Following Sustainable Passions with Oren Ellenbogen, VP Engineering at Forter

(Intro Narrator at 00:00:03) Hello, my friends. Today, Joel is talking to Oren, builder and curator of Software Lead Weekly. And they discuss how to build a sustainable career while balancing a family life and pursuing fulfilling side projects, Oren's framework for only spending time on things he'd want to do for the next forty years, and how to approach leading without leveraging authority. All of this right here, right now, on the Modern CTO Podcast.

(Oren at 00:00:35) Here we go.

(Joel Beasley at 00:00:36) This is the Modern CTO Podcast. I want to discuss, you know, because we're talking about family here, I know you have a lot to say about building sustainable careers, but keeping your family life good and making sure that you both progress your career, but also have a great relationship with your spouse and your children. Can you share a little bit with me about that?

(Oren at 00:01:09) Yeah. You know, to be frank, it's a real struggle. I think that we all face this notion of, have you heard about the term "good enough"? Yeah. The good enough parent. Right? Like, good enough dad, good enough spouse, good enough worker, good enough, you know, friend. So I'm thinking a lot about this framing of how can I give myself some slack, you know, this good enough? Let me be good enough. And, because, you know, all my life, I really tried. I'm still trying to do multiple things, like working on multiple side projects, doing multiple things at work, doing multiple things at home. And it's incredibly hard to feel that you're doing everything right. You know that you can't. It's impossible. So how can I feel that I'm doing good enough? Like, how can I feel that I'm building healthy relationships with people around me and also with myself? Like, I know that I will be dissatisfied if I will want to be working on some side projects and let my creativity spark. So there's, you know, great excuse. I have a family. There is pandemic. You know? There is the job. Like, I have day to day work as a VP of Engineering, and that kind of consumes everything. But I know that to feel good, I also have to somehow work on side projects and build things from scratch. Like, this is part of me that really has to take place.

(Oren at 00:02:38) So I have this framing that I've been using for the past few years, and it really helped me. Again, I'm not sure it would be helpful for anyone out there, so don't take my advice. It's just things that I'm thinking about. So I'm starting to think of almost everything on the term of will it be worth doing for the next ten years, or even, you know, forty years. So I'll give you a few examples that are incredibly strange for most people. So I decided to start eating almost the, well, the same food every work day. So Sunday to Thursday. In Israel, we're working Sunday to Thursday. I'm basically eating the same food during lunchtime. So, you know, healthy, good food. I have someone that I found during the pandemic that tried to basically earn more money because she couldn't work. She's quite, you know, a bit older and she was at risk, so she was preferring to see if she can find some work that is less dangerous, being with people. I said, like, I'm looking for someone to cook food for me. It will be, you know, it's not a huge income, but it's something. And for me, it's extremely important that I'll have someone that I can rely on to prepare the food. I know that I'm super busy, and I won't have the time to prepare everything. And, like, my wife said, like, you're crazy. Like, why eating the same thing every day? And I'm saying, like, it's peace of mind. I know that I can keep it up for the next forty years. It doesn't bother me. It doesn't mean that during the weekends or during the night or during the morning, I can't, you know, eat other things. But during work time, like, during lunch, I just want to know that I'm eating healthy food that I know that I'm reacting well to. And I started to look at the same about, you know, going to the gym. So, you know, I found someone. I knew that if I'll go to the gym myself, I will quit after a few months. Right? So I need someone to basically push me, like preparing food. I knew that it will be on me to prepare the food at some point, maybe a few weeks, maybe a few months, I will stop. Now I want to do that for years, for many, many years. And the same with the gym. I knew that if I need to go by myself to the gym, I will quit after a few, you know, whatever it is. So I said, okay. I need to find a trainer because the trainer will basically hold me accountable for that. That's great. So I found someone to train me and the first question they asked, like, you know, what's the goal? Do you want to run a marathon? Do you want to lose weight? Do you want to gain some muscle? You know? And my answer was no. I want to come here for the next forty years. Like, this is the plan. Right? So coming, like three times a week or two times a week for the next forty years, that's the plan. So don't try to break me. Don't try to, you know, squeeze everything into this two months of chaos so I'll be able to run, you know, this 10 miles or 10 kilometers, whatever it is. It doesn't interest me in any way. I want to feel that I'm investing in, you know, in a healthy sustainable life, but I want to come here for the next forty years. And it kind of drove him insane. Like, he said, well, you know what? So let's do this theme that this year we'll do this. And I said, no. No. No themes. Like, I'm not looking to try and, you know, get to some goal here. This is me trying to be healthy, and you are the person who will hold me accountable, so that's great. And I will hold you accountable not to break me. So it's okay to, you know, push me and to try to do things a bit different and change things. That would be great. But I'm not trying to hit some goal of, you know, hitting this percentage of, I don't know, fat or muscles or whatever it is. And it really made me, like, so I'm going to that person for two years now. And we have a very good solid relationship where we can talk about, you know, the type of changes that he wants to do. And I'm thinking of how we do that in a way that I will be enjoying that. So, again, like, thinking about habits, how can you change the habit so it will be fun for you? I don't like exercising that much. I like to play, you know, basketball or to play football, soccer. I don't like to exercise that much. But with him, that he knows that I'm going to do it for many, many years and that's the goal, he tries to make it more playful for me. So again, maybe it's not the best exercise to gain all the things that people sometimes put this goal ahead of them. But he knows that it needs to be fun to the best ability that I can when exercising. And that's the type of framing that I'm looking more and more into. So it helps me with picking side projects. It helped me with picking, you know, how I want to eat things or how I want to go into the exercise. It's quite radical. So some people say, like, why should you pick something for ten years or forty years? And the answer is that I don't know, to be honest. But that's how my brain operates in a way. And it really calms me down to know that I'm doing things that I would enjoy doing for many years. And it also means that I'm going to say no to many, many things, which is, again, very comforting in a way that I don't want to do things that will squeeze me for the next six months. Like, it doesn't sound like something that I would enjoy. And so this is the framing that I'm doing. Like, I'm asking, is that worth doing for ten or forty years? That's a very, very hard question. And if the answer is no, then for me, I probably reduced 90% of my motivation to do that to start with. So this is the first question. And the second question is, like, do I have the intrinsic motivation to do it myself completely for the next ten years, or do I need to find an accountable partner to hold me or to keep up with this? So for example, you know, finding this coach to work with me during the gym or to find a mentor that I can talk about, you know, about something with them. So that's how I look at it.

