Effective Remote Work with James Stanier, Author and Director of Engineering at Shopify

Published on Feb 27, 2022

17 min read

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In this episode, I speak with James Stanier, Author and Director of Engineering at Shopify. We talk about working remotely, various best practices, team building, valuable resources for working remotely, how hiring has changed, and his new book Effective Remote Work. In addition, James offers advice for managers who are just starting out. You will also learn how James manages his time and a book recommendation for engineering leaders.

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Transcript

[00:00] Vidal: All right. So good morning today. I have with me James Stanier. He’s a director of Engineering at Shopify. Welcome to ManagersClub.

[00:10] James: Hey, thank you for having me.

[00:11] Vidal: Thanks for coming back on. I know that I interviewed you back in 2017 (see Interview with Dr. James Stanier, VP Engineering at Brandwatch), and James you’ve recently written a book on remote work.

Like such a timely topic. And so I was wondering, in researching the book and writing it where there may be some surprising things that you learned yourself about working remotely or working remotely the last couple of years?

[00:34] James: Yeah. It’s interesting like this my second book. So the first book that I wrote was about engineering management and that’s something I felt really experienced in. I’d done it for many years. And the book came from a place of knowledge, I think, but I think the second book, which is called Effective Remote Work came from a place of discovery and I think a place of trying to figure it out. And I think I’ve always learned by writing.

And I know that going to a publisher and saying, Hey, I’ve not figured this all out yet. Can I write a book on it? It’s probably not the best strategy, but that was partially why I really wanted to write this book because I felt that the pandemic forced everyone to go remote. It forced many companies to change their policies on remote working. And it very much felt like we’d reached a tipping point that this was going to be important for the future.

Be sure for people to understand these skills, but really it came from a place of figuring this out in my own job at the time. And also from life experience in the, we did a fairly significant move across the country to a fairly remote location to be narrowed of all family who are getting a lot older now, both sets of parents.

So it was a combination of things that were happening in my life, things that were happening in work and things that were happening, with the pandemic that led to this book being created. And yeah, I’m really pleased that I did. It feels like it’s solidified. A lot of the things I’ve learned a lot of things I want to do more of in the future, for sure.

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How is working a company that’s fully remote?

[01:54] Vidal: Great. So Shopify is a fully remote company and I think a lot of companies are wanting to be that way or maybe move that way. Could you maybe say a few words? Like how is that working at a company that’s fully remote?

[02:09] James: Yeah, that’s a good question. So Shopify went fully remote about one month after the pandemic.

So I didn’t work there at the time. I’m newer than that, but yeah, Toby made the decision to make that change to stop the leases on the offices to be fully remote, to fund people to have the home setups that they need and the equipment they need at home. And what’s interesting now that we’re coming out of the pandemic is, and hopefully, in the future, when people listen to this, the pandemic is no longer a thing and it’s endemic and we’re just living with it.

But fully remote is not a solved problem. We have decades of knowledge of how to work co-located and offices, we have communication patterns and collaboration habits that you have to do very mindfully differently in a remote world. And certainly, you can’t change physics. The fact that somebody is on a California time zone and someone is in Germany, you can’t bring them together in any way that there are laws that are acting against you.

So I think good remote work is around like really good mindful communication practices. It’s about sharing within teams with outside the teams of how things are progressing and how they’re doing increasing discoverability of information. . But fundamentally at a team level, there still is a lot of synchronous work that has to be done and people have to be online at the same time.

They have to be able to talk. They have to be able to meet. So it’s a shift from synchronous to asynchronous and filling in the gaps in between it.

[03:38] Vidal: Yeah. I remember reading that in your book, you have the spectrum of the synchronous and asynchronous communication methods, and then you also discuss the different kinds of artifacts.

What do engineering managers either misunderstand or have the most trouble adapting to in working remotely?

So I think that’s really interesting. What is something perhaps that engineering managers either misunderstand or have the most trouble adapting to in working remotely?

