Cate is currently the Engineering Director of Mobile at DuckDuckGo and prior to this role, Cate was the Head of Developer Experience at Automattic, the Director of Mobile Engineering at Ride.com, and a Software Engineer at Google.

Cate’s diverse experience has brought her all over the world, working from places like China, Colombia, Canada, the US, and Australia. Listen to this episode (or read the transcript below) to learn how you can leverage asynchronous communication to thrive in a remote environment.

1 How did you get interested in the world of remote work?

I was nomadic for about three years and before that I was moving all over the place. I lived in Canada and in Australia and I went fully nomadic after I left Google, splitting my time between South America and Europe and my first management job was in Colombia. When it came time to start looking for my next job, Matt Mullenweg automatically reached out to me and then I ended up at Automattic, which has obviously been fully distributed from the get-go.

2 Was it easy to adjust to the way Automattic was operating?

It was super natural. One thing to understand about Automattic and this is also true about DuckDuckGo, is that it was built on this premise of open-source software, and this is how open-source communities work and how they’ve always worked. You accept a little bit of chaos and there’s an acceptance of text-based medium because there’s a need to document everything because people come and go in an open-source community. When you build companies on top of those open-source principles, it makes a lot of sense.

3 Who has been your favorite or most memorable boss?

I reported to my friend most of the time at Automattic which was obviously an intense learning experience. Additionally, if you report to the CEO, you learn to manage really well and you also learn how to meet your own needs because they have a really hard job, and they may not have time for you. I had a coach that I’ve worked with since I was at Ride which has been really helpful to give me a sense of continuity when I can’t necessarily get it from the people above me.

My most memorable manager was probably my worst manager and when I became a manager, I thought about him a lot. I know that I didn’t want to be anything like him, and it helped give me a much clearer direction of what a bad manager looked like which helped me really understand the importance of understanding and defining myself.

4 Do you think authenticity is a spectrum of discovery?

For sure, and especially right now because everyone’s priorities have fundamentally changed. Who I am authentically as a manager in a pandemic is very different from who I was authentically as a manager when I was nomadic.

5 What did the harmful manager that you had do? What is something that people should try to avoid?

The biggest thing was gaslighting and not delivering or having no accountability. There were major deadlines that nobody talked about. It got so bad at one point that we got fired by the internal client at Google and you had to be performing really poorly for it to get to that point. I really wanted to believe he was doing a good job because it was so early in my career, and I wanted to respect my manager but I literally couldn’t.

6 What were some of the early mistakes you made when you were just starting out?

Something that I took from one early experience was the lesson of always interviewing my managers or telling everyone that I interview that they should interview whoever is interviewing them. Asking people that were potentially going to be my managers all kinds of questions really taught me a lot and I always encourage people to do the same.

7 What kind of interview questions should people ask their managers? 

Well, first, people need to decide what they care about. When I joined DuckDuckGo, I really wanted to get back to working on a product team so I could deliver a product that was really important to me, and I also really wanted to have a manager and peers that I could learn from. There were obviously red flags that could easily have been deal-breakers for me, but I looked the other way because there were other things that they had that were really important to me.

8 What is an asynchronous meeting and what kind of meetings can be asynchronous?

Any meeting that is boring should be asynchronous because zoom meetings are exhausting. Before, you could put people in a conference room and if a meeting was going to be particularly boring, you could give them some doughnuts or something, but you can’t do that anymore because everything is online. Boring meetings are a major source of negative energy and they’re draining which is why it’s so important to get rid of them right now.

9 If a meeting is asynchronous, how do you truly know that you’ve read and consumed it?

I realized that my likes are important to people and it’s one of the powers I have in my position, so I make a point of liking things and going the extra mile, and adding a genuine comment if someone has really put a lot of work into something. I also like to ask a question because it shows that you’ve read the content and really absorbed it. It also models that behavior and encourages other people to do the same. I also send a lot of private compliments and I make sure that I follow up with some kind of validation, both publicly and privately so people know that it’s real and authentic.

10 Do you think people can bond in a remote setting through a static meeting?

We’ve been adjusting our team call to run experiments so we’ve been trying to adjust and approach things with the expectation that some things will fail, and some things will need to be adjusted. One of our major areas of focus has been team cohesion because there are so many people on our team that haven’t actually met each other and we’re always hiring more so we’ve started a watercooler chat where everyone can get together and chit chat. We like to start every one of those meetings with something called feelings of the time which essentially means that everyone starts out by talking about how they feel and what’s currently going on in their lives.

11 Can you elaborate on the process of providing people with feedback during the hiring process?

Companies often provide candidates with projects or request samples because doing so is extremely unbiased when looking for a candidate to hire because you know you’re looking for certain skills and we started to evaluate these projects or samples and provide feedback. I’ve noticed that people that I’ve given really blunt, honest feedback to are the people that have gone on to really excel.

12 Do you have any words of wisdom or resources for leaders or managers that are looking to improve their craft?

The simplest thing I can suggest is to get a coach and also to really five deep into every situation and determine what you learned from the outcome. Another piece of advice would be to write and be honest about the situations that you’ve been in so you can really dive into what you learned from the entire scenario. The more you find yourself in positions of power the less you will get valuable feedback so it’s really important that you work on self-reflection and learn about implicit feedback.