#82: Paul English on Hiring, People, and Time Management

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This is a podcast episode titled, #82: Paul English on Hiring, People, and Time Management. The summary for this episode is: If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. ----- Paul English is a serial entrepreneur and philanthropist -- and you probably know him as the founder and CTO of Kayak, which was acquired by Priceline for $1.8 billion (with a B) five months after they went public in 2012. Today he is the founder of Lola, a Boston-based travel service. DC invited Paul over to Drift for a conversation with the team and we recorded it Seeking Wisdom — but it’s not the conversation that you might have expected. Instead of asking Paul about his career and story, we went deep on one topic: people. This episode of Seeking Wisdom is all about hiring. Here’s how you can support Seeking Wisdom if you’re a fan of the podcast: 1. Get your tickets to Hypergrowth using the promo code SEEKINGWISDOM at hypergrowth.drift.com 2. Subscribe on your favorite podcast app. 3. Leave us a five-star review. Here's how: bit.ly/5-Stars-Only.

D.C: I'll turn it over to you. Intro Paul.

Speaker 2: Sure. So this is Paul English. Paul is a crosstalk.

Dave: We got to give it up. Give it up for Paul.

Speaker 2: Yeah. Paul is a friend and a five time entrepreneur. He started some small companies like Kayak, Lola. I'll let him tell you more, but we're lucky to have him on board. One of the things that I circulated recently that you mentioned was this post from, I think is it 2002?

Paul English: Yeah.

Speaker 2: Yeah. 2002 that Paul wrote on hiring. That was something that we looked at as a model, many times at Performable, HubSpot, many companies. And so we're honored to have him here.

Dave: It must be pretty good, because he doesn't remember anything. So for him to be like, " Yeah, that was article from 2002." This must be a important moment.

Speaker 2: Yeah. Yeah. Well, thanks for coming.

Paul English: Yeah. Great to be here.

Dave: All right. So actually, right when we set this up, you tweeted out, " This article on hiring from my friend, Paul English, is still one of the best that I've read." So there's so many things that we could talk about with you, but I think we'll go deep on hiring first. What made you like, why write this? You're an engineer by trade, right? Like why sit down and write this manifesto on hiring and people?

Paul English: So, I'm a programmer. And earlier in my career, when I first started managing, which I resisted for years, but then once I started managing, part of managing is hiring and I'm obsessed with hiring. I think about it every day, seven days a week. And when I meet people. I'm trying to think like, " Am I going to hire this person? Or they know someone I'm going to hire?" And someone once asked me why I'm so obsessed. And I think I grew up in a family of nine. So my parents had seven kids and growing up in a large family, there's a lot of dysfunction that goes on. And I think you kind of observe human interactions and behaviors, and teams are in many ways, just a different model for a family. I think really high functioning teams are model of a good family. And for me, it was all about how do you build a team with as little dysfunction as possible and with a lot of really phenomenal collaboration? And I've just seen the difference. I knew what it's like as an engineer to be in a team that functioned really well or to be on a team that was really stressful because a lot of interpersonal stuff going on. And I just wanted a lot more of the former, none of the ladder.

Dave: This actually goes back to something I saw. I don't know if this was because you were prepping, but this morning you tweeted something that we've talked about a lot, that the complexity in business is not the business, but the people. It always comes down to the leadership and management of people. Why did you say that?

Paul English: Random thought. I was not prepping as crosstalk.

Dave: There's no prep.

Paul English: There's no prep, but it's something same kind of thought pattern. I did not grow up one of nine, but one of six and introverted engineer growing up. And so like the observing people and figuring out kind of patterns and systems of for so long, I think I spent all my time worried about technology and then realized like technology is like the easy part. It's like nothing. And the hard part is the people.

Dave: What was that shift for you though? You mentioned you didn't ever want to manage people. Was there something that happened, like you reached a certain point of success in your career as engineer and then the only next step was to manage people or did something change?

Paul English: Yeah. My first management job was at a company called Interleaf. It was a document publishing company and my boss and my boss's boss kept asking me to manage teams. I didn't want to, because I just wanted to code. And back then I was 25, I was kind of an arrogant engineer, I thought I could out code in with the company. I'm like, " Why would I manage when I could just code and compete with the whole team by coding?" And finally, they convinced me to manage, and it was actually kind of brutal the first year. I think I was still coding full- time and managing. And I think by the end of the year, I had 15 programmers direct reporting. But I modeled that team a little bit off of the team that I had been a member of. And I looked at just things that worked really well, things that didn't work well, in particular engineers or people who are problem seekers. And I think many times as an entrepreneur, it's more important to pick the problem to attack than it is what the solution is you're building. I think most tech companies fail not due to building bad technology. They fail because they built technology that no one gives a shit about. They fix stupid problems. And for me, I was always focused on what are the big problems? And not just in products or technology companies, but what are the big problems in teams? And when I would see things that were dysfunctional in team, I would just say, " I'm not going to have that on my team." As a manager, you're both a member of a team, your boss and your peers, but you also run a team. And I always wanted the team I ran to be strong and the team I was on.

