A name so synonymous with radical tech leadership, he hardly needs an introduction. But we’re going to anyway, because we’re incredibly excited that none other than Jason Warner – CTO at GitHub – is giving a keynote talk at our forthcoming conference CTO Craft Con: The People One on 1-3 December. And we’re extra chuffed that he sat down with us in the middle of moving house to give us a snippet of his insights on all things distributed teams, remote working tools and an endless supply of books.

Hi Jason, thanks so much for joining me today! Apart from moving, what’s keeping you busy at the moment?

Everything in general around what the future of software will look like. I go to bed thinking about developers and wake up thinking about what they’re going to need not just today and tomorrow but what they need in the future. I’m constantly on the hunt because, you know, inventing the future doesn’t look like we think it does in the movies. It’s not just sitting here pontificating on something and then bringing something new out. Mostly it’s an aggregation game of figuring out all of those different signals that are happening in the world, and then trying to piece them together like one large puzzle. We have to say this is what we think this puzzle will look like when it’s complete in five years. That’s the game. That’s what I do on a regular basis. I’m really thinking about what is going to happen for developers in three-to-five years’ time.

Wow, busy! So tell me a leadership lesson you’ve learned this year?

Github has been distributed for a while, so a lot of the things other companies might have had to go through, we didn’t have to. However, there was one large change. I have never lived in San Francisco [where GitHub is headquartered]  – I’ve been a distributed executive for over a decade at this point, but I’m one of the few. And the biggest change was for GitHub executive leadership who have never worked remotely before. It really highlights the differences between onsite and remote working: there are things that you can do in the office that allow you to bypass good company hygiene – things that you cannot get away with when you are fully distributed. From a leadership perspective, we’ve all realised there are certain fundamental things that we were only doing half-heartedly and we had to do more of those things. The core of those things is communication: writing down our long-term objectives and ruthlessly focusing on our priorities, and then putting together a process that allows those things to become visible.

What’s the best leadership book you’ve read this year?

There’s a couple I like, the first is Jocko Willink’s Extreme Ownership. You don’t need to read the whole book – it’s not one of those – but it is all about taking ownership. While it’s something that I have personally always done in my life, I’ve never really understood the broader concept in organisations [until reading it] and I think it’s a great read. 

The second is The Inner Game of Tennis: The Ultimate Guide to the Mental Side of Peak by W. Timothy Gallwey, that I saw someone recommend on Twitter. I really like it. It’s very similar to The Score Takes Care of Itself by Bill Walsh, which is a very famous Silicon Valley-applicable book which I also love. 

The Atomic Habits by James Clear is also very famous these days. I happened to meet James earlier this year because we were living in the same area and I got to hang out with him for a couple hours; it was fun. So I always plug that one whenever I can.

And finally, Creativity Inc, which is the famous book about Pixar and that was just a fun read. There’s a lot of lessons you can take away from these books and that may not be tangentially, or directly related to leadership, but that’s just another thing I like about them.

What is your top tip for goal setting in 2021?

I could go a lot of different directions with this one but I think it’s actually rather consistent year-on-year, which is to write down your long-term plan first; three to five years, or what I like to call the ‘In the fullness of time’ plan. So, in the fullness of time X company should do Y for… And if you understand what that looks like when you’re successful, you’re off to a good start. If you don’t have that you’re basically sailing to unknown territory; you don’t know whether to go north, or south. And that’s a non-negotiable. If you don’t have that, then do it. 

If you do have it then the really critical thing for goal-setting for the next year is to understand that 10 things are not going to get done and your plans will change. So you need to understand what the three most important things to achieve this year are, from a hiring/product/revenue/retention/progress perspective. And then you also need to understand that 2021 is likely to look a lot like 2020, so temper your expectations and don’t assume that people are going to be 100% capacity for 2021 either.

That’s brilliant, thank you and finally, what’s your top tip for remote team building?

That you need the right tools for the job! Everyone wants to talk about tools when it comes to remote teams, and do have them, but Slack is not the number one tool you need to get right, for what it’s worth. I believe Slack is one of the more destructive remote team tools, to be clear.  I want to say out loud that synchronous communication in a remote environment is actually destructive for people’s productivity; you need async tools. 

Going back to my earlier point which is communication, if you can do nothing other than understand what your calendar looks like as a construct, understand what you do every year, every quarter, every month, every week and every day from a company perspective – I call that the rhythm of the business – you’re well off. Understand: what are we doing this year, what are we doing this quarter, who is doing it and is there progress? I call that the Corporate Communication V. The CEO needs to be able to articulate what is happening and an individual engineer or marketeer or salesperson needs to know what they’re doing that day to achieve those objectives, and then it needs a progress status back up to the CEO. If you can do that, and close the gap between the vertices of the V, you’re a good company, if the vertices of the V are too wide, you’re a bad company. It’s pretty simple when you say it, but it’s not until you experienced it for a decade that you understand what that looks like.

Thank you so much, Jason!


Catch Jason and some incredible other speakers at our forthcoming CTO Craft Con 2020: The People One on 1 – 3 December.

Find out more and get your tickets here!

If you or your CTO / technology lead would benefit from any of the services offered by the CTO Craft community, use the Contact Us button at the top or email us here and we’ll be in touch!

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