's a that's a dangerous spot to be in, I think. [52:34] For people that get anxiety hearing this, where they're feeling they're going to be left behind,

[52:37] and like, oh my God, I don't have time to do this, or I don't know what I'm doing here. Give me advice for how [52:43] something someone can do to [52:45] not fall behind [52:47] I think that's a good thing. [52:48] Use the products. [52:50] 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, what isn't. And the same goes even more for AI. [53:08] Use ChatGPT. If your organization has Glean, use Glean. Use Claude. Try them all. Like, try them and see what they do. I was talking to a product manager I know. [53:20] who is more forward-thinking and loves playing with new products. And he had this use case that blew me away. So he said, [53:26] 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. [53:36] And he took the transcript from the Discord channel, which was huge, right? And he fed it into Gemini. [53:44] 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? Like this never would have occurred to me. It's like, that is so smart. And he's like, it was like a gold mine. Do you know how long it would have taken him to read? And he just wouldn't have done it. Right. So you're, [54:07] Think about like for the argument. Oh, I'm too busy. Well, if you use these products, I

[54:12] you're actually not going to you're going to it's going to be leveraging your time. So you get a lot of articles sent to you. [54:19] 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. [54:32] 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 gone calls. [54:43] And it took a while to get it right. [54:45] Like at first it would the summarization, the prompt wasn't good enough and would give us features that like 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. [54:59] But then we got it to the point where it worked and these things, [55:03] Really save time. [55:05] And you have to use your creative juices as a PM. [55:09] to figure out how it can help you and have patience to iterate and keep trying. [55:16] Because... [55:18] The models that we have today can do a lot already. Yeah. I love your example of the PM and what they did with the Discord channel. [55:26] Is there anything else along those lines that either you've done [55:29] to leverage some AI tool to be more productive or focus on your team. [55:33] have done to be more productive if there are product leaders or other folks? So many examples. [55:41] So one that I did really recently is I wrote I wrote a prompt in in Glean to help me get the status of features. And like you have a launch cow and you can look at launch cow and we'll say a day. But then, like, is it really the day? What are the outstanding issues? So it will look at our launch cow.

[56:00] And it will look at see if there are any open year tickets, what the Slack conversations are to see. And the customers who are beta testing it will bring all these together to tell me, OK, launch date is this according to launch jail. 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. [56:22] 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. [56:30] two weeks ago because we're advancing our prompting capabilities. [56:34] And so I was testing it out and I was like, oh, I could do this. So that's like and that's another example. And engineers are using it for automating part of the incident management of like I got an incident. How do I see all of where 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 say. [56:59] Uh, to, to help you. Um, but like the simplest, simplest is there's so much news. Let me just like paste in all 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? [57:15] what's what's impacting me and potentially competitive to any of the products that I have [57:21] and putting that into, say, collage at jpt you're saying. [57:25] Yeah. [57:26] Yeah, I think that beginning of the prompt is something a lot of people don't know is the power of just giving...

[57:32] it a role like you are a product manager at glean [57:36] from that perspective, give me this summary versus just summarize this. And that ends up being really powerful. Right. A hundred percent. And you can compare and like, what is Claude's, you know, PR saying that they just launched Claude Enterprise? How is Claude Enterprise different from OpenAI Enterprise? [57:55] and what are like because this is they again you can do it yourself but these micro improvements in your productivity [58:03] help. There's a, I, for my newsletter, I interviewed Claire Vo, who came out with chat PRD. [58:10] And so product managers are using it. We're just starting to evaluate it internally. I haven't personally used it yet, but it's super cool. And you can use chat VR, chat GPT to. [58:22] to do a PRD and Chad PRD gives us more templatized and more frameworks of how to do that. And these again, these things are going to keep getting better. [58:32] Claire's been on the podcast. She's going to be speaking at the Lenny and Friends Summit coming up October 24th. Oh, cool. Yeah. And she, a crazy statue shirt, she's making six figures off this product that she builds on the weekends, chat PRD. [58:44] So cool. But it also shows what you can build with AI. [58:48] Right, and it's just her. I think she just recently hired some engineers to help because she has like three kids, CTO, launched Darkly, and just is building this on the side, making $100,000 plus. [59:00] Incredible. I want to add a couple things here. So one is for folks looking for ideas for how to use

