Daniel Lereya: How a 30-column rival reset monday's ambition

1. 0:00 – 4:20

   Introduction to Daniel and monday.com

   1. DLDaniel Lereya0:00

      (instrumental music) A great PM basically for me is someone that is relentless until he gets this impact, until he validates that this impact is in place. In some cases, doing the biggest impact is not developing another feature. It's about making the current value more accessible.

   2. LRLenny Rachitsky0:15

      You've been at this for eight years. You said there's 250,000 customers at this point. What would you say is the most counterintuitive thing you've learned through this journey of building Monday?

   3. DLDaniel Lereya0:25

      We really have an approach of very radical transparency about everything. Before we went public, we actually shared every bit of information with our employees. Instead of demoralizing people, I think that this is something that gives them a sense of deep partnership. We really want everyone's brains in the challenge and not just one centralized brain and a lot of working hands.

   4. LRLenny Rachitsky0:48

      You basically realized that y- your competitors were shipping a lot faster than you were, that made you shift the way you think about product and the way you operate.

   5. DLDaniel Lereya0:57

      Some of our competitors did something that we can only imagine. We said, "Okay, we need to treat it differently." We received a gift from our competitors. They showed us that it's possible. Use your competition, know it, and take it, and set ambitious goals, and believe in yourself, and you can do amazing things.

   6. LRLenny Rachitsky1:14

      Today my guest is Daniel Araya. Daniel's currently chief product and technology officer at monday.com. He joined when they were just around 40 employees. And a few years in, Daniel and the exec team realized that their competitors were able to move a lot faster than they were and ship a lot more often than they were, and that spurred a transformation in how they build and operate their teams. Very few companies are able to transform like this and even fewer recognize that something is wrong. In our conversation, Daniel shares a bunch of very specific insights and suggestions into how to go about making change or even recognizing that something is wrong. Daniel shares moments when it felt like everything was going to crumble, why it's important to know that the skills that got you to where you are today aren't the skills that are gonna take you to the next level, why it's so important to orient all your teams around impact, and so much more. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of paid accounts at Superhuman, Linear, Notion, Granola, and Perplexity Pro. Check it out at lennysnewsletter.com and click bundle. With that, I bring you Daniel Araya. This episode is brought to you by Interpret. Interpret unifies all your customer interactions from Gong calls, to Zendesk tickets, to Twitter threads, to App Store reviews, and makes it available for analysis. It's trusted by leading product orgs like Canva, Notion, Loom, Linear, monday.com, and Strava to bring the voice of the customer into the product development process, helping you build best in class products faster. What makes Interpret special is its ability to build and update customer-specific AI models that provide the most granular and accurate insights into your business, connect customer insights to revenue and operational data in your CRM or data warehouse, to map the business impact of each customer need and prioritize confidently, and empower your entire team to easily take action on use cases like win-loss analysis, critical bug detection, and identifying drivers of churn with Interpret's AI assistant, Wisdom. Looking to automate your feedback loops and prioritize your roadmap with confidence like Notion, Canva, and Linear? Visit E-N-T-E-R-P-R-E-T.com/lenny to connect with the team and get two free months when you sign up for an annual plan. This is a limited time offer. That's interpret.com/lenny. This episode is brought to you by Airtable Product Central, the unified system that brings your entire product org together in one place. No more scattered tools, no more misaligned teams. If you're like most product leaders, you're tired of constant context switching between tools. That's why Airtable built Product Central after decades of working with world-class product companies. Think of it as mission control for your entire product organization. Unlike rigid point solutions, Product Central powers everything from resourcing, to voice of customer, to road mapping, to launch execution! And because it's built on Airtable's no-code platform, you can customize every workflow to match exactly how your team works. No limitations, no compromises. Ready to see it in action? Head to airtable.com/lenny

2. 4:20 – 8:50

   The pivotal moment: competitors shipping faster

   1. LRLenny Rachitsky4:21

      to book a demo. That's airtable.com/lenny. (instrumental music) Daniel, thank you so much for being here and welcome to the podcast.

   2. DLDaniel Lereya4:32

      Thank you so much for having me.

   3. LRLenny Rachitsky4:34

      We're gonna get into the story of Monday. We're gonna talk about your journey over the last eight years building and scaling this company and all the things you've learned along the way. But I want to start with a very specific moment that you shared with me where you basically realized that y- your competitors were shipping a lot faster than you, or able to get stuff out a lot more quickly and more often than you guys, and that made you shift the way you think about product and the way you operate. Can you talk about that moment and that, and that lesson and, and what you took away from that?

   4. DLDaniel Lereya5:06

      Yeah. Well, you, you take me a while back, you know, uh, I think it was when we were relatively a small team. I think we were something around like, uh, 30 people and, uh, you know, including engineers and product and everyone. It's actually that back in the days, we did so many things and actually we had an amazing, amazing execution, where there, you know, a weekly update where we would share everything that we did with the company. And it was alw- always, you know, super long and super, like, we have so many different things, uh, and really felt good about ourselves at that point, uh, to be honest, about the, the execution. And then I remember one day, uh, you know, coming to the office and just looking on one of our competitors, and with Monday we have, uh, like, one of the main things that we have in the product is our boards. It's like the, the heart and soul of the product and it's... You can think about it, it as a table.And it has different column types, data types that you can capture within the board and work with. And you know, back then we had five of these and I was actually coding the sixth one (laughs) eh, to be honest. And each and every one of these, like, took us, like, four months to develop, you know, together with defining the product and everything. And at this morning, we actually saw that one of our main competitors back then has actually launched 30 new columns.

   5. LRLenny Rachitsky6:39

      30?

   6. DLDaniel Lereya6:40

      Yeah. (laughs) And you know, we said, "Okay." At first we, we didn't really know what to do and, you know, we thought about it and I remember that even we said, "Okay, we are going to take even some time out of the office." So back then, Roi and Eran, which are the founders and also, uh, together with me and Tal, which is, uh, uh, w- was one of the main tech leads in monday for a long time, and few others. We went outside the office and we said, "Listen, we need to do things differently. Something doesn't make sense." And you know, I remember back then that for me, this realization of, like, understanding that we are doing so much but suddenly some of our competitors did something that we can only imagine and actually transform the product because it's a different type of platform, if you think about it. Eh, it, it was really hard, personally. First of all admitting that although you worked like crazy, you didn't do something that really transformed the product because I remember back then when we did a conversation, we said, "Okay, we're doing so much. What is the most meaningful thing that we did over the last three months?" And you know, suddenly the answer was, "You know, there's so many things." But it wasn't something specific. And after like, uh, you know, acknowledging that and, you know, it's a very hard thing personally, especially when you work so hard and you put your entire heart in, in what you do, eh, we said, "Okay, now we need to treat it differently." We received a gift from our competitors. They showed us that it's possible. Now we f- we need to think how. And in order to do that, we need to think differently because remember like we said, "Okay, if we're going to add 25 more multiplied by four months, we are a small team, we, we lost, okay? We can't make it." So

3. 8:50 – 17:44

   Setting ambitious goals

   1. DLDaniel Lereya8:50

      we said, "Okay, we need to take upon ourselves an ambitious goal, like 25 columns in one month." And this is the goal that we took upon ourselves. And you know, I think that the fact that our competitors did it give us, like, didn't give us the excuse of saying it's not possible. So in a way it was the biggest favor that we can ask for. And you know, long story short, month and a half afterwards we had 30 columns in monday. And we did it, you know, by thinking totally different. And by the way, afterwards, you know, we did it over and over again. So if you think about monday, it's basically a platform for work and you have different building blocks. Columns is one of them. But we did the same drill exactly with, eh, dashboards and widgets and then with automations and so on. So I think this was so transformative because A, we understood that you need to constantly think, especially at these phases, how will you, how would you transform completely the product in the next three months? And if you can't answer that and you say, "Listen, I'm doing so much thing," but you can't point this exact thing, you have a focus problem in my eyes. And second that, is that, you know, put ambitious goals. It will make you think differently. And you know, we really love now to do it even with, when we don't know it's possible. And it actually, like, works for us time after time. And last thing about it, you know, the team that was there suddenly became invincible because, you know, it's such an amazing, amazing experience that you have a goal that you don't know how you're going to do it and you succeed, and then it makes you feel that everything is possible, so.