Speaker 2: What do you think were common dysfunctions? Your book of the Five Dysfunctions of a Team.

Paul English: Yeah. It's just too much ego. I think humility is underrated. I think the smartest people have... there's a term I use, arrogant humility, which is, if you're gifted and you've accomplished a lot, you know you're good because you've been successful in a bunch of things. But if you're really, really bright, you recognize there are definitely people way brighter. And there are definitely people who you can learn something from. And I've often said you could parachute me anywhere in the world. And I guarantee you, the first person that I met, two things, one, I could find something they know that interests me. And two, I could find something they know that they're expert at more than me. So there's something I can learn from them. And when ego gets in the way, people stop listening and they do more talking than listening. And it's frustrating for me. And I also observe a lot. My team has joked that I'm five percent therapist at work, sort of psychotherapy. I've two siblings who are psychotherapists. My mom was a social worker and I definitely do a lot of debugging of personal interactions. And I look for things like why does this person always interrupt that person? Like why to men interrupt women more than women interrupt men? Or I just look for things that I think are dysfunctional. And then I jump on them, and rather than ignore them, I try to debug them and say, " I want to fix this. I don't want to do workarounds. I want to fix the dysfunction."

Dave: How do you actually do that, if you notice something happening at work?

Paul English: I call it out either in real time or I grab someone right after the meeting. I say, " Can you hang out for a minute? I want to give you some feedback." And I'm always asking for feedback as well. And I think being good at giving feedback, you have to model what it's like to accept feedback. So I try to model listening really careful when people give me feedback and echoing back to them what I'm learning from them. But I also am not shy. It's probably the most difficult thing for a manager to do is to give feedback. And there's a lot of reasons why that's difficult, but I try to give realtime feedback and say, " Hey, this interaction I observed, I think I'm sure what you're trying to do. That might be a better way to achieve that without pissing off the other person."

Dave: Talk about feedback and like the mantra that has been circulating here recently about getting defensive in feedback and how that's kind of been now built and related to that.

Speaker 2: Yeah. So many things are related. I feel like this is an episode of Seeking Wisdom, but it is like a meta episode, because we talk so much about the ego humility thing. And so one thing which you mentioned was on feedback, we talk a lot about it internally and we started to use this phrase. That's like, don't get defensive, that could go the wrong way, but we're trying to use it in a loving way of like, something's coming, we're giving you feedback. And the way we talk about it internally is that without feedback, there's no growth. And that has to do with the ego humility thing. We all have egos. And so, what we have to learn is how do we balance them and how can we turn them off just enough so that we can keep growing? And the minute that you stop being able to turn it off because of whatever, maybe some success or some experience, that's when you're growing stops. And so we're always encouraging everyone to take that feedback because without that, there's no way that you can improve.

Dave: One of the examples is like, if I was sitting here right now and I had a big piece of broccoli in my teeth, I would want him to tell me that.

Speaker 2: And Dave tells me that often.

Dave: I tell him crosstalk.

Speaker 2: Because like you have something in your teeth. That's sure.

Dave: crosstalk something in your teeth, RX bar's glued to them.

Speaker 2: Yeah, that's true. Yeah. Often. My wife tells me that too, " There's something in you're teeth."

Dave: So I think that's a different lens. It's natural. I get defensive. It's not easy. DC comes at me and says, like this thing, this, it's easy to be like, " What the hell man? I'm out here working so hard. Can you please not do that?"

Speaker 2: Yeah. Yeah. Don't get defensive. Don't do that.

Dave: But I think it's just natural to... so, I guess my question for you both is like, how do you manage through that? And like, look, I'm going to be a hard ass. This is going to come across as hard, but it's really feedback to help you grow. How do you manage through that?

Paul English: I think it's, as a manager, you have to have confidence and humility. People follow confidence. And if you come across as too insecure or too humble, people don't listen to you. So I think when you give feedback, you have to be confident. And like, " I've seen this movie before and I've worked with teams like this. I just want to give you some feedback based on my observations of what's worked well on teams that I've been on." So having some confidence, but also listening to the person you're giving feedback too, and make sure they understand it and look at their interpretation of what happened. And it could be that I misinterpreted something. And so feedback is, I've been managing now for 25 years, I guess it is. It's kind of hard to believe, but I have seen a lot.

Dave: What's your oldest internet story? Because DC loves to like break out some old technology or something. What can you dig in the crates with?

Paul English: So my oldest internet story is-

Dave: It's pretty crosstalk.

D.C: If I ever said that.

Paul English: I recently found an article that I wrote in 1989.

Dave: Look at him. He doesn't know what that is. That was a year. It was called 1982.

D.C: Did you print that? I was two.

Speaker 2: Look at Connor. Connor was not.

Connor: No.

Speaker 2: No. No.

Dave: Sorry to derail this conversation. But something always comes up on this podcast and I won't even mention it, but that's called Netscape. You ever heard it?

Speaker 2: Yeah.