(Oren at 00:08:29) I'm trying to apply it at home in different things. So I have this, again, very strange thing that I'm doing. It's called binary versus incrementals. The binary part is zero to one. I want to try every quarter, I'm taking a couple of days off. I'm sitting with myself, and I'm starting to say what will be an interesting binary activity to do in next quarter. Binary means it will be the first time that I'm doing that. So, like, you know, I've never done that for the first time. I did something. It can be very trivial thing. It doesn't have to be, like, very, you know, big and scary, but something that will make me practice something for the first time. And the incrementals is what I want to do better. So if, you know, if I feel that I'm doing it well, I want to do it better. And just taking the time every quarter to take a couple of days off and spend this work hours instead of work at work, spend it with myself and start to think on, you know, what do I want to do better? What do I want to do that is fresh? And again, for me, it feels very comfortable, comforting that it's one binary. It's two incrementals. It's not here are 10 things that I want to do this month. Here are, you know, 100 things that I want to do this year. I want to be very easy on picking things that I can actually commit to. So just, you know, a few small frameworks that I can think of that I'm doing that are really helpful for me to think on the longer horizon.

(Joel Beasley at 00:10:03) I'm taking notes here. Alright. So what I was, here's something that I got from it. You help correct me if my interpretation was right or not. So you have these frameworks, you look at things, and you'll say, you know, will I do this for forty years? And you decide to put it into your recurring events, essentially.

(Oren at 00:10:20) Mhmm.

(Joel Beasley at 00:10:20) You put it into your schedule. But then you have one of those things that you're doing is giving you variety on other topics quarterly. So that way you can, like, you could, a binary could be, like, you never played guitar, so you pick up guitar. You just go do a little bit of guitar, and then you're free from it the next quarter. You can continue to do whatever you want. But is that correct? Is that how it works?