[59:07] AI tooling for their PM job. There's a couple of posts I've written. [59:10] that I'll link to in the show notes just to put that out there. Just a bunch of PM sharing. Here's what I've done with these various tools. [59:16] Another thought I'd love to get your take on, there's a lot of fear that the PM job will be replaced by AI. And I recently realized that it's the opposite. [59:25] I think the PM role... [59:27] is the best positioned to thrive in a world of AI, because if you just think about it, you have a tool that can just build a thing for you, [59:35] Just like you're staring at this blank thing that can build anything for you. [59:38] which function would you think would have the best chance of asking it [59:44] of what to build and how to articulate what to build best. [59:47] To me, it's clearly product people. [59:49] They're best at figuring out what to build, what matters most, where the impact is going to be, what customers need. [59:54] Not to say other functions don't also have these skills, but I feel like of all functions, PMs have the [59:58] most [59:59] of that specific scale i'd love to get your take on i i think that ai the one thing it's not good at is being creative [1:00:04] So if you're a PM who's doing the kind of route work, [1:00:10] It's going to take your job away. [1:00:12] 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 is going to differentiate, because it's not going to give you that leap. It'll say, here's what customers are asking for. [1:00:25] Here are the problems today. [1:00:27] But you have to figure out how to solve it. So in some ways, it might weed out the good from the bad PMs. So there's a significant number of PMs who are more like just execution.

[1:00:38] And I think that part of the job hopefully will be lowered because I hope that [1:00:43] a lot more of the execution will be able to automate, like, updating Jira and, like, you know, all these things that just take time and creating even though, 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 going to blend because the best designers I've worked with. [1:01:06] are product thinkers and a lot of really good PMs can also design. It depends on the what kind of product you're PMing for. But so I agree with the caveat that it will become harder to be a great PM. [1:01:20] Wait, say more about that. It'll be harder to be a great PM because... [1:01:23] Uh, [1:01:24] this [1:01:25] Many PMs are doing things that are mostly like project management, and that's the stuff that you use. 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 PM's jobs will go away. The great PMs will still have great jobs. Yeah. [1:01:41] I totally hear you. So in a sense, there might be fewer [1:01:43] you might need fewer PMs, but I think that applies in theory to every function. You might need fewer engineers, fewer designers. [1:01:49] I don't think you'll need fewer. I think you'll be able to do more things. [1:01:52] Mm-hmm. [1:01:53] So, like, 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. Like, when have you ever worked in a company where you thought that, like, [1:02:05] you didn't need more engineers. Like, you always...

[1:02:09] 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. [1:02:16] A lot of people are building AI into their product. Glean is obviously an example, which integrates LLMs, which innately are non-deterministic and non-deterministic. [1:02:25] Hard to know if they're going to provide anything [1:02:27] good. Sometimes something really dumb comes out. [1:02:30] Do you have any advice on... [1:02:32] working with these very complicated systems that don't necessarily you can't control [1:02:37] and building them into your products. Anything you've learned that might be helpful. [1:02:40] 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. [1:02:49] So Glean was started as Enterprise Search, which is... [1:02:53] So 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. Then when and using AI. So it was an AI search using BERT models and using vector embeddings in 2019. [1:03:23] And so it was obvious that they would be using ML techniques for search. Then GPT-3 came along and added a natural language interface, a chat interface. So you can ask a question in actual language and get an answer. And it basically is a knowledge graph of the organization. So you can ask any question. Think of chat GPT for your enterprise. Ask any question about your enterprise.

[1:03:43] Thank you. [1:03:44] So search people understand search. [1:03:48] 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, [1:04:03] the retention is fairly low. Like 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 [1:04:12] what they can and can't do for it. When I got to Gleam, [1:04:16] The first week I met with the assistant quality team. [1:04:21] And one of the biggest issues they have is, [1:04:25] people trying to use Glean for things that there's like no way it could know. Like, what should my top priority be next week when like we don't even know what your priorities are? And but then there's golden cases that are just amazing. [1:04:42] So we're not the the example of refining queries and search years for people to understand how to do it. And I took a lot of features of like autocomplete and refinements at the bottom of the page. So we need to build in those things to guardrails to help with the change to help suggest, oh, Lenny, here's what you could do. Here's a here's a prompt to find out the status of your feature that Tamar built. [1:05:12] 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, like an enterprise CIO will go use ChatGPT on weekends, but they come to work and they expect their software to be deterministic. So how do you how do you help educate users about that?

