#173: Replacing Yourself

Media Thumbnail
  • 0.5
  • 1
  • 1.25
  • 1.5
  • 1.75
  • 2
This is a podcast episode titled, #173: Replacing Yourself. The summary for this episode is: <p>DC's goal in life? To replace himself. On this episode, he's joined by Leo Tenenblat (Drift's Chief Product Officer) to talk through what this means in the context of a scaling company. Together, DC and Leo talk about their approaches to hiring and team building, projecting yourself into the future, and the one thing Leo thinks DC should stop doing. Digressions include some Portuguese lessons (for DC) and comparing astrological signs. </p><p><br></p><p>Like this episode? Be sure to leave a ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ ⭐️ review and share the pod with your friends. You can connect with DC on Twitter @dcancel @DriftPodcasts or text him to share your feedback at&nbsp;+1-212-380-1036.</p><p><br></p><p>For more learnings from DC, check out his weekly newsletter, The One Thing. You can subscribe here:&nbsp;<a href="https://www.drift.com/insider/learn/newsletters/dc/" rel="noopener noreferrer" target="_blank">https://www.drift.com/insider/learn/newsletters/dc/</a></p>
Experiencing Hyper Growth, Project Yourself Into the Future
01:33 MIN
Hire for the Future
00:54 MIN
How to Think About Who You Should Hire
00:31 MIN
How Leo Thinks About How He Can Replace Himself in What He Does Each Day
00:42 MIN

David Cancel: Before we get to the show. Did you know you can get more insights just like the ones you're listening to right here on Seeking Wisdom, delivered right to your inbox. Sign up to get my weekly newsletter. It's called'The One Thing' at drift. com/ dc. Leo, thank you for joining us today.

Leo: Happy to be here.

David Cancel: Me too. So for people who are listening to this podcast, I have some Easter eggs in here that you need to log into our YouTube account to see, and subscribe, and click that little notification bell. One is this homemade hat that I just made, just now. Look at that, what do you think of that Leo?

Leo: That's pretty awesome. Does it have some... How did you home made that?

David Cancel: That's holographic, look at that. And then it matches my cup holder.

Leo: That's pretty awesome.

David Cancel: It's amazing. This has never been seen anywhere. I just made it myself. And you cannot see it, you cannot know what it is unless you log in. And the other is this that I'm pointing right behind me is, I finally hung something on my walls here. And you have to log in to YouTube to see that. All right, today, enough Easter eggs. One more, Easter egg. One more. Third, it's always the rule of threes. I'm reading a new book. This is the book. Beware, Leo.

Leo: All right.

David Cancel: 'WhatData Reveals', this book is called'Super Founders'. I have not opened it yet.'What Data Reveals About Billion- Dollar Startups'. You know what's the problem with this book?

Leo: What is it?

David Cancel: It's going to give me more ideas, and more tabs, and more conversations with you, Leo. Good luck, saludos.

Leo: That's good. Looking forward to it.

David Cancel: All right, here we go. We are talking about, this episode is called replacing yourself. I will tell you the first thing, I would love nothing more than to replace myself. That is my goal in life.

Leo: Sounds good. We could all do that.

David Cancel: Yeah. What is your astrological sign? I only learned of these things in the last two years.

Leo: Sagittarius, I think.

David Cancel: Look, you had to think about that.

Leo: Well, I'm a math guy, science guy. Astrological science is not going to be a big thing for me.

David Cancel: Me too. I was like," What is this nonsense?" And then in the last two years, mind blown.

Leo: Really? Wow!

David Cancel: That's pretty interesting. Not in the way that I think most people who are into them, interpret them, and think about them. But more in this thought of just, well, there are patterns, there are cycles in life. And there has to be something to the cycles of when we were created, when we were born. Maybe there is something to cycles that we don't understand, right. And so, from that aspect, very, very loose aspect.

Leo: Yeah. I think this reminds me of when you look at the Incas and Aztecas, and that kind of stuff.

David Cancel: Exactly.

Leo: When you're in college. Learnings... A lot of smarts that they had thousands years ago. It's pretty insane.

