Remotely Remoting

Meg Robichaud
Shopify UX
Published in
13 min readOct 24, 2017

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I like to start most things by saying I have no idea what I’m doing, but John asked me for some quick tips about remote leadership and I accidentally sent him a novel, so turns out I have some opinions.

Credentially speaking, I have led two teams remotely; reported into a remote lead; and worked remotely as an IC on other teams. I also did (read: am still doing, sort of) the whole nomad-travel-the-world-while-freelancing thing for two years. In other words: remote is all I know. There are actual books on this stuff, and entire companies built around being really good at remote, so it’s on you if you pick my advice over that plethora of knowledge. But here we go here are the things that I think about as a remote lead.

You’re either built for it, or you build for it

I’ve been trying to find the words to articulate why I like to work remotely for a while now. For a while I’d say “ehhhh well my job is just kind of one of my favourite things to do, so I don’t really have to keep myself in check, I naturally just go back to work when I find pockets of time” but that didn’t feel right. Then I’d say “oh I just have different values. I’m really motivated by control over my time, not money. I always negotiate time > money; that’s how I make it work.” For a while I even tried talking down about myself “oh sometimes I totally blow it on my projects, remote is hard yo” (I don’t. That’s not a true thing) just to make up for this thing I honestly don’t find that hard, since everyone else struggles with so much.

Two deep dish’s and one impressive feat of man vs. pizza later, Mackey finally broke it down for me (although he was not the pizza slayer). There are people who are happiest when their life is divided in sections, and there are people who are happiest when their life is fluid. Neither is better, unless being able to work remotely is our only unit of measure, in which case: fluid lifers emerge the king of the world. I’ve planted my feet firmly in the goo, where my happiest days look something like work-run-work-friends-work-dogs-tacos-work, and the idea of coming home at the end of the day and having literally nothing I could be working on is revolting. But so is working all day. If you’re the other way around, and really enjoy turning off your work brain at the end of the day, but still want to work remotely, well, it is my professionally uninformed opinion that you might be trucked.

KIDDING. You’ll be fine. You’ll just have to get your advice from a different self important listicle. All that advice people hand out about building your own office, setting a schedule and putting on pants—it’s probably good advice (except for the pants part), but it’s really a choose your own adventure kind of thing. As far as I can tell, like snowflakes and puppy noses, no two remote workers are alike. The successful ones ignore most of the advice in favour of self awareness, and a lot of neurotic habits of their own invention.

The important part is to figure out what style of working fits you, and set clear boundaries accordingly. It’s part of your job as a remote worker to take care of yourself long term. Understanding how you like to work, and articulating it clearly—both for yourself and the people you’re working with—will set you and your team up for success, and help you avoid the plethora of unhealthy habits of working remotely.

Put in the hangs up front

Joining Shopify was a really hard decision, with my personal identity largely rooted in “freelancer” and “nomad” I basically said “thanks this is going to be great, you said I don’t have to be there, you said it. I’m going to Jordan kbye” because I had to prove—to myself more than anyone else—that my life wasn’t about to change (spoiler: life still changed, nothing proved, no one cared).

If I had my time back.. I would change nothing at all, Jordan was the best, I galloped a horse across Petra, slept in the desert and hugged a baby camel.

Okay no try that again tho: if I had my time back, I would have worked in the office for at least a month just to get to know everyone. I would prioritize building deeper relationships as the first step to being really good at my job. That’s not to say that you can’t get there remotely. You can build a sincere wonderful working relationship from anywhere, it’s just harder if you start remotely. There are harsh opinions from an avatar who looks kind of angry and only chimes in when they disagree. Or there are harsh opinions from the an avatar who looks kind of angry and only chimes in when they disagree, who you also caught checking if they still know all the words to Baby Got Back because they thought everyone went home already. It’s not like you’re different people when you’re working remotely, you were always going to get to more or less the same relationship eventually, but for the sake of the work, the efficiency, and general i-want-to-love-my-job-now-not-later-ery: I think it’s worth your time to add general hanging out to the to-do list, (even if all you want to do is get to work already).

I think about this every time I start working with a new team now. It sounds like it makes sense to kick off in person, and then everyone goes their separate ways and you can continue on slack. Well, I mean, it does make sense if you already know how you’re going to literally work together. Like, gritty details, how do I edit your work; how do you edit mine? Who owns the files? What if I change my colours, will you change yours? If you’re so early in a project that you need to riff off each other, then you need to be damn comfortable riffing before you leave the office. I need to be able to ruin your work, and you need to be able to ruin mine, and somehow all we see is the good work the other person was trying to do.