   2. LRLenny Rachitsky10:40

      There's so much here and, uh, I have so many threads I want to follow on. One is just, there's the kind of this, there's this metaphor of the four-minute mile where no one thought it was possible and then someone did it and then everyone started beating that record. So I like that this is highlighting there's just so much power in seeing somebody else accomplish something you thought was impossible and that unlocks the way you think. And, uh, I love that you saw it as a gift. A lot of people, a lot of companies do this. They're in this place and they're like, "No way." It's like when the iPhone launched. Like, "No. No one, no one needs that. That's not... there's no keyboard." And a lot of people, like, are, uh, like deny that it's a, a thing they should be paying attention to. I love that you saw it as like, "Okay, we need to, we need to move. Things have changed. We're not doing things, uh, we're not gonna be competitive long term."

   3. DLDaniel Lereya11:23

      I think it's also very much about focus and I think that, you know, it's very hard to get to very good execution but it doesn't guarantee that you are working in the right way. And many times in my eyes, you know, simple questions can provide the most and the deepest insights about your work. And I think that for us, the fact that we managed to leverage it, as you said, and see it as a gift is one of the most important things. Use your competition, know it, use it to your advantage and you know, take it and set ambitious goals and believe in yourself and, and you can do amazing things.

   4. LRLenny Rachitsky12:00

      Another, uh, I think, uh, piece a lot of people are probably resonating with here is, uh, starting a company that's small grow- growing, things are going great and then all of a sudden things start to slow down.And in some cases, you don't realize that they've slowed down in, that's what had happened in your case, sounds like. In a lot of cases, the founder's like, "What the hell is going on? Why is it taking three or four weeks to ship one type of co- new column."

   5. DLDaniel Lereya12:21

      (laughs)

   6. LRLenny Rachitsky12:21

      And so is there anything... By the way, what was the scale of the company at this point?

   7. DLDaniel Lereya12:26

      Uh, it's a good question. Eh, if I'm not mistaking, it was around, eh, 2018, eh, back then how, I- I- I- I... It's safe to assume, like, 150, 200 people in the company, but we, we were relatively small.

   8. LRLenny Rachitsky12:43

      I recently had Bryan Singer on the podcast, who created the Shape Up method from Basecamp, and hi- that's kind of his, uh, piece of advice too, is around, like, 50 to 100 people, things start to really change and slow down, and that's where a lot of companies start to go sideways. So that resonates. That's really interesting. And by the way, this, these columns you're describing, just to make it clear, this is like a new type of, like, data, like, new format of column. Like, it's a new data format that you're building. It's not like just add another column to some database.

   9. DLDaniel Lereya13:10

      Yeah. So, so actually, like, the, exactly. It's a new type of column, but it's a whole product around it. Like, if you think about it, for instance, you have a column that captures dates. So it's pretty straightforward, but you can also have, like, formula column, which is, like, more complicated and has, like, more complex product around it. I think one of the best benefits for us as platform is that suddenly when we will, like, w- when we set the goal of adding so many different columns, we actually stopped for the first time and say, "What is a column like?" And we also, like, organized all the product architecture around it. And, you know, these kind of things, like, sounds really trivial in retrospect, but, you know, we really defined, okay, each column need to have, like, specific capabilities. It should be able to export into Excel. It's- it should be able to be filtered and sorted and so many different other things. But basically, we defined what is it and then create an infrastructure for all these shared things, making the work of adding a new column just thinking about the specific product that you want to provide with each one of these columns. And the story about it is actually even more interesting. We... The way we actually achieved it is that we said, "Okay, in two weeks, we are going to have an accaton in which each one of our developers is going to take one column and implement it in one day." And you know, if you think about it from four months to one day, it's, like, mind-blowing. And back then, I remember people said, "How can it be?" But then, Tal, that I told you about, eh, build an infrastructure. He send it to me. I did a column at night, you know, just to, to see the how the- how it works. And on the day that we did the columns, like, everyone knew what they are going to do, what they are trying to solve, and we just did it. And two weeks afterwards, it was in production, which was amazing.

   10. LRLenny Rachitsky15:11

       What we wanna do here is help people avoid these moments where they're almost, like, too late in realizing that things have slowed down. So I think a really, another important lesson here is the power of ambition and thinking crazily big. A lot of people think that when you ask your team, "We need to build 25 columns in a month," or whatever it was, people would be, like, uh, burned out or feeling super depressed. But really, people get excited. There's all this opportunity to think really differently. It reminds me at Airbnb, Brian Chesky was very famous for, you give him a goal, "Here's our goal for the year," and he's like, "What would it take to 10X this goal? Just, like, what would it take to do that?" And he's always pushing you to think a lot bigger when you're, like... 'Cause your first reaction's like, "What? No, no. (laughs) Why would you... Leave us alone." Uh, but then you realize, if you really think big, it changes everything about how you approach the problem, as you described, where it's like instead of-

   11. DLDaniel Lereya16:03

       Yeah.

   12. LRLenny Rachitsky16:03

       ... like, in a day, what, what would it take to build this in a day?

   13. DLDaniel Lereya16:05

       Yeah, and, uh, and I think by the way, this is something which is really important about setting ambitious goals. If you set a mi- like, a different goal, I want to reduce it from four months to three months. So many times this translates in people heads to, "I want you to work harder. I want to, you to work longer hours." And this is not a message here. It's about working smarter. And I think that many times when we talk about speed of execution, you know, there's fake speed, which means trying to do the same work by skipping stages or not doing the high quality that you want. But there's the real speed and speeding, like, organizations and speed of execution. Many times, it's about doing things right. It's about understanding, A, what is going to move the needle and work only on that, not working in a lot of things that you tend to invent when you trying to solve a problem. And B is, like, you know, about, like, thinking, as you said, like, eh, thinking differently. And I think that for the goals, this is why we really wanted the goal that you really understand from the first minute that if you work the same way, you cannot achieve it, even if you will sleep in the office. So you need to change dramatically, eh, how you think. And you know, the advanced phase of it is that today we're doing it on things that we didn't see others doing. And you know, we have the confidence because we have the experience of, like, trusting ourselves that this is an exercise for us that will make us actually think about different

4. 17:44 – 27:07

   Focusing on impact rather than features

   1. DLDaniel Lereya17:44

      solutions.

   2. LRLenny Rachitsky17:45

      I know another element of this that is really important to you, that you have shifted the way you all operate, is focusing on impact. There's a lot of focus on just building a lot of stuff and you realized there's a lot of power in thinking from perspective of how do we have the most impact. Talk about that.

   3. DLDaniel Lereya18:00

      This is the call and the, the main thing that we also measure, like, our teams, and this is how I see a great PM. So a great PM basically for me is someone that is relentless until he gets this impact and it... until he validates-... that this impact is in place. And, you know, for us, it really change how we think about things, it really changed how we set goals for our teams. So in many ways, PM in monday, first and foremost, is responsible for creating the shared understanding on what would be impactful for our customers. Okay? It's not about, uh, the solution and what we are going to build, it's about, what's the problem? What's the opportunity? And second, how we will know that we moved the needle? And without these two things, you can build so many different things and, you know, it's like, uh, songs for the door. Like, I built so, you know, such huge part of what I build was never used by our users th- the way I thought it was going to use. So I think that, for me, having the... this understanding of what we want, uh, to change for our customers and also how we know we did it is a huge, huge part of the, uh, the PM role. And for us, you know, uh, it means that we pay a lot of time in setting goals, in making sure that we really understand both, again, the opportunity, but not only that, but how we'll see and we'll know for sure that we moved the needle. In many ways, you know, it changes the, the conversation. So PMs, you know, and their teams, many times like, are spending a lot of time at the problem area before they think about the solution. The solution is not the case anymore. It's not... Like, there are so many different solutions. And once you do that and you have these goals, suddenly, it reduces also a lot of the discussions that you have about the different solutions, because everyone knows that everything is going to be tested on real life. So they make, m- make it, everyone treat it differently. And also in that way, you know, it makes you think much more holistically, which I also think is something that is very special at monday, is that we give our teams, like, real life goals as much as we can. And then, you know, in some cases, doing the biggest impact is not developing another feature. It's about making the current value more accessible. It's about connecting better to the go-to-market motion that you have. It's about understanding how your customers are going to learn what you built and use it. And, you know, this realization is something that we try very hard to stay, uh, on it. And it's hard because, like, people tend to build things... L- like, we all love to build things, right? And when you start to build things, you get excited, and suddenly, you lose track of why. Why you're doing it and what do you need to change. And I think that in that sense, this is the most important part about, like, uh, this point of impact. And, you know, this is also how we measure ourselves. So we can work extremely hard. It doesn't mean that we are successful, it doesn't mean that we are doing our work right. Okay? Uh, and it's not only for the PMs, it's for the entire team. So the entire team succeeds or fail together based on the value that we bring to our customers. And we have a lot of, like, different ways in order to make sure that we stay honest to this principle.