Dave: So something that's interesting. I have your article up about your hiring. And one thing that you mentioned here is like, you look for people who have a fire in their belly, who are outwardly competitive, and who are very goal and results driven. Those are very like in harsh contrast to some of the softer skills like of feedback and being a good teammate. And that's been a challenge for us. Like how do you find people who have that fire, but at the same time aren't assholes to work with?

Paul English: So one of my techniques that I do in interviewing, probably my favorite thing is I ask people about teams I've been on before. And what I'll do is I'll first of all, always read your resume or LinkedIn profile before I meet with you, because I think it's really obnoxious to be reading it in front of a candidate. It shows like I don't care enough about you to have done research on you before I met you. So I research before. And then I'll find something that intrigues me that I'm interested in. And even the interview is going to be awful and then not a good match. I at least want to be entertained for the half hour or hour or whatever I'm going to spend with the person. So I find something in that background that's interesting and I'll ask them for the team around that. And I will say, " Name four people who worked on that, just give me their first name, or you can make up a name. Because I don't really care who they are, but give me four names and four titles." And then for on that specific project, let's say you've built an eCommerce website for Converse or something. And I want to know what it was like to launch a website with a big ad campaign behind it. And I'll talk about the people on that team. And I'll say, " On that launch of that website, tell me something that Stacy did, which blew you away and something she did which was awful." And the thing that I look for is one, I want to make sure that everyone I hire, people that can be really afusive of about other people. And sometimes when people are so wrapped up in their own ego, they're not actually afusive enough. They don't get excited about other people and that's a fatal flaw to me. And the second thing is when they talk about, well, I want to make sure that the thing that impresses them about that person that I'd be impressed to. So yeah, that sounds like a cool thing. And then when they have critical feedback to say, " Yeah, that would annoy me too." And if you have a candidate who basically can't think of anything negative about anyone, that's a warning sign too. So I want to make sure that they can talk about a team articulately and that they have really passion for a team. I also, like, I think I may... it's been a long time since I read that article. But I think I've talked about that I also like people who are musicians that have played in bands because to be a good musician, a lot of it is listening, not just playing. And then also I like athletes, not so much tennis players, but athletes who play on big teams.

Dave: Not tennis players.

Paul English: No. Not runners. I'm just saying, people played on a team.

Speaker 2: Team sports, team sports.

Dave: You have something similar in the listening. So you don't say, " I like that, that's it like, tell me about four people on the team." You have something similar and you listen to how they're talking about a prior work, right?

Paul English: Yeah. I think one thing that I've mentioned in the past is just that when you're talking to someone who's leading people like how often are they mentioning other people, referencing or how often are they just mentioning themselves because they get wrapped up in that. And so, one thing that we've talked about in the past is like I've had extreme examples where people, I could not get them to mention another person. They only said everything was them, even though they may have led 50 people. And they just say, " I did, I did, I did. I did. I did." And I turned that into a game where I try to trick them and get them to say someone else's name. And there have been people that will never say it, but they would always say, "I, I, I, I, I." So, that was the thing. That's the towel. They're almost in autopilot during the interview process that they don't even realize what they're doing. Work should be fun. I tell this story, when I had a routine with my kids, when they're little and one morning I had to leave for work really, really early. So I got a phone call from my daughter, Nicole, as I was on to work. And she's like, " Daddy, where are you?" And I said, " I had to leave really early. I had a meeting at work," and we chatted for a minute. She's like, " Okay. Say hi to uncle Dan, for me." I'm thinking, " Uncle Dan, why does she assume I'm working with my brother who's an electrician?" And so I had to explain to Nicole, we didn't work together. I'm like, well, I had to explain to like a four year old what you do for a living. So I said, " Dan fixes buildings," which is sort of true. And I fixed computers, which is not really true. crosstalk. But then-

Dave: That's what you describe it. Anytime asks like at a house party you say, " I work in computers."

Speaker 2: It bores them.

Paul English: Anyway. So I hung up the phone and I started thinking about it, like, what does Dan do for work? And what do I do for work? And I realized like we do the same thing, which is, he's in construction and I'm in software. We manage teams and I was away from my kids during the day because I'm working. And sometimes people ask me why I start companies. Because my kids go to school. I need something fun to do. Work should be fun. And if you're not getting excited by your colleagues and your peers, what are you doing? So I always look for people who get excited by their job and find people that they're just thrilled to work with.

Dave: We think about that a lot because it's not... I'm not a math guy. I'm not good at math, but I know that I spend more time here than home. And so if you just think about the hours, you have to genuinely love the people that are going to sit next to and work on. And this is where you're going to be frustrated. This is where you're going to be off, this is where you're going to have fun. I think that's a piece of advice that a lot of people often gloss over. Like it seems corny on the surface to be like, "You have to really like the people that you work with," but it's true. This is hard enough on its own. If you don't actually enjoy the team that you're going to be around, it's going to be even harder.

Speaker 2: So how do you deal with like problems, problems with no matter how good you are to hiring, you're not 100%?

