Remote work thoughts

remote.md

Some random thoughts about making remote employees successful

• have an advocate, ideally at the VP or C-Level, who is personally invested in making remote work. When I started at Etsy, I remember Kellan asking me directly "what can I do to make working remote better?" and Marc repeatedly checking in with me about remote qua remote. This has the obvious benefit of people who have power to make changes knowing about what changes to make and pushing things in a remote-friendly direction, but IME it also has an incredible effect on the morale of remotes. Remote morale is even more subject to perturbation than onsite morale, so this matters.

• Avi Bryant said something once that really resonated: try to hire extroverts as remotes. I'm an introvert AND I'm shy and lots of the things I struggle with as a remote are, I think, tied up with that. My default action is not to reach out to people; it's a thing I have to nudge myself to do every time I need to do it, and minor barriers can grow in my head. In a way Slack feels like a step backwards in this regard: with email I can assume asynchronous communication, and I don't feel like I'm interrupting someone when I use email to ask questions. With Slack, there's a weird pressure both that I'm maybe interrupting someone and also -- I'm gonna be honest here -- I might get pulled into a conversation I'm not fully prepared to engage in. I find in-person conversation profoundly more natural, and I second-guess myself far less frequently in person. Slack has a strangely anxiety-inducing aspect of being in this uncanny valley between in-person conversation -- where some ambiguity is given and space is given to say the wrong thing and correct it in real time -- and email (or gists) where there's time to edit and refine your message without feeling like someone's waiting on you. I guess my point in this entire thing is that for early hires especially, hire people who are less neurotic about this thing in particular than a shy introvert like myself.

• I'll echo Brad and say one of the things that'll go the furthest to ensuring that remotes are successful is hiring more remotes (I think this was the answer I gave Kellan when he asked me during my first or second week at Etsy, too). There's nothing worse than being the only remote on a team -- conversations inevitably happen without you, social events happen without you, you're forgotten in random morale events or swag distribution. This seems, writing it down, like the most irrational, childish thing to complain about, but it's real, especially as these tiny things pile on top of each other. If that's coupled with the knowledge that the org isn't committed to hiring more remotes, it can lead to feeling even more isolated.

• give remotes projects where the default state is collaboration. The times I've felt absolutely best as a remote have been when I'm working very closely with someone else. Whether they're remote or not is mostly irrelevant, though working with someone at HQ can be great for reasons outside the scope of the project, like hearing rumors/gossip/good news/inside baseball etc etc. I've had this dynamic both in collaborating on moderately complex projects where each person's work is very dependent on the other's, and also projects where the actual work is split but you become really good code review/rubber-ducky/sanity-check buddies.

• sorta related to the above, try to "ship" your work (whether it's code or documents or thought-leadering or whatever) in the absolute smallest increments possible. This is, of course, good advice no matter what, but I think it's particularly important for remotes because it's a forcing function for human interaction. It's also a forcing functions for making mistakes in public, which I think can be really positive as a remote, because it's a way to enlist help (more human interaction!) and also to a degree a way to show yourself being your best, which I truly believe for most people is when they're righting their own mistakes (again, whether code or writing or whatever)

• if you're remote and an introvert, try to set up some regular 1:1s with peers or just random people in the org. Manager dens at Etsy were amazing for breaking me out of my introvert shell and connecting with other folks in the org, who I might've had no contact with at all otherwise. Another thing that was great was the perf team at Etsy did biweekly peer 1:1s, so every IC on the team had a 1:1 with every other IC on the team approximately every 2 weeks. These were the sorts of things that shy/introvert me dreaded beforehand and which always put me in a fantastic mood afterwards. (I need to set this up for myself at MailChimp, speaking of)

• I'm a huge advocate for getting yourself an office outside of your house. In my ideal world, the company would pay for this (and a nice desk, and a nice chair, and maybe even a nice keyboard) but even if they don't, just spend the money. It's way too easy, when you're working at home, to completely blur the lines between work life and home life, and the bad news is home life will invariably lose when those lines are blurred. I try to leave my computer at my office a couple miles away from my house unless I'm on-call. I can read my work Slack and work email on my phone, but not on my other personal devices (home iPad and home Macbook). I try to leave my phone out of reach when I'm at home so I'm not tempted to slip into work-mode. If you have to work at home for financial or logistic reasons, at least have an office with a door that closes, so you can close your door and leave home behind when you're at work, and close the door and leave work behind when you're at home.

• I've found it's super super super important to have something outside work that give me some sense of community and an implicit time to interact with people in real life. For a while after I started working fully remote at Etsy, I got this from my gym, and when I stopped going it was (in retrospect) devastating. I didn't wrap my head around why this was at the time -- the reasons I stopped going to the gym were tied up in working too much and traveling too much (see below) and it was hard to separate the various strands at the time. But the gym gave me a place where I felt a sense of belonging, in person, and a place where it felt like I got to be part of a group of people doing something (in this case, something dumb like picking up heavy things, but still!) together. I think there is a HUGE qualitative difference between the belonging you feel in person and the belonging you feel online. The latter is real, and valuable, (I love my Fiasco people so damn much!) but different and, I'll be honest, incomplete.

• don't try to fix broken-because-of-remote-things by traveling to HQ. I fell into this trap at Etsy and Slack and for I believe 3 years in a row spent over two months of each year in a hotel. Again: hindsight is 20/20 and I didn't see this at the time, but that kind of travel is a band-aid for whatever work stuff you're trying to address, and it's physically and mentally unhealthy. I started sleeping worse and worse, I neglected exercise, I ate bad food, etc. etc. All these things are possible to do well when traveling but it takes conscious work and if the reason you're traveling is a stressful situation at work you're making things even worse for yourself. Instead: stay home, and force yourself and the organization to fix hard problems when you're not at the office. You'll thank yourself, and other remotes (and teams with remotes on them) will thank you too.