   4. LRLenny Rachitsky21:37

      There's a lot of people listening to this th- that work at, say, modern tech companies, very high growth tech companies, that are just like, "Duh, this is how you should work." A lot of people hearing this are like, "I don't really understand. What..." Like, "How..." Like, "What am I doing wrong? What am I missing maybe?" Uh, what's a sign that you're not oriented around impact?

   5. DLDaniel Lereya21:56

      I think the, the most obvious sign for me is that you are building something without the aim or without the initial aim of what it sh- should change for your users and how you are going to, to measure it. So in my eyes, it's many times the fact that you don't have a goal or the goal is, is like... Many times, you know, for me, a smell for death is that I hear people use the word, "We're going to enhance, we're going to augment, we are going to extend value," and this and this and this. No, it's not enough. What is it going to change for users and how you are going to see it that it actually happened? And then you start asking yourself all the questions, right? Because once you have a goal that you are committed to, suddenly, you think about the target audience because you need enough... Like, like, big e- big enough target audience, for instance, in order to, to get your, uh, you know, uh, to your goals. You need to make sure that what you build actually going to touch all of these people. And, and I can share just a recent example. You know? And, and, you know, these things sound trivial and maybe an example would, you know, like, uh, help resonate with that because I know many people are thinking like that. And, you know, we, we have a very, like, uh, uh, interesting offering that we just introduced with AI. It's called, uh, AI Blocks. Okay? And basically, me- it means that with no code you can integrate blocks which contain AI actions within your existing workflows. And, you know, 70% of monday's customers are non-tech, and for them, this makes AI accessible for them and has a huge, huge value. And we started building these blocks and we released it to customers and we measured, you know, uh, discoverability and adoption and retention and so on. And something that we do in order to, to stay connected to the numbers, so each team at monday has like, what we call the daily numbers update. So we have a... Think about it like a, a message that the team is building with all the numbers that care... that they care about because we really want people to leave these numbers. So for AI, for instance, for the AI Blocks, it was the AI Actions. So we had the AI Actions, how many accounts, like, uh, are using, uh, these AI Actions and so on and so on.And, you know, we got amazing responses from our customers. We see g- great success of them getting value from their AI actions. But, you know, one day, like, in this, like, uh, it's, uh, we, we use a Slack channel in which, uh, one of our internal systems, BigBrain, is sending us these messages every day, and then we have conversations about it, okay? And, you know, one day we saw, we noticed that the amount of accounts that are using AI is super, super low comparing to the entire population that we have. And you know, we have 250,000 paying companies that use monday, and we saw only like few thousands there. And, you know, until this point everyone will like in a very good feeling that we are making an amazing product. We get v- really good feedback, we're building great value, we're adding value. But we sat down and say, "Okay. Why it's only like this and this?" Then someone said, "Yeah, you know, uh, since AI is new, we need to do change of, uh, the terms of service for, for customers before we are opening it to them." And this is planned, you know, for, like, i- in the next quarter or something like that. And said, "What? No, we need to do it now." (laughs) You know, we need to now open it for everyone, because this is actually what would be the most impactful thing to do. And then, like, you know, the team went and sat with legal and sat with everyone, and with two weeks time it was open to 98% of monday customers, you know? And I think in that sense, you know, this is a very good example because we could have continued building value, and it's great, but the impact wouldn't be the impact that we were, were aiming for. And this is a very important point. And you know, we, I think in that sense, staying really connected to your teams, uh, to your, uh, numbers, sorry, this is something that I really feel strongly about. I feel that you need to get your numbers in push, you need to live by them. And you know, for me it's, like, so exciting to see a conversation that says, "Oh wow, uh, today there were a lot o- of new accounts that are using what I'm building. Let's see why it happens." And you know, these kind of things that I see the conversation about, uh, it's amazing. And also, you know, for in this case seeing the AI actions go, it's like you want to drive it and push it forward. And in many ways I feel that this is a very good example on where you can actually build a lot of value, you can work really fast, you can deliver a lot of features, but the problem lays in other place in order to get the impact that you want.

5. 27:07 – 32:07

   Transforming your product quarterly

   1. DLDaniel Lereya27:07

   2. LRLenny Rachitsky27:08

      Yeah. There's so much joy in watching, (laughs) watching your number go up. Uh, so just to close the loop here, to help people see if they're impact driven, working from a perspective of how do we drive the most impact, is one simple way of thinking about it is, uh, you're working backwards from a goal that is gonna drive business growth and revenue basically in the end. If you're working backwards from a number and a metric and a goal and then thinking through what are the levers that will most move this metric, that's a sign you're thinking impact through, by impact versus let's just keep shipping features that the sales team wants.

   3. DLDaniel Lereya27:43

      Yeah. And I think another thing for me, like it's an exercise that I really, you know, I really encourage everyone to do. For me it was like, uh, after the columns hackathon and everything that we talked about, I said, "Okay, each quarter..." And this is when we were much smaller, but it can be each month, it can be each two weeks. But how do I imagine the company and the product, uh, is going to be different and better for our customers in a quarter from now? And from that, you know, work it backwards. But if you, if you are just saying, "We'll have better security, we'll have better performance, we'll have less bugs, we'll have more, uh, like, enhancements to the, I don't know, this and this feature," it's not enough. You need to constantly build value which is pivotal to your customers. And if you don't do it and if it's hard for you to answer about this question, uh, it's a, it's a very good sign that you are not impact driven. And you know, I love to do it also with teams and individuals. Like, what are the things that you are most proud of that you did in the last three months? And if it's, like, takes you a lot of time to think, you are not very focused and you are definitely not maximizing the impact that you want due to that, in my eyes.

   4. LRLenny Rachitsky29:01

      I like that exercise as a kind of a, like, versus waiting for your competitors to do something and then realizing-

   5. DLDaniel Lereya29:05

      Yeah. (laughs)

   6. LRLenny Rachitsky29:06

      ... shit, we're be- way behind, it's forcing yourself every quarter to think about this. So do you do this as like a, you have a meeting or, or something in your calendar? Or how do you, how do you actually operationalize this?

   7. DLDaniel Lereya29:15

      So it's actually ve- Y- you know, today we are like, uh, under the builder's organization, which is the engineering product management, product design, we're 700 people. Uh, so we have a lot of different, like, uh, ways and methodologies to do it, uh, in different levels. But I'll give you an example from the company level and from the team level maybe, because these are the most interesting ones. So we just recently had our yearly kickoff. Each, uh, each and every year we do a yearly kickoff for our company. And one of the most, you know, exciting sessions obviously is what we are going to do with our product as a product company. And I really to, like to have a slide in which I, like, write and I just share it. When I'm going to stand here in a year from now, what is going to be different for our customers? And you know, this is on the company level. And I have one slide and it talks about, like, our offering and it talks about the value that they are getting in a way that next year I want to, you know, each year to start-... eh, my, my presentation with the slide from last year and see where we are. And, you know, in, in this level, it can be something like, our CRM continues with a very strong momentum and becomes a product suite when we give much more robust value to our customers. This can be an example, okay? With a, an additional product of CRM marketing, I would just say. But, uh, on a team level, what we did, and maybe I'll take an example from the early days, you know, we really did, uh, we really loved to do, eh, each ev- each and every two weeks, I told you we would write like a, an update for the entire company about what we did. And the way we did it, is that each and every one of our team members actually thought, write what, uh, is highlights, and then we would share it with the, the company. And this exercise really made us sit every two weeks and think on an individual level, but also on a team level. And you know, every one of our team members used to write, uh, to, to read these updates and say, "Dan, we had a good two weeks or we had a bad two weeks. We did a lot of impact or we did, uh, not, not enough impact." So I really encourage to create these points in time where w- you sit down and you force yourself to understand whether what you did is what you thought you're going to achieve or not.

   8. LRLenny Rachitsky31:46

      That's great. I really like the, the slide idea. It's basically, there's all this power in just working backwards from something in the future, uh, however you come up with it. So it's just like in a year we're gonna have... There's just, like, working backwards from a goal, working backwards from a big vision. Tho- I think those are such good exercises. You know, obviously Amazon's famous for working backwards. There's a whole book called Working Backwards-

   9. DLDaniel Lereya32:05

      Yeah.

   10. LRLenny Rachitsky32:06

       ... from their PR

6. 32:07 – 39:14

   Scaling monday.com: challenges and strategies

   1. LRLenny Rachitsky32:07

      approach. Uh, okay. I wanna go in a slightly different direction. I wanna zoom out a little bit. So you've been at this for eight years, building Monday. You said there's 250,000 customers at this point. What's like the revenue scale? Give people a couple of stats to give them a sense of just how large this company has gotten.