David Cancel: Yeah. That is the context. That's actually the lens that I look at it through. Which is fascination with that, with the Incas, and the Mayans, and et cetera, et cetera. All these ancient civilizations and how much was tied to lunar and solar events, and times in the year. And how much meaning there was that I don't, we don't even understand how they understood. Which we're trying to interpret now from a scientific standpoint, and they're actually on. And so, thinking about that from a human standpoint of, maybe there is something to the timing of things. And so anyway, that's it. That's all I'm going to talk about it. Anyway. The reason I asked you is because I'm an Aquarius, and Aquarius' seek freedom. AKA, I would love to replace myself.

Leo: Okay. Sounds good.

David Cancel: That's the thread. Yeah. Replacing yourself is something that both of us think a lot about. Especially as we are now in the midst of scaling a company. And you have been in very large companies. The company you were at before this, twice, was Salesforce. So you saw massive scale, massive change. And through that experience, I'm sure you had to replace yourself. And you saw others constantly working on replacing themselves. And in order to give people room to grow.

Leo: Yeah. I've been fortunate enough to be in multiple situations where it's like hyper growth, and replacing yourself is the norm. You have to do it. If you don't do it, you're going to be left in the dust. And you don't scale, like people around you don't scale. You have to constantly be thinking about that. I still remember the early days at Salesforce, where I, first day I arrived, I had my cube. I brought all my stuff and arranged it. And within six months I was in a different place, different job. After the second move, I'm like, I'm not even taking my stuff out of my box. It was just in a box. And the second time I came back to Salesforce, I didn't even bring a box to the office. I'm like, this is going to be constantly changing anyway. But it is, yeah. Replacing yourself is super, super important.

David Cancel: I love that visual. I think the important thing that we can talk about in this episode is this context that you have, and it's context that you've gone through, right? This experience is history. Because for a lot of people, they maybe have only had experience in slow moving companies. Or maybe they haven't had experience yet, if they're new and they're early in their career. And for them, the idea of this constant change is constant flux. This, the visual that you painted of, forget even setting up your desk, because it's going to be moved to another area, another floor, another what have you, before you know it, is scary to them. There is something that's, that is amazing. That is where the growth opportunities are. So how would you coach someone early in their career? Someone coming from a slow growing company that is scared of doing this.

Leo: I think you have to kind of sort of project yourself into the future. Like when I joined Salesforce, it was a thousand people. When I left six years later, it was 10,000 thousand. And we just-

David Cancel: 10, 000 people?

Leo: 10,000 people. And I came back, it was 30, 000. And then when I left again, it was 50, 000. Yeah.

David Cancel: That's insanity.

Leo: When you join and, you're like us, 500 people. But you think a year ahead, it's going to be a thousand or 2000. If you start to think about that, your whole brain starts to, oh wait, hold on a second. It's like, what I'm doing right now is not going to work six months from now. As soon as you start to project the path, you start to realize that things have to change. You have to start thinking differently.

David Cancel: Yeah. I, you know, exactly what you mentioned is something that's on my mind. Which is like, we're at 500 people now. My mind is already at a thousand people. Because I'm like, I'm going to blink and we're going to be a thousand people pretty soon. It's going to be overnight. When I went from that 500 to a thousand journey at HubSpot, it was like a blink. And I think, to your point, I moved... I didn't even know where my desk was anymore. Literally. I didn't even know where the desk was. I was never at a desk. I don't know. It just kept moving, floors, buildings, across the street, across to a different campus. I had no idea where my desk was anymore. We were just in this... But that was a blink of an eye. That seemed like now, it was just like one day you woke up and it was 500, 1000, then it was a thousand to plus, and then just kept going that way.

Leo: Yeah. And I think you, when you've gone through some of those things... Well, when you even just think about it, you start thinking about the mechanics of, hold on, I can't just hire for now. I have to hire for the future. I have to hire for the future of the future. And so it changes how you think about the volume of hiring that you need to do, and how you actually think about hiring. Thinking about people who can grow very quickly and have that mentality, as opposed to, oh, they're good for the job I have right now. They have to be good for the job I'm going to have two years from now, or a year from now. They have to have the mentality of bringing that kind of, more of those kinds of people, into the team. It's a very, very different way of thinking.

David Cancel: So, how are you tackling that now? Coming from seeing that thousand person journey, doing your own startup, then leaving. I think you said 50,000 people, finally at Salesforce. And now zooming all the way back down to a 500 person company, who is now beginning to having this problem, or this opportunity I should say, to scale. How do you think about your hiring? Because I know you're knee deep in it.