Paul English: No. Some people say hire slow, fire fast. I actually think if you're disciplined, you can hire fast, fire fast. And the discipline thing to me, like I have the seven day rule, which I talked about back in that article. And it's still true. When I meet someone the first time I hear someone's name, like a clock starts ticking. I have seven days to hunt them down, convincing them to meet me. If that goes good, convince them to meet my team, back channel, convince them to meet my team again, making them an offer the same day. And people will say, " Don't you make a lot of mistakes if you move that fast?" And my analogy is, if you watch formula racing and you look at a pit crew change tires, if they make a mistake... They have to change cars pretty quickly. If they make a mistake, someone dies. So they become really good at changing tires. And even though like hiring isn't necessarily a life changing crosstalk decision, if you're disciplined about it, you can get good at it, but you do make mistakes. And I think that when I've made mistakes, I'll often say it's not a bad person. It's a bad hire because there's something about this person that I liked during the interview. They're awesome at some things, but that's not fit for the company. I try to coach them really quickly when I see things not working out too well. And if it doesn't work, we separate. And I've often said that if you get fired in Boston, you want to get fired by me because I do ridiculous things to try to take care of people after we fired them. So I help them find a job. I'm always available. I give them my home phone number, my cell phone number, whatever. And I take care of them because I feel responsible responsibility as a hiring manager to have changed their job. And if you can change it again, I don't know. I just feel like you should be good to them.

Speaker 2: Are there common things aside from being an asshole?

Paul English: I think being an asshole is probably 90% of it. It's rare. I would say this of all the people I've fired. And unfortunately being a manager for 25 years, I've had to fire a bunch of people. I'd say 10% were due to incompetence, but 90% were due to team dysfunction, and it's really hard. And when you see people have bad interaction and you try to coach them on it, it's like to be an effective person at Lola, let's say like my travel company, you need to influence people around you. And if you are having this harsh reality, where you're walking down the hall, people are diverting their eyes away from you, like huge, dangerous sign that people aren't gravitating towards you. So I think people should be concerned. If their peers aren't gravitated towards them, it means you need to work a little bit more on the EQ.

Speaker 2: Definitely. Are there patterns, you mentioned Lola and are there patterns you're doing now versus 2002 that are different or from Kayak?

Paul English: One big difference between Lola and Kayak, so Lola is about the same age as Drift. About two years old, about 50 people, about the same size. With Kayak, Kayak was my fourth company I had started and the first 10 hires were 10 people I've worked before. So I just hired the best people I could possibly find. With Lola, I went out of my way to hire new people because I didn't want to do the same movie again. And when I left Kayak, I told friends that I would never work in travel again, because been there, done that, spent 10 years of my life. Yeah. But then the Lola idea came and we decided to go for it, but I didn't want to do it with the Kayak team. So I went out of my way to try to find people that were outside my network. And it's been amazing. It's one thing to bring someone from a prior job that you know is a rock star and that rock star for you in the new company. But it's unbelievably gratifying to take somebody you've not worked with before and to watch them excel in ways that you haven't seen. Because as a learning CEO, it allows me to learn when I see people who have executed in a different space than I've executed in. So I get really turned on by people who perform successfully in a completely different space than I've been in.

Speaker 2: What is learning CEO? I like that.

Paul English: Every interaction you have to be learning something. It's not just about lecturing. I've often said, I only hire entrepreneurs. Like even my assistant is an entrepreneur. And I think that if you're good at hiring entrepreneurs, entrepreneurs are people that are learning people and every interaction with an entrepreneur, there's something unique about the way they look at the world that I can learn from. So it's everything from when I give them feedback to brainstorming and product. I also spend a bunch of time with people who... so I think I have a pretty good filter for hiring people that are smart. I definitely make hiring mistakes, but I think the smart thing I can get, I think you can get that in an interview in background check. But occasional, I hire people that are really smart, but I disagree with them a lot. I end up spending a lot of time with those people because I'm like, there's a guy in my team right now. I guess I won't name him, but a really sharp guy, young guy. And when I hired him, I was blown away by he was just really, really a sharp guy. But I disagree with him a lot, and rather than cutting him out and just ignoring him, I decided like he sees the world differently than me. I'm just going to spend a lot of time with them to try to figure out how he sees the world. And we're in the midst of it right now. I work really close to him every day. And I'm learning something from him every interaction.

Dave: Do you still disagree? Because where I'm going, there's like, is it possible that you guys are just completely different people? Or can you just get closer to the same thing?

Paul English: Usually when two smart people disagree, it's because there's variables they're seeing which are different. So they're looking at the world slightly differently or they have a different goal. So if you're transparent with what your goals are, sometimes that'll diffuse tension. If you're fighting about something, you don't realize it, you're optimizing for CAC and I'm optimizing for customer sat. You can be just wired to think about problems differently. In this case, I had a new product idea yesterday, which I thought it was like the greatest thing in the world. Turned out my team just shat all over it, including this guy. And I went to him immediately because I was super excited when I said, yeah, I first drafted an email to my team saying, " Please implement this by next week." I literally wrote that. And I sent it to five people. I'm like, " Before I hit send, I should probably run it by this guy, this really sharp guy on my team who I always disagreed with it." So I went over to talk to him. He's like, " This is the worst idea ever." And I spent probably a few hours trying to sell my idea to other people, but going back to him and ultimately I decided he was right. And my idea was stupid. I'm not going to do it.

