Building Trust and Safety in Remote Teams at Shopify

Transcript

Shane Hastie: Hey, folks, QCon London is just around the corner. We'll be back in person in London from March 27 to 29. Join senior software leaders at early adopter companies as they share how they've implemented emerging trends and best practices. You'll learn from their experiences, practical techniques, and pitfalls to avoid so you get assurance you're adopting the right patterns and practices. Learn more at qconlondon.com. We hope to see you there today.

Good day, folks. This is Shane Hastie for the InfoQ Engineering Culture Podcast. Today, I'm sitting down with Jesse McGinnis from Shopify. Jesse, welcome. Thanks for taking the time to talk to us today.

Jesse McGinnis: Thanks, Shane. Thanks for having me. Excited to be here.

Shane Hastie: Now, we met when you gave a talk at QCon San Francisco last year on building high trust and high performing teams at Shopify in a remote world. Before we get into that, who's Jesse?

Jesse McGinnis: Great question. I don't know. Who is Jesse? I mean, there's so much to that question, but the usual answer, I work at Shopify. I'm a senior lead. I've been here for approaching six and a half years, which is wild to think about. I love helping teams and people figure out how they can be the best versions of themselves. It's been a joy chasing that the last couple of years. Before that, much more focused on building products, getting into code much more, waxing those sets of skills. I'll go back there at some point in the next some number of years and continue that pendulum, but right now it really is about helping people figure out how to do the best version of the work. And, yeah, I'm in very balmy southern Ontario right now where we have about a foot of snow outside and a wind chill of minus 30. It's great.

Shane Hastie: And I'm sitting in a summery Otaki in bottom of the North Island New Zealand.

Jesse McGinnisL Sounds horrible.

Shane Hastie: Isn't technology wonderful that we can be together and I don't have to be in a foot of snow? So what does trust look like in a remote world?

Being deliberate about enabling trust in a remote environment [02:01]

Jesse McGinnis: I do think in many ways it's not any different than what it is like in person. Can you have candid conversations? Are people willing to show up? Can people bring their authentic selves without having to be guarded or heavily guarded? Will they challenge their peers, their leaders? I think it's a lot of that. And then, in remote, you just have to put a lot more work into creating space to let that build and develop. That might come naturally when you sit beside someone or get to have lunch with them every day or bump into them in the hallway, because none of those opportunities exist automatically when you're remote.

Shane Hastie: What does that deliberate look like? 

Jesse McGinnis: Part of it is being willing to set aside space for creating that initial social connection, creating that really, to some extent, almost surface level trust, the small talk, the opportunity to play a casual game together. And it can feel really weird to say, "Here is our regimented 45 minutes to have fun together", but you just have to get past that because if you don't set it up, I mean, you might get really lucky and have a team that's very outgoing and hungry for it and will do it of their own volition, but my experience has been that there's not a ton of those humans. Because they'll also feel the same trepidation that you might be facing in creating fun time except for they're not in a position of authority and it's like, "Well, am I allowed to go book a thing on everyone's calendars?"

Enabling time for people to get to know each other on a deeper level [03:20]

So it's creating space to let people be human together, to socialize, have that on some recurring cadence and rotate through different kinds of lightweight activities to help break the ice and still create opportunity to do surface communication conversation and have that first initial introduction. You can go deeper than that, and I think you should, but I'll also say, I think even having time for "fun" is more than what a lot of people do because they feel like it's work. "We're here to do a job. I'm not supposed to set up time to socialize with my coworkers or my team." And so even if you just stop at creating space for fun, you've already done better than a lot of people that I've seen. Where I think magic happens though is when you go deeper and you create very intentionally set up spaces where humans can reveal a little bit more about who they are behind the curtain, show their full selves. And this is something that I think even in office a lot of teams didn't do.

Again, it might have happened naturally if you had board games in the office or drinks around and people could hang out together or you went out together for a social activity or you'd been working with someone for a really long time and had just naturally built up that really deep trust. But a lot of teams in office or in person didn't set up dedicated space to expedite deep trust building. And in remote I think it's even more important because you have so many less natural opportunities. And so if you've established a little bit of that surface trust building, help break the ice, help us know who we all are and can feel comfortable having a conversation with each other, then you can start layering in deeper conversations. And there's a lot of different prompts you can use. The New York Times Questions To Fall In Love is my favourite default one because it has a nice progression of what's your favourite superpower, up to things like, what's the relationship with your mother? And everything in between.

