How to Design Remote Serendipity

“Defining moments can be consciously created. You can be the architect of moments that matter.” ~ Chip Heath, from The Power of Moments

As a leader who has run a very collaborative, face-to-face agency for 14 years, I vividly remember the defining moment of 2020, for my business at least. It was when we decided to temporarily close DISTRICT, the innovative coworking space that’s home to Digital Surgeons, among other creative and entrepreneurial companies.

That day, now more than a year ago, feels burned into my brain. And my heart, truthfully. It was the moment that transformed us into a remote company literally overnight. (Happened to the best of us…)

So what does one do when faced with an unprecedented challenge?

Honestly… at first, I panicked.

Then I saw it as an opportunity to design a new way forward. We were already using so many digital collaborative tools that flipping into all virtual communication, whether synchronous or asynchronous, went pretty smoothly.

But then life settled into a predictable pattern. After a while, it started taking on a Groundhog Day-esque flavor. My team and I were getting things done, but I couldn’t help notice how much was lost without being together in person. Commiserating about Zoom fatigue is its own special kind of bonding, but it certainly doesn’t help with morale.

Now that vaccines are starting to become available to more people, we’re all hoping that life will go back to “normal” in the next few months. Many of our teammates have been sharing how much they miss the in-office environment. Others have commented on how much they love the remote workflow. I believe part of the new normal is keeping a fair amount of flexibility in our schedules and embracing distance and remote work, at least some of the time, as part of our culture.

So, for business leaders who care about having a close-knit crew (I know I do), the paradoxical question is, how do we plan for serendipity? Those moments that crop up organically in person are harder to come by without physical proximity.

This post is as much a question as it is a series of experiments and answers — many of which I still have no clue about.

All I know is it all starts by taking things moment by moment.

Before you can replicate what occurs naturally IRL, it helps to understand how memorable moments happen from an intellectual, social, and environmental standpoint. Luck and happy accidents aside, as professors, brothers, and bestselling co-authors Chip Heath and Dan Heath show in their book, The Power of Moments, there are evidence-based steps you can take to make profound connections.

According to the Heath brothers, the four main elements of defining moments are EPIC. That is, an anagram that stands for:

E = Elevation: Foster opportunities that help others rise about the everyday doldrums to inspire joy, delight, and engagement. For example, look for ways to transform a Monday morning meeting from an energy suck (“Here’s the list of things we need to get done this week”) to an energy spark (“Here are some cool things coming up this week to look forward to”).

P = Pride: Celebrate accomplishments and milestones, from large (i.e., completing a project) to comparatively small (i.e., implementing a new system to support smoother-run projects). A little recognition goes a long way, particularly when we literally don’t see each other face-to-face. (Well, without a mask, anyways.) Letting people know you notice and care about their progress is a significant motivator.

I = Insight: This gets to the bigger context and truth of things. Insight takes you beyond the face value of what you do to understand your place in the world better. For example, when I think about our client Naboso, who makes proprioceptive insoles and mats, I don’t think about the product itself — I focus on how many lives are changed by being able to move better. This is the stuff that lightbulb moments are made of.

C= Connection: The ties that bind are incredibly crucial, again, especially at a time when we’re physically scattered. Interpersonal relationships can be transformative, particularly when working with others on a shared goal.

Here are some of my sketch notes I drew on my iPad when diving into this.

While you don’t need to have all four things happening at once to create a “defining moment,” the Heaths recommend you use all of these elements liberally.

Another aspect of a defining moment is that it tends to go in one direction or the other: peak or pit.

That’s just what it sounds like: a peak is an overload of delight — as the Heaths put it, “the best moment in a positive experience.” A pit is a moment that’s full of negative emotions, like fear, sadness, or anger. (All of those feelings, for example, came into play when we closed District because of the pandemic.) Both are equally memorable, and there’s no way to avoid either extreme.

That said, the negative route gets the bad rap. For example, when I asked my team members what starves their inspiration, negativity was the first thing that came up, followed by “negative vibes” and “bad vibes.” (I see a pattern here…)

However, when it comes to pits, you can have the chance to make them memorable in a good way by responding with empathy and support. The thing is, most won’t just bust out with what’s bugging them. You’ve got to know how to read your people — and this is especially challenging by distance work.

Research shows that nonverbal communication is critical to convey emotions, and while video meetings can help, it’s not the same. And asynchronous work loses the nonverbal factor completely, making it difficult to read a team member’s emotional states.

Riding the wave of the peaks and easing the sting of the pits is a leadership challenge, which is where EPIC moments come in. It gives you a guide to take back the power of memorable moments and harness them for good.

It’s very different when you start working fully remote versus flipping to distance working. But as we say, change is the only constant.

I think about it as a challenge to seek out what people are proud and passionate about and elevate it. I try to look for unique insights into how people feel and behave, then design them into our company’s O/S. And I work hard to hold space for my team to share thoughts and ideas and make sure that they know they are valued, appreciated, and not just a row on a timesheet.

Here are just a few ways that innovative technology can help you strengthen connections in a casual way — say, like it used to be in your office kitchen at lunchtime or after-work happy hours.

  • Make onboarding more personal.
    I love this idea from Pitch — instead of just hopping on a Zoom call, have everyone on the team make a personal video introduction using Loom or another easy video messaging app.
  • Revive bonding rituals and events that have fallen by the COVID-wayside.
    For example, at Digital Surgeons, we do a Quarter Hack, our unique take on a hackathon. Back when we could physically shut doors, we’d hole up for a full day to collaborate on exploring new business-building ideas for our partners. But it really wasn’t about producing work for clients — it was all about challenging time, space, and process. This is what leads to experiments and newly formed collaborations. While a little more challenging online, tools like the online whiteboard Miro can help. I’ve been planning our first-ever entirely remote version. I’ll share more about this soon. (Wish us luck!)
  • Ditch the Zoom fatigue with immersive video chat experiences.
    Platforms like Kumospace allow you to have multiple simultaneous conversations in wacky and fun settings — without having to be split into breakout rooms.
  • Inject your collaboration software with some fun.
    Emojis are so not a substitute for real emotional connection. You can add an app like Donut to your Slack to jumpstart one-on-one discussions about non-work-related topics.

This helps people bond over both individual and shared interests/passions.

The bottom line: design the opportunities for your people to express themselves, and they will come. And along with those connections will be serendipitous opportunities to expand the boundaries of creative collaboration.

The world now, more than ever, seeks connection. Contrast. A way to break out of the Groundhog Day world that we’ve all been forced into with the pandemic. And after a full year of working remotely, a laugh, a smile, or a flowing moment of collaboration is, in my book, epic in its own right.

How are you creating serendipity in your work? Hit me up in the comments — I’m particularly curious about what platforms or programs you’ve started using that inject a little epicness into your day-to-day.

Founder and Force-multiplier @digitalsurgeons. &

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