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The Pains of a Remote Team

One Startup. No Secrets. Start at the beginning.


“I feel like you two are off running a tech startup and I’m here running a food manufacturing business all by myself.”

In a little over a year of working together, this comment from Casey during a catch-up phone call hit me hard. It was the closest we had come to a breaking point that wasn’t related to a flood of sales or overwhelming number of backorders.

That comment might not sound harsh on its own, but the implications certainly were. As far as Casey was concerned, the three of us might as well be working on entirely different companies. I gulped, knowing he was right. After all, this was the first time in three weeks we had talked in person (if you count the phone as in person). Having spent many years working remotely in the past, I knew we were letting the downsides of our “distributed” team get the best of us.

After a number of escalating emails went back and forth, I called Casey to figure out why we were so misaligned. I knew there were challenges with the three of us being spread out (Casey: Brooklyn, Morgen: Germany, Ted: Connecticut) but I didn’t realize how poorly we were managing our remote team. Here’s what we realized:

Our Communication Sucked

You know this one: the key to a healthy relationship is good communication. Well, that goes for business relationships too.

Since moving to Germany (for my wife’s job) I had been nearly off the radar. It sounds unbelievable given that this is 2015, and I’m embarrassed to admit it, but I had not been able to get dependable wifi or a reasonably priced international phone system in our apartment for the first three months! This meant that I was online only sporadically, not overlapping with US working hours much and almost never available on the phone.

  • The three of us had no scheduled or regular contact
  • We had no standard system for communicating, switching randomly from text to email to Skype to G-Chat
  • None of us actually knew in detail what the other two were working on

Paradox of Three: many parts of our business are easier with three people. But it created an even bigger gap in communication at times because it was too easy to assume talking to one about a given project was as good as talking to the other. What I failed to realize was the number of other topics and needs that we frequently cover on any given call, in addition to the key items on the agenda. All of these second tier topics and needs were getting completely ignored.

I’m happy to say that within a few weeks of our breakdown we made some changes and were on our way to being a happy (well-communicating) team again. Here’s how we did it:

  • The best systems / platforms are the ones you’ll use

  • We tried using hipchat to stay connected. Ted and I used it for a few days while Casey never used it at all. Casey had enough to worry about with production and fulfillment and didn’t need another login and chat platform. Instead, we should have just said “We all use G-Chat. Period.” Or picked any of the other platforms all three of us already used as our default.

    Scheduled communication allows for spontaneity

    Each of us now chat on the phone at least once a week. We haven’t felt the need to schedule a standing call, but do make a point to check in if the week is coming to an end. Roughly half the time we cover high-priority issues like new product, pricing, or finances. However, the other half of the time is where the magic happens: “oh, I almost forgot to tell you…” turns into a valuable conversation with related action items nearly every time.

    Communication style matters as much as frequency

    It’s no surprise that the three of us communicate quite differently. But it was surprising to realize that the differences contributed heavily to creating a divide. We’ve had success doing more of the following:

    • Acknowledge what each other are saying / doing. Sometimes a quick “Got it, thanks for keeping me posted” goes a long way to letting each other know you’re being heard.
    • Give the benefit of the doubt. It’s easy to think you know what’s going on from you seat, but there are always a number of factors happening around your partners you can’t possible predict.
    • Be kind. It sounds trivial, but it works.
    • Swap perspectives. Again, your perspective is correct from you chair, but it’s certainly not the only perspective. Before expressing your argument or desires, put yourself in your partners’ shoes.

    Business isn’t all business

    During our less-than-fun phone call I had a realization. Not all the problems that were expressing themselves as the byproduct of poor communication needed better communication to be resolved. On any given day, one or more of us was simply lonely working alone for most of the day. No business calculation would have illustrated this. Sometimes, it’s just really nice to talk to someone for a while. And sometimes, when that person can empathize with your situation, it’s really really nice to talk to them for a while. 


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