Leo: Yeah. So first of all, I try to hire as senior as I can. Because it's people who can bring other people that, and build out whole chunks of the department. And so hiring folks who have seen the game before, and can expand really quickly. But also looking for junior folks who have that growth, and have that hunger. Because that is super important also. Both hiring, and looking internally, for people who have that hunger as well. Because you need to do all three of those things. It's some sort of a game of you need to meld in experience with folks who are hungry, to see that experience and grow from it. And altogether you start to see the whole thing kind of take shape. So it's, you have to be firing all cylinders in all directions.

David Cancel: I know. How do you counsel the existing team that may be there, maybe seeing all of these? And you're going through this right now. So this is perfect time, bringing in these senior people. Also bringing in younger people or bringing people kind of in the middle of their career. You've come into probably a situation where almost all of the team was kind of the same age thing, same tenure, same kind of experience level. And now you're filling in, not only people that look like them, which they're used to, but people that don't look like them from either younger in their career or older in their career. And so, how do you counsel people through that?

Leo: A lot of it has to do with diversity. It goes back to diversity of thought, as I see it. It's like, look, you have a way of looking at things. Maybe there's some other people that have different ways of looking at things. When you put those things together, it's all good. It's all, it just makes it stronger and better. And so, telling people not to be too afraid of change or a different opinions. But also to be strong, to put their opinions on the table. Because they have a fresher way of looking at things and can add to it. So I think when you start combining things like that, it just becomes more powerful. But you have to coach people in, look, it's going to be all right. It's okay. You've got something to add. The other people have something to add. It's going to be okay. It's all good.

David Cancel: The coaching is the hard part, the interesting part, right? Because it's easy. Like you mentioned when you started, diversity, the word diversity. Diversity of thought there, in that case. But everyone likes diversity, or most people like to talk about diversity. But not when it affects their job. Like not when it affects them, right? Not when it inconveniences them by introducing the right thing, which is to diversify the system, diversify the team. You are introducing things that are affecting people.

Leo: Yeah. I think that there, the idea is you have to paint multiple options in the future for people. And then they become a little more calm. So maybe in this space, you're kind of reaching your limit. We need something else that's a bit different. But look, there's another option over here, there's another option over there, or discovering people's talents. Like look, you've been doing this thing here, but you have a talent that's undiscovered. You could completely blow this up in a different direction here. And then the moment people start to see, oh, there's options. And again, in that picture of growth, look, if you're going to be a thousand people, there's going to be a ton of opportunities. So the moment you paint that picture for them, and you come down to about the immediate situation and their personal view on it, they can relax a little bit more and focus on the options that they have ahead of them.

David Cancel: Have you thought about, in your recent career, thinking about how you replace yourself in what you do each day? I know you're thinking about that even at this scale.

Leo: Yeah. I mean, it's constant, right? Do you always want to be figuring out who... Like it's important for many reasons, right? It's A, you never know when you're going to get hit by a bus. So you always have to inaudible it up. You never know when you're going to reach your limit. Everybody has limits, strengths, and weaknesses. At some point, when you reach a moment where you're like, all right, I've done this. I'm kind of tired of this. I'm going to go do something else. Maybe there's other people who are stronger than you. Look, they could do a better job than me. By all means. It's the best thing for the company. I am just a piece of this. And I'm pushing it along at where my moment, where in that moment, I am the best person. At some later moment, it might not be ideal. And it's perfectly great to just move along, get somebody else to take the ship forward. So it's key. We have to be thinking about it.

David Cancel: Yeah. It that one frame that I always use for myself, is just that every year I want to be a different version of myself. And that I have to then therefore replace some of the things that I was doing professionally within the company, if I'm going to be a different version next year. And so I'm thinking about the next version for next year now. And I'm thinking, okay, how do I start hiring? Or how do I start giving away... As Molly Graham and say, giving away some of my Legos. And if you don't know Molly Graham, you have to. She's an advisor to us at Drift. She's an amazing speaker. Look up her article and her video, her talk, that she's given on giving away your Legos. Which is an important thing that she learned during her time at Facebook, which was constant change, constant growth. And just being willing to, again, give away your Lego sets. I'm always thinking about like, how do I give away Legos? How do you give away Legos? And some people are more predisposed to it. And so, I'm happy to throw my Legos. Hey, Leo. Here's some Legos, take them. I'm happy to give them away. Because I'm looking for the next growth opportunity. And some people are a little bit more hesitant and want to protect their Legos. That's their kingdom. That represents them.