(Oren at 00:10:48) Yeah. Yeah. So I would pick very carefully the thing that I want to do for the next ten or forty years. Right? So it doesn't have to be a lot of those. It, by definition, needs to be very little amount of those. But I let myself explore more in the binary and the incrementals to play with that a bit more, just to make myself more balanced. So it doesn't, like, I don't want to make sure that every decision is so crucial and big. Like, is that a forty year commitment? It's very hard to live life like that. But, you know, when you're thinking of, let's say, you know, we all earn money. Right? So I'm extremely grateful and lucky that working in the industry where I actually love everything I do. I love the, you know, the profession. I love the challenges, technology, the people. Like, I'm so lucky that people are actually paying money for that. And the question that comes to mind is, okay. So, like, what do you do with money? Right? So let's say that you earn money. What do you do with it? So, again, a very good question to ask. Like, if you think about it from the, you know, what's your next goal? I want to buy an apartment. I want to buy a car. I want to buy, I don't know, whatever it is. The question that I'm looking at is, like, what do I want to have in the next forty years that will make me excited. And that's the interesting thing. Everything that I need to buy for the next year, like a car, the car is not a forty years thing. So it's not interesting for me to even think about it at all. An apartment, maybe. Like, if you want to say, this is the dream apartment. I want to live here until I'm 70 and then maybe change it. Okay. That's interesting. But maybe, for example, I really want to take the family, so I want to take my entire family to a vacation and pay for that or to at least be able to do so. So to take, you know, the entire family to Spain for a week and be able to pay for everyone. Doing that for, you know, a couple of times a year sounds for me, like, for the next forty years, sounds for me amazing. And maybe that's because I had this experience as a small kid where a lot of my family are living in France, in Paris. And many times they were inviting us to join them for a vacation. They basically paid for everything. So as a kid, I grew up going twice a year to Paris and being with the family and, you know, having some great, great vacation time with them where everything was kind of taken care of. And the way I see it is for myself, you know, if I can give this type of experience to my family and my wife's family, we'll remember. And again, doing that for the next forty years, not just for 2022. That sounds like a, you know, great way to invest my money in terms of nurturing relationships, developing, you know, interesting experiences together. So, like, that's for me extremely interesting to think of. Okay. So what's the budget for that? Right? So how much money will it cost us? Can we do something interesting as a family together? So this is kind of, you know, the way that I want to make sure that I'm picking very few things in this grand scheme of forty years career or how to enjoy and build life. And I want to let myself at least a quarter every quarter to play with things on a very, you know, smaller scale and be completely fine that I'm ditching them completely. So the guitar is a great example. Right? So I can take a few lessons. I can play with it for a few months. And then if I want to change after quarter to something else, there is no part of me saying, you know what? I should have stuck around and done it for longer. It's like, no, this is an experiment. That's great. Like, I really enjoy that. It was fun. I discovered things about myself that I like and things that I don't like, and I can move forward. So that's the type of thinking that I'm doing in my head. And again, like, when I'm talking with my wife on, you know, let's imagine forty years that we're going to take two times a year the entire family to, you know, different places. And she was like, 40. Like, are you crazy? What's going on? And I'm saying, no. No. Like, think about it. Like, you can take them twice a year. Like, she says immediately, it's a lot of money. I'm saying, right. So let's actually calculate how much money it is just to show that it's actually not that much. It is a lot of money. Right. But converting it to achievable, you know? Yes. It is achievable. Right. And, you know, do I want to invest in that versus investing in a car versus investing, very clear. So it does create this deeper conversation between me and my wife sometimes on, you know, how do we see ourselves in the future? Very strange conversation sometimes. I will admit that. But, you know, once she gets across this, you know what? I'm not sure if we want to commit to this type of length. And I'm saying, like, why not? We're going to have our kids and their kids talking about it for years. You know, this family activity of us going to Spain together to some nice place and having fun together. Why is that not a great usage of our money? And she's like, actually, that's interesting. So anyway, I don't know. A bit crazy. I know.

(Oren at 00:15:45) Yes. So it worked mostly because I told her, like, I'm going to plan those vacations, and they're going to be remarkable. So I'm going to rent a villa that you wouldn't even imagine. I'm going to rent a castle in France that is remarkably cheap. It's much cheaper than any hotel in Israel. And we're going to have—she said, like, a castle in France?

(Oren at 00:16:05) Like, is that even possible? I'm saying, yes. Like, look, just open up Airbnb. You have multiple. She's like, holy shit.

