Prior to Gitlab, Darren was the managing editor at Engadget and the Director of Global Communications at Dolby laboratories. In addition to his in-depth knowledge and expertise in the remote work landscape, Darren also famously holds a Guinness World Record as the planet’s most prolific professional blogger.
Listen to this episode (or read the transcript below) for an inside look into Gitlab, their core values, and what it means to be transparent by default.
1 You have the Guinness World Record as the planet’s most prolific professional blogger, can you expand on holding this title?
I was Managing Editor at Engadget which is a consumer technology publication, and it was really the golden era of tech blogging. I started writing about tech the year before the original iPhone came out and I really fell into my niche. My superpower is distilling information and writing it down really quickly, we were also one of the earliest all remote teams. We had people scattered all over the world, so we were very efficient.
To capture the record, I wrote and published an article every two hours 24/7 365 for four consecutive years. The record was bestowed about four years into my tenure at 17,000 or so articles and 6 million words. It’s up to the 25 30,000 range now and well past 10 million words and the record still stands.
2 Who has been your most memorable boss?
Tim Stevens was my boss at Engadget, and he was by far my most memorable boss. At the time, Engadget almost fell apart, we had almost the entire team left to go from another publication, there were only a handful of us left and we decided that we were going to rebuild it from the ashes and Tim was in lockstep with me on that vision. We were suddenly a startup all over again and being with my manager through that entire trial by fire experience was crystallizing. The magical thing about him was that he was such an empowerer. He recognized my strong suits and my flaws, and he taught me how to harness my energy in a positive way. He let me make mistakes and would always point them out with grace and was always there to be a mentor and help me connect the dots in my career.
3 Is there something that you’ve been great at that you’ve hired for in the past?
For sure. Long-term, project choreography, or anything requiring a Gantt chart. If we’re trying to wrap our heads around a massive six-to-nine-month project where we would need to coordinate dozens of people with a very syncopated list of due dates where things have to happen for another gate to open is something I would much rather give to someone who is in the weeds or someone that thrives on making sure each one of those gates gets lifted at the right time. I thrive on being able to live in that visionary world and it’s amazing when it’s coupled with someone that is very tactical that can make sure things get done.
4 How long did it take you to figure out that you had to partner with someone tactical?
It took forever, maybe even ten years. When I was at Engadget, it was necessary for all of us to be a jack of all trades, so I really found myself being an individual contributor on a lot of very important projects, but I didn’t love it. I would do it, but it would be at the expense of a ton of energy because I was always doing something I wasn’t necessarily called to do. It took me a long time to realize how I could spend my time in a more effective way which wasn’t just to train someone but to hire someone that specifically wants to do the job that has to get done because it won’t be an energy vampire for them.
At GitLab, what has really crystallized for me is that we work in draft, we work in public, and we have an extremely low level of shame. People are always sharing early ideas and asking for input and feedback and that allows people to grab hold of an idea early and run with it. It also means that people can harness their strong suits and run with something that excites them. It’s really been a game-changer for me because I don’t have to spend time wondering if people are working on an idea that speaks to their strong suits.
5 How many synchronous meetings do you end up having in each week or what kind of meetings would you do synchronously?
Before COVID, I did very few synchronous meetings and after COVID, there’s been a huge spotlight on GitLab being an all-remote company, in large part, guiding the world and making this transition so there’s been a lot of opportunity to connect with people synchronously to then scale that knowledge in a big way.
Even now, I try to keep these meetings to less than half of my day. As a leader, I find that my energy starts dropping precipitously and the quality of work and the quality of my mood goes down if I commit more than roughly half of my day to synchronous meetings. Thankfully, we work in a place where people can be honest about that, and they can block time in a way that they can manage their energy.
6 Do you have general guidelines around how async meetings work?
We do, we actually did a three-month project that we’re dubbing Async 3.0, and we have an entire page of our handbook dedicated to it. We essentially list the entire company and ask managers around the company how they’re leveraging async tactics to make their teams more effective. We then collected all of those ideas and shared them to create a sense of cross-team visibility. Which enables us to learn about how other leaders are using asynchronous workflows in a very unique way.
7 Do you have any resources, tips, or tricks for any leaders or managers that are looking to get better at their craft?
I would recommend taking a look into the remote section of the Gitlab handbook that you can download or access through the out-of-office report. Our handbook has lots and lots of resources that may be useful to managers that are trying to wrap their head around managing and leading in a remote world. Additionally, I recommend Coursera where you can search for remote team management courses. A lot of our management training comes from there and it’s completely free and optional to upgrade to a paid certificate at the end.
On a personal level as you’re managing remote or even co-located teams, I try to recommend that people envision themselves as an unblocker rather than a director. It’s important to unblock your direct reports right away so they can run as fast as possible because remote work is all about empowering your people to do their best work.