The state of remote work at iwantmyname, 2019

team map

A job is a job. No matter what position you are in a company, there are certain tasks that need to get done, and a general expectation that you’ll responsibly earn your paycheck.

But this generation of workers — a generation I’m a part of — has a particular fascination with personal empowerment, and a distinct lack of respect for how things were done in the past. We see “make X great again,” and think of insane gender/racial disparity, rampant corporate exploitation of workers, and global war. The past sucked, 80’s greed brokers are still running the present, and it’s our lot in life to make it better.

Nothing is sacred. Everything is disposable. And first on the chopping block are workplace expectations. If we’re going to maximize efficiency, we need to A. be comfortable, B. eliminate distractions, C. not waste time. The solution doesn’t even require that much imagination — get rid of the traditional office, eliminate the rush-hour commute, and let people do their jobs from home.

We — as a generation — didn’t get together to do a bunch of studies to gauge its effectiveness (although we did pull from the best practices of the earliest adopters), we just started making remote work happen. A company here. A company there. It’s clearly the solution to the problem, we just have to bend the general expectation of work to our will.

The most fascinating thing about being a Millennial/young Gen-X’er is seeing our willingness to throw caution to the wind meet reality. We know it should work — it will work — but we won’t generationally reach our potential until we iron out all the kinks. Remote work is great for all the reasons you’d think it’s great, but it presents a number of challenges that probably weren’t anticipated.

It’s like we’re beta testing a societal shift. Someone has to do it.

Here’s our version.

Could you see yourself going back to a traditional office setting?

F%#$ NO. Kill me now if I ever have to.

(The block quotes are answers to an internal poll we did recently… you’ll see them throughout the post.)

General organization

At this time, iwantmyname has a board of directors that pass down general goals and expectations, a team lead (me) who manages all the work getting done, a support team, a dev team, a designer, and a person in marketing. Because of our team size, most of us moonlight as different things at different times. I’m slowly rewriting most of our site content, the support team is managing our documentation, all our TLDs, and even taking on finance tasks, and etc. for the rest of the team. It’s an all-hands-on-deck situation — as many businesses are.

Day-to-day tasks are mostly self-guided, poked along gradually by an ever-evolving list of to-do’s in Basecamp (some still exist in GitHub as well), my mouth noises in video chats, and a surprisingly efficient system of checkins in Slack by the support team to ensure no gaps in coverage. From a project management perspective, I’ve found it to be nearly impossible to build out to-do’s with due dates in such a small team because that sort of rigidity just isn’t realistic (for reasons I’ll get to later), and it’s generally better to not ship garbage without external pressure forcing your hand. Instead, we list out tasks in order of when they need to be completed to unblock the next task, and when we ship is dependent on the situation — we usually ship when our work will help our customers rather than harm them.

On an operations level, most things tend to get done in Basecamp as well. The underpowered calendar has become a catch-all for everything from meetings to scheduled time off. And we have an open leave policy we don’t police at all — people just schedule off and remind the team in meetings when the time is coming. (I know there are plenty of companies that make a big deal out of time off… we just don’t. At most it’s a minor headache for managing products, but no one here abuses the policy, and I don’t see it slowing us down in any significant way.)

Intermission 1: Kevin’s desk

Kevin's desk

Meeting culture

At the start of each week, we have a Zoom meeting called ProdChat where we talk through the week and try to unblock people who are stuck. Ideally people have been chatting in Slack up to that point so the problems we’re facing aren’t out-of-the-blue, but getting together once a week for ~30 minutes has been extremely helpful.

We also have a once-a-month team meeting on Zoom where we talk about bigger-picture stuff. Honestly, at this point it’s more of a face time exercise — it can be hard to have empathy for people you don’t know face-to-face, so it’s a critical way for support (which is semi-autonomous) and product to interact.

