If You Don’t Know Your Co-Workers, Mix Up the Chairs

This interview with Dennis Crowley, co-founder and chief executive of Foursquare, was conducted and condensed by Adam Bryant.

Q. What are some leadership lessons you’ve learned since you started Foursquare?

A. I learned early on not to feel badly about reaching out for help, and not to feel embarrassed about saying that you’re in over your head. We have a fantastic group of investors, and I’ve always felt comfortable asking for guidance. Early on, everyone in the organization became really comfortable with the idea that if there’s something you can’t do, just talk to someone about it or find someone to help you.

Q. Other things you’ve learned?

A. The importance of overcommunicating. We’ve been working in this space for a long time, and it’s taken me a while to realize that just because I understand things doesn’t mean that everyone else understands them. In our company meetings, I’ll say things that sound repetitive, but you have to do that. You have to make sure that everyone is on the same page.

As the company has grown, I can sometimes start to feel disconnected, and I’ll decide to randomly meet with one person a day, and we’ll go out for a half-hour coffee. You do that for six weeks or so, and then all the channels of communication are open again. People feel like they can come and talk to me. I learn about the things that are troubling them or challenging them, or questions they might have.

I always ask them for feedback, too. “Is there anything that I can do better to make your job easier? Is there anything I can do to make the company better?”

Q. How do you make sure you get honest feedback?

A. We’ve taught people that it’s O.K. to be critical. We try to air all that stuff in public at company meetings, and I think it creates a really healthy environment so that people aren’t running off to a conference room and saying, “I can’t believe we’re doing this.” If you want to talk about that, talk about it in public. That’s one of the things that have made it easier for us to be 120 people and still feel relatively small.

Q. How else has your leadership style evolved?

A. I’ve learned to have more discipline in the way we talk about certain things. I keep a notebook in my pocket and I write down all the stuff we could ever do with Foursquare. I used to go through the process of sharing that with everyone. “As soon as we finish this, we’re going to go on to this, and then we’re going to go on to this. ...” I get really excited talking about that stuff, but for people whose job it is to execute on the current plan, I’ve learned that it can be distracting — as in, “Whoa, I’m supposed to be doing this, but the C.E.O. is really excited about this. Should I do this instead?” So I’ve learned when to bite my tongue about things I’m excited about.

Q. Tell me a bit about the culture of your company.

A. We mix the seats up occasionally so that everyone gets to sit next to other people. And I’ll move my seat around so I’m sitting next to different people. They can ask me questions, and I get to know everyone better.

I started to feel a bit disconnected from our San Francisco office, so we got two big screens with cameras there and here in New York. They’re on all day long, so you just walk by and say: “Hey, Pete, what’s up? Can you get Ben?” It works so well.

Q. You worked at Google for a couple of years. Anything you’ve borrowed from that culture?

A. A lot of it. One of them is this idea of weekly snippets. Every Monday, you send in a bullet list of the stuff you’ve been working on, and the software compiles a list and mails it out to the entire company. So you can quickly scan them to find out the status of a project or what somebody is working on. It gives you a nice general overview of the company. So you follow the people you want to get updates from, but we make sure that everyone automatically gets them from me and our C.O.O. and our head of engineering and our head of product.

When I send out mine, the first heading is, “Things I’m Psyched About,” and the next is, “Things That I’m Not So Psyched About” or “Things I’m Stressed About.”  The next thing is usually a quote of the week — something I heard from one of our investors or maybe overheard from an employee — and then I have my snippets below that.

I’ve been using this system for about a year, and it works out great. I get a lot of feedback from employees. It only takes them a minute or two to read, and it’s like a bird’s-eye view of what I think is going well at the company and areas where I think we could improve. It’s also a good way to start a conversation. So I might write, “Hey, I heard someone say this, and so let me address why we’re thinking about it this way.”

Q. What else is unusual about your culture?

A. We’re pretty critical and self-aware about where we are as a company. We always talk about when the company feels broken — let’s say you have 10 employees, and suddenly you have five more, and the stuff that worked at 10 doesn’t work at 15. So we’ll say, O.K., the company is broken — let’s step back and figure out how to fix it, and it might happen again from 20 to 50, from 50 to 70, whatever the numbers are.

But we’ve been very transparent as an organization about how we’re going to have to change some things. The teams might be too big. Maybe there are too many reviews. There are all these little levers that we can tweak, and that’s how you take something that’s feeling a little bit broken, or not as efficient as it could be, and right it.

And the way we’re self-aware really helps when you get to this stage because you’re not embarrassed to say, “The way we’re doing this is not working right now, and we have to change some stuff.” Then it doesn’t rock the boat when we mention it to the staff. It’s easier because we’ve done it before.