Assisted Serendipity, Random Coffee and the power of the unstructured meeting

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We have some of the best conversations when they are unstructured and happen by chance. That moment when you bump into someone when you are out and about, and they happen to mention something that really helps you. Or you sit down to lunch with a work colleague, and it sparks a great new idea.

These serendipitous moments are where relationships are built, and magic can happen. Something organisations and communities can really benefit from embracing. Recently I have been looking for ways to help create opportunities for serendipitous moments. This is called assisted serendipity.

What is assisted serendipity?

This is a term I have borrowed from a blog post by John Goulah from Etsy.

First, it’s worth saying why it’s important that people talk to each other. For this, I tend to look to Alex Pentland. His books on Social Physics, talk about our organisations in the context of social systems, and the power of connections between people across divisional or discipline boundaries. It is easier for people to share ideas and work together if they know each other.

If a building doesn’t encourage [collaboration], you’ll lose a lot of innovation and the magic that’s sparked by serendipity. So we designed the building to make people get out of their offices and mingle in the central atrium with people they might not otherwise see.”

Steve Jobs

Assisted serendipity is about changing our organisations in some way to make it easier for connections to form, either through creating the space for unstructured conversations between peers or allowing new connections to form between people that wouldn’t otherwise meet. It might be through physical space design, for example, Steve Jobs talking about the Pixar building, through reinforcing messages, like Tony Hsieh from Zappos talking about collisionable hours or through creating community activities like meet-ups.

Random coffee

Aside from communities of practice, one of my favourite easy to set up assisted serendipity hack is random coffee. Where two people are paired randomly to have a coffee and a chat. I took part in random coffee when I was at GDS and always found the conversations really interesting and massively useful.

Hootsuite wrote about the power of random coffee on their culture here:

And the University of Michigan talk about how their random coffee programme has created new innovations across divisions here

I use (remote) random coffee with my Agile in the Ether community slack channel as a way of deepening relationships and connections over a distributed community. For that I use the donut slack app to set up fortnightly pairings. To keep the community feeling, we follow up in the slack channel with remote coffee selfies and a thank you to each other.

Random Coffee Selfie

Remote working and serendipity

At the time of posting, the WHO has declared a pandemic leading to many people self-isolating, and governments advising or mandating staying at home. Suddenly people are finding themselves working from home, which has ignited an interest in how to deal with remote working. Not being in the office means that those serendipitous moments rarely happen. We might interact with other people, but it’s mostly over meetings with set agendas or outcomes, which makes it more important to create those serendipitous moments.


A useful addition to this post is group remote coffee breaks. See global canteen from Matt Ballantine for group and virtual fika from Lisette Sutherland


So what about you? I’m really interested to hear if others have experimented with assisted serendipity and what results you saw in the comments below.


  1. Barbara walker

    12 March 2020 at 12:28 pm

    I do agree with random meetings in coffee shops you always leave with a smile and feeling lighter on the inside talking is the most important thing to do even in families .

  2. I’ve been taking part in the random coffees from the Agile in the Ether Slack. Great chance to get to know people and hear ideas that might be useful for me to try too. I’ve really enjoyed people sharing topics and links from their coffees afterwards – spreads out the interesting conversations further!

    Loads of interesting context about where else similar ideas have been useful, I’ll definitely be trying it out in more contexts.

  3. Random coffees are great, they are agreat way if breaking down siloes in large companies, and in remote companies they provide the much missed ‘watercooler chat’ opportunities. It’s really nice to do this in communities such as agile in the ether too, I learn so much from peers in other organisations, it’s like a giant community of practice!

  4. Really love the random coffee meet ups as a way to meet and interact with new people. Lots of ideas shared and top tips received!

    Thanks Emily for setting this up.

  5. thanks for information to random coffe, keep healthy, keep safe

  6. Marshall R. Haycraft

    7 October 2023 at 4:20 am

    What an insightful article! “Assisted serendipity” is such a fascinating concept, and I can see how it could lead to innovative ideas and connections.

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