I love (our team meetings)! Even though I have to drag my ass out of bed for them haha. I haven’t met a lot of the team in person yet and I am definitely the type of person who likes to be able to see people’s body language when talking to them. It makes the rest of the team seem like real people and not just textbots in Slack ;)

I’m one of the people who thinks a social component is valuable, and since the bulk of our work is done within smaller groups and/or asynchronously, there isn’t that much that the all-hands monthly meeting is critical for aside from generally touching base and company-wide updates. Beyond that, I think teams and groups have a pretty good handle on when they need regularly scheduled meetings or ad hoc ones. It’s unfortunately that it’s never ideal for one time zone, and I tend to support a rotating schedule to alleviate that somewhat, but I also understand sticking with a specific date/time since it’s such a pain to schedule.

Are they successful though? “Meeting culture” is the thing people most loathe about traditional offices, and they can easily get out of hand in a remote setting. Especially when people are in different time zones — there’s always someone who is forced to join in late at night (in our case, it’s our Europeans), and more than one late meeting a week can be a real problem. We all work remote to have more personal time, and so many of the workarounds we’ve created to make remote work succeed chip away at all the time we’re supposedly saving.

Meetings in general are very often a giant waste of time. That’s why I don’t like them, neither “IRL” nor remote. As we came up with agendas and stick to them, it has become less of a pain. It’s a good thing that we stick to as few meetings as possible.

Being on each side of meeting culture — as an employee and now a manager — I can really empathize with everyone. For management, meetings feel like a crucial part of ideation and getting things done. Most importantly, it’s hard to feel like you know exactly where the team is on a project without getting them in a room to report on it. But as an employee, I know how these meetings go. You say what you need to say to get out of the meeting, then ignore nearly everything and do whatever it is you need to do to get the job done. For most employees, frequent group meetings are a giant waste of time, and for managers, they’re at best a temporary dopamine hit. An attaboy for doing boss things, and a good way to get talking points for the next meeting with management further up the chain.

I tire quickly of reporting for reporting’s sake, so we do our best to keep meetings infrequent, short, and focused. It hasn’t always been that way, but it’s starting to feel like our meeting culture, which I think is healthy.

They are a super important: as an efficient method of information exchange, with spontaneous questions/clarifications. Also can boost morale and team cohesion. They’re on late which can be tough, but they are kept as short as necessary, and mostly only once a week, for a period they were later some weeks would be 3-4 late night chats - much better now!

Intermission 2: MJ’s desk

MJ's desk


Communication goes much further than meeting culture, and it’s where most remote companies struggle. Speaking from my own experience at iwantmyname, I have a solid report with the people working in my orbit (design, dev, marketing) and in my general time zone, but have a harder time with support and people on the other side of the globe. We have casual chats in the “#social” Slack channel, but I don’t know them as well as I’d like, and I don’t know if I ever will.

Our annual trip helps (we meet once a year for a week or so to plan the year and have a bit of fun), but so much of getting the job done relies on asynchronous communication, which doesn’t really necessitate relationship building. Last year we moved into a more traditional project planning environment and chose Basecamp because of our strong cultural alignment (content marketing works, folks!). I went over Basecamp a bit above, but the most interesting takeaways are that A. mapping out a project is easy, B. having someone tasked to have a permanent overview of everything is essential (like a Janet, from The Good Place), C. ensuring things get done in a way that eliminates roadblocks is exceedingly difficult with a small team.

I think we’re most productive when everyone’s aware of who’s counting on them, and how their role fits into the larger scheme of the business. Currently, we have bottlenecks that I’d like to see opened up to prevent one person from having to wait on others for results.

Once you hit a certain size, everything is go go go — when one person is having a slow day, the rest of group is picking up the slack. But when knowledge isn’t spread evenly, or if the skillsets are siloed too much, so much can fall apart so quickly. Stagnation due to roadblocks kills morale faster than everything else combined.