Speaker 2: That is awesome. I think I know who that person is. I'll ask you later who it is.

Dave: What is your hit rate on hiring you think these days? Because we've talked a bunch of people and they said, " It's you just have to accept that hiring is fucking hard and it's always going to be 50% or 70." Do you have a sense of what yours is?

Paul English: So when you hire people, you say they turn out to be As, Bs or Cs. A are the superstars, Bs are the supporters, and Cs are people who either become As or Bs or your crosstalk.

Dave: Do you guys actually go and grade people out after you hire them?

Paul English: We do. We rate people on two things, their impact on the team and their impact on the customer. So everyone gets rated-

Dave: crosstalk after a month or?

Paul English: We do it formally twice a year in I think it's January and August, but we also do it... Sometimes we do it during the interview. We actually have a spreadsheet, it's different in each department, but in engineering, we have a spreadsheet and we would guess what people are going to score on team and work. And sometimes I literally with my CTO, Dennis this is really harsh, but sometimes 24 hours after they started or a week after they started, we're like, " How did we think we did in this assessment?" Because when you see them actually working with people, it's different than them talking about working with people.

Dave: So different.

Paul English: But if you say A, B, Cs, I think if I'm going to hire someone like this person is absolutely A plus, like rockstar, I think when you really feel it, I think I'm probably 70% right. If someone who I think is like really solid fit in with the team, I don't know, maybe a little bit above that, maybe 75% right. But the people who turn out not fitting obviously I'm zero percent right. So I've had a bad hire because I've thought they were going to fit in really well and they didn't. But I don't know, just try to get better all the time and make corrections as it need be.

Speaker 2: And do you try to screen on... like the interaction part, totally agree. So important and you can't figure that out in the interview process, you have to, and we used to do in the past, like working projects or like have them come into the office and see, especially with engineers, see how they work with someone else and you can see right away, like how's it fitting? Like how's the styles? And do you do any test projects like that to try to simulate that?

Paul English: If someone is really awesome, they might be like, " Fuck you. I'm not going to do work for you."

Speaker 2: Totally. Totally.

Paul English: One thing I like doing is it's also can be intimidating, just hand someone a keyboard and say, " Go write some Python code to do whatever." But sometimes what I'll do is I'll have them sit next to me in the same side of table with a laptop looking at. So I'm controlling the laptop, doing things. And then I'll say, " Well, how would you do this?" I'll slide the laptop over to them. And if I'm interviewing an ops engineer, I want to see like, do they know how to configure web servers? I watched like literally can they type fast enough? Stacy, our head of people ops and customer service, when we interview customer service people, part of her interview processes, she does live chats with people to see, are they funny? Are they fast? Are they succinct? And I like engineers to be able to be all those things too. And I look for that. But another thing I like doing in interviews, I'm really into pair interviewing where there's two interviewers with a person. And there's a couple of reasons I do that. One is, so I'm really guarded of my time. We can talk about time management and things I do to manage my time, but I want to make sure that if this interview is going to be a bomb, I better at least have fun for the next 30 or 60 minutes, whatever it's going to be. Usually it's 30, but sometimes 60. So if I invite some of my team who I'd love to sit in, it's like, okay, well the interview candidate is not a fit, but at least I got to spend half an hour with crosstalk. But the other thing we're trying to is we fight, I fight amongst someone on my team. It's like Lincoln Jackson's my design chief. And he and I've sat next to each other for like 15 years now. We work together, sat next to each other at Kayak. And now he was the design chief at Kayak. And I was designed chief at Lola. And we will fight with each other in front of an interview candidate and it bewildered some of them. But I like to see how they deal with conflict.

Dave: We need to write this down. The new interview playbook at Drift is David and Elias.

Connor: And me.

Speaker 2: And they sit between us. That's your job.

Dave: That's my job.

Speaker 2: That's his job. You sit between us.

Dave: It's like fighting with parents. One of them looking at you like, "You know what drives me crazy about him?"

Speaker 2: Has that ever happened with us? Never.

Dave: He's sleeping.

Speaker 2: He's sleeping. Yeah. See?

Dave: Let's talk about time management. Hiring and time are two good topics. So what was your thought on?

Speaker 2: I need secrets for this.

Dave: Give him your crosstalk.