   2. DLDaniel Lereya32:24

      We recently announced that we crossed the, the $1 billion in ARR. And we are serving, as I said, 250,000 customers across the globe from virtually any industry that you can think about, like more than 200 different business verticals. It could be, eh, both tech and non-tech savvy customers. Eh, the vast majority of our customers are non-tech. And you know, from like a customer that is building airplanes and cruise ships, all the way to real estates, construction, finance, tech, and everything you can basically think of. And if I, like just for reference and seeing our growth pace, so when I joined Monday eight and a half years ago, eh, where we, back then, we were called The Pulse. Eh, we had around 4 million in ARR, and we, you know, eh, scaled from the, from there to one billion, eh, and from like around 30, 40 people in the company to 2500 right now.

   3. LRLenny Rachitsky33:29

      Awesome. When you talk about the product you're building, so a lot of people it's like, "Oh, it's like project management soft-... All this like column, like what's the big deal?" But I had Drew Houston on the podcast, and he made this really interesting point when he talks to people working at SpaceX who are like launching rockets to Mars, and he talked about people building ships. Like, if you really boil down what are they doing day to day, they're sitting in tools like Monday, putting together tasks and doing to-dos and sharing documents. Like, this is kind of what the world runs on. So it's important to have that perspective. With that, putting that aside for a second, I think very few people have seen what you've seen, is having a, seeing a company scale this way. Also, the transformation you just shared of just like almost sh- shipping too much and being slow to like, "Okay, let's rework things to shipping 25 columns in a month and all these things." Like, very few people have seen this, so there's a lot to learn from this journey that you've been on. So I have a bunch of questions and a different, bunch of different ways of approaching some of your biggest lessons from this journey. The first is, let me just ask you this question, what would you say is the most counterintuitive thing you've learned about building product and leading teams through this journey of building Monday?

   4. DLDaniel Lereya34:39

      Maybe first of all is about like something that we really care about, which is transparency. Eh, I, I'm like, uh, let me tell you a story. Like, I, uh, sat down for dinner at my family and many, many different members of my family are like entrepreneurs or like, uh, working as an executive in, uh, tech companies and so on. And, you know, back in the days with Monday, before we went public, eh, we actually shared every bit of information with our employees. You would get into our office, and you would see a dashboard with how many paying accounts do you have, how many people have churned today, how many signups do we have, and so many different things. Even if you came for an interview, you'd see these numbers, and I remember sitting in this dinner and everyone would tell me, "Listen, you are making a mistake. How can you do it? When thing goes south, you know, you'll demoralize the team and people like, eh, you know, will get upset about it." And I think this is, eh, you know, for me, one of the most important things, eh, when you hire and you have such a talented team, you want to share them... You want to share with them everything. And the reason for that is that then you are working on every challenge together, and instead of demoralizing people, I think that for the right people and the people that like, you know, eh, are working at Monday, this is something that gives them so like, you know, a sense of deep partnership. And as a leader, you know, there were many situations in my professional life that I knew some bit of information...... and I felt, you know, all the weight on my shoulders and... I love to call it the dark side of the moon. You are there alone, right? Like, you are coming to the office, there's nothing, you know, like, more demoralizing as... or, like, depressing as a, as a leader that you feel awful because something that you know, and you're coming to the office and everything is great and everyone (laughs) are, like, happy. And I think in Monday, we, we really wanted to do it differently and we really have an approach of, like, very radical transparency about everything. And this actually makes everyone part of what we are doing. And in a way, we like to say, we really want everyone's brains in the challenge and not just one centralized brain and a lot of working hands. And I can share examples. You know, when, for instance, suddenly people would come up to the office... We have dashboards across everywhere in the office, like, each team has its own dashboard. We have our company dashboards with all metrics and so on. And I remember cases in which someone said, "Listen, what happened to the conversion?" And you know, think how powerful it is when you have everyone at the company looking at these things. And many of the things that we discovered, many of the things that we saw as challenges and problems is things that people saw due to this transparency. Uh, so I think that maybe the, you know, counterintuitive part is that, um, don't be afraid to share the information. It's exactly the other way around. And I can probably share, share that, you know, even today as a public company, uh, we really share everything that we can. You know? And also, like, if you are product manager at Monday, you are signing, like, a 10b5 program for selling your stocks, meaning that we found a way to make everyone still see the data because we think this is the most important part. And I think this is one thing that I really believe in and really changed how we work and also how people are feeling about being partners in building Monday and not just working at a company.

   5. LRLenny Rachitsky38:37

      Is that thing they sign that's just, like, auto-sell stock, so they're not-

   6. DLDaniel Lereya38:40

      Exactly. Yeah.

   7. LRLenny Rachitsky38:40

      ... selling based on information, based on-

   8. DLDaniel Lereya38:43

      Yeah.

   9. LRLenny Rachitsky38:43

      ... announcements that's coming? Okay, got it. So every PM basically has to automatically... Uh, can't, like, decide I'm gonna sell my stock tomorrow 'cause this number's tanking.

   10. DLDaniel Lereya38:51

       Yeah. So, so you know, like, uh, we want to give people the choice but, like, usually we really feel that in most cases you really need to know this information in order to do your work. Uh-

   11. LRLenny Rachitsky39:02

       That's so interesting.

   12. DLDaniel Lereya39:03

       Yeah.

   13. LRLenny Rachitsky39:03

       And I, I, I think people even prefer just, like, dollar cost average sell. You know, it's like-

   14. DLDaniel Lereya39:08

       (laughs)

   15. LRLenny Rachitsky39:08

       ... (laughs) makes life easier not having to try to time all these things.

   16. DLDaniel Lereya39:11

       I definitely think so, yeah. (laughs)

7. 39:14 – 45:40

   How monday.com maintains transparency as a public company

   1. DLDaniel Lereya39:14

   2. LRLenny Rachitsky39:14

      (laughs) That's really interesting. Uh, and that's, and that's just product managers or how far does that all go?

   3. DLDaniel Lereya39:18

      No, so basically wha- when we became public, you know, uh, I remember still, like, one of the conversations that we had with, uh, like, uh, the bankers and the lawyers about, like, uh, "Listen, guys. Things would need to change. You cannot have a dashboard with all your financials at the entrance of the, the building. Uh, it doesn't make sense as a public company." And we understood it, but we didn't want to let go of what we cared about because we really believe this is one of the main drivers to the business, having this transparency and having this, like, shared brains, uh, you know, uh, mode. So, we tried to think about ways in order to do it. And so, uh, now, if I'll, like, fast-forward, you know, we're almost four years public, uh, and we have, uh, an internal app called Monday Morning. And in Monday Morning, you have two parts, part A and part B. Part A is for the every, uh, company employee. It contains a lot about engagement and a lot of data that can be shared with everyone, and part B is confidential and it's by role, okay? So it's the company management. But I think the important point is that we see product management as something that got to have these numbers, so we thought about it really hard and, you know, it's, uh, it's a lot of logistics to do, like, so many plans, uh, 10b5 plans, but I think it worth it. Yeah.

   4. LRLenny Rachitsky40:45

      This is so interesting. Like, a lot of companies talk about transparency (laughs) and, and you guys are, uh-

   5. DLDaniel Lereya40:50

      (laughs)

   6. LRLenny Rachitsky40:50

      I think radical transparency is a good way to describe this 'cause I've never heard of a company doing this (laughs) where you have to-

   7. DLDaniel Lereya40:56

      Yeah.

   8. LRLenny Rachitsky40:56

      ... sign this-

   9. DLDaniel Lereya40:56

      They, they didn't hear about it as well apparently (laughs) and-

   10. LRLenny Rachitsky41:00

       (laughs)

   11. DLDaniel Lereya41:00

       ... yeah. It wa- it, it took time to, you know, (laughs) to get to these solutions.

   12. LRLenny Rachitsky41:05

       That's so funny. So for people that are listening to this who are like, "Hey, maybe we should explore this," what's, like, one thing you'd suggest they, that they could do to start moving down this road? And the benefit, again, is you... I guess, maybe again remind pe- people of the benefits of doing this 'cause it sounds like a lot of work and, and risk.