[1:05:34] And then the other thing I'll say about using LLMs, [1:05:38] is the industry is transforming so rapidly [1:05:42] that you need to make sure that your product gets better as the LLMs get better. [1:05:48] 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 OK to do it to understand that it's going to go away, but that can't be your differentiator. [1:06:01] you have to understand that your differentiator is something that will continue to be there. [1:06:07] as the LLMs get better and smarter. [1:06:11] And as part of that, because the LMS get so much smarter, everyone else will become awesome. [1:06:15] And to keep up, you need something that is actually outside of the LM that continues to differentiate you and is better than what other people are doing. [1:06:24] Well, yeah, that your whole product gets better as the LLMs get better. Yeah. And that, I think, is a frame of mind of how you approach the value add you're having. [1:06:37] Awesome. [1:06:38] Tamar, to close out our conversation, is there anything else that... [1:06:42] we did not cover that you think is important to share or you think might be helpful to leave listeners with. [1:06:48] before we get to our very exciting lightning round. [1:06:50] Thank you. [1:06:51] I, in my decades of working in tech, have never been working in an environment that's moving so quickly. [1:06:57] Thank you. [1:06:58] And it's really exciting. [1:07:00] I mean, it's super energizing and it's also scary. [1:07:03] But you have to change how you're working.

[1:07:06] You have to change how you're working so that you can keep up because it is going to be 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 much how many products we can build. [1:07:36] Thank you. [1:07:36] I love that. I can't help but drill in one level. [1:07:40] deeper, is there anything you found to help you stay ahead and help you stay... [1:07:44] you know, aware of what's happening? Are there like newsletters you find useful, chat, podcasts that just like help you keep up to date on where things are going? Is it like a person you look to like, hey, what's new? There are definitely like AI newsletters that I look at. There's AI 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 [1:08:14] perfected this, but the chat GPT voice mode where you can load it. Somebody who I just hired 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

[1:08:36] like Ben's Bites and the Neuron. And I love I like those are good summaries. And like I let Gil and Sarah goes podcast. I listen to Cognitive Revolution. There's there is a kind of too many of them right now, but I pick and choose. [1:08:51] Also, okay, we'll link to those ones you just mentioned in the show notes. The Elog Gil and Sarah Guo's podcast is 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. [1:09:02] She's going to be moderating a panel between [1:09:05] Kevin Whale and Mikey Krieger, who are the CPOs of Anthropic and OpenAI. So there we go. Another quick plug for LennyandFriendsSummit.com. I think it's LennySummit.com. Awesome. [1:09:17] With that, Tamar, we've reached our very exciting lightning round. Are you ready? I am ready. Okay, let's do this. First question, what are two or three books that you have recommended most to other people? [1:09:29] So one book was recommended to me by Shashir, the CEO of Coda. When I started at Slack, [1:09:36] He recommended the book Switch, How to Change Things When Change is Hard by Chip and Dan Heath. [1:09:42] and [1:09:43] It's such a good book. [1:09:45] And it's about like, how do you set a path for people? [1:09:50] to follow 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 remember the [1:10:04] all up in arms about that we had to do and i just read the book and after the all hands i went up to store it and i'm like you did that all wrong like

[1:10:13] You need to read this book. That is not how to get people motivated. [1:10:17] 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 Team of Rivals. [1:10:31] It's a book about Lincoln and putting together his cabinet. [1:10:38] 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... [1:10:49] uh is fascinating [1:10:51] Don't think anyone's recommended either of these, so... [1:10:54] Love them? [1:10:55] Next question, do you have a favorite recent movie or TV show you've really enjoyed? [1:10:59] I don't know if you like British murder mysteries. [1:11:05] It's kind of 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 like kind of an intricate story, so I enjoyed it. [1:11:20] Very niche, but amazing. [1:11:23] Do you have a favorite product you've recently discovered that you really like? [1:11:25] Well, I'm going to give two. One is tech and one is non-tech. So non-tech, I really like dark chocolate. [1:11:34] - Or just like a dark chocolate bar? - A really good dark chocolate that's simple, like no frills, none of this, just dark chocolate. And I discovered this chocolate called Bazoo Chocolate. And 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 were like a simple,