Paul English: Okay. I use Google calendar. I color code my appointments. One of three colors. See the Lola, which is the most important thing that if I was going to be at Lola 40 plus hours a week, I need to make sure on a given day, I'm spending time actually working on Lola. Those I color in purple, actually I have four colors. Then I have non- profit work, which I color in yellow. I do a lot of work in Haiti and with homelessness in Boston and different groups in Africa and elsewhere. And I color code that yellow and I want to make sure I do a certain amount of nonprofit work every week. Sometimes it turns out to be too much. I think I had four hours of non profit meetings yesterday, so I have to keep a check, keep balance on that. So I'll glance at my calendar week to week and see, am I spending too much time on one thing versus another? Green means personal investment. So it could be working out at the gym. It could be like today we had a meditation seminar. I brought in an amazing woman from Cambridge Insight Meditation Center and gave a lecture to 15 of our people about how to meditate. And that was awesome. And I want to make sure that when I glance at my calender of the week that there's a number of green boxes there, that I'm doing investment in sort of personal growth, health, whatever. And then I have personal time and I do look at my calendar regularly when I meet with my assistant. I talk to my assistant constantly. But we have one meeting in particular the beginning of the week and at the end of the week. And we'll glance at my account for the next two weeks. And I'm looking for balance. And if I see spending too much time with one or not enough with another, I'll make it sort of course adjustments along the way. One of the dangers in calender management these days is it's too easy to accept a meeting. And one thing would be interesting is look at your Google calendar for the last month and try to say, " Okay, for all of the meetings you did last month, what percent were meetings that you requested and what percent were meetings that you accepted?" I think a lot of us end up getting in a trap where we just accept meetings coming in and then you're not controlling your destiny. So if you're reactive instead of proactive, if you have extraordinary people around you, you might get lucky in bouncing around like a pinball and maybe you'll score. But I think sort of the master of time management is proactive, not just reactive.

Speaker 2: So teach me this. How do you filter outside requests, whether they're personal or professional outside of Lola that come in for your time without being an asshole?

Paul English: So I have a blow off template.

Dave: Can you share that?

Speaker 2: Can I have it?

Paul English: Yeah, sure. I'll send it to you. And I edit it a little bit, but I'm also a big fan of... do you have an iPhone and Android?

Speaker 2: IPhone.

Paul English: Okay. Do you know what auto text macros are?

Speaker 2: Yes. Yeah.

Paul English: So I have-

Dave: Can you explain to me?

Paul English: Yeah, so you go in settings, general, keyboard, auto text, and you got other things like a lot of my emails online with kind regards Paul, but I would set up something I type KRP. It is, kind regards, Paul. But most of my them I can setup with the letter Q and then just a letter. So after like QM, is my mobile number, QA is the address to my house. QD is directions to get to my house. Q busy is my blow off template. And I'll edit it per person, but it allows me to be really quick with emails. So I get hundreds of emails a day, but my inbox at all times has about 10 items or fewer because I'm just maniacal about keeping up with it. I have a whole email handling thing too, but there's a lot. But I think when a meeting comes in, you have to think of like, " Yeah, that person's really cool. I did meet them before and I enjoy enjoyed spending time with them. But if I spend an hour with them, it's an hour I'm not spending with the designers at Lola and I could be fucking up Lola a little bit by not helping on that." So it's an opportunity cost where there's all this eye candy and interesting stuff coming in. But just have to say, " What's my number one thing for the day, or what's the one of two things I've got to get done this week?" If it's not on that list, you shouldn't do it.

Speaker 2: That's awesome. My technique is just not answer so it just goes into this like...

Dave: And there's one day-

Speaker 2: That's not a good technique.

Dave: Then there's one day a week where I can tell he's going through his email.

Speaker 2: Anything else in your mind?

Dave: All right, let's do questions. I know a bunch of people got questions. We'll relay them back. So what do we got? Everybody has an opinion about everything at this company. Now, nobody has a word to say? I find that hard to believe.

Speaker 2: Afterwards they'll be like, " Why didn't you ask this? What's going on?" All right, Kara.

Dave: I'm going to repeat it for all the loyal listeners.

Kara: So, you talked about how do people relate with teams. But how do you really instill that in inaudible.

Speaker 2: Cool. Can you answer it? Can you repeat that?

Dave: How do you sum that up?

Speaker 2: So how do you instill culture? So, how do you instill culture?

Dave: My real question is how do you make people value team? How do you make people see that working on teams, is something they should work on?

Paul English: I've two kids, both college, and there are some, not everything, but there are some things in common with parenting and managing, and part of it's carrot versus stick. And I'm a big believer in positive feedback. And when you see something awesome, celebrate it. And a lot of people don't do that. And if you see someone do a positive team interaction, tell them, " That was amazing, what you just did there." And if they're getting positive feedback, being directed by a particular thing, it works really well. I've got an example of one positive feedback that I got once in my career. This is back in 1994 or'95 as I was recruited away from Interleaf to run engineering at an internet startup. And when I first met this, the founder of this company's name is Sean Sullivan. The company's called that Centric. Halfway through the interview, maybe 10 minutes through the interview, Sean, he's this crazy Irish guy, really fun. He said, " You're bigger than me, but I used to play rugby. And I'm not letting you leave this room to till you sign this offer letter."

Speaker 2: That's an elite's technique.

Paul English: It's a line I've used many times, actually, since then. Stacy introduced me. I keep talking about Stacy because she's sitting here. I had to put crosstalk.