Those kinds of questions allow you, to some extent, expose more about who you are to your peers. In many cases, when I've run it, I've seen people not realize things that they have in common with each other that they can then take away for their own one-on-one. And, again, digital environments, people should have one-on-ones that aren't manager report related. You can have a coffee chat with a friend. You should. But now that you've had this space where you expose more of who you are, have these conversations open up, that gives fodder for one-on-ones. That helps teams feel heard. I think it makes it easier for people to feel comfortable being honest about how they're doing or how their day is going. Once you've talked about the relationship with your parents or your beliefs about death or some of the scariest moments of your life with people, a lot of other stuff is easy as well.

That's the raw stuff about you as a human after you've been willing to open up, had the space to open up, had moments to have these kinds of conversations multiple times. A lot of other conversations are in many regards trivial, emotionally at the very least. So then it's really just about the work at hand. I think intentionality and purpose built spaces can be magic for a lot of different things, and trust is one of those.

Shane Hastie: What does a great team look like?

Great teams form on the foundation of trust where working together is fun [06:31]

Jesse McGinnis: I think it depends on the type of work you're doing, but I do think as a default, any team that I would want to be a part of is one that people have fun. I really do think work isn't always rainbow and sunshine and joyful, but I think it should have lots of moments of fun and engagement and interest. And so you need to know the people that you're working with. Hopefully, you have a level of trust with them where you can be honest and authentic and unguarded about how you're feeling, what you care about, what you're passionate about. You can bring your full self and you don't have to put a whole bunch of energy into being really careful with what you say or how you present yourself or how you challenge or how you shy away. You have fun and fun not just in, again, the surace level.

I think you should have some of those fun game things, but working together itself is fun, and I do deeply believe, when you have capable people that know the fundamental skills or are interested in learning how to get good at those skills and have the opportunity to do so, if you have people that you have fun with, with the work that you're doing and you trust, that team will get very good, very fast. And maybe fold in some reflection and introspection moments so that the team can identify where it's not as good as it needs to be or where the rough spots are or where there's opportunity to improve and you've created this environment, this pot that's just going to bubble over into a fantastic team.

Shane Hastie: And how, from a team leader perspective, do we set up these teams to be successful?

Things team leaders can do to set teams up to be successful [08:02]

Jesse McGinnis: There's a lot of different things that you pull into. I'm trying to figure out which one is my favorite pull in here, but what I'll go with is, how do you set this up? There's a few core ingredients that have to be established to get to one of these kinds of high performing teams. I think everyone needs to know what their purpose is. You need to know where you're going. You need to know why you're going there. You need to care about whatever that is, or care about something. Maybe you're consulting and you don't actually care about the consulting project that you're attached to, but you care about some interesting piece of technology you're exploring or the particular client or the team you're working with. You need to identify something that as a team you can be excited and passionate and energized by and know that it is important or valuable or meaningful in some way.

Know where you're going. Know why that matters. That gives you direction. That gives you a sense of purpose. That anchors a lot of other pieces. You should set up and create intentional spaces for the team to build trust. Again, create those avenues. Be the strong facilitator if you don't have one already baked into the team to create service level conversation and then well facilitated safe spaces to have deep, honest, authentic conversation and build that real trust.

Process matters

 And then, depending on how you work, the type of work you do, the scale of the work, you're going to have different kinds of processes and rituals around it, but don't ignore process. Process is often I think tagged as a dirty word in our industry, but everything is process, everything. If you don't do something, there's still a process that exists whether you want it to or not. It just might be something very chaotic and very not well suited to the work that is actually happening.

And so take some time to think about, given the kind of work we're doing, given our team size, given the context of the work that we're doing and the space that we exist within, what systems or processes or nudges can I or should I set up to help this team be successful? That can be something like the full textbook answer of Scrum, which works for very specific kinds of projects. It can be something like Kanban. It can be something completely free form with a check-in every couple weeks because you're doing deeply emergent and explorative work that's very independent. You have to be willing to pick and set that up intentionally. And I think, regardless of what process you have, you should have some system for retrospective and reflection. I really do think being self-aware and looking back at how things are going and having that avenue for the team to self-identify how it can get better is really critical to building a sustainable, high performing team.