[03:58] James: Yeah, that’s a good question. So I think one, you have to set yourself up for success. So what we’re trying to do here is make sure that people within the teams are within plus or minus a few hours time zone of each other, because going completely remote and deciding that people can be anywhere in the world on any time zone on any team might work for some individuals, but a majority of people find that really challenging. So certainly set yourself up for success to make sure that you can talk to each other on a short term notice if you need to in your day to day activities and then have more of an asynchronous interaction with people that you talk to less frequently to say outside the team, your division, your department, and so on.

I think also going back to management in general. I know a lot of new managers find it really hard to begin to relinquish control and delegate more and trust more. And that’s a, we’ve been hard enough to do just in the office even when you can see people and you can see what they’re working on, but doing it in a remote world, especially for new managers is even harder because they can’t see the stuff.

They can’t see what people are working on all over the world at any given time. So really getting comfortable with letting go, comfortable with delegation, and putting in the right practices to make sure that everyone’s informed on a basis that’s enough for the team. So they can feel comfortable with their progress is being made.

[05:17] Vidal: I think that’s a great point. Yeah. It’s a more high trust environment you have to have, right. Cause you have to relinquish control. You’re not there. Let me ask you this. So one challenge I find has to do with team building. So since people are dispersed and they’re not all together I’ve been doing some online team building with my teams.

What are some best practices for remote team building?

Like we play some games, sometimes we’ve done some online experiences, but I’m curious, what have you found are some best practices on doing team building?

[05:45] James: So I don’t have too much more to give other than what you’ve already suggested in terms of online team building. I think it’s never the complete thing. I think no matter how much metaverse we have in our lives, in the future, we are social creatures as human beings, regardless of how introverted or extroverted we are. And just being able to get together, but various points during the year, if you can, is probably the best team building that you can still ever do. That is how us humans have evolved, tribal collective nature of human beings.

group of people wearing shirts spelled team

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So certainly, yes, we can all play virtual billiards every two weeks or play virtual chess or whatever fine, but it doesn’t replace things. So I think sporadic virtual meetings with your team, creating the space in your calendars to do fun things online, Pictionary so on are great. But I think the really important thing and the thing that requires, influence and buy-in from people who are leading the company, it’s like, how can a team if they want to get together once a quarter to spend some time and not to spend some time sitting next to each other programming because they do that all the time anyway, but get together to do some team building, get to know each other, discover more about each other and put a human to the avatar that they see on Slack every day.

Tools or resources useful in working remotely

[07:01] Vidal: Are there any tools or resources you might recommend that you found really useful in working remotely?

[07:10] James: Sure. One, I really liked just because I’m a visual person is Miro and there are plenty of others, like remote drawing tools that are useful. But I think people often think that asynchronous means written and that’s it, there’s no other asynchronous communication method other than writing humongous messages and emails and yes, there’s a time and a place for writing for sure.

But there are also plenty of other tools. Pages and pages of texts can be replaced by one really excellent diagram. And remember boxes and arrows are still super useful. Use them. Also recording video tools like Loom, or even just, recording your own zoom meeting or Google meet as a way of asynchronously communicating information in a way that doesn’t require writing pages of text is also really useful.

Cause I know that personally, I really like writing, but then I’ve done quite a lot of it, so I can do it quite quickly. But for people who maybe English, isn’t their first language. For people who may be just not great writers in the first place, all of these other messages of communication, are just as good and often.

How has hiring changed working remotely?

[08:11] Vidal: I think that’s a good point. Yeah. Because it’s easy to default to just writing. So you’re trying to use these other mediums. What is your approach to hiring these days and has it changed, in the new environment?

[08:24] James: That’s a good question. So I guess, my approach to hiring is now Shopify’s approach to hiring and we are hiring a lot of people.

We’re going through a really big growth phase. So we’re hiring from all teams in all parts of the world at quite a rapid pace. And certainly, one thing we are doing differently is the engineering leaders at Shopify do spend active time sourcing as well. So typically, you’d imagine that the engineers and engineering managers are getting involved in the interviews, but like one thing that I know, I’m spending time doing.