   13. DLDaniel Lereya41:20

       So I think that as a young startup, it's actually not such a hard work. Uh, when we were very small, you know, back in the days, we had a, like, like the daily numbers concept that we now have for the teams, we had the daily numbers for the company. How much bank accounts, how many upgraded, downgraded and so on daily. And you saw people reacting to it, like, on a daily basis, so this is something that you can do in virtually one hour and it, like, changes how people see, you know, their role within the company. It focus everyone to the company's KPIs because everyone understand what you care about and so on. So this is one thing that you can do extremely fast, and I don't see any disadvantage at a- aside from the fact that people are afraid. Many time you are afraid. And I can share, like, it's so much... Like, it's even, like, a, a big relief that you don't need to think, "Can I share it? Can I don't share it?" Like, can I... Like, you just let it go and everything would be okay. And I can share from my experience that we shared everything. And the second thing, which is really practical, you know, it's the office dashboards. We really believe in it. So, you know, you buy a TV, you put it on the wall-

   14. LRLenny Rachitsky42:32

       (laughs)

   15. DLDaniel Lereya42:33

       ... you start a conversation due to it, what do we want to show on this TV? And you know, when we was like, eh, a smaller startup and we sat all in one office space, we had our company goals, eh, dashboard, and it also had like, eh, we, we programmed it to have sounds on meaningful events. So when you had a, like for instance, new paying account, you had a Homer Simpson saying, eh, like the, the saying with the $1 million, "I will become a millionaire," or something like that. Eh, for, you know, a new sign-up you add a tick and so on. So suddenly everyone are living it, you know, it becomes part of the cadence of the company. So these are l- just two ideas to make it super easy and the change happens immediately.

   16. LRLenny Rachitsky43:17

       I love how that connects back to the whole point about impact, people all aligning around, "Here's what we're trying to drive." Like if the Simpson sound is going off all, that's a sign that this matters and it's something we should be driving up.

   17. DLDaniel Lereya43:29

       And it creates such a partnership, you know, I remember like reaching to the first time where we had one, eh, million dollar collection in one month, breaking the record of like new paying accounts for one day. Everyone are living what in many companies, you know, only the management or the founders are like feeling, and I think that in that sense you already feel that you have a great power because everyone around is the same things and it makes conversations different because everyone understands what matters to you at that point.

   18. LRLenny Rachitsky43:57

       This is awesome. Uh, really cool counterintuitive lesson, I feel like a whole podcast could be, uh, done on like how to do this effectively. Uh, I wanna move on, but if, I guess if people wanna start implementing this at their company, let's just say they should go talk to you and you could probably give them a bunch of advice.

   19. DLDaniel Lereya44:10

       I would love to.

   20. LRLenny Rachitsky44:11

       This episode is brought to you by Vanta, and I am very excited to have Christina Cacioppo, CEO and co-founder of Vanta joining me for this very short conversation.

   21. NANarrator44:20

       Great to be here. Big fan of the podcast and the newsletter.

   22. LRLenny Rachitsky44:23

       Vanta is a longtime sponsor of the show, but for some of our newer listeners, what does Vanta do and who is it for?

   23. NANarrator44:30

       Sure. So we started Vanta in 2018, focused on founders, helping them start to build out their security programs and get credit for all of that hard security work with compliance certifications like SOC 2 or ISO 2701. Today, we currently help over 9,000 companies, including some startup household names like Atlassian, Ramp and LangChain start and scale their security programs and ultimately build trust by automating compliance, centralizing GRC, and accelerating security reviews.

   24. LRLenny Rachitsky45:01

       That is awesome. I know from experience that these things take a lot of time and a lot of resources and nobody wants to spend time doing this.

   25. NANarrator45:08

       That is very much our experience, both before the company and to some extent during it. But the idea is with automation, with AI, with software, we are helping customers build trust with prospects and customers in an efficient way, and you know our joke, we started this compliance company so you don't have to.

   26. LRLenny Rachitsky45:24

       We appreciate you for doing that. And you have a special discount for listeners, they can get $1,000 off Vanta at vanta.com/lenny. That's V-A-N-T-A .com/lenny for $1,000 off Vanta. Thanks for that, Christina.

   27. NANarrator45:39

       Thank you.

8. 45:40 – 51:02

   The importance of taking risks

   1. NANarrator45:40

   2. LRLenny Rachitsky45:40

      Any other big counterintuitive lessons from the journey that you think would be fun to share?

   3. DLDaniel Lereya45:45

      One thing I really love about what we do in monday is that we really love to take risks. Not for the sake of it, but we are not afraid to do bold moves. And many times when you want to do bold moves you have a lot of concern, especially when you start to be successful because you, you are afraid that you are going to break everything that you built till now. And for me, you know, one of the most pivotal moments in the company life is when we decided that, you know, back in the days as you said, we, we were a platform but we had a go-to market of a project management tool. And we said, "Listen, people are doing so many different things on top of monday, they're building a CRM of monday and they are building a software for managing their dev cycles and they are building so many different things." And we took a decision, strategic deci- decision to become like a, a multi-product company which is built on top of this platform. And we actually did something which is really counterintuitive. You know, the, the first thought that comes to mind, at least for me, is why maybe not just launch a new product, do it relatively on the side, gradually understand if it's successful? And if it would be successful, double-click on it. But we actually did it in a very different way. We actually announced five different new products, eh, simultaneously on the same time. And you know, we had so many like, I can't stress enough how, you know, how hard it is to think about it because like I remember when we talked about and doing it people say, "What? But we're going to confuse our current, eh, users and it's going to help conversion. And how are we going to do the marketing now when we have so many different go-to markets? And the sales, they don't know how to navigate people to different... And what about pricing?" So many different concerns, um, but we decided to do it because we really want to create a pivotal leap. And I think that in that sense, you know, fast forward to, to this da- day, like part of these products were really successful. Eh, for instance, monday sales CRM is like, like going faster than monday back in the days like, you know, when it's amazing to see it. And some of them we understood that they don't need to be separate products and we, eh, collapsed them back to the main product. But the point is, is that we managed to learn and to change both internally at the company our, the perception of everyone around what we are building, but also externally. Like this move changed dramatically the competitive landscape that we live in. And, you know, I think there was a lot of friction, many people at the company were, eh, like having a lot of friction with it. It was real- really, really hard. ... but looking back, it's such- I'm so happy with this move and the fact that we did it like that because just imagine what would happen if we would choose one of them and it wasn't the successful products, and our conclusion can be that multi-product won't work for us. We really managed to transform the company in a very short amount of time and also to create new reality, uh, you know, and I think that people need to remember that, and I'm constantly reminding it to myself, and I think this is something that we are constantly working, you know, uh, with each other in order to make sure that we, we remember it that not taking bold risks, not m- making bold moves, it's a risk for itself, okay? And many times like, you know, people want the inertion. People want just the incremental value, but if you want to do leaps, many times you need to let go of things that were successful for you in the past. And this is very counterintuitive and we did a lot of, you know, a lot of mental models to help us cope with it. So I remember that when we were small and we had, for instance, like 20, uh, 2000 paying customers. So I said, "Listen, but most of Monday's customers are not customers of Monday yet, so we need to think about them as well." You know, and this is something that really helps you because many times you need to do things that affect like the current success that you have. Eh, but I think it's- this is another very, very important thing that I'm constantly reminding to myself.

   4. LRLenny Rachitsky50:07

      There's kind of this other recurring theme that I'm noticing of just like thinking big and taking leaps, and I love this point you made of not doing that is actually a big risk. Not taking risk is a big risk. That's a really powerful point, and it's innately scary to do something risky. And so I love the push here of just like take more risks because it's so easy, and this comes back again to the beginning of the conversation where you- we're just like building things the way they've always been built and looking back and like, what have we even done? What have we done over this year of hard work and tons of features? I think a lot of companies get in that place where they're just like, what are we... Like at Airbnb, I had this exact

   5. NANarrator50:44

      (laughs)

   6. LRLenny Rachitsky50:44

      ... Brian is constantly like, "What are we even shipping? All these billions of experiments that are moving the numbers, like what are we even doing?" Like, I don't know anything that we ship that's really exciting. And so I think this is a really good reminder and push to just like think bigger and take- and you need to take big leaps. Um, so love that. Is there,

9. 51:02 – 54:33

   Counterintuitive lessons in product development

   1. LRLenny Rachitsky51:02

      uh, any other big counterintuitive lessons before we move in a different direction?