And that invites the team in to fix and improve itself. It's not your job as a lead to make a high performing team. That's the team's job. Your job is to make sure that they have the tools they need, the space they need, the opportunity they need to get there.

Shane Hastie: This is not a skillset that technologists are renowned for having. How do organizations help our technical leaders, the people who want to move into that space, build these skills? You mentioned for your own journey from coding and development into this leader position now, the team leading, what do you need to learn to do this?

Leadership is a skillset that can be learned [11:12]

Jesse McGinnis: I believe organizations can accelerate it for you. You have to want it, first and foremost. So that is actually maybe even the first step. Make sure this is a thing that you want to go spend time learning and getting good at, because if it's not a thing you're excited about, it's all going to be a slog and you might get good at it, but you're not going to enjoy it, which means you're not going to be energized by it, which means you're not going to want to practice all of the things that feed into becoming really excellent. And so make sure it is a thing you want to explore. Where organizations can help, I think mentorship programs, peer groups, and then I would say accelerators. So when I think about Shopify, the way we approach this, there is a pretty strong expectation that the people who are already in this craft of people leadership are mentoring and growing the people that are aspiring to be people leaders, is an expectation that exists.

We have a dev manager accelerator though that focuses on what I would say are your management fundamentals, self-reflection, how to run successful one-on-ones, how to give good feedback, and all of them have explicit space for practice with a facilitator present. And that maybe that's really what the actual answer here is, is that all of this is just stuff you have to practice. There isn't a cheat code. I mean, there's books you can read that speak to different strategies to take or different ways to show up as a facilitator, but, like many of the things that we have in this industry, practice actually will get you there really fast. That's not going to be great the first few times. If you have someone nearby who can give you feedback on how that went, you'll get there faster.

And if you don't have that someone and you're in a position where you have to do these things, I've done this in the past and I have seen other leaders do this where we shy away from admitting what we're not good at yet, the sense that we need to show up perfect or well established or we know all of the answers. And people see through that. And especially when you're new to something, just being upfront like, "Hey, I'm going to try something this week that I've never done before with a really hard, detailed, deep conversation. And I've read a blog post that talked about a way to run this and I don't know how it's going to go, but this is what I'm trying to do." Being honest and authentic about your aims, about what you're worried about opens the door, first of all, just by being upfront like, "Hey, I'm going to do this thing that I'm really unsure about, but I'm really excited about what it might do for us," you've already been honest and authentic. You've already opened the door for other people to be honest and authentic.

You've invited the room to give you feedback, or you should invite the room to give you feedback afterwards, which means you can learn, and then you've gotten some practice in. And then the second time you do it, you can still be honest with where you're at. Hopefully, you will have got feedback that you can refine and iterate on, and then ask again. And you're creating your own space to learn and grow with your team. None of that was specific or tactical. I think tactically, when you are facilitating or when you're showing up as a people leader or when you're working with other humans, what's really important to always remember is that you are dealing with other humans. We are all complicated. We are all nuanced. Communication is hard and things won't come across the way that you want and you won't hear them the same way that they intended. And so give yourself grace, give yourself space, give yourself an opportunity to learn and fumble and hit a whole bunch of walls, and just be ready to learn from it and carry on.

Shane Hastie: Standing back a bit, looking outside of where you are now, what's happening in our industry at the moment?

Reflecting on the macroeconomic climate in early 2023 [14:31]

Jesse McGinnis: It's chaotic with the macroeconomic environment and companies I think getting wary about longer term prospects around revenues and all of that. As they should, they're doing very heavy introspection. To me, I see some trends emerging of people getting very critical about do we have people working on the most important things versus stuff that maybe isn't as critical or core to our business. I have seen some trends around, our people hate the word, but utilized the most efficient for humans. We're not machines or resources that we throw at things, so it's a gross language, but are people positioned and set up to do their best work, as maybe a nicer way to frame that? And so what I'm seeing happening is companies are, I'm going to ignore the layoff piece because that gets into a whole other complex macro piece, but companies are redirecting humans to their most critical pieces of their business and I think looking for ways to clear overhead or distraction.