It’s a hot jobs market at the moment. Everyone’s hiring compensation is going through the roof everywhere, which is a great time to be looking for a job, so that’s fantastic. However, it does mean that if you are hiring the competition is quite fierce and it’s hard to stand out. Often everyone on the job market, and even people who aren’t getting so much inbound that they don’t even need to look for a job it’s just coming to them.

So yeah, one of the things that I do is I do spend, a good portion of my time every week looking through LinkedIn with recruiter access finding people that I think look great fits for us, spending, especially time on diverse candidates to make sure that we’re getting in touch with them saying that we’re here telling them what we’re doing.

And then just offering my time, just allow people to very easily book 30 minutes in my calendar for a chat. Completely, no pressure from my side, but just to say, Hey, like we have. I’ve talked to you about what it’s like to work for Shopify and some of the things that we’re doing. And it’s a long game.

It takes time, often you might have someone say, Hey, I’m not looking right now, maybe later in the year, but planting those seeds and then over time, I think it does definitely yield.

[09:59] Vidal: Okay. You have a lot of experience as an engineering leader. And you even wrote a book on engineering management.

What advice would you have for managers who are just starting out?

So a lot of people who listen or read managers club, maybe they’re new managers or they want to get into management. What advice would you have for managers who are just starting out at the very beginning of their careers?

[10:20] James: Yeah, that’s a good question. So something that I had as, as a tool when I made the switch which I think often people might not know is available to them unless they ask, but going from an individual contributor to a manager, it is different.

Yes, it has the same scaffolding underneath it. It still has technology and people and building things for sure, but the job is different. And going into the industry, people have often done education courses, boot camps in order to get good at programming and computer science in general. But they often go into management without having had the same amount of time learning those subjects.

So it’s a lot of what you can read a lot of what you can discover on the internet. So you might not actually know that you like it until you do it. That’s the main problem. So I think something that’s a really good idea is if you do have the opportunity to be promoted into a leadership role, to be an engineering manager at your company, do discuss with your manager if there is the possibility of having some kind of safety net if you don’t like it.

So setting some goals between you and your manager to say, Hey, like, why don’t we come up with a 30, 60, 90-day plan of if I’m going to do this role, here’s what I’d like to see if I’m going to be successful. And what, if we get to the end of the 90 days, And either I’m not performing as well as I want to be, or I just don’t even like doing it.

It’s not for me then I can just very safely and without any kind of shame, just go straight back to doing the IC role, because I think that takes a lot of the pressure off and some people sometimes either find themselves stuck. and worried that they’re going to get fired because they don’t want to do the job or they’re going to have to leave because they’ve painted themselves into a corner they can’t get out of it. I think a safety net is a really good thing to discuss.

[12:08] Vidal: I think that’s great. So like trying out management for 90 days and seeing, some people who become managers and they’ve actually gone back to being ICS because once they have the job, they realize it’s a totally different job.

What’s your workday like and how do you manage your time, emails, calendar, etc.?

And maybe it’s not the one I want. So you’ve written two books, which I know takes a lot of time because I’ve written some books too. It’s a lot of time plus you are a director of engineering. How do you find time to do these things? How do you manage your time emails, all the stuff you have to do?

[12:36] James: Yeah, with difficulty. Both books were written in either early mornings or late nights or weekends. There’s no shortcut about it. You’ve put the hours in. But fundamentally the books came from a place of passion. So you don’t mind spending the time. When it comes to sitting with a day and just general time management I do have to be very strict with myself and in terms of the calendar. I block out my time.

