Making remote work work

Do’s & Don’ts: For video conferencing does not a remote culture make


Trade sitting in traffic for latte’s at your local posh cafe while organizing your backlog on Trello.☕️

Swap yucky uncomfortable pants for your favorite pajama bottoms while negotiating with clients via video.💃

Reject your cube and get a tan by the pool while chatting about the next release on Slack.👙


There’s a certain je ne sais quoi to remote culture.

It is the joie de vivre for our technological zeitgeist and other fancy words. Being remote offers a view into a more progressive workforce. Into a more enlightened society who– through the power of the internet– are able to work smarter not harder. Happier, even.

For an organization adding a remote workforce can be another way to attract talent it normally couldn’t. Sometimes it is used to unintentionally solve a distributed team problem. The worst it can be however, is a checkbox to “cool.”

For some companies offering remote is listed under “benefits” alongside free snacks and ping-pong tables. It’s not an ethos. It’s a perk. Doing it well though. Now that is the ultimate acclaim to a company’s ability to offer autonomy, independence, trust. 🙌 The Holy Grail of culture. 🏆

After working remotely for pretty much the last 3 years I’ve seen the good and the bad. Between my experience at an enterprise, a startup, and then consulting on my own I can attest to the following experiences and offer guidance for those companies interested in breaking away from the confines of cube farms and into a more progressive workforce. Let’s start with a don’t.

👎 Don’t:

📺 Rely on equipment.

Spending thousands of dollars on fancy video equipment or robots with iPads on them will get you some ooh’s and aah’s for about a second. Ok a week. Tops. I mean… They are pretty sweet honestly.

But if the process isn’t there– if the culture doesn’t actually live and breathe the mantra of remote– it doesn’t matter if you’re communicating through tin cans and string or $5k screens (ooh that rhymes).

Spending a couple hours literally just talking on the phone the old fashioned way with my coworkers or staring at each other on a minimized window on a laptop screen totally helped us bond regardless of the backdrop of where on the planet we were. There were awkward silences. Lots of shared screens. Sirens in the background. Text messages. Whatever the medium was didn’t matter. It was the message and LOTS of communication that was important.

👌 Do:

🙋 Communicate like you normally would.

Too many times talking in remote land means creating these little private perfect little moments for you and your coworker. Making these little finely curated delicate experiences of perfectly crisp video and precious compartmentalized time together.

Fuck that.

We’ve literally got a bajillion ways to talk to one another. People’s lives are messy. This is why asynchronous communication wins. Bouncing from Twitter to Slack to Github to email to a Hangout and back again across time zones and oceans is just normal. Embrace talking to each other when and how you need to. Again the importance is LOTS of communication.

🚫 Don’t:

😷 Expect remote to solve culture.

Over the course of about a week I participated in two remote conferencing workshops. Both had design-thinking elements and both had around 10 people in them.

The first one accomplished everything and more and finished early. The team was aligned. We had group buy-in. Everyone knew individual next-steps and dates. We were energized about what we were making. We all shared the responsibility of taking notes during the meeting to capture everything that happened. A couple people wrote down ideas and posted them for everyone during any design-thinking activity. Information was all well documented and uploaded to a shared folder for all to see until the end of time. There was plenty of room for discussion and flexibility in the schedule. Everyone participated.

It was awesome.

Fast forward a few days later and I was part of one of the most soul crushing meetings where time literally stopped. I gave myself an Academy Award at the end of the day for staying engaged and interested over video (where everyone is watching!!) for eight whole hours.

Channeling my inner Meryl

So. Boring. One person controlled everything. There was so little structure that no one understood what was happening. I’ve had happier days at the DMV or doing my taxes.

Yet, for some reason the meeting was lauded as a huge success!

“Look! We’re doing remote!! We’re hip! We’re cool.”

News flash: You’re not. You’ve just moved a crappy meeting from the office to my home.

💩 Lesson learned: Remote will expose weaknesses and amplify any crappy in your culture. 💩

✅ Do:

🤘Go all in

The absolute worst thing to experience when working remote is hearing about a decision made that you weren’t a part of. Crushed. Meetings that happen but aren’t documented or shared. Excluded. Fun jokes or events that everyone goes to that you get to decline time and again because #RemoteLyfe. Lonely.

The rubber really hits the road when everyone is either remote. Or not.

Remote needs to have ultra transparency. Over communication. And recorded engagements as much as possible.

  • At the very least make best-practices and guidelines for communication practices super easy to find on a shared drive or cloud. Update and iterate on the reg and be liberal in asking folks to contribute or discuss.
  • Share notes from your meetings even if they’re sloppy or incomplete. Something is better than nothing.
  • Have shared experiences. I’m a fan of the Brady Bunch window during video chats where everyone is on their laptop even if they’re in the same place. It’s equalizing. Being the token person on the laptop can be awkward.
  • 😢 Be careful with phrases like “we’ll just talk about this next time you’re here” or “hey when are you here again?”. Those are tough. Somehow it invalidates the present time and creates this “real work only counts in the office if I see it” vibe. No bueno.

🙅 Don’t:

👨‍🎨 Forget that your coworkers are people too. 👩‍🌾

A team I was on was fortunate enough to all go to Vegas one year for a conference. I honestly don’t remember much about the conference itself, but I do remember the dinner we went to. For me I was meeting some of the newer team members for the first time. For others I’d met maybe once or twice in person but had literally talked to everyday for like a year.

I really didn’t realize how important that was until after I got back and saw my teammates in new ways. I didn’t realize Chris felt that way about so-and-so executive!! Hilarious! And Michelle and I share a love of conspiracy theories. Super rad. Also: Matt wears killer sneakers and we love the same newsletters (Names changed to protect the innocent of course). I felt we were all maybe just a little more relaxed. A little more candid and friendly.

Working remote can be incredibly freeing. Teams can be super successful and never meet. Building trust and rapport however are fundamental to great teams. It’s more than just a cat walking across a keyboard to realize your coworker is a human. It’s actually learning about the people you work with as people.


In summary, I absolutely loved remote work. At best I was ultra productive, totally happy, and absolutely felt like I was part of one supportive respectful totally kickass team. At the worst I felt completely isolated, unsupported, and different. Why… I might say the two experiences weren’t even remotely close. 🤓😁

For a company to offer remote work and be successful requires ensuring that it’s an actual culture and not a symptom of the 21st century workforce. Taking that responsibility might mean making some real change which I can empathize as quite a daunting task not to be taken lightly.

That said, I’ve seen the successes of remote and can absolutely say the benefits far outweigh the negatives if done appropriately. Of course, standing on the shoulders of giants helps. Here are some of my favorite resources with friendly folks from the companies leading the way.