   2. DLDaniel Lereya51:06

      I really believe that many time, like, uh, spending more time on working on something will not yield to better results or to better products. And, you know, I think that many times like, um, we as people that are building products for others, eh, get to a point where the feedback that we, we want to get in the bottom of our heart, you know, is like, "Wow, what an amazing product you have built." And I think this is a very bad feedback to get (laughs) for initial things that you are doing, eh, because it means that, you know, I, I feel that in many ways the, the point in which you make real people use your product is really scary because you, you suddenly, you know, put your work out there and then in order to, to like actually... And you, you are afraid that they will say, "Listen, it's a lousy product. It's not a good product." But actually, we really encourage people to get really fast to production, to put traps for themselves that is scored by time and not by effort. And, you know, many times I saw that more time creates more questions, it creates more complications, it creates more assumptions that we put for ourselves in thinking what our users need, and we invent things, you know, and we, we do it all from good reasons. We want people to like what we build. We want them to get value. But for me, like this is a very important point that many time, many times using like the setting traps mechanism of saying, "Listen, we have three weeks, let's think about it," and score it by time, it makes you extremely focused. And you know, this is very important because, you know, uh, we really want to get feedback from customers that say, "Yeah, listen, this is on the direction. I'm still missing this and this and this." And also, we really love the fact of this is not a good product. And I can give you a recent example. You know, even when now we, you know, we work with big customers and, of course, like there are different ways to implement what I said, eh, than you are a small startup, but we are building like a new offering of enterprise work management. Think about it like a way of managing projects at a huge, huge scale, you know, thousands of projects, like tens of thousands of employees and so on. So I really love using the deadline trap, and it makes you focused, it makes you sharper in thinking. And we just had a recent example with the offering I was telling you about of like enterprise work management, managing projects at scale and, you know, this is an enterprise product. So you have all the reasons in the world to say, "No, I can't release it yet. I need more time. I need to do more things. They won't use it. They need this and this and this." And I think that we actually released the first like alpha version to them and we got a feedback of, "Listen guys, this is premature. We need more like more comprehensive value," but we got exactly the feedback of what, and this is priceless. And, and my response to the teams is, "Well done." Like, I think you did an amazing job in like releasing it and making sure, because, you know, many times being so afraid of releasing it and like, uh, thinking, "If I just have one, two, three more weeks, eh, I will build a better product," I think it's not,

10. 54:33 – 57:28

    The value of timeboxing and deadlines

    1. DLDaniel Lereya54:33

       it's not true.

    2. LRLenny Rachitsky54:34

       This is such good advice. It resonates so much with recent other conversations I've had. So just to clarify what you're saying, basically you...... have a time box. When you say traps, it's basically a, a set amount of time. We're gonna spend three weeks on this feature, and if it doesn't, if it, we don't hit the three weeks, we just cut scope essentially. Is that the idea?

    3. DLDaniel Lereya54:51

       I think, yeah, it's, it's like this is the basic version of it.

    4. LRLenny Rachitsky54:55

       Yeah.

    5. DLDaniel Lereya54:55

       But now for us, we really want and we really love doing, doing it as an exercise for ourself. For instance, let's say now as a public company we say, "Listen, we're working on something. We want to announce it on the next earning." And put a trap for ourselves. Why? Because again, it makes you sharp. It makes you super focused about things. And you know, I think that in many ways, this results in a much better product because you are not building things that you invented. You are staying really true to what your users needs, the real, you know, core of the value. And it's really funny to see the dynamics of teams, you know, when they are planning, you know, from the bottom up, so it starts like, you know, with something that, uh, like let's say you done everything great, okay? You have the opportunity, you understand, you have the KPIs, everything is in place, but now you're starting to plan it. And suddenly people are raising, you know, concerns and issues and becomes, uh, a sport to say, "What can go wrong?" And like being fear-driven and then you tend to, you know, protect yourself and adding more content and more cont- and then when you see what happens, it's actually like, it's going to be shipped in two years.

    6. LRLenny Rachitsky56:10

       (laughs)

    7. DLDaniel Lereya56:11

       Then we say, "Okay, no. Okay, we have earnings in two months. What can we ship to these earnings? And let's put a, a tab." And then you suddenly see the conversation changes. First of all, it makes everyone really focused on what's the core of the value, and it removes all the theoretical discussions that people have and things like that. And you know, the results are amazing and you need to remember when you do it, you need to continue afterwards if you, like according to feedbacks and, and not let it go just but what you did in the first version. But in many ways I really love the fact that, you know, the first version get a feedback which is not everything is perfect because if this is the, the feedback, it means that we built too much and probably it's not focused product enough. And when you build a lot of features, this can be like, you know, the death by a thousand cuts because in each corner of the product you add more than you need, like...

    8. LRLenny Rachitsky57:08

       Yeah, there's so much here that, that connects to other conversation we just had. We had a Gaurav Misra from, he's CEO of Captions and he made this point that if people aren't complaining about your pro- like, you, you want to see people complaining 'cause that means they care. Like, there's something there that they care about if they're... If you're not hearing any complaints, they could care less about what you're building and that's not, that's a bad sign.

    9. DLDaniel Lereya57:27

       I really loved

11. 57:28 – 59:54

    Embracing user feedback

    1. DLDaniel Lereya57:28

       it. Yeah.

    2. LRLenny Rachitsky57:29

       Their company actually goes to the extreme of what you're describing. Every engineer ships a feature, a, a marketable feature every week. That's their pace. (laughs)

    3. DLDaniel Lereya57:37

       I, I really connected to it. And by the way, about user feedback, I think, you know, uh, it's really, it's really nice because like, uh, many times, you know, people associate like, uh, they, they only measure themselves by user feedback, uh, the specific point. And I think this is also maybe, uh, you know, something that is, uh, counterintuitive. Not every customer feedback is the feedback that will drive you to the, you know, to the end result of the best product out there. Uh, there are many aspects to it. I, I can share, you know, just one example about us. We as a, you know, in the beginning of the company, we for instance, uh, didn't want to have a free trial. And part of it is that we really wanted to hear feedback about our product only from people that the product means something to them. The, the best proxy for that is that they are paying because it means they get real value and you know, in that sense it helps us, it helped us at the beginning to be, to stay super focused about like, you know, separating the wheat from the chaff in the, with the, the customer's feedback. So I think, uh, it's a super important point and we need to take customer feedback in context.

    4. LRLenny Rachitsky58:51

       The other really interesting point here that you're making is this idea of we had, uh, I think I mentioned this already, Ryan Singer, he's the creator of this method Shape Up, which is very centered around appetites over deadlines. There's so much, like so many, everyone listening to this has probably gone through an exercise where like, "Let's redo our landing page." And it's like, "Yeah, it'll probably have some impact. Let's spend some time on this." And it ends up taking like six months and everyone's like, "Why did we spend six months redoing this freaking landing page?" Like, "Look, I would've given it three weeks and then moved on." And the way to do that is you just commit upfront, "We will spend three weeks on this. We'll get as much done as we can in three weeks and then we'll move on." People talk about this, very hard to actually do, so I love that's how you actually approach some of these bigger features you work on. Do you guys practice Shape Up by any chance or this is just like a thing you do?

    5. DLDaniel Lereya59:38

       Uh, no, actually I wasn't-

    6. LRLenny Rachitsky59:39

       Okay.

    7. DLDaniel Lereya59:39

       ... uh, familiar with it, but I definitely going to check it out. Yeah.

    8. LRLenny Rachitsky59:42

       Okay, cool. Yeah, it's, uh, it's a whole method. Uh, and we'll have I think the episode right before this is actually that episode. Okay, let me go in a different direction and kind of keep extracting lessons from this journey 'cause that was a really fruitful place to go.

12. 59:54 – 1:04:43

    Adapting leadership styles

    1. LRLenny Rachitsky59:54

       So let me ask you this question. What's one thing that you wish you'd known before stepping into the role you're in today?

    2. DLDaniel Lereya1:00:00

       This is an interesting question. I think, uh, you know, there are many aspects to it and maybe if I'll take the, the personal aspect. So, you know, I've been in charge of like the, the product and technology from, from like since I joined the company. But with that, my role has changed I think like dozens of times. Like I've, I feel I'm very fortunate to work in one company but actually work in dozens of different companies. Think about the scale that we talked about, like each point is a different, uh, it's actually a different company and a different role and different challenge. And I think that, you know, something that maybe is counter- counterintuitive personally for me was that...In many of the phases that we undergoed with, I felt that what got me to this phase isn't, is not necessarily what's going to make me successful in the next phase. And if we want to be even more blunt, you know, there were, like, personally, times when suddenly I saw how my biggest, you know, strength, uh, for instance, like, mastering all the details and having everything in my head, knowing exactly what's happening on every corner of what we do, this is, was probably something that gave a lot of value when we were small. But as we got bigger, I think, like, it suddenly created, you know, even damage, you know, continuing to do the same thing. And in many ways, it takes time to do this realization, and I think that a good advice that I would love to have is that, don't be afraid, again, to, to let go of things that you, uh, think are super powers. Many times, your super powers that brought you to this point and made you successful, many times you think that if you let it go, you won't be successful, and it's frightening. But I really feel that you need to constantly evaluate what your current role, eh, is actually, is actually ... What, what is the role, like, and what is needed in order to be successful in it, and not continue with the inertia? And, uh, this is, uh, something that I wish someone had told me, yeah. It took me time in many cases, you know? (laughs) Many cases, I did it too late.

