Leading with empathy | Keith Yandell (DoorDash, Uber)

Keep going if you believe in the business is critical, absolutely critical. I mean, we were weeks of runway situation and had been told no by everyone, and it was just Tony's drive really to keep going. And the way he explains it to me is it's just the difference between a founder and a non-founder. Like if you're really a founder, you just have to find a way, you have to keep going, there's no question. And I mean, that's the only advice I can give folks is it only takes one yes, so you've got to keep going.

Definitely as ready as I'm going to be. And those are two good folks to talk to.

Culture. And I'm not one to swear a lot, but after interviewing Ryan Sokol, who's now our VP of Engineering, he was just kind of aloof. He came across as aloof to me, really curt answers, and I just didn't have a great feeling about him. And I pride myself on being able to discern when people are really engaged or not. I went to Tony Shu, who's our founder and CEO, and I said, 'Tony, I think this guy's a jerk. I don't think we want him at the company.' And Tony was great. He said, 'Keith, I want you to just have dinner with him, please, because I got a completely different impression. And if you have dinner with him and you still think he's a jerk, we won't hire him.' So I ended up meeting Ryan down the street. We actually live in the same... He said, 'I'm super embarrassed. What could I do differently? Regardless of how this works out for me in this circumstance, it's just not how I want to be perceived.' And we talked and joked about the things he had done, and he kind of told me the background for how he reacted or why he reacted the way he did. By the end of the dinner, we ended up staying super late, we had a couple beers afterwards. Ryan and I have become really good friends. And like six months later, he told me that one of the reasons why he joined DoorDash was that we were going to blackball him potentially from joining just because of his attitude. Because his perspective is life's too short to work with people you don't really enjoy, and a lot of people pay lip service. And he knew he was going to be a tough hire for us at the time... If someone really was a jerk, they probably wouldn't have taken it very well, right? It's just like when you're interviewing someone, giving them tough feedback after the interview, if there's an area of concern but you otherwise liked them, can be a really great way to see how they would interact with you personally as well as how they take feedback. So that was my learning from this situation: if you really enjoy an interview except for maybe something on the culture side, give the direct feedback and see how people engage.

Any time with our founder Tony Shu, you realize that he's a humble leader, he's competitive, he really wants to win, and he'll do whatever it takes to win. And the example you're referring to, I think, is when we raised our Series D funding, which was a really tough fundraise for us. We had very little runway left, we almost went out of business. And it was a huge relief when we had finally gotten the funding secured. I remember I was in a meeting, I was running policy and communications among other things at the time, and I was in the meeting with a couple other folks and we were talking about the press release strategy. Tony was there, and someone ran down and got some... He put together the champagne flutes, and he called the other two co-founders, Andy Fang and Stanley Tang. They came and stayed up all night, put together I don't know, 500 plastic champagne flutes for this cheap champagne, and let the people who are closest to the problem try to work out the pieces. And I do think that's one great example of the culture. The other thing I think that really exemplified DoorDash's culture is a level of customer obsession, and that manifests in a few different ways. We have a program called WeDash where four times a year all employees are required to go do deliveries. And I love doing it, I do it more than four times a year, and I usually take my daughters with me. One time I was out with my daughter who was eight at the time... The customer it didn't make sense for us as drivers, and she'd gotten to know Tony over the years. And she said, 'I really want to call Tony and tell him this thing's broken.' I said, 'Honey, I like my job. I'd like to keep my job. Can we not call Tony right now?' But she was adamant, and I was so proud of her for feeling so strongly that she wanted to fix this thing that was broken. I figured he's not going to answer anyway, we can just call him. So I call, Tony picks up on the first ring, and I'm like, 'Oh, this might go badly.' And she just lays into him. She said, 'This is going to take us 36 minutes to drop off. The coffee's not gonna be hot. How could you allow this experience if you really care about your customers?' I kind of sucked in my breath and said, 'Well, that's how my time at DoorDash...' One of the most insightful pieces of feedback I've gotten recently, and you've only been dashing for like a few different times. By the time we got home, he'd actually sent an email out to the product organization calling out the problems, suggesting the fix, and they were already working on it. And that shows the bias to action that I think really is at the heart of DoorDash alongside that customer obsession. And it's not unusual for Tony to do customer support. It wasn't like just because he heard this from my daughter that he actioned it. He does support every day, and again, this goes back to that level of humility and companies really taking on the ethos of their founder.

