You’ve probably learned something useful by chance. A stranger at a café mentions a tool that turns out to be exactly what you needed. You overhear a colleague in the elevator describe a project that touches your own. You sit through a compliance course, and the real value turns out to be an offhand comment on something else entirely.
If serendipity plays a real role in learning, why isn’t it part of our learning and development strategy? Can we engineer more of it on purpose?
Principles of Serendipity Engineering
Serendipity flows from simple principles:
- Let conversations follow people’s interests. Don’t force an agenda.
- Don’t aim for action plans or specific outcomes.
- Bring together people who wouldn’t normally meet.
The second point may surprise you. Most of us push hard for clear actions and outcomes. Conversational leadership pioneer David Gurteen argues the opposite: insisting on outcomes can choke off the free flow of ideas where serendipity actually happens.
Think of this as a search problem. Some questions have a known place to look for the answer. Most don’t. For those, you cast a wide net across people and topics, watching for something useful. This isn’t random. You choose who to talk to because they come from a different background and might expose you to something new. You range over many topics, then follow the ones that connect to something you actually need. It feels casual, but there’s a search logic underneath.
Methods of Serendipity Engineering
The methods of serendipity engineering are familiar:
- Communities of practice
- Networking events
- Lunch and learns
- Social events
- Slack channels
It’s all about creating a time and place for people to connect.
Why the Name Matters
If you’re already running events that encourage connections why give the underlying idea a name? The name matters because the mechanism that makes them work gets lost without one. An informal community of practice looks like a nice-to-have next to a formal workshop. A networking event without clear outcomes may seem a poor use of time. You need to name what this type of L&D intervention is doing—it’s engineering serendipity to reach insights that won’t arise from scripted workshops. A strong name earns credibility. Use it.
How This Fits Into the Broader L&D Program
None of this replaces standard training and workshops. Those still matter for skills many people need at the same time. If many of your managers need training in giving feedback, don’t wait for serendipity. Build the workshop.
Serendipity engineering matters now because of AI. AI is moving too fast for the usual training mechanisms to keep up — if a course takes three months to design and roll out, it’s obsolete before employees see it. Plan for the skills everyone needs. Engineer serendipity for everything else.
Related ideas: You might be interested in Cohen, March & Olsen Garbage Can model of decision making, which discusses serendipity in decision-making, and Herminia Ibarra’s work on loose connections in networking, which can be seen as a way to enable serendipity.
David Creelman is CEO of Creelman Research. Currently, he focuses on helping organisations build their capability for adapting to AI. Connect with him on LinkedIn or at dcreelman@creelmanresearch.com.