(Oren at 00:16:13) That's remarkable. I'm saying, so don't worry. I will prepare those. Like, I will make the vacation remarkable. You show up and, you know, so you can surprise and you can add this mystery back. But I don't know. This is what makes—look, this is what makes me tick in many ways. It just makes things look a bit bigger and more interesting, or if they're not, my mind is like, well, you know, it's nice, but I don't have the mental energy now to actually entertain that for the long run.

(Joel Beasley at 00:16:46) I started doing this thinking in terms of decades thing about five years ago. So I had, you know, up and down success in my personal life and my work life. Success is very subjective, right? So I had up and down success, and I was trying to figure out why and why I was failing a lot.

(Joel Beasley at 00:17:10) And it was because, simply, I was giving up. Like, I was giving up too early. And I would start something, I'd be on it, I'd be going for it, and then I would get interested in something else. And so I'd kind of drop it, and then I would see other people that didn't drop it, and they had huge success. And I just kept seeing them get these big payoffs for staying with it just, like, longer than me.

(Joel Beasley at 00:17:30) And so I got so frustrated by that. I said, okay. And I was in my twenties. I said, I'm gonna do a five-year plan. It was like the biggest deal in the world to me.

(Joel Beasley at 00:17:41) And so I made a promise to myself, and I stuck with this five-year plan. And at the end of that five years, oh my goodness, it was so amazing. And so then I said, alright. Well, I'm gonna start like doing things for like ten years or committing to them. That's what I—that's the word I use.

(Joel Beasley at 00:17:57) I use ten years constantly. I'm like, alright. If I'm gonna go to a jiu-jitsu match thing, if I'm gonna learn to do some martial arts training, I'm just gonna say that I'm gonna go into this for ten years. Because that allows me to walk in freely, not get burnt out, not get frustrated that I'm not making progress because it doesn't matter. I'm just doing this for ten years.

(Joel Beasley at 00:18:16) Yeah. I could be a white belt for ten years. It doesn't matter. I'm just gonna go through. And inevitably, the experience just stacks up and you just leverage the compounding, you know, interest, the compounding nature of time.

(Oren at 00:18:28) Yeah. Yeah. I think, you know, it's exactly that. And you find ways to enjoy that. Maybe not in the first year, maybe in the second year, maybe in the third year, but you're finding this rhythm where you're happy.

(Oren at 00:18:40) And I think that happiness, you know, it should be something you should aspire to look deeper into yourself to see what makes you happy. And I don't try to judge that. Like, why am I happy doing that? I just say that it is what it is. Like, I'm having fun having people to do barbecue at my house, and I like, you know, preparing the barbecue.

(Oren at 00:19:03) I don't know why I like that. I usually don't like to cook. So, but there is something about the barbecue, and I don't know what it is, but it is what it is. And I'm finding a lot of joy in getting friends to come and preparing some good barbecue for them. I wouldn't do that to prepare some other meal for them.

(Oren at 00:19:23) So I wouldn't try to cook something for them. Like, so it's specifically barbecue. And I don't know what it is, but it is, again, what it is. And, like, there is a tradition now where, you know, I invite friends every month to my house, and we do that. Like, every person brings—so I bring the meat and bring the wine and someone else brings something like, you know, fish and someone else brings some salads.

(Oren at 00:19:44) And I'm saying, like, why can't we do that for, you know, for many, many, many, many, many years to come? So I really do like this framing, the ten years where you're saying that, like, I don't need to rush. I don't need to burn out. I don't need to feel frustrated that after two months, I'm not whatever, you know, this belt or that belt. That's fine.

(Oren at 00:20:03) I have time.

(Joel Beasley at 00:20:05) What was your root? What was, like, the very first time you started thinking about this type of study? You haven't been doing this since you were born. Right? This is something—

(Oren at 00:20:13) Yeah. You're absolutely right. But I think it started when I was quite young, not thinking about decades, but thinking in framework. So I remember that I was reading—so I'm going to celebrate 38 next week. And I've been, you know, twenty-five years ago when I wanted to learn to write code professionally.

(Oren at 00:20:37) So I started, like, to get to being paid for that when I was 16. But when I was 13, I knew that this is what I want to work at. So I was asking myself, what I need to know so people will actually pay me money to build software for them? And back then, you have to read books. Right?

(Oren at 00:20:53) Like, there wasn't Stack Overflow. There isn't this abundance that there is today where people actually need to improve their sorting algorithm to know because there is so much, you know, so much content. Like, how can you sort through? Back then, it was there are a few books you can go and, you know, pick it up. And I was reading a lot back then just like I am now.

