The first time our remote team ever met in real life

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WP Buffs is a distributed company. That means we all work from different cities, different states, and even different countries. We hop on a secure WiFi connection and use tools like Teamwork and ManageWP to work from wherever we live or from our travel destinations to help our clients increase their site speeds and improve their site security — among other things.

I’m in Washington, DC, but people check in every day from New York, Florida, Kentucky, California, and the Philippines.

But for the first time at WordCamp Miami this year, 3 members of our team got the chance to come together and meet not just via video chat, but IRL.

😮 When a remote team meets for the first time IRL... #remotework #WordPress Click To Tweet

Nick was coming in from Rochester, New York and by pure coincidence, he was flying through DC and was on the same flight as me.

When my Lyft dropped me at the airport, I was admittedly a bit nervous. I really felt like Nick and I had gotten along great the last 6 months we’d been working together, but there was still a tiny sliver of my brain that was asking that question…

What if you don’t get along in real life?

That voice in my head immediately evaporated when we met at the gate. One big bear huge and that was that.

We flew to Miami together, got lunch and relaxed the rest of the evening before the first day of workshops. We showed up on Friday morning eager to meet Cindy and it was that same relaxed feeling alongside a big hug.

This was a big moment for WP Buffs

As somebody who’s worked hard to build a successful remote team, I’ve followed many other companies that have come before us. I was always reading about how Buffer spent $111,874 on a team retreat or how Baremetrics ran their first getaway.

Then, of course, there’s Automattic, and they don’t disappoint either.

To me, the ability for a remote team to bring people together for in-person meetups is a sign of success for two reasons:

  1. Part of this is a financial milestone. When a remote company is doing well enough to afford to buy plane tickets and a place to stay with all expenses paid for, it’s a big deal. The fact that WP Buffs has the financial flexibility to put 3/4 US-based team members in the same place is something I’m proud of.
  2. Then there’s simply the concept of investing in getting the team together in the first place. The biggest investment I make in my company is in the people, so paying for people to get to know each other and build that trust just seems like a terrific way to invest capital to move a business forward.

Although this was never an official goal for 2018, allowing a distributed team to meet IRL is a good indicator for any remote team. To me, it’s positively correlated with growth, making smart investments, and making the business an attractive place to work.

🌎 Meeting IRL is a big step for any #remote company, especially as the team grows and it becomes more expensive. #WordPress Click To Tweet

Why get everyone together?

Although this wasn’t as much of a retreat as it was a conference, having the 3 of us meet face-to-face allowed us to really get to know each other, and not just about our WordPress backgrounds.

It was refreshing to chat about things besides work

When you learn that somebody on your team grew up in the same neighborhood your sister lives in, it’s just another thing to add to your connection.

When you learn that someone homeschools their 2 children and they both graduated Summa Cum Laude from college, it adds another dimension to them you never would have thought about before.

These are the things that don’t come up as often when you’re working remotely because sometimes, you really just don’t have a chance to bring it up while on chat or having video calls. But when you’re sitting and drinking a beer at a WordCamp afterparty, you really get to chatting and these are the kinds of things that come up.

And work discussions were even better than doing video

When talking about certain troublesome customers, systems we need to improve, or just parts of the business we’d like to see get better, the in-person conversations were pure gold.

It became clear to me one of the big disadvantages of working remotely is that it’s extremely difficult to convey all your emotion and body language via video chat. I think this is something I knew before intuitively, but this experience made that fact crystal clear. Speaking with people IRL made it easier to understand exactly how passionate somebody is about something.

This was a great experience for two reasons:

  1. It’s taught me that we need better ways to influence our remote work with strategies and tools for conveying this emotive language. As of a few months ago, we’re using a new feedback system called 15Five to drive a high-performing culture. I think this will help tremendously here.
  2. Now that we’ve met face-to-face, it will be that much easier to converse via video chat like we’re just two people having a conversation. Real life conversation will lead to a deeper connection when working remotely.

Everything we talked about, be it WordPress-related or not, helped our team build trust, and that’s the most important ingredient for any remote team to be successful.

⚡️ Building culture as a remote team is extremely challenging, but meeting in-person accelerates that process. #WordPress Click To Tweet

What’s next?

While getting together and meeting some of the people I work with the most every day was 100% worth it, the next time we get together, we’ll have to do more.

I’d like to make sure we can go on a real retreat with the team so we can do more than just a WordCamp. I want to organize a retreat that we can use to push WP Buffs forward by:

  • Getting together in the same physical location and tackling some projects that might be simpler in person.
  • Working on the business instead of in the business by reviewing our mission, milestones, and our big, hairy, audacious goals.
  • Doing what we did at WordCamp Miami and having fun. Once you’ve done that with somebody, you realize they’re just a regular person like you. And getting along, asking for help, and building a strong relationship becomes that much easier.

Now, that still leaves the question of our non-US team. If we do our retreat here in the US, those plane tickets are way more expensive. Full transparency: I haven’t figured this part out yet so it’s something I’ll have to think about and budget for.

Getting even 3 people on our team together was well worth the investment and we’ll have to get to planning another get-together later this year as WP Buffs continues to push forward.

And if you’re managing a remote team, be sure to give this a read: 25 Tips to Help You Manage a High-Performing Virtual Team

Onward and upward!

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