How To Create Serendipity on Remote Teams

I’ve consulted with dozens of remote companies since 2018, and one question continues to come up again and again:

“I love remote work, but I miss the serendipitous moments in the office when I caught up with a coworker while getting coffee and had a breakthrough. How do I make this happen remotely?”

Let’s dive into this problem, starting with: Those weren’t truly serendipitous moments.

Serendipitous moments are ones that happen by complete chance. But that coffee chat moment in the office occurred due to structure. You worked in the same physical office as your coworker and had the same work schedule. This structure is what brought the two of you together, not chance.

This is important to recognize because you’ll need to create some structure in order to introduce breakthrough moments into remote life. The structure is typically derived in one of three ways:

1. Time — A specific time when people take a certain action

• Coffee Breaks — Schedule recurring 15–30 min calls where anyone can jump on and talk about informal topics
• Lightning Talks — Each week, a person presents on a topic they’re passionate about for 15 minutes (it doesn’t have to be work-related), then answers questions for 15 minutes
• Chat Office Hours — One hour a week where everyone commits to being available and checking Slack at the same time

Live in action: Tom attended a lightning talk Alice gave on her interest in AI. Later in the quarter, he’s added as a PM to a new project with an AI component. He reaches out to Alice, who provides him with helpful resources and solutions.

2. Place — A specific zone where people connect on certain topics

• Interest Group Slack Channels — Allow employees to create clubs around their interests (book clubs, tv shows, hobbies, etc.)
• Virtual Coworking Space — People can drop in whenever to cowork together
• Internal Podcast — Record conversations with team members and share their stories internally

Live in action: Jessie and Alex are on different teams but both drop into a virtual coworking space. They are able to bounce ideas off each other and get a new perspective that their teams hadn’t considered.

3. Opportunity — A ritual that takes place following a trigger

• Slackbot Connections — Use a Slack bot like Donut to connect random team members together to meet
• Meetup Budget — Budget for coworkers to get together for lunch/coffee when nearby
• Experience Bonus — Reward team member wins with a day off and a budget for a nice experience out of the house (ex. Day trips, nice dinner out with family, mountain climbs, etc). Have a channel dedicated to sharing experience bonus trip stories.

Live in action: While browsing the experience bonus channel, Sarah reads about how Monika used her experience bonus at a nice restaurant in Munich that looks delicious. Later in the year, Sarah is in Munich for a conference and reaches out to Monika for the restaurant details. They decide to catch up in person and use their meetup bonus to grab lunch together. Monika finds out about an opening that would be the perfect fit for her in Sarah’s division through this lunch.

What do these things have in common?

• They’re optional. People can attend if and when they want. The above ideas will be good for some people and bad for others. That’s normal and okay. Offer a variety and let people choose what’s best for them. Serendipitous moments will never be created through forced interactions (like icebreakers).
• They’re regular. People know what to expect from them, and they are consistent. Serendipitous moments will only happen if team members can count on your chosen structure.
• They’re not about the work. You’re building connections by encouraging people to get to know each other on a personal level. Serendipitous moments will not happen without letting your team members be human.

So, with that, step 1 is complete. You’ve created the structure necessary for these breakthrough moments to happen. Now for step 2: provide the permission for them to happen.

When teams go remote, the company’s first concern is that their employees will start slacking off. In actuality, people end up overworking because they’re always trying to prove this is not happening. This means they won’t participate in anything outside of their job responsibilities, they won’t chat with coworkers about non-work topics, and they won’t build bonds with their coworkers. But informal, open-ended conversations are required for serendipity.

Company leaders must provide explicit permission for team members to talk about non-work topics and have fun together. It won’t happen otherwise. Create policies that encourage taking part in the connection structures, build them into your onboarding process, and ensure managers lead by example.

The “serendipitous” moments you miss from the office can absolutely still happen remotely. It’s as simple as adding structure and permission. Remember: People need to be humans instead of machines in order for very human moments, like serendipity, to happen. Create an environment where that is okay.

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