Maintaining Culture Through Hyper Growth with Chad Dickerson

Intro: Welcome to The Daily Bolster. Each day we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Welcome to The Daily Bolster. I'm Matt Blumberg, co- founder and CEO of Bolster, and I'm here today with my friend Chad Dickerson. Chad was a relatively early employee at Etsy, who became CEO of Etsy, scaled the business and took it public. He is now an executive coach, working with CEOs and other senior executives, mostly in New York and in the tech area, but I think broader than that as well. Chad, welcome to Daily Bolster.

Chad Dickerson: Glad to be here, Matt.

Matt Blumberg: I was very excited to ask you a specific question today because you were at a company that scaled a lot while you were there. I'm thinking from like 50 or a hundred employees to close to a thousand over your tenure, right?

Chad Dickerson: Yeah, 40 to a thousand.

Matt Blumberg: 40 to a thousand, okay. That's considerable so-

Chad Dickerson: Yeah, close.

Matt Blumberg: The question I have, and our audience is mostly CEOs, some senior executives, is how did you stay close to employees with that kind of growth? So being connected to the team is so important for so many of us. What are your top three tips for doing that as you scale?

Chad Dickerson: Yeah, as you said, I saw a lot as we grew from 40 to a thousand. So three key ways, and I think pretty much everyone can adopt these. The first is random skip levels. I encountered this kind of randomly myself. An engineer inside Etsy inaudible built a tool called Manager Mixer where you would get matched with a random manager in the company every week, and no one expected me to opt in as CEO, but I did. And over the course of a couple years, I would say on average, I did like 40 to 45 skip levels, and I learned so much about how the company worked.

Matt Blumberg: Totally. So all level, all levels?

Chad Dickerson: All levels.

Matt Blumberg: And like 15 minutes?

Chad Dickerson: Mostly managers. 30 minutes. Some people were really excited to talk to me, others were shaking.

Matt Blumberg: Who would be scared to talk to you, Chad?

Chad Dickerson: I know, but maybe it's because, some of the data that I gathered actually made major decisions in aggregate. So reorgs how different teams were doing and super, super helpful. And I think having the people who didn't opt in to talk to me and the people who maybe even at first were a little afraid kind of corrected for the problem that you have in large companies when you have some people who speak pretty loudly and others who don't.

Matt Blumberg: That's great. All right. What's number two?

Chad Dickerson: Yeah, number two is to do an AMA, ask me anything session. All hands that is separate from your all hands meetings. I started-

Matt Blumberg: So just like open mic night?

Chad Dickerson: Open mic. And I started doing that at Etsy because I felt like there were always things that we didn't get a chance to cover in the all hands meetings. And when you frame the discussion, the all hands meetings and you do Q and A at the end, a lot of times people want to ask questions about those things. So I found the AMA that was completely separate to be kind of like a pressure release valve. It allowed me to be a little less formal in what I was talking about. And we did an engagement survey after the first year of doing that. There was no question about that particular weekly event, but in the verbatims, it was mentioned dozens of times.

Matt Blumberg: That's great. Yeah. And presumably vary that up if you have multi- locations and you're varying up time zones and where you physically are to get you in front of more people?

Chad Dickerson: Yeah, absolutely. And it became kind of a tradition and people asked me hard questions. And there was a time when, for example, an announcement went out that Amazon was launching a direct competitor against Etsy, and I didn't want to call an all hands to talk about it because we weren't competitively worried, but it was a good chance in that AMA to talk about it with the team and tell them why I wasn't worried.

Matt Blumberg: Yeah, that's great. Okay. And what about number three?

Chad Dickerson: Number three is participate in social channels. I think for a lot of CEOs, especially CEOs who are maybe not Gen Z, millennial, the idea of doing emojis with back flips and smiles and everything in Slack might seem a little kind of beneath the office, but I think especially with distributed teams, it's really important that CEOs participate where communication is happening. And so I think you can use that not just for strategic pronouncements. A lot of that will happen in different channels, but I think you can do that to wish people happy birthday or pass along piece of news or even just put a smile emoji next to something interesting or insightful that someone said there.

Matt Blumberg: Well, one thing I have learned over the years as a servant leader or practice of servant leadership, practitioner of servant leadership is there is nothing beneath the office.

Chad Dickerson: I totally agree.

Matt Blumberg: All right, and on that note, thank you for being here. Will you come back and do one of the longer form ones next time around?

Chad Dickerson: Absolutely. Anytime.

Matt Blumberg: All right. Thanks, Chad.

Chad Dickerson: Thanks, Matt.