Speaker 2: Hello, Stacy.

Paul English: But Stacy introduced me to a woman once. Her first name is Rachel, who Stacy was really excited about me meeting to interview. And I was looking at resume before I went in and I'm like, " Okay, it looks interesting, but why the fuck am I wasting my time meeting this person? She has no relevant background." She was a military commander in Iraq and Afghanistan, young woman. And I definitely am big fan of military. People that have military training, I think is a real positive. By the way, I meet her, and in five minutes, I'm like, " Okay, I'm going to like redesign the company around this woman. Like, she's so fantastic." And I think I used that line on her. I'm like, " Okay, you've probably like killed people in battle, but you're not leaving this room to till you sign an offer letter." And to me, what I learned from Sean that day was if you see something awesome, just say it. And it's amazing how often we forget to do that. And sometimes people are really smart. You assume like, okay, they know they're smart, so you don't have to tell them. And sometimes people who are really smart don't actually get a lot of positive feedback. So what I try to do is when I see something amazing, I just, I'm very childlike in many ways, but when I see something amazing, I just stop and say, " That was amazing." And if they see that, the things I'm really amazed out of the team interactions more than anything else, in many cases, they'll model themselves after that.

Dave: What'd you got Will?

Will: When you think about hiring anybody, like really talented people want to grow and develop inaudible. And I think a lot of that done on the job, but a lot of it's approaching. How do you think about employee development and growth?

Paul English: So a couple of things. One is, do use the concept of skip manager? Do you know what that is?

Dave: Yeah. I know.

Paul English: So skip managers is your manager's manager. And I think the skip manager has career accountability for people. So that, for those of you who don't check in with your manager's manager, you should because hopefully, and I'm assuming that all the managers here are amazing, just because I'm a huge fan of DC and Elias and others here. And I'm assuming these guys are once again, build a really strong team. But while your manager is looking out for you, your manager's manager by definition is looking the wider set of things every day. They look across departments, not just your department and chatting with them every now about, " How do you think I'm doing, what can I do to impact the company more?" I think is really useful. I also encourage people to learn outside of the company. So I am a big fan of learning from other leaders, bringing people in, sending people out to talk to other companies. I'm always networking to find people who've been at other companies. And I think that if you train your people to do that as well, that helps them sort of chart a course.

Dave: Do you have something that you dig into in the interview process to see if this person is a learner? Do you ask them about things that they're doing?

Paul English: Yeah. Okay, it's not that everyone I hire is a big reader. I'm a big reader. I'm biased towards people that read.

Dave: Me too.

Paul English: So I'll ask like, " What are you reading?" That question intimidates people, probably not as much as it intimidates Sarah Palin, because she probably doesn't know how to read, but sorry. Sorry. I can't believe I went this far without a political comment.

Speaker 2: I know. This is good.

Paul English: But I do-

Dave: Why does that intimidate people? Because most people don't read?

Paul English: I think either they don't read or they think that I want them to talk about some-

Speaker 2: Elite.

Paul English: ...like really elite, really fancy book. And I think that's a good sign of people who are learners. I also ask them for role models outside of their company. I'll ask them who inside the company's inspirational to them and why, but I'll also ask them like who in the industry is inspirational to them and see if they have ever looked outside their company.

Dave: Love it. We'll get everybody. We'll go back, Pete. And then we'll come up.

Pete: If you inaudible some like coaching or handling on ego management, advice on ego. Where my email or interacting inaudible.

Dave: How do you manage your own ego? What's the process for coaching that? That's Pete.

Paul English: Yeah. So there's ego and super ego. There's sense of self and how you relate to other people. And I would just ask for feedback and you don't have to necessarily ask everyone for feedback, because that seems a little weird, but you should pick people to model yourself after here. And I'm not talking about the org chart. So don't necessarily... I don't really care where people are in the org chart. But if there are people here who you think have a good team skills and it could be one of your customer service people just as phenomenal at getting stuff done and getting people to do stuff for them. I have another story about product management about EQ. But track everyone you want to model yourself after and ask them for feedback, like, " How do you think I'm doing?" And I like specifics too, rather than generalities. Always like, " How do you think that meeting went?" Because I think the more specific you are, the easier it is to give direct feedback.

Speaker 2: That's good.

Dave: Do we have a minute for your product manager EQ story?

Paul English: Yeah. I'm an engineer, but I more think of myself as a product manager now more than anything else and particularly focused on design. And I've often tried to coach other people new to PM about what it's like, what you have to do to be successful at PM. And one of the things are like our PMs come to me whining saying, " The engineers didn't do what I asked them to do."

Dave: crosstalk.