It's a good point that not everyone is able for a host of reasons at DoorDash to do it, and so there are alternatives. So you can do customer support, for example, in lieu of actually going and doing deliveries. It's just about making people have empathy and get closer to the product. It's also going back to the culture point, it's a great way to weed out people that maybe we wouldn't want to work with, right? Because not everyone wants to... not every software engineer wants to hop in their Tesla and go out and deliver McDonald's to some kids, right? It takes a certain level of humility, a certain amount of customer obsession to even sign up for that. So we're really vocal during the interview process that this is something that's... Did a much worse job, I think we're doing much better now. Nice. And Airbnb was always... something okay.

This is a good one, and I had massive imposter syndrome the first time Tony asked me to take on something that I wasn't a subject matter expert in. And I told him I didn't want to do it, and he had me read this book called 'Range' by David Epstein. And the general thesis is that generalists are better than specialists, and it goes through all these examples about how Nobel Prize winners are usually amazing in something other than the field that they actually win the Nobel Prize in. Tony believes pretty deeply in this philosophy, and the way he explained it to me is as follows: if you want to achieve a 10x outcome, hiring someone that's an expert in the field, it's maybe unlikely you're going to achieve that 10x outcome because they're likely to do things the way things have always been done. So you might achieve... What I did was believe that I could add value here. And then the second thing for me was to go out and find the best people that really were the subject matter experts and add the value I could to help them be successful. And I found that they were actually really attracted to wanting to work with someone like me who came into the interview process and said, 'Good news, bad news: I don't know your field anywhere near as well as you do. Here's the ways I intend to help you, here's what I think you can provide, and at the end of the day I'm going to get out of your way.' And that's really proven true. So I ran marketing, hired initially a brand person, Kofi, who now is our CMO; hired ahead of legal, who's now our GC, Tia Sheringham.

Yeah, 100%. I run a 12-person org today, so I've gone from running 1500 people in the company to 12. And for me, people talk a lot about hiring people better than you are. People don't talk a lot about what you do when you hire those people. And if you really care about the company and your long-term brand as an individual, as a manager, you realize what you want to do when you find the person that's better than you is you want to slowly get out of the way. And it's really good for the company. It's my favorite part of my job is... That comes from the fact when I joined DoorDash, we were getting our tails kicked. We were in fourth place in the space. Uber had just launched food and rocketed to market share leadership. And I think that was really good for us as a company because we realized unless we all work together and it wasn't about who was doing what or things like that, we weren't going to have a shot at being successful. And I think that ethos has really pervaded and persisted since then.

Yeah, I mean the category chart I've seen is consistent with what you said. By a lot... Hard. You try, and we read those experiences. We do customer support and we understand that there's a long ways to go, so we're just getting started and we know that.

One thing I've learned is it's super hard to scale culture, especially when you're growing as fast as DoorDash has since I joined. We were 2-3, exiting the company from a headcount perspective for... And one thing that Tony taught me is one thing that scales really well is written work product. So I put together this document. There's three basic subject matters: it's kind of my expectations slash what I've seen as traits in successful people within the company; two, how I can improve, like basically feedback I've given and gotten and things I'm working on. For example, I'm a litigator by training, so I tend to argue about things even if I agree with people to test levels of conviction. And I got feedback from my team that was really confusing because I'd be arguing against something and then we would execute that exact thing. So I try to be transparent about that and explain how I work through problems, but also in... That's not at DoorDash. Life's too short to be in a job you don't like. Things like that.