(Oren at 00:21:13) And the books, what it gives you were—and I think that, you know, I love Twitter and I love reading blog posts and, you know, listening to some videos. But what books has is you can have some depth in thinking. So you can pick up a topic and you can go really, really deep in that topic. And that's quite fascinating.

(Oren at 00:21:35) So I was always starting to think on which are the topics that I want to go deep at, and it changed during the years. Even management, like, for me, management is not something that, you know what, I'll just play with it. Like, it's fine that I will experience, but I want to read about it. I want to think about it. I want to talk about it.

(Oren at 00:21:52) I want to ask people, other people that are more experienced than me, on how do you think about things, like how they make, you know, difficult decisions, how do you come up with interesting frameworks to prioritize, like, very big and complex areas. Like, some people have amazing insights and depth. And what I found out is that usually it becomes through reading a lot, whatever the medium is. And just books provide you this medium where you read with depth and not only with this breadth. So the notion of decade probably started when I was around 25 or so where I started to understand that I really like this concept of helping others in a meaningful way.

(Oren at 00:22:42) That means that I'm helping you or others not by showing only what I am doing, but also giving you some framework to think about the problem. And when that happened, frameworks, you know, the problems with them is that it takes you years to understand what is the framework that you apply. So this is when it started to make it clearer to me that I need to start thinking years because frameworks requires years of experience and then how you can make it into something more concise. And as I grew older, things started to shift more and more. So when I decided to start working on the newsletter, it was nine years ago.

(Oren at 00:23:20) And, like, I told my wife, I'm going to do this forever. And she said, like, you know, why? I'm saying because I'm reading anyway, and I'm already sharing some helpful things to, you know, my friends who are in the industry and asking me for books and asking me for, you know, for great posts. So I'm basically already doing that. What's the difference?

(Oren at 00:23:37) It's just me sending an email. That's the only difference. And she said she's saying, well, you know, that's great, but why are you thinking that you're going to do this for so many years? And for me, it was because I'm going to do this forever. Like, this is what I like doing.

(Oren at 00:23:51) There is no burden. There is no—it's almost 90% or 95% happiness and joy. And these are when the things started to click more and more. So the framework thinking takes you from, you know, days and weeks and quarters to years because frameworks usually take years to think of and apply. And then when you're starting to think on what I want to work on and build, it usually takes me at least into is that really something I want to work on?

(Oren at 00:24:18) Is that fitting into my purpose the way that I see that for the next, you know, forty years? So the side projects that I have today, I've built a few along the years, like, you know, the weekly Software Lead Weekly, Leading Snowflakes, Down Left, which is a different thing. Manager README that I know that some people really hate the READMEs and some people really like, and I completely understand both sides, and that's fine. Did you—

(Joel Beasley at 00:24:43) Did you do the Manager README? Was that yours?

(Oren at 00:24:45) Yeah. Oh, nice. Yeah. Managerreadme.com, downleft.com, things that I've done. And for me, it all fits into this thing of I want to help build better software organizations.

(Oren at 00:24:58) I want to help managers, but not only managers, also like technical leads. And it's not because I think that I'm the best at it or even, you know, partially okay at it. I'm just saying that I think that software has a lot of room to improve many, you know, many things in our life. And if I can help people in that transition to start more great companies—so, you know, back then, like ten years ago in Israel, at least, I don't know how it is in the US maybe or in other places in the world.

(Oren at 00:25:27) When you asked someone, you know, can you tell me about great managers that you had? It was very common to say in Israel, great managers? I don't think that I had one of those. And I was, like, I was really excited to hear that most people never experienced a great manager. And I think it's really changing a lot, and I think in the past few years, there are many, many new books that are coming along, and people are actually reading those and starting to think on how to be—how to become better, you know, servants to their teams and help others versus thinking that this is a place for them to, you know, to get power over others.

(Oren at 00:26:05) And for me, like, that's great. Like, even if the weekly or the book had the tiniest portion of helping others to think about their role as managers or as technical leaders, even if it's like 10 people in the world change their mind about something or learn something, the way that I see it, like, that's for me a huge, huge, huge motivator. So Manager README—there are a lot of terrible things you can do with the README. That's not my purpose.