Paul English: I'll say that's one of two things. Either your idea was stupid or you have no influencing skills. So what I need to coach you as a PM is one, how to refine your ideas to make sure they fit company goals and to fit what customer needs are. But two, how do you influence engineers? And so I teach them tricks and techniques about how to get engineers, I don't mean to say, to do what you want, because I care what the engineers think about too. But to be a good PM, you have to be able to get people to follow you, and to be a good customer service person, you have to get people to follow you. And a lot of times, customer service people should go walk up to the engineer and say, " When a customer does this and the code does this, that seems really fucked up. Can we fix that? Is there some way to fix that?" And if that customer service people can get engineers to make those fixes, it means it's two things that a customer service person is doing. One is they're really good at problem identification, like discerning important problem versus stupid problem. And the second thing is they have good influencing skills. And those are probably 50/ 50, as far as importance of the company. You need both of those things.

Dave: I love it. Danielle.

Danielle: inaudible. Do you have a favorite book or top three books that have helped your personal growth or personal learning?

Dave: You have to go top three, because that's what the people want. Top three books. Maybe not top three books, give us some books, leave us with some books.

Paul English: I don't know. Just some recent thing. I like Sheryl Sandberg's book. I like reading books about leaders. I liked the Elon Musk book. I thought it was interesting. I have a friend who works for Elon Musk for eight years. So I've learned lessons about him from my friend who worked around him. But it's fun to read about him. Of course, everyone is influenced by the book about Jobs. I think that was not a great book, but there are great stories in that book. And I don't know, I just read biographies a lot.

Dave: When do you read?

Paul English: Usually at night about an hour on a Kindle. And then when I travel incessantly on planes.

Dave: Love it. Alicia, you got something?

Alicia: inaudible.

Dave: How do you maintain culture at early stage company versus big company?

Paul English: So my thing is, culture is not something you write on a wall. I'm kind of glad. I thought there was going to be motivational posters. And I'm trying to go out with no motivational posters.

Speaker 2: Why did you think he's a motivational quote guy?

Paul English: David's actually my favorite people on Twitter. I love his tweets. I don't know where he comes out with this shit.

Speaker 2: Me either.

Paul English: I love, love, love following him on Twitter. But I've always said that culture is not something you write on a wall. Culture is how you're treating people, treating each other every day. And that can be practiced on a two person team or a three person team or a 50 person team. And it's something that you have to be mindful of all the time. So if nothing else, if I were to give someone advice, whether they're working at Wayfair or Drift, and those are two very different companies. But I would give him advice about how to improve the culture at Wayfair, how to move the culture at Drift, I would say just observe interactions and try to figure out how can I be a better teammate and how can I model myself and how I reward and shine a light on people who are doing well? So I just focus on the interactions.

Dave: I have a question for you, then we'll wrap it up, unless we got one more. What's something that you hate doing as a founder and CEO that you still have to do?

Paul English: Anything finance related. I hate micro- managing programmers. Like I get really worked up about product issues, but when we've had the meeting, we fight about stuff, and I like fighting about product, but we have the fight. I leave the room and I trust the engineer to make the right decision. They might go and disagree with me, but I'm not good at following through on... Some people, I have a guy who used to work for me, phenomenal VP of engineering and he never trusted anyone. And he had this crazy system for how to use Gmail with labels. So, when he would send me an email, he would label it and then check back a week later to see if you followed up on that issue. I thought that was a disaster because just created incredible inefficiencies. I think you should trust people. So I'm terrible at detailed follow- through. But part of it is because I don't believe in it. I believe in hiring really good people, have the fight, don't hold back, really speak your mind, and then leave the room and let them decide what to do.

Dave: Love it.

Speaker 2: Great ending. That's a great way to-

Dave: Send us out of here.

Speaker 2: Right. Don't forget everyone in this room we leave six star on Seeking Wisdom. Leave us a rating on Apple Podcast and please check out Lola Travel. What's your URL?

Paul English: Lola. com.

Speaker 2: Lola. com. That's pretty badass. That's one last letter.

Paul English: Yeah, we got five.

Speaker 2: That's pretty good. And check out what they're doing. Follow Paul on Twitter. And don't forget to come to hyper- growth from out group, Seeking Wisdom and where you can meet awesome people. Not as awesome as Paul, but pretty close.

Dave: Thank you, Paul. Let's give it up for Paul. Thank you.

Speaker 2: Thanks a lot.


If you liked this episode, we bet that you’ll love our blog content. blog.drift.com/#subscribe Subscribe to never miss a post & join the 20,000+ other pros committed to getting better every day. ----- Paul English is a serial entrepreneur and philanthropist -- and you probably know him as the founder and CTO of Kayak, which was acquired by Priceline for $1.8 billion (with a B) five months after they went public in 2012. Today he is the founder of Lola, a Boston-based travel service. DC invited Paul over to Drift for a conversation with the team and we recorded it Seeking Wisdom — but it’s not the conversation that you might have expected. Instead of asking Paul about his career and story, we went deep on one topic: people. This episode of Seeking Wisdom is all about hiring. Here’s how you can support Seeking Wisdom if you’re a fan of the podcast: 1. Get your tickets to Hypergrowth using the promo code SEEKINGWISDOM at hypergrowth.drift.com 2. Subscribe on your favorite podcast app. 3. Leave us a five-star review. Here's how: bit.ly/5-Stars-Only.