Leo: Yeah. I think it's both for you to scale, but also to look at other people and say, look, I want to give more opportunities to more people. And so for that, I have to give them Legos. I have to give them. Otherwise, they're not going to have those... Or they're going to look elsewhere for it. And if it's someone who's strong and you want to grow them, you have to give them pieces of your pie. I was going to say kingdom, but it's not a kingdom. It's just holding it for awhile.

David Cancel: Yeah. You just hired two executives on your team, two VP level people. Is part of giving, replacing themselves ever part of the conversation when you're recruiting? In terms of framing it for them as I would imagine that they would want growth opportunity. Right? Because that's the reason to come to this size, or this stage, of a company. They want to grow in some ways. So is that part of the conversation when you recruited them?

Leo: A hundred percent. It's like, when you look at bigger companies and you see people who are a GM of a big, big part of the company. In oftentimes you get someone who is not that big, but if they get on the ground floor in a company like ours, they have that potential. And so I brought it up with both of them. I was like, look, this is, you've seen this, you weren't at that level in these other companies, but here you could be. And so that becomes a growth opportunity for them. And between them and other people onwards. And you know, the cycle keeps going. As we say in Portuguese, like foreign language, the line has to keep moving.

David Cancel: Wow. I like that. I wish I knew Portuguese.

Leo: I'm sure you do. Come on, you need to stay close to Spanish. I'm sure you'd understand it.

David Cancel: I can understand parts of it, for sure. Speaking of which, I just signed up to go back to one of my favorite locations, countries, ever hidden gem, Portugal. I'm going to Portugal in November to speak at Web Summit. Which I went right before the pandemic. Blew my mind. Because I had no expectations going to Lisbon, and it just totally blew my mind. So I need to bone up on my Portuguese. Portuguese.

Leo: Portugal is amazing. That culture, the people, the food.

David Cancel: Love the people. The food is amazing. Everything is just great. So see you all in Portugal in November. I hope you'll attend. And okay. If you were going to give me one, we're going to close this with one piece of advice that you would give me, that I need a lot of advice on how to replace myself. What would it be? How can I replace myself? And this can be within the context of Drift. Or something that I'm doing there. Or maybe what job do you think I need to replace myself in that I'm doing today?

Leo: I would say, it's the deck inspector. You need someone else to be the deck inspector.

David Cancel: I am the deck inspector.

Leo: The stories. The stories. I think the stories are super powerful. You have that mindset. You have to find a way to multiply your force and not be the only one who's who's nitpicking at stories, and how we tell stories.

David Cancel: That is true. All right. I need, if you're listening to this and you're a world- class storyteller, please hit me up. I need to replace myself on storytelling and nitpicking at Drift. I am chief nitpicker at Drift. Leo felt that deep in his gut. All right. You know what to do? Leave a six star only rating. Shout it out to Leo. Subscribe on YouTube so you can see my homemade hat and this painting in the background. And get a Gander at a young Leo here, and the old uncle on screen. And don't forget to click the little notification bell so that you know when new episodes are dropping. Saludos. How do you say goodbye in Portuguese?

Leo: foreign language.

David Cancel: foreign language.

Leo: foreign language.

David Cancel: foreign language. Cheers. Let me know what you thought of this episode by texting me at 1- 212- 380- 1036. Again, 1- 212- 380- 1036. Now, if you're looking for more leadership insights, sign up for my weekly newsletter,'The One Thing' at drift. com/ dc. Every week, I'll share a habit, tool, or mental model that's helping me reach my goals. I hope to see you there. Text me, hit me up.


DC's goal in life? To replace himself. On this episode, he's joined by Leo Tenenblat (Drift's Chief Product Officer) to talk through what this means in the context of a scaling company. Together, DC and Leo talk about their approaches to hiring and team building, projecting yourself into the future, and the one thing Leo thinks DC should stop doing. Digressions include some Portuguese lessons (for DC) and comparing astrological signs.

Today's Host

Guest Thumbnail

David Cancel

|Co-Founder & CEO, Drift

Today's Guests

Guest Thumbnail

Leo Tenenblat

|Chief Product Officer