I've wanted to write a piece forever outlining my thoughts on how startups can build successful remote cultures. As with many things on the internet, if you wait long enough, someone else will express your thoughts better than you would.

Everyone should read Stella Garber's piece on the OpenView blog.

I'll offer a few additional thoughts, in case you make the mistake of not clicking through to read the whole article.

The shift towards remote work is real. A combination of modern tooling and millenial workforce has created a perfect storm for the desirability of remote labor. However, remote cultures are easy to screw up, and are no more a panacea than adding ping-pong tables and dog-friendly policies were to a traditional workspace.

The two more important elements of remote work are:

  1. Trust - your team, your mission, and (maybe most importantly) yourself and your ability to self-regulate focus and motivation.
  2. Tooling - chat, email, Google Docs, code revision control: it's not just about having the right tools, it's about using them the right ways for your team.

Don't be 50% remote

The mistake I see most companies make with remote culture is that they get caught in between fully co-located and fully-remote. You can't thrive at 50% remote.

If only a few people are remote, and you aren't thoughtful, they will become second-class employees. This happens insidiously. For example, a typical interaction might look like:

  • Bob: Alice, are you still blocked on that bug you mentioned at standup this morning?
  • Alice: Actually, I think I've got it, should push a fix within the hour.

Now imagine how this is different when it happens across the desk vs. in a Slack channel. If it doesn't hit the Slack channel, none of the remote workers are aware. They miss some key things: Bob was paying attention in standup and cares about the bug; Alice got a nice win by cracking through the issue; code changes are coming shortly and other developers should pull in that change; their team of fellow humans are alive, well, and a productive inspiration for us all.

You can still have a great office, of course. But your goal is to create a 100% remote culture, where people can be effective anywhere anytime. If you have such a great office environment that many people choose to come in (for the perks, the social, or the balanced separation of work/home life), it's icing on the cake.

Also, for goodness sake, discuss what it's like to work remotely. Too many companies just work remote without addressing that it comes with a unique set of challenges. Remote work is just like any other cultural or process issue. Apply the kaizen principle of continuous improvement, having open retrospectives on how it's going. Don't attach a stigma to having an unproductive remote work day. If your team isn't sometimes complaining that they got distracted doing laundry and babysitting the furnace repair guy and got nothing done, you aren't having honest enough discussions about your remote culture.

A dangerously blustery remote success story

When I was CTO at Thumb, I was commuting weekly from Boston to our NYC Union Square office where most of the team was located. A number of our employees lived in NJ, and worked from home sometimes. But we mostly had a typical startup office culture (yes, a nice ping-pong table).

While we worked a lot on our culture in general, we didn't stress too much about what it meant to be specifically remote. This was 2011, a time when remote was accepted, but most you just “made it work”.

Our trial by fire came with Hurricane Sandy, which dealt a major blackout to our area of Manhattan, but far more personally, destroyed the homes of some of our employees on the Jersey Shore. I stayed away from NYC that week, and everyone worked remotely.

The revelation that came from that week's struggles was that we were shockingly effective working completely apart! Granted, it wasn't a fun week, per se. But communication remained strong, we pushed code, kept out customer support running smoothly, and bonded as a team facing this new challenge. We effectively leveraged GitHub, Hipchat, and phone calls. For a whole afternoon, we found out only later, one displaced developer worked from a park bench in their powerless NJ neighborhood, tethered to a cell phone.

The remote-readiness experiment

To test your own culture for remote-readiness, run this experiment:

Some unremarkable week in the near future, announce to your team on a Thursday

Heads up: The office will be closed for the following week.”

Not a holiday, mind you, everyone is still expected to meet all their deliverables. But no one is allowed to come in. Work from home, work from a coffee shop, doesn't matter to us. But you can't work here.

And with that, enjoy a week of careful observation. Ask questions as you watch this experiment play out:

  • Did all the expected work get done? Was the completed work skewed to certain kinds of tasks?
  • Did everyone still attend their scheduled meetings remotely? Were they comfortable contributing over conference call? Did they use video chat gladly/begrudgingly/not-at-all?
  • Did the week still feel productive? Did it perhaps feel more productive than a normal office week? (This happens more than you might think…what does it say about your office environment??)
  • Did communication patterns change? Was there more or less email traffic? Slack chatter?
  • Most Importantly: Did people reach out to collaborate and remove blockers right away, or do they lean on the crutch of “I'll just wait until Monday when we are all back in the office…"?

Let me know if you run this experiment, would love to hear about your conclusions and surprises!