Instead, every time you form a new team, don’t just stay for the scheduled two day kick off. Leave yourself some time do develop a short hand. Get comfortable in someone else’s files. When you’re editing someone else’s work, remind yourself that the smaller the change: the bigger the slap in the face. Take the time while you’re still sitting next to them to tell them 50 times why you changed something, so when you’re working apart, they already know why you probably did it on the 51st change.

Make a reason to talk to each other that IS work

I’m a new(ish) manager, so I spend a lot of time listening to and reading about wtf I’m supposed to be doing to not ruin everyones time. One piece of advice that comes up again and again is that it’s really important to use one-on-ones to talk about things that aren’t work. And I’m like, sure, great advice. Just, I dunno, YOU try to ask someone about their feelings even though you just met and also I think hangouts is lagging again did you say Barak Obama or taco lasagna? And what about when you need something? And then you need another thing? and then you need another thing? And omg do I only message him when I need something? I am the worst. Shit I need another thing. Should I ask him how he’s doing first? No that’s weird now. Dammit why isn’t small talk in my personality? Maybe I’ll just skip this one.

And that’s when remote leadershi- hits the fan.

I don’t know if I can realistically hand out the advice “work on something together” you know, since that’s not really how you should decide who works on what, but damn does it make your life easier. When you’re actually talking to each other all day hey I wanna see my thing? what about this? BTW I have a you’re-my-lead or I’m-your-lead thing I need to talk to you about. But wait I have another update to our thing look its cool I rule. Also I definitely took a screen cap of you in that last hangout.

It’s just easier.

Learn to type like you talk

It’s 2017 and you work on the internet. Don’t pretend like you don’t know how pissed off you seem when you suddenly switch to short declarative sentences. You’re a professional communicator and we’re supposed to believe you’re oblivious to how draining a giant block of text feels? Come on. Did you just double dot at me..? There is no plausible deniability in that passive aggressive chatter any more. Take the time to develop some freakin’ awareness and get a better understanding of how you come off when you type. “Oh he’s just curt in email” is no longer a viable excuse. You are the person behind your avatar. Your avatar is you. You should be precise in how you are perceived in your primary means of communication. It is your responsibility to foster real conversations and real relationships as much as possible within the constraints that remote working provides. You might miss the water cooler conversations, but your gif game is the new water cooler, and you were only planning to drink La Croix anyway.

You have to be that guy who shows up uninvited to everything

I felt bad is a stupid reason to not get invited to things. It’s thoughtful. It’s kind. It’s someone trying to be respectful of your time. And it’s the main reason you’re not in the right meetings when you’re remote (ignoring that whole women-dont-get-invited-to-meetings-in-tech thing, I mean). But it’s stupid. You signed a contract where you sold your time to an organization, and they are trusting you to manage it appropriately. You can’t do that if you don’t know about the things you’re supposed to be at.

So start inviting yourself. Like hey who’s running a sprint? Cool send me the schedule, I’m coming. I have never encountered someone who doesn’t want me there, only people who don’t want to be the one to make me fly across the country for one day—to which I say: fair, thank you. Invite yourself to three things and you’ll get an invite to the fourth. Let people know you are good at setting your own schedule and boundaries; and that you know how to say no, and they’ll stop feeling so bad.

Or maybe all these feelings are just a Canadian thing.

Be A-synchronous AF

If it were up to me, this would be this would be advice for every team, not just the remote ones. But hey, I have to start somewhere. Part of being respectful of peoples’ time, while still facilitating a smooth transfer of information, is creating tools and practices that are a-synchronous. Not just to account for different timezones (although that is an issue), but to account for different working habits. I like to start my day by checking and updating all the projects that are active or pending on the illustration team; someone else might prefer to end their day that way. Why make a meeting to talk about it if someones head isn’t in the game just because it’s a time that works for me?

Some actual things we do because that’s probably why you’re skimming this article:

Request form (Google forms)
Where we were previously using some terrible combination of random slack messages, meetings and emails, we now use a google form that populates a project for us in Asana. It serves us two fold: it walks the rest of the Shopify UX team through building a proper brief for us; and it collects the projects into one place so that we can self-assign and update as our schedule allows.

Project board (Asana)
IknowIknowIknow this isn’t ground breaking, but I didn’t say the Shopify illustration teams new and zaney a-synchronous practices, did I? I don’t mean to be all Asana’s number one fan here, but it is what we use to track our projects, and I am efficient project tracking’s number one fan. At a glance we can easily see where a project is at, what new projects have come in, who is working on what, and if there is anything that is high priority that is approaching it’s due date. Using a thorough project board releases the pressure to keep up with every slack conversation. If you missed something, that’s okay, everything you actually need to know about to do your job today is right here.