(Oren at 00:26:31) My purpose is to say, can you start and see and articulate the way that you think about your philosophy, you know, philosophy as a manager? You don't have to share it with anyone. You can share it with yourself. You can share it with someone you trust. You can share it with your—you know, whatever it is.

(Oren at 00:26:47) You can share it with new people. You don't have to. You can do whatever you want. But my purpose is to make sure that—or to try to get people to think on how they can build better software organizations. And a lot of it is by understanding that it is humans who build the software that is running in production.

(Oren at 00:27:06) So that means that humans are part of this equation of production systems. And if that's correct, we have to make sure that the human element here is being thought of. So for me, every side project that, you know, hits on that mission of building better software organizations, for me, it's like it's a good side project to think of. Everything else, like, you know, I have an idea.

(Oren at 00:27:33) I want to improve, you know, the way that LinkedIn is doing, you know, sourcing over LinkedIn, sourcing for candidates. Well, okay. Like, you know, it might help building better organizations. But for me, like, I'm lacking this excitement of—I just don't see how it really completely changes the way that companies are being built in the future. And if that's the case, even if it's a nice idea and I have some nice, you know, thinking on how to approach it very differently, it doesn't really move the needle the way that I look at it.

(Oren at 00:28:04) And, like, for me, it's like, well, it's a nice idea that someone else maybe should build at some point, but that's not for me. So this is the type of, like, thinking that's really shifted in the past ten to thirteen years. And, you know, the weekly is one of them. And the book—so the book came and the weekly—the weekly was before the book. So the weekly was there.

(Oren at 00:28:25) The book was there. And then I was kind of saying, like, how can I pick the future side projects that I want to work on, which led me to think on, you know, what do I want to do in the next, you know, ten, forty years in this industry that I so love and appreciate? And that's the type of mental framework that I like to use when picking ideas. So Manager README fits well into this place. And Down Left, which is kind of—it's actually like a game of, like, you know, most companies are talking about up into the right.

(Oren at 00:28:57) Like, everything is perfect. Everything is solid. Right? Like, we're growing. We're hiring.

(Oren at 00:29:01) We're raising money. So Down Left is to say, well, we want to have this support group for people who feel alone in this journey. So as a VP Engineering myself, I'm feeling sometimes lonely in this role. It is sometimes a very lonely role. Like, how can I build a support group full of VP Engineers who can meet together and share things that are extremely personal, extremely sensitive?

(Oren at 00:29:26) And talking about the down left parts on, you know, the opposite of up into the right is, like, things are not working. Things are breaking. I am breaking. My team is breaking. And I need to think of an advice here.

(Oren at 00:29:37) So this is how I kind of see, you know, the type of projects I want to build in the next few years, and I have a few more coming. One of them at least will be this year. But that's what makes me excited about doing so.

(Joel Beasley at 00:29:51) The VP of Engineering group, is that already together, or is that something you want to do?

(Oren at 00:29:54) Yeah. It's been running for the past three years now, a bit more than three years, four years. So there were, like, four pods that were meeting, and we are starting to kick off a much more scale-out type of version in Israel now. So, hopefully, there will be more groups and more groups of not only VP Engineers, but also, you know, tech leads and eventually people like, you know, chief, like CPOs or CTO or CEOs.

(Oren at 00:30:24) Like, I'm aiming for people to feel alone in this journey. And, again, don't have any desire to scale out to millions of people. I'm completely fine—if it will change, you know, 20 companies in Israel, I will be extremely honored to say that I have, you know, the tiniest, tiniest, tiniest, tiniest portion of that because of, let's say, Down Left was, you know, something that helped them think about how they build their company. So that's something that we are doing, and we'll see how it goes.

(Oren at 00:30:57) It's quite fantastic. And if you go to downleft.com, you can see that I did show, like, the structure. So sometimes people are kind of surprised that the structure is extremely, you know, detailed. But that's how I think about things. Like, I'm starting to think about the experience.

(Oren at 00:31:15) Have you heard about the 11 Stars Experience? The Brian Chesky, the Airbnb CEO. Have you heard about the 11 Stars Experience? No. So the notion—I hope that I'm not going to completely kill it, but the notion is like we all know about what is the five-star hotel.

(Oren at 00:31:32) Right? So we can say we go to the hotel, things are clean, you know, food is good. Trivial things. The room is ready on time, things like that. So the question is, what is the six star experience?