What I’ve learned is that in an asynchronous environment, instead of worrying about perfecting communication, a product manager’s primary task should be to empower everyone with tools to do as many jobs as possible without friction. If your content team gets too far ahead of development and wants to tinker around with meta descriptions, empower them to do that easily. If marketing wants to spin up a landing page to run a campaign, don’t force them to wait for a free developer — give them the tools to roll that out independently. And don’t ever underestimate the power of easily searchable documentation. If you have someone on staff who seems to enjoy writing and organizing documentation, never let them leave.

Communication is a big deal, but you don’t need to herd a small group like they’re a room full of cats. They know what needs to get done, especially if you list the required tasks out in an easily digestible place. The key is empowering people to get their parts done asynchronously.

Here’s where things get exceptionally tricky though — if you thought siloing was bad in an office setting, wait til you see a remote office. From a management perspective, there’s literally an endless list of product enhancement tasks I’d like to see done in my lifetime. But sometimes you have to pump the breaks to sync up with support because there’s always an escalated queue of cases that need to be addressed. And if there’s one thing that’ll break the spirit of a support team, it’s seeing the same crap come in day after day, and not having any confidence the problems will ever be addressed.

With a big enough team, this is a no-brainer — you just assign some people to the EQ and rotate them out after their time is done. But in a small team, every person you put on the EQ puts an aspect of product development on pause. There’s no perfect solution (I don’t think), but what seems to be working is something Ley dubbed “Bughouse” (which I like to say in that “Swishahouse” drawl because I’m a 90’s kid from Houston). Every month, we drop everything to spend the final W-F pairing up to tackle bugs. As product changes become more or less a vanity task, we might move Bughouse to twice/month, but the current situation seems to be working.

I’d recommend something like this for every remote team, because silos are a force of nature you have to protect yourself from in advance. If you don’t support support, support will never be able to support efficiently.

Support, support, support. (I’m just getting it out of my system.)

The support team I feel are super productive — they’re the ones I have the most visibility over (being one of them!) The rest of the company, the reality is I don’t really see what they’re doing (unless something is horribly broken, then I see the devs). I assume productivity is happening though!

I still feel like there’s a bit of silo’ing between dev and support. It’s getting better than it was when I started though, for sure. But like I said above, I don’t really see what the dev team are doing. Customer support queries that have to be escalated to the devs are still an issue.

Staying sane

I can work from ANYWHERE. Because I’m support I have a set shift, but as long as I’m happy to work whatever hours my shift works out to be in another location, I can do it. I’ve worked from Wanaka a few times, am off to Perth next month to work there and spend time with my little siblings (not much point in burning leave if they’ll be at work/school during my shift anyway!), and will be spending Christmas overseas as well. I also really love that I can work with my music blasting at 5 billion decibels if I want to, stretched out on the couch if I want to, in my pajamas if I want to (the first couple of hours of my Sunday shift is almost always in my PJs.)

It lets you say “sure, why not to things” like impromptu tramping, because you can make up the time later.

Again, remote work is awesome for all the reasons you think it’s awesome. And if you have friends who also work non-traditional jobs that can meet occasionally for extended lunches, it’s even better. And if you have a Mario Tennis addiction, only a remote job will let you consolidate your breaks enough to be world ranked (not even a humble brag).

mario tennis

But there are drawbacks, and they’re very real.

We have a very Europe/North America heavy dev team, so there’s a LOT of conversation that happens in Slack while I’m asleep that I then have to try and catch up on. I have to make a point to get myself out of the house (the dog helps with that). I also have to deal with people who seem to be under the impression that “at home” = “not actually doing anything”, and don’t seem to understand that while yes, I’m at home, and that’s amazing, that doesn’t mean I’m free to do whatever — I am, in fact, working.

Can be hard to define the parameters, temptation to check slack at night, weekends, on holidays is there. Harder to switch off, leaving work behind at an office and commuting home creates clearer boundaries of where is what, without that any time can be spent doing something work related, or just finishing off that one thing. I also tend to think about iwmn stuff all the time, pretty sure I dream about it as well.