One thing I’m doing a lot more now is blocking out space in my calendar that people can’t touch for me in order to progress on all the sorts of things that are still the IC parts of management. So for me, I wrote a lot of things that are the future and strategy and thoughts of how we can make things better.

white paper with note

Photo by Bich Tran on Pexels.com

And definitely, advice for managers that are slowly finding that their calendar just becomes like a salad of all these different meetings is to block out time for themselves to make sure they progress on the things they want. You just have to accept also that some days you will try and get three or four things done that are really important and something happens, you get none of them done, but you have to be in it for the long term. Three months, six months, nine months, 12 months, you can do a lot if you’re just consistent every day.

What’s a personal habit that contributes to your success?

[13:43] Vidal: What would you say? Is it a personal habit that contributes to your success, James?

[13:49] James: Before this interview, we would go when I answered this by email in 2017, I said like a deep dissatisfaction with my own performance or something.

I think there are still parts of that that are still true. I am a very competitive person, but mostly with myself. I have quite a high bar for myself and things I want to do. Not in terms of things I want to achieve, or just a sort of quality of output or quality of doing a good job. I think it’s really important as a work ethic.

So that definitely helps. That definitely helps. But I think now it’s more to do with trying to every week think of two or three big rocks that I want to move in terms of my work and then as long as I get those done by the end of the week, I’m happy. That gives me flexibility if things are happening throughout the day.

And then the really important things as well as making sure that I have a lot of time away from the computer, relaxing, doing things, my family and so on. I always try and exercise every day. We walk the dog together twice a day, make sure that we’re cooking anything together every evening.

And even though, it’s very easy to keep getting pulled into work. Your work suffers if you do too much of it. So making sure that those boundaries are clear and as of the last year or so, I don’t have work email on my phone and I don’t have anything like that. So I keep it away in the evenings to make sure that I’m in it for the long run. I don’t burn out with time.

If you could recommend one book to managers, what would it be and why?

[15:06] Vidal: I think that’s great advice. I think that’s one of the challenges people have to now working from home is they’re easy to blur work and home. So just give me a really crisp boundary. James, besides the two excellent books that you’ve written if you could recommend one book to managers, what would it be and why?

[15:26] James: So the book I recommend is The Staff Engineer. So this is fairly new. I think it’s a staffeng.com is the site. So the reason that I would recommend that book to managers, even though it’s a book about the higher levels of the IC track is that managers are in a great position to champion the progress of their ICS and also companies that maybe have put less thought into the IC track to really proactively champion staff engineering positions, principal engineer positions, because this is what we have in larger tech companies.

There’s really great IC progression, but it’s something I’ve noticed in smaller companies that haven’t really thought about it. And you get a lot of really fantastic engineers, but end up leaving to go and get job title progression elsewhere when maybe they’re already doing that.

But the progression framework. And also, more importantly, the compensation framework that comes along with those promotion steps just isn’t in place. So understanding what the top of the IC track is all about is really important. And I think if, over the last 10 years, we’ve had a great collection of management books in engineering coming out.

I think we’re beginning to see a great sort of selection of IC-related books. I think staff eng is fantastic. It would be brilliant if someone could break principal eng at some point, an equivalent book because it demystifies these parts of the track. And also it gives ICS a really clear guide as to, how do I really influence as an IC in a company? And there are so many ways, but sometimes it’s not completely clear.

[16:58] Vidal: I think that’s a great point and yeah, smaller companies, usually they don’t have a career ladder. You just haven’t gotten to that.

Where can we go to learn more about you?

James, you’ve been really generous with your time. Thank you so much for coming on. Where can people go to learn more about you if they wanted to connect with you afterward?

[17:16] James: Sure. So there are a few places. I still maintain my website, which is theengineeringmanager.com because I’ve been writing the books. I’ve written a bit less on there recently, but it’s still updated. And you can find all the archive of writing I’ve done over there.

And also the other places on Twitter, which is JStanier, one word, or just search for “James Stanier Twitter” on Google and find it. And I’m fairly active on there. I’m pretty responsive too.

[17:40] Vidal: All right. Again, thank you so much for coming on. Really appreciate it.

[17:43] James: Likewise. Thank you.

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