(Oren at 00:31:45) So the six stars is that I'm getting to this room, and I've been waiting with champagne in the room, and there is a small card saying, "Hey, you're in Tel Aviv. The beach is like five minutes walk. We took the liberty to set some surfing lesson for you. So, you know, be at 3 PM. There'll be a guy there waiting for you, and you're going to have the best time of your life learning to surf." Right? So that's something you remember. Right? So the question is, what is the seven stars experience?

(Oren at 00:32:15) So the seven stars is entering the lobby and there is a band playing for me saying, "Hey, welcome, Oren, to the hotel or to the whatever Airbnb floor." Takes me to the room. The room has, you know—and you can go crazy with that, and the post actually covers that. But I'm saying that because it's actually quite fascinating to think about almost everything you do. It's like, what is the five star of, you know, Down Left or a weekly or something like that?

(Oren at 00:32:43) And I'm not saying that I'm good at it on everything, but I'm using this framework that Brian Chesky—this is what I've seen him doing. I think it's quite remarkable to see what is a six star experience of listening to a podcast. What is a seven stars experience of experiencing a podcast? It's not only listening. It's maybe something bigger than listening to a podcast. And it can go really crazy when you think about the 10 stars experience or 11 stars experience. And the thing that, you know, Brian is trying to say is try to think bigger about the experience, and it's okay to finish at five stars or six stars or seven stars. You don't have to go to 11. But the fact that you spend the time actually thinking completely crazy, like, you know, I'm going to this hotel, so I'm going to have this band waiting for me in the airport, not in the hotel, right? And then they're holding my hand and, you know, entering and taking me to some Porsche. And this Porsche takes me—so you can go crazy with it. And I really like that because it kind of opens you up into how great looks like and how ridiculously, you know, great something can look like. And then you can start and say, you know, how do you want to pick that?

(Oren at 00:33:56) And with time left, I do have some crazy ideas that I would like to explore. Given COVID, the next, the last couple of years were extremely hard, personally in terms of just, you know, taking care of my family and work and things like that. So the creative side of me on side projects was kind of held back, and, you know, I'm okay with that. But now that I'm feeling that COVID, maybe, knock on wood, I don't know, would be better, I already feel the creativity juice coming up with so many ideas that I want to explore. And some of them is taking Down Left, which I think has quite a unique setup and experience. And how can I get much, much more crazy with that and provide an experience that people will remember and enjoy and recommend others? And I'm doing that because I think it would be fun for me. So if I wouldn't think it would be fun for me, I would completely ditch that and say, you know what? Doesn't matter. But this is the type of thing that, you know, I hope to play with more and experiment more this year, hopefully, once COVID will get into this better place.

(Joel Beasley at 00:35:05) I love it. Yeah. And then we have this group called Elevate 150. So we have like 150 or so. We found out that the reason why these Slacks, like Michael Lopp's Slack is very amazing, right? But there's like 15,000 people in it.

(Oren at 00:35:21) Yeah.

(Joel Beasley at 00:35:21) And we found that when you get to this certain number, the attitude in the group changes because people ask the same questions, they almost get frustrated at them, and it just gets weird online. Yeah. So we did some research and we're like, "Oh, okay. There's this psychologist that says community sizes for each..." Yeah. The Dunbar number.

(Joel Beasley at 00:35:40) And so 150 was one of those numbers. And so we're like, "Alright. Let's cap it at groups of 150," and we just finished our first group of 150. So I just spent the past two years figuring out this whole community thing with this guy named Etienne de Bruin, who has Seven CTOs. So if you ever have questions about what we've learned with the community stuff or whatnot, more than happy to share with you because I'm a firm believer that there is more than enough out there. There is more than enough lonely people out there. And if anything, we need more people figuring out ways how to start in their communities to bring these people together to share because it literally, in the least cheesy way possible, it literally changes people's lives when they get a new perspective of how to think about work, how to interact with their families. And things can go from horrible, brink of divorce, to best life ever, you know?

(Oren at 00:36:34) Yeah, yeah, yeah. I'm completely—yeah, I would definitely love to stick with you a bit more and share some lessons and thoughts from Down Left and to hear about 150 a bit more and understand better, you know, your takeaways from that and how you think about it. So let's grab some more time together next time.

(Joel Beasley at 00:36:58) For sure. I want to wrap up here with this one question we didn't get to. How do you approach leading without using authority?

