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Remote Work with Gonçalo Silva, CTO of Doist

During the coronavirus pandemic of 2020, Gonçalo Silva, CTO at Doist, generously offered 15-minute time slots to discuss remote work strategies as a way to help promote and improve remote work globally. I took him up on his offer, and asked him if I could summarize our conversation in a blog post. He graciously agreed, so here’s the condensed version of what we discussed, recreated from my notes and memory.

Q: Do you use or encourage pair programming at Doist?

A: Pair programming at Doist is rare because it requires that both people be at the computer at the same time. Asynchronous communication is primary at the company, because they don’t want to leave people out. They have employees all over the world, and part of building an inclusive culture is ensuring that everyone can work on their own schedule. There are several benefits to pair programming, including knowledge sharing, multiple modes of thinking about a piece of code, and rapid code review. Doist uses other processes to achieve these benefits, including a strong code review process, and keeping pull requests small so they can be thoroughly discussed, analyzed and reasoned about.

Q: What is your approach to mentoring engineers?

A: Doist has an intentional culture of mentoring, where the mentor is proactive about guiding the mentee. They do a 3 month onboarding process, which includes weekly meetings and daily checkins where the mentor seeks to understand “how’s it going?” with the mentee. They also have a monthly block meeting to go over progress and process more formally, to ensure the onboarding is thorough.

Q: Connectivity and support is essential, especially during difficult times like this… where do people connect with others not on their immediate teams?

A: Doist uses their own tool called Twist that they created because they couldn’t find any tools that would suit their fully async communication style. They use it for general interactions, as well as group communication centered around projects. They also use the #general channel as the “watercooler”, where anybody can talk about whatever is on their mind.

Q: So do you have an all-hands type meeting?

A: No, they don’t have any kind of all-hands meetings, again because there’s not a good way to make it fair to everybody. They considered several different strategies for an all-hands, including rotating time zones, recording it for later viewing by people outside of the main time zone, and so on. They came to the conclusion that the drawbacks outweighed the benefits of any kind of synchronous, companywide meeting. Instead, they make company announcements and build culture on Twist, and less commonly, via email.

Q: How do you discern when people are discontent on a remote team, and what strategies do you have to bring them out and address them?

A: Culturally, we all have a habit of emphasizing the good, and diminishing or ignoring the bad. As an example, when you’re having a not-so-good day and a coworker or neighbor asks, “how’s it going?”, we almost automatically answer something like “good, and you?” even though that’s not actually true. To better gauge how people are doing, Doist uses a stoplight check in. They’ll ask something like “is today red, yellow or green?” It’s much easier to respond with a color and start the conversation from there, which helps address issues and needs early on.

The processes and practices at Doist all center around communication. For engineers, it includes the ability to talk to team and other stakeholders, reason through code that you write and how you plan to write it. These skills aren’t innate or automatic, they need deliberate practice. But they are magical in a way, through the power of compounding. As Gonçalo put it, “the more people understand you, the broader effect you can have on others.” Communication isn’t just a tool, it’s the backbone of our ability to be effective at work.

I deeply appreciate Gonçalo offering up his time to strangers like me in an effort to help advance the cause of remote work and the betterment of work relationships in general. Remote work is empowering, liberating, and a much more efficient way to practice our craft so we can help drive technology and humanity forward. The pandemic has forced many people to at least try it for a while, and perhaps with intention and practice more of us can embrace the new future of knowledge work.

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