Making space in calendars by removing meetings [15:32]

And so I think a pretty common trope at this point is every year around the new year, there's a lot of energy around, "Call out all of the meetings. Get rid of all of the distractions. Let everyone just work." And I actually do agree. When you're doing large scale communications, you need to be bold so all meetings are bad. Cut them all. Delete them for three weeks and then figure it out afterwards. That's how you turn a giant ship. But, obviously, there's nuance in here and it's really hard to communicate that nuance. The media, at least in its headlines, is never going to have a nuanced headline. It might exist in the article. And so this trend towards dramatically scaling back meetings, I think to me the takeaway shouldn't be, "All meetings are bad." It's, "Make sure that meetings and moments together serve you." That they're useful, that they do what you want them to do, and they're not a thing that you have become a slave to.

It's the same with all process. When we go into our rounds of, "All process is bad. Agile has become a horrible thing. We need to get back to just the work," it's when we become a slave to the thing versus the thing being a tool that serves us is where you start to see it go bad. And so, with the current meeting trend, yeah, Shopify cut all those meetings at the beginning of the year. I cut all of my meetings personally every quarter. I just delete my calendar and then reschedule stuff back in because that's just how I make sure that all of the stuff serves me and I'm not just falling into a trap. So I thought it was useful. I found it good. I have not told my teams to not add back meetings that were critical to them or important to their work or help them socialize or help them connect deeper or planning meetings that help them coordinate so that they could spend the rest of the week being focused on good work instead of having to have 30 one-on-ones to coordinate.

I think what it ultimately comes down to is intentionality and awareness. In this meeting, what do I want it to do? What does it need to accomplish? Is it doing that? If it isn't, can I fix it or should it go away, or is there an alternative way to approach this? And maybe one last call out, at least thinking about my own experience at Shopify, I do think we had relied on meetings in the early days of our transition to being a remote company to work in similar ways that we did when we were an office-based company. And a transition that we are still going through and figuring out is, what does it mean to really be a remote first company that's globally distributed? What are the different patterns that we should adopt for how we communicate, get on the same page, jam on ideas? I still think even in that world synchronous time together is super valuable for certain things, but what things were we doing synchronously that maybe we would be better served by doing in a different async way?

Shane Hastie: Tell us about the book, Embrace Uncertainty.

Jesse’s book – Embrace Uncertainty [18:09]

Jesse McGinnis: Yes. I would say a field Guide to Scrum that me and a few coworkers wrote seven or eight years ago really centered on trying to get to the good parts. If you've never done this before or if you've read lots of books and it's been a while, you need a refresher, can you read this on a plane ride and get some good practical tactics to help a team work better? It has a little bit of a centric focus on in-person work because it was written in the times when I was personally completely against the idea of remote work. But if you fuzz your eyes around the parts that anchor on that, it still actually applies pretty well digitally. I would say it still is the defaults that all of my teams run with on how to use I would say Scrum Light in a way that can be very productive without too much overhead and keep the team in charge of how that all runs.

There's a foreword that we added to the book a couple of years after we published it. The real thing for all things process related is, again, that intentionality and awareness of, what are you trying to achieve? You can carbon copy if you have no idea what to do, but you can't stay in that carbon copy. So I like the defaults that, that book proposes because they've worked really well for me. But all of those defaults change with every single team that I lead or have been attached to because each team is different and needs slightly different things to be successful. It's a starting place, not an end state.

Shane Hastie: Jesse, thanks very much for your time today. Some really interesting conversation. If people want to continue the conversation, where do they find you?

Jesse McGinnis: I have all of my various social links and messaging platforms are on my personal website at J-C-M-C-G-I-N-N-I-S.com, but Twitter, LinkedIn, and increasingly Mastadon are the places that I reside on the internet.

Shane Hastie: Wonderful. Thank you so much.

Jesse McGinnis: Thanks, Shane.

Mentioned

• QCon San Francisco
• Shopify
• The New York Times Questions To Fall In Love
• Jesse’s book – Embrace Uncertainty
• Jesse’s website