(Oren at 00:37:09) Yeah. So it's an extremely difficult question to answer quickly or briefly. I will say that there is a video that I've made specifically about this topic. So if you Google my name, which is a very difficult name sometimes to write, but if you Google it and you look at "leading without authority," you'll see a video that I gave covering that. What I think, you know, if I need to give the short version of it, is to basically understand how to learn from customers or to learn from people who actually are in pain and trying to help them. Meaning, even if you have a very strong agenda and vision, one of the most difficult things to understand is people need to trust you that your vision or your agenda will take the company into the right place. And I often see people who are extremely gifted and, you know, capable and smart, but they're not investing enough time to build the trust yet. And when they're bringing these thoughts into the table, people sometimes are not ready. So first, it's like you need to build the trust and take the time to actually understand the pains, understand the business, understand what the company is actually trying to achieve, understand what the people, you know, what people are suffering from or what makes people completely excited and happy, and then see how you can take and bring your agenda and your vision to that. So the leading without authority, for me, the way that I see it is if you want people to listen to you, you have to earn their trust and their respect. And the way to do that is to speak their language and to make sure that that language aligns with the business needs. If you do that, I think that this is, from my experience, 90% puts you in the right place. Then you need to figure out how to bring your agenda and vision in a way that is coherent, that is relevant now, that you know how to split it into milestones, you know, you know how to get the buy-in. So there are many, many things around it. But what I'm seeing people doing often or too much is investing too much in the 10% that is "I'm going to convince you, and I'm going to explain to you, and I'm going to prove you, and I'm going to show you." And not in the 90% is that "I understand you. And I can repeat the pains that you say, and I can understand about the business you're trying to achieve. And I know how to connect the dots between what I have in mind and what the business needs and what you need, in a way that you can relate and speak to." And this is what I think that people kind of sometimes miss when they're thinking about authority is like, "If someone will give me the authority, I will be able to make an impact." And the way that I see that is that you need to practice this leadership without authority because it will teach you to be humble. It will teach you to listen. It will teach you to ask questions. It will teach you to ask better questions. It will teach you to take notes and maybe to reflect on those and maybe to share with others. It will teach you to be a facilitator sometimes between people and, you know, between business people and product people and engineering and engineering and others. To help you to become a better facilitator because you need to explain how others, you know, perceive something in a different way. When you do all of that and then you bring your vision and your agenda, then people will listen. So it will seem like you have the authority without, the leadership without authority. But, actually, what you will have eventually is also the authority because the company will look at you and say, "You know what? This person deserves the title." So, but it shouldn't change you. So when someone, you know, moves into these ranks, if they want to, it doesn't have to be. But if they shift between the ranks, it's the same process. So when you're an engineering manager and you want to convince VPs or convince the C-level that something needs to happen, how do you do that? You don't have the authority of a director or a VP. Right? You have only as an engineering manager. It's the same journey. It's the same skills, just a different magnitude or a different level of complexity to understand and to reflect on, but it's the same muscle that you need to apply. So this is how I see that, and I try to give some practical, you know, ideas and suggestions for people who want to listen to the, I think it's like a 40 minute talk. And I think there is a version in English. There is for sure one in Hebrew, but I think that one in English as well. So if someone wants to listen to that and see that, and there is a deck that I presented there that is available online as well. But that's the short version, the short version that I have in mind. And I recommend people to start early and practice it on the small things because they will need to do it again and again and again and again and again as they change their roles. It doesn't mean that once you're becoming this authority, you're getting to be a staff engineer, a principal engineer, an engineering manager, a director. Doesn't mean that it ends there. It just, the level of complexity, the level of vision that you need to bring to the table changes. So it's not a vision of a year. It's a vision of two years or three years or five years, but the muscle is the same. So the muscle is learning to listen and understand the voices of others, not to agree with them, but to be able to articulate that and figure out then how your vision connects the dot between how you want to see the world and what the company needs to achieve and how people want to go there. So that's my thinking about it.

(Joel Beasley at 00:42:39) Thank you so much for listening. And if you found this episode useful, please share it with a friend or colleague who you think would get value from it. And if you have topics that you'd like to hear discussed on the podcast, either add me on LinkedIn, or send me an email [email protected]. Every time I get an email or LinkedIn message, it absolutely makes my day and inspires me to keep going.