This might speak more to my management style (or lack there of) than remote specific, but I think using a system where we largely self assign is really important for creating a sense of autonomy (ew that sounds like we’re faking autonomy, I mean it just creates autonomy, and also: it feels that way) which then distributes the ownership and successes (and failures) to everyone on the team. Also, I don’t want to be handing out projects all the time, I want you to tell me what you think you should be working on all the time, ya know? This just creates the structure for us to do that, while also sleeping in.

Multiple channels (Slack)

Public channel
I mean do I have to explain this one? It’s the illustration channel. It’s for questions and sharing and junk.

Private feedback channel
We have a private channel which includes the full time illustrators, as well as anyone with an interest to learn illustration. It’s not specifically hiding anything, there’s just a different tone when you’re in a channel of 8 instead of 80. People are more willing to talk through problems/half ideas, share work that is actually WIP (instead of those “oh nbd just a quick sketch” that obviously took you forever), and give direct feedback, when they know everyone in the room.

Of course yes we also have actual reviews because what kind of design manager would I be if we didn’t have reviews, but if I’m being honest, I think the Slack channel yields more candid and thoughtful feedback. It opens the floor up to feedback from anyone, instead of just the person running the reviews. It gives you an opportunity to question your own feedback, instead of operating exclusively on instinct and gut reaction; and it gives you the opportunity to organize your feedback, which softens it without detracting from the actual feedback.

Pulse channel
Keeping people up to date with what you’re is doing is hard. Staying up to date with what everyone is doing is also hard. We use a pulse channel. A place where everyone just drops whatever they’re working on at the end of the day, finished, or not; looking for feedback, or not. Within our team, it created a space for everyone to share what we’re working on without asking for approval. It changed the conversation from “what do you think of shipping this” to “I shipped this” ✨hellooo autonomy✨ Externally, it became a window into what we’re working on that anyone can access. It gives people who need to have a sense of what we’re working on, without needing the day-to-day something they can access on their own time.

Master files (Google drive)
I don’t know how to say this without feeling kind of silly for stating the obvious, but it is a thing we do that helps us work on different schedules: organize the shit out of your shit. Shopify is a freakin’ ecosystem: everything is being updated constantly, and guidelines get dated quickly. Gathering up all the work relevant to a project you’re about to start is cumbersome, and chasing people down to find out if the things you gathered are still true, sucks. Where we previously had many single artwork files, across many folders, we began a series of master files: a source of truth that everyone can contribute to, organized according to what they need to stay consistent against. Basically does the work of gathering and truth checking for you, so you can start a project on your own schedule. Anyway, welcome to the low rent version of Github for illustrators, I guess.

Some other things we have tried that worked okay but obviously not great or we’d still be doing them
* Weekly email updates
* Slack standups
* Office hours

Except when it’s dumb to be a-synchronous

Okay I do get that we can’t be a-synchronous like 1000% of the time, although my inner introvert says but what if we can? We sync up IRL or over video regularly, with no ground breaking tactics, so I’ll just tell you them.

* Weekly illustration reviews (hangouts)
* Bi-weekly illustration team
* Ad hoc (usually week long)(usually every 4–6 weeks) in office visits
* Ad hoc in office sprints
* Attend conferences together

Junior mentorship is hard; Senior mentorship is also hard; general mentorship is also hard

Yes, junior mentorship is hard. You can’t be next to someone. You can’t always type out how you got to a conclusion like you might IRL. You will never approximate “hey meg can you take a look at my screen for a second” and honestly, as far as I can tell, that just sucks. We send sketches, talk through ideas, and spout opinions, but it will always be a new kind of mentorship built around not being in the same room.

The rest however, the rest I can do. I mean maybe I’ve just got this mentorship all wrong, but as far as I can tell the rest of mentorship is not one size fits all. It’s a relationship built around a pillar of I’m fucking rooting for you. I’ll be on your side when you’re not around, and really just want to help in any way I can. Don’t tell me I can’t do that remotely.

Some tools

I dunno this list probably exists a million places on the internet, but here we go: all the tools I use to make my life easier as a remote worker..

Clocks
’cause timezones are hard

Tripmode
’cause data is expensive

Twitter
cause crippling isolation & general longing for human interaction

That’s it really. That’s all I use.

Note: it occurs to me at the end of this article that I use the word lead and manager interchangeably in this article, because my part of the Shopify organization does not differentiate. I am definitely a technical lead who also manages a team, and not a straight up manager. Which means that I think of myself as a resource who is eager to help, but I expect my team to let me know when they need help. I can only speak to managing a team from that perspective; a lot of the leads at Shopify are more active in their individual team members growth, which I think would be decidedly more challenging to do remotely.

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