    3. LRLenny Rachitsky1:02:21

       Is there anything that helped you realize this or get good at this? Is it, like, coaching? Is it just doing it and surviving and failing and be like, "Oh, I see"?

    4. DLDaniel Lereya1:02:28

       (laughs) Eh, I think all of the above. Eh-

    5. LRLenny Rachitsky1:02:31

       Mm-hmm.

    6. DLDaniel Lereya1:02:32

       ... I think that, uh, one sign for that for me was that in many cases, I felt, eh, I'm doing a very good job, but then people ... Like, uh, it can be, like, uh... I, I'll give you an example, okay? Like, uh, for instance, doing a company, like, leadership QBRs, okay? Quarterly business reviews. So when we just started it, with it very early, you know, I would actually tell about everything and, you know, I remember one meeting that I went out of the meeting and I say, "Wow, I really managed to, you know, convey everything and explain everything in very, like, in a very articulated way." And, like, one of, uh, my colleagues in the, the co-leadership team said, "Eh, wow, I didn't understand anything." (laughs) Like, eh, "Wh- what is the bottom line of all of this?" And, you know, it was like, eh, y- you suddenly realize that what you thought is, is good is not necessarily what the other people needs from you at this point. And, you know, like, eh, after understanding that, I, I went and ask, like, "What would be beneficial for you?" He said, "Listen, I want to keep in my head, like, the three most meaningful things that you are currently facing with. I don't want to n- hear everything." And, you know, e- like, it's hard, (laughs) but, uh, but this was a point for me that I realized that I need to change and I need to change something and the, the, like, the requirements are different. And, like, at the beginning, you know, I tried to say him, "But listen, it's very, it's important that you know, like, you, you're sticking to it, right?" But, uh, we need to let it go sometimes and think f- like, from the beginning.

    7. LRLenny Rachitsky1:04:22

       There's this phrase that someone shared on this podcast once where in, as you rise in your career, you often go from the person that is pitching leaders on something to the person being pitched, and that's a really weird place to move-

    8. DLDaniel Lereya1:04:35

       (laughs)

    9. LRLenny Rachitsky1:04:35

       ... from, you know, having to learn how to be, give great feedback, delegate, let go of things, and I love that this, this is a good example

13. 1:04:43 – 1:10:41

    Personal reflections on leadership

    1. LRLenny Rachitsky1:04:43

       of that.

    2. DLDaniel Lereya1:04:44

       Yeah.

    3. LRLenny Rachitsky1:04:44

       Since we're getting a little vulnerable and open about stuff, I wanna try this question. You haven't, you've done a lot of podcasts, you've done a lot of interviews, you've been all over the place. Is there anything you haven't shared anywhere else that might be helpful to share here about the, the journey you've been on?

    4. DLDaniel Lereya1:04:58

       Yeah, so maybe continuing with the same point, you know, like, uh, it's a crazy journey and it's crazy personal journey. If you think about it, like, uh, I remember, uh, Roy once said, "If someone would've interviewed me to a public company worth, uh, you know, eh, like, uh, I would say $10 billion, uh, in market cap and managing 2,500 employees, I'm not sure that I would interview myself and get myself to the job." Eh, and I can... You know, for me, there were a lot of moments – and it's constantly happening – eh, you know, when things, you know, are going sideways and things doesn't work and you see so many things are breaking down and, you know, you can be on the same day super happy and suddenly on the lowest point there is. And I can share, you know, many times I've a- I've asked myself, like, eh, whether I'm the right person to lead it, whether we need, like, someone that is coming with all the experience to this phase. And I remember, like, a talk that I had, uh, with Eran. He tell me, he told me something, "Listen. First of all, as the one who built it, no one would be able to do it like you." And I think it's an important, you know, thing to remember when times are tough. I really believe that, you know, if you have the passion, and if you have the will, and, and if you are willing to do the hard work in o- order to constantly adjust and evolve and, you know, to be vulnerable and also, you know, to say about yourself, like, "I didn't understand something. Now I need to learn it, and I need to do things differently," eh, you know, it's a very important point if you want to do this kind of, uh, of, uh, journey, and it's hard.And something I can share, you know, I can reassure everyone that are listening to us, you know, if you are feeling it, you are not the only one. Everyone are feeling it from once in a while. Be confident about yourself, be vulnerable in order to learn and to evolve, and I really love to do like a, a mental, you know, mental exercise of, like, saying, like we, we said about the product. So let's say I'm, eh, I'm, eh, Daniel of, like, next six months. How do I want to look back on these six months, and what do I want to say about myself that I learned, that I evolved? And this help you get out from the state of, like, "Everything is okay, I'm good," and it makes you, like, want to learn and want to evolve. Eh, and also, like, stay in doing mode. Like, I don't believe in, eh, like, I think the one, one thing that really characterize me is that I can be, like, very, you know, it can be very difficult and very challenging time, but on the next day, I'm already bouncing back with energy and in order, like, to come and do things and win it. And, you know, there are a lot of things that we as leaders needs to do in order to, to help ourselves to keep, like, this mental, uh, you know, state, so I like to run, I like to do things that are unrelated to work in order to get back to my center, but then quickly bounce back and to really believe in myself, in the team around me. Eh, so this is, yeah, this is something maybe very personal, but, eh, I'm pretty sure I'm not the only one, you know, feeling it. (laughs)

    5. LRLenny Rachitsky1:08:37

       I appreciate you sharing that. There's a, a post that I did a long time ago with a coach, and she... It was about imposter syndrome-

    6. DLDaniel Lereya1:08:44

       Yeah.

    7. LRLenny Rachitsky1:08:44

       ... and she made this really powerful point that, uh, like, you are actually an imposter in the role you're in. You've never done this before. Like, most people are imposters in their role. They've never been as chief product officer. In a lot of cases, they've never led teams this large. And first of all, just realize that you actually are, and second of all, that's okay, and most people are, like you said. And then third of all, this advice you shared about how to work through that is really powerful. Just, like, know many people feel this way. Uh, work hard I think is a really important part of this. Just, like, know there's another day and that you can bounce back.

    8. DLDaniel Lereya1:09:21

       Remember that everyone are people. No one is born to be, like, in the role that he's currently at. And, you know, another thing that, you know, in Monday we are scaling so fast, so even people that are coming with experience, and I had, you know, the chance to see it over and over again, because we're going so fast, each one of us will get to a point which is the first time he's doing it sooner or later. So, experience matters, and we have, like, uh, a lot of people that are coming and bringing experience from, from the outside, but also remember that, and remember that every one are people and, like, no one was borned in a position. Eh...

    9. LRLenny Rachitsky1:10:02

       Yeah.

    10. DLDaniel Lereya1:10:03

        Yeah.

    11. LRLenny Rachitsky1:10:03

        And, and at companies like, like yours, it's, I've... People have described it as, like, every six months you have a new job.

    12. DLDaniel Lereya1:10:09

        Exactly. Exactly.

    13. LRLenny Rachitsky1:10:11

        We had... Sheryl Sandberg once did a talk that I was at where people were complaining or, or just, like, so much is changing, we're growing, every, the culture is not as strong as it was and there's just, like, things not working, our processes are no one was... Hiring is hard. And she's just like, "This is the problems you want because you're growing very fast and that's very good. Versus if you were not growing, it'd be much more painful and hard. So ple- be thankful to see the problems you're facing."

    14. DLDaniel Lereya1:10:39

        I couldn't agree more.

14. 1:10:41 – 1:17:28

    Handling crises and strategic planning

    1. DLDaniel Lereya1:10:41

    2. LRLenny Rachitsky1:10:41

       Mm-hmm. You talked about things breaking along the way and things you had to deal with. Is there an example of something? I love these stories of just, like, maybe a moment of crisis along the journey where you thought like, "Okay, things are gonna fall apart. This is over. (laughs) See you everyone."

