Gonçalo Silva is CTO at Doist — the bootstrapped, profitable, and globally distributed company behind Todoist and Twist. He’s been working remotely and asynchronously for over a decade and leading distributed teams for most of that time. He loves long-term ambition, asynchronous communication, programming, and cats.

At our CTO Craft Conference, he’ll present on The art of distributed work: Harnessing strengths & mitigating weaknesses for asynchronous success.’

Hi Gonçalo, welcome to the CTO Craft Spotlight Q & A. You’re a day two speaker at CTO Craft Con and CTO at Doist. Can you give us a teaser about what you might share with our audience at the conference?

The puzzling thing about distributed work is that it has been around for centuries. It’s one of the oldest and best-established ways of working, especially for creative work. And yet, unless forced upon by a global pandemic, it has always been uncommon in the tech industry, possibly because it’s a recent industry born during a time when colocated synchronous work was at its peak… and it shows.

In the end, excelling as technology leaders requires us to make sound decisions and leverage all of our tool belts. The way we work is a tool just like any other. Understanding the trade-offs and, most importantly, how to make the most of each is key.

So, how do we adjust? And what do we adjust? Which practices do we need to adopt? Which books should we throw out?

I’ll review some of history’s most interesting lessons, some of Doist’s most interesting lessons, and a couple of personal anecdotes, ultimately aiming to provide the audience with some of the most important pillars that make distributed work work.

In a nutshell, what is your experience of asynchronous communication at work?

I transitioned to working remotely a few years into my career and have practically not worked in person or seen a live chat log since.

First, as a freelancer, primarily using email with multiple clients abroad.

Then, joining Doist’s founding and globally distributed team, using Wedoist and, more recently, Twist. We did try Slack as a sanity check for about a year around 2014-2015, but it became very clear very quickly that it was a significant downgrade to the way we worked and our collective performance. Daily lengthy deep focus sessions allow me to perform at the level I aim to perform, and this is an opportunity that an asynchronous communication culture can uniquely accommodate.

When encouraging or implementing an asynchronous working environment and culture, what criteria should you consider?

Join me on May 9 at 14:00 to learn more!

A small teaser: documentation, transparency, trust, flexibility, autonomy, and a clear vision all triple their importance when working asynchronously effectively.

How can tech leaders ‘sell’ and communicate this style of communication to achieve buy-in from others in the company?

Getting buy-in on asynchronous communication requires a frank conversation.

It’s not an overnight transition, not when done right. Teams need time and effort to shift their culture and their habits, starting with their leadership. The truth is that most companies don’t document ideas, discussions, and decisions nearly often or well enough. They don’t build processes and incentives with full autonomy and independence as core goals. They rely on intense collaboration to perform… including things like daily standups, frequent meetings, and constant interruptions.

All of which are difficult or outright bizarre in a distributed workforce working asynchronously. In the end, asynchronous communication requires a set of habits that don’t come as naturally to the traditional workplace.

But here’s the key idea. All the upsides, like thoughtful communication and more opportunities for deep focus, lead to higher quality work, more throughput, and improved quality of life from flexible work arrangements. This benefits just about every organization. And that’s the pitch: Even if the transition isn’t successful, the organization will be significantly stronger just by giving it an honest go.

Changing the subject completely, please tell us an interesting fact we don’t know about you.

I almost pursued astrophysics instead of computer science. There is something luring about the cosmos that had me conflicted up to the day I had to choose (and beyond). I also almost refused to dive into leadership when I was asked to step into the role.

In fact, I did at first but conceded on a subsequent try. There is something luring about going deeper and deeper into a field over the course of decades that I knew would be difficult if I didn’t constantly focus on it all the time.

Both reminders that we’re all here somewhat accidentally, so we better make the most of it. 🙂

In your opinion, why should someone come to CTO Craft Con?

CTO Craft Con is a much-welcomed in-person manifestation of an otherwise fairly unique community. When or where else will hundreds of CTOs be under the same roof, discussing pertinent issues and opportunities?

What talk are you most interested in hearing?

Tough question! There’s a lot to like on the agenda! If I’m forced to choose one, I might go with Laura’s “Driving positive cultural change through developer insights”, as it’s an area I’ve been meaning to dive deeper into recently.

Finally, can you recommend a book or a podcast that every technology leader should read or listen to about strategy, development, or leadership in general?

I’m a fan of the usual suspects in leadership like Andy Grove’s essential High Output Management or David Marquet’s insightful Turn the Ship Around. I’m also a fan of some heavy hitters in technical leadership, particularly Camille Fournier’s thorough The Manager’s Path.

However, one book that’s not quite as popular in technology leadership circles but has been just as foundational for me is Bill Walsh’s The Score Takes Care of Itself. This book was a revelation when I read it over a decade ago, and its ideas continue to shape my thinking to this day.


We’re proud to announce the launch of CTO Craft Con: London 2024 at the prestigious QEII venue. Grab your tickets now.

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