The Quest #150: ๐ŸŽ‰How to Engineer Surprise in Your Live Session

Hello friends,

Greetings from Barcelona where we are enjoying some surprising sunsets.โ˜€๏ธ

Pop Quiz!

Do you prefer when things