Isolation, the likelihood you’ll find yourself working in a silo for any amount of time. For small, timezone diverse teams: team camaraderie has to be drummed up. Morale is needy.

There’s no magic pill for being ok sitting by yourself all day. Some people love it, but others — like myself — are fairly social by nature. Not being able to go get coffee and blow off steam with your coworkers is admittedly hard. But there are plenty of ways to make it better. Here are a few that are common:

  • Video chats (with coffee). Just because you can’t drag someone into a coffee shop doesn’t mean people won’t talk. Have a “buddy” of sorts in your timezone and don’t be afraid to call whenever you’re lonely.
  • Work out of the house. I really don’t like coworking spaces because they tend to feel like working in terrible open office environments, but for some reason I can sit at coffee shops for hours on end. Find a place you like to go, and do it a few days a week if you can.
  • Exercise. Don’t just use all that time you gained not driving to work sitting on the couch. Lift something heavy. Sweat a little. Exercise really does make you happier. It’s science.
  • Eat better. I don’t want to get too far into the healthy lifestyle thing, but you have so much more flexibility at home to eat healthy than you would at a typical office. And I’m 90% sure your mood is 55% tied to your gut bacteria. Also science.
  • Keep your space clean. A common occurrence — especially if you’re married — is having your wife/husband come home vaguely upset because there’s a bunch of dirty dishes sitting around. “I was in work mode and lost track of time!” I sheepishly say. Every home situation is different, but I’ve found that cleaning up for 15-30 minutes at the end of the day leads to more peaceful nights.
  • Set up a routine. Some people walk their dogs. Some people take naps. I make myself espresso shots throughout the day. What I’ve found is that establishing a small set of norms keeps you grounded, and that’s usually a good thing for consistency. Remote work is known for letting people live these exotic digital nomad lifestyles, but most of us work best when things are exceedingly normal.

My last thought is about vacations. I read a lot of advice in tech circles about taking more vacations, and they usually go like this: “If you’re burned out, go on a trip and you’ll come back recharged.”

Utter crap.

When something is grinding your gears, you can’t just walk away and hope for some kind of Office Space zen moment to make it all better. You’re just postponing your misery — it’ll be right there when you get back. Instead, identify your problem and address it head on. A good manager should be flexible enough to make a miserable situation better, and if they can’t, you should save your sanity and quietly start looking for a new job.

Vacations should be their own thing entirely. Instead of taking a vacation to recharge your engine for work, you should be taking vacations because you have interests outside of work entirely. Pursue them. Go to the spa because you really like going to spas. Go to the beach and surf because your soul needs the ocean. Sit on your couch and watch all of Game of Thrones because you want a distraction-free refresher before the new season starts.

Whatever you do, don’t go on vacation just because you’re burned out and can’t take it anymore. Vacations won’t fix that. Only action will.

Intermission 3: Melle’s coworker


Would you wish this upon others?

I asked a very specific question to the team, which I’ll end this lengthy post with: If your best friend owned a company, would you recommend a remote-only workplace?


It would depend on what the company did and the particular friend. I don’t think it’s for everyone or every company. Generally, though, I would say companies that’re dead set against it are hamstringing themselves.

I believe it could be hard for a new company to be fully remote from day one while building out the initial product, unless people have worked together previously and know each other’s work style.

It’s a big trust-fall exercise which I guess can go both ways, if you hire the right people and harness the right culture - they’ll catch you and help grow the company; if they’re not the right people you’ll face-off with gravity and likely come of worse.

It would depend on the what they made/did, how mature the company was, whether people were already in the same timezone, etc. A one-size-fits-all answer would be a lie here I feel. The things I would say to the friend are, the problems will probably be things you don’t expect, and try and hire someone who’s already worked remote if you can.

With a LOT of pro-tips and recommendations. I don’t know if anyone has perfected it.

My desk for the day