How to build serendipity into your community

Jul 29, 2021

Have you ever been dragged last-minute and unwillingly out by a friend, expecting to not have a good time, only to end up meeting possibly the coolest person you’ve ever met who ends up changing your life in numerous ways?

That’s a special moment. It feels like the universe is on your side.

Incorporating that feeling, that high-ceiling of possibility, into your community is achievable and is a reason why members will spend time in your community over others. That's the magic of serendipity.

  • Serendipity is unexpected, addictive and memorable. This helps deep bonds to form within your community and improves engagement, advocacy, and retention.
  • If you can foster it, serendipity is an unfair advantage at a time when there are more communities than ever.
  • Use community data to create meaningful introductions between members and predict their needs before they ask.

Serendipity: "the occurrence and development of events by chance in a happy or beneficial way."

You've probably seen the term 'serendipity' used to refer to inventions that happened by accident. The microwave oven and penicillin, for example, were pretty serendipitous outcomes. Yet the word also translates well to social interactions and events.

While there is no magic blueprint for serendipity, which by definition is unpredictable, it is possible to create environments conducive to collaboration, mutual benefit, and support in order to build something memorable for your members.

You want your members to be frequently thinking about your community. This does not happen by simply having a unique purpose. Providing a great member experience is an active, not passive, job.

Being memorable is critical. The hard truth is that your members have other options. There are more digital communities than ever, right at the same time that people are starting to spend less time online and more time re-connecting in person with people they haven't seen during the pandemic. Serendipity is more important than ever if you want to differentiate yourself.

Unfortunately, there is little information available on how to cultivate serendipity successfully. If you put the time and effort into adopting it within your community, your community can experience some unique benefits:

  • Deep bonds are formed: Serendipitous moments and encounters are memorable. Whether you are meeting new friends or simple having a joint experience, these special moments will create nostalgia over time and keep members from churning, improving your long term retention.
  • Word of mouth spreads: Serendipitous events are things that members don't expect to happen and, since they're unexpected, experiencing them will naturally lead to members talking about them with friends and online. This kind of advocacy will result in community growth.
  • Engagement increases: Serendipity is addicting because it's both beneficial and surprising. Members will be more willing to spend time in your community, and engage with others (as well as you) within it.

If serendipity is based on random chance, how can you create it?

Rather than trying to force it, build structures that allow your community to be a vehicle for it to happen.

Promote intentional one-on-one interactions

1:1 interactions are essential for building meaningful connections. This goes beyond simply pairing people up, as a single bad match can lead a community member to opt out for good.

Executing this step well means collecting data on your members when they sign up. Learn about their backgrounds, why they're interested in your community, what they hope to get out of it, and what they’re most looking forward to. Make matches based on whether two people can actually help each other (tools such as and Covalent can make this step easier).

Deliver answers to questions they don't even know they have

As a community leader, your goal is to connect members with the right answers, or people, in order for them to achieve their objectives quicker.

Try to tailor your content to the questions you see people asking in the community. I do this with the BSP and the email replies I get from you all each week. Sometimes, like this week, I'll change what I plan to write about after chatting with members.

Consistently collecting community data will help with this. The more you know about your members, the more you'll be able to predict their needs.

Normalize small sub-groups

I have mentioned before how important it is to minimize the number of places people have to interact in your community, especially in the early days. Doing this effectively creates social proof and keeps engagement high. However, while a larger number of public channels is bad, intentionally designed small groups can be a community's superpower.

When creating sub-groups, there needs to be a clearly defined objective. While the purpose of 1:1 meetings is immediately obvious, the purpose of recurring group conversations is not. Develop a framework and provide a reason for small groups to exist within your community. It’s okay for these reasons to vary wildly between communities, or even between sub-groups within your community.

For example, if your community is made up of startup founders, you could have smaller groups focused around the company stage and industry that the founder is in. Finding people who have gone through the same thing as you can be magical.

Getting feedback from these groups is crucial. Watch out for members who are providing lots of help to others but not getting any in return. They will most likely move on. Every member needs to be bringing the same amount of value to these conversations.

Leverage your community

One of the most used channels in many of the best communities that I've been a part of is the "asks'' channel (we also use this at Launch House).

Community members can share problems or questions in the hope that someone else in the community can help them, or at least connect them with someone who can.

These channels are very simple and effective, and members tend to check the channel even when they don't have questions in order to learn from others in the community.


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