    3. DLDaniel Lereya1:10:54

       (laughs) Yeah. To be honest, we have so many, eh, like, eh... But again, this is the problems, eh, that you are lucky to have. Eh, but, eh, yeah, may- maybe I'll give you an example. Like, eh, you know, I remember this day that, eh, someone from our customer success team has approached me and say, "Listen, Daniel, we have a spike in performance issues wi- in the board." And, you know, again, like, our boards is this table of, like, think about it, like, of data, and on each time we, we add new functionality and we make the platform more mature, people are taking it to the extreme. So if you look back eight years ago, so these kind of tables usually had, like, let's say, five columns and 100 rows. And if you look about it today, it's, like, hundreds of columns, you know, tens of thousands of rows and, like, so performance was always a challenge and struggle, like, in making sure that everything works, eh, smoothly, and this is also of value to us. We really believe that performance is the number one feature, eh, that makes people use your system. So, you know, he came to me and I remember that, like, suddenly seeing the spike in the tickets, you know, it's super hard, right? Like, you say, "Wow, it's something super hard." Y- you don't necessarily have a magic wand of, like, fixing it, eh, immediately. And what we did, we actually, again, connected everyone to it. The first thing I did was, like, taking this graph to everyone in the team and showing and thinking together what we can do. And we did a lot of things and we, we worked really hard and we managed to, to make this situation better and, eh, you know, and then time passed by and you, you are, like, continuing and then it happened again. Eh, and I can share that on the first ti- on the third time...I said, "Okay, we had enough." Like, uh, we need to think totally different, uh, in a different way. And, um, back in the days, this is where I think, uh, like, many of our core, like, long term projects have born. The signature one would be MondayDB. It's like, uh, it's an, a name we use for, like, an underlying data infrastructure that we've been building in the last three years or so. So, think about a very small team and a very small startup. I remember the day that we said, "Listen, we need few of our most talented people, they are now not going to contribute features anymore. We're putting them on, like, uh, a separate, like, uh, place, and let's think and solve this problem while thinking about 100X." And, you know, it really, like, in many ways, so different from what we talked about in so many other of the examples, right? Uh, and I think now w- we said, "Listen, instead of being, like, uh, fixing an issue, we want this to be our competitive edge." We have a very unique, uh, product architecture where everyone can build their own schemas of the table. And, you know, it's like a crazy thing in terms of technology behind it. We want to do something that will not only solve the problem, but also will serve us as a competitive edge, edge. And we took a huge risk because, you know, we took a lot of people and put them aside, uh, for that. Or, like, not a lot of people, but the very talented people. And I think in retrospect, uh, by the way, we released MondayDB I think, uh, one and a half years ago, like the, the first version. It did a huge, huge change to our customers. And in many ways, this is what, like, actually makes us today a platform which is enterprise grade. Uh, so my lesson from that is that if you feel about something, it is strategic, you need to not only solve problems, but be super proactive. And also again, like, uh, this contradicts the fact of, like, what are the goals? What are we going to achieve? Because you need to lean on, like, something which is strategic. So with the, everything that we said at the beginning of the conversation, there is also things that you need to do because this is the company you want to build, this is the product that you want to build, and you don't necessarily get the, you know, uh, looks as if getting, uh, conviction from things that happened in the past or from data. You need to just go with your, uh, intuition and take this risk. And I'm super happy that we did it. Yeah. But this is an example where things really broke, you know, and, uh, what we did with it.

    4. LRLenny Rachitsky1:15:39

       There's a couple other stories of crisis I've been thinking back to. And they all seem to be a database started reaching capacity and we're about to f- (laughs) fall apart 'cause this growth was too fast. So that's an interesting lesson for people to hear, just like try to anticipate this a little more. And, uh, sounds like that's what you realized is like, let's think a 100X from now, not, not just like a couple years from now. There's... It reminds me of, so Bryan Johnson, he's this, uh, dude that's trying to live forever or as long as he can. And he makes this really interesting point that I promise connects to what you're talking about. Which is, he's like, "Okay, what is, what is your goal?" He asks everyone, "What's your life goal?" And so they're like, "Oh, I wanna do this and this and that." Okay. To accomplish that, the base goal you're not even thinking about is you need to not die.

    5. DLDaniel Lereya1:16:22

       (laughs)

    6. LRLenny Rachitsky1:16:23

       And that's actually the number one goal everyone should have. Don't die. And I feel like that's infrastructure (laughs) in companies-

    7. DLDaniel Lereya1:16:30

       (laughs) .

    8. LRLenny Rachitsky1:16:30

       ... is like, you have all these metrics and goals, but really the goal underneath that is your infrastructure needs to scale. So it makes sense why this is outside of like, okay, we have all these metrics and goals. Like, there's this, this-

    9. DLDaniel Lereya1:16:39

       Yeah, not, not necessarily treating it as a, as a tax or as a risk. But rather like, you know, for, for our offering, like as a platform, this is like actually now one of our core advantages.

    10. LRLenny Rachitsky1:16:50

        Mm-hmm.

    11. DLDaniel Lereya1:16:51

        So it's super important as well that value to customers comes in different ways, shapes and forms. And you need to, to think about the experience and not only about like, uh, you know... And many times the general experience start with things that are reliable, performant, that you can count on them. And suddenly, you even use them differently because they are fast. So I think this is another important, uh, like aspect to it.

    12. LRLenny Rachitsky1:17:16

        That's such a good point. When you have a problem, something that's slowing you down or might crumble the company, just not flipping it from how do we just put the bandaid here, it's how do we turn this into a strategic advantage if we really invest the time.

    13. DLDaniel Lereya1:17:27

        Yeah.

    14. LRLenny Rachitsky1:17:27

        I, I, I like that

15. 1:17:28 – 1:22:13

    The role of AI in work and personal life

    1. LRLenny Rachitsky1:17:28

       a lot. Okay. To start to close out our conversation, I'm gonna take us to AI corner, which is a recurring segment I try to get to more and more with this podcast. And the question is, how have you... What's an example of you using AI tools in your day-to-day work to do better work, to do faster work, that you think might be helpful to other folks?

    2. DLDaniel Lereya1:17:49

       Uh, maybe I start with a personal one, you know. Like, uh, I'm a- (laughs) it, it's not, it's not about work, but I think it really shows that for me it was like a moment of like, uh, really saying this, this has so much potential in it. Uh, so I actually prepared myself for a marathon. And unfortunately, I got, uh injured in my knee. So yeah. So I went to do an MRI scan, and I finished the scan and they gave me this disc with the results. And then they said, "Listen, uh, you need to schedule a doctor appointment five days from now." Okay, I said, I took it, put it in ChatGPT and asked for like the results, uh, and explanation of line by line what, what does it mean. And then I of course went to the doctor and said, "These are the results." But I think like for me, you know, this is a, this is something that I was really happy about using it. Uh, and it also opens my mind a lot because I think that if you think about it from the product perspective, and this is how we think about AI in Monday-... the technology is amazing. Uh, you, you can do so much with it. But, you know, there's still the part of, like, productizing it. Because every person that I talked with them about this example, like, with enthusiasm, and said, "How do you think about putting your MRI there?" And I said, "I don't know, like, I just did." But this is all, like, creating products that actually allow people to leverage this technology. And more on the work side, you know, I use it a lot. I think, like, uh, for me, like, one recent example I would say is, like, uh, we really worked hard towards, like, uh, determining the, the pricing for our AI offering, uh, that I was mentioning earlier. And just in, like, two hours, I was manage- I- I managed to get the full perspective on what everyone else are doing. You know, and we have analysts and we have product managers and s- but the fact that I was independent and managed to get, like, you know, the initial thoughts and, like, all the information in just a bit, it was mind-blowing. So, I use it a lot in order to understand things that are, like, very extensive, like what the competitor's are doing, what is the history of this and that. And I think it helped me a lot, uh, in that sense.

    3. LRLenny Rachitsky1:20:16

       These are awesome examples. And is this all ChatGPT? Is that the tool of choice?

    4. DLDaniel Lereya1:20:20

       Um, you know, it's hard w- I have, like, uh, my own periods right now. It's changing from one week to another. Uh, it is true, uh, actually, wi- with, uh, ChatGPT, yeah.

    5. LRLenny Rachitsky1:20:32

       Very cool. The first example, my wife does all the time. My mother-in-law was in the hospital and we were waiting for the doctor to show up, and she just put the chart in ChatGPT and was like, "What's, what's the problem?" And it's exactly what he told us.

    6. DLDaniel Lereya1:20:43

       (laughs) Yeah.

    7. LRLenny Rachitsky1:20:44

       And it feels like, like, it feels like we're in a world now where an engineer without, say, Cursor or one of these tools, is just not ... Like, that's not, that's not, uh, possible anymore. And it feels like now, with going to doctors, is like if you don't do this and see what it says, like, you're missing out on a big gap. There's this New York Times story, I don't know if you've seen, where they actually compared a doctor's analysis versus a doctor plus ChatGPT, plus just ChatGPT. And, uh-

Episode duration: 1:32:06