[1:11:59] like no nuts no anything just and he's like great pride in the beans and resources and from wow it's called busy with a b yeah bazoo as in kiss in french um okay and then on the tech side [1:12:15] Thank you. [1:12:15] I mean, the honest answer is clean, is, [1:12:20] I was listening to your podcast with Nikita, who said that people over 22 don't use new products except at work. And that like stuck with me. And I I. [1:12:30] the products, new products I usually use are at work and I use Glean 10, 15 tons a day. Like I use it so much and it changed the way I onboarded, it changed the way I work. I like, I just, [1:12:42] Even like the simplest questions, you don't bother people, you don't, you know, interrupt people on Slack. You're like, you know, 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 and or without asking an engineer, where's the latest design doc? It's just, it has really transformed how I work. [1:13:04] So I know it's cheating in that it's the product I work on, but it's the actual honest [1:13:10] is the actual honest answer. [1:13:12] And for folks that haven't heard of Glean, it's one of the most successful B2B AI companies out there, right? It's like... [1:13:19] a very large successful business and company that if you haven't checked it out, you should definitely check it out. [1:13:24] As our investors say, it's one of the AI companies that's actually making money. [1:13:29] Very few of those. Awesome.

[1:13:32] 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? I have one that my father told me when I was being really indecisive about what college to go to. He was really kind of bored of the conversation and he said, there are no right decisions. You make a decision right. [1:13:55] Okay. [1:13:55] And it is so true because you never know what's going to happen in life. [1:14:00] You just have to commit. [1:14:02] to whatever you're doing [1:14:04] And have no regrets about it. You can't be like, oh, you know, 10 years later, what if I had taken that job over there? It's like you you make it you make your success based on how you approach the decisions that you've made. [1:14:17] So if you feel regret about something, [1:14:21] This is a good one to pull out of just, I will make this the best I can make it, and that's the best I can do. [1:14:27] You're going to move forward. Move forward. I love that. [1:14:32] Last question. [1:14:33] I know you're a parent, I'm a new parent, I have a 14 month old at this point. [1:14:37] 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? [1:14:46] 14 months. I think the best parenting book I read is [1:14:51] Besides the how to talk so your kid will listen to how to listen to your kid will talk is I think it's called healthy sleep habits. Happy baby. [1:15:00] Like we are much happier when we sleep well.

[1:15:04] We perform better at work when we sleep well. Children need to sleep. [1:15:09] Like so making sure that they sleep well and sometimes that's like I did the whole sleep training like cry until you fall asleep and my kids still speak to me. So it was OK. And so you just like that is like. [1:15:23] the basic things like, [1:15:25] make sure that their basic needs are met. And then as they grow up, [1:15:31] Share your life with them. So a piece of advice I was given was. [1:15:37] Kind of analogous to Talk So Your Kids Listen is – [1:15:40] When they 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. Like if you share. [1:15:57] your life with them, they will share their life with you. [1:16:02] Such good advice. I really appreciate it. [1:16:04] Tamar, thank you so much for being here. You're awesome. We got through so much great stuff. Everything I was hoping we'd get through. [1:16:10] 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? [1:16:15] And how can listeners be useful to you? [1:16:17] Find me on LinkedIn and I have a subset 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 they be helpful if you're a customer of Glean? I'd love to know what you think, what works and what doesn't work.

[1:16:40] What's the best way to share that with you? Is it like message you on LinkedIn? [1:16:44] Subscribe, subscribe. Message on LinkedIn or comment on your post. Yeah, those would probably be the two ways. [1:16:53] Awesome. Tamara, thank you so much for being here. [1:16:56] Thank you for having me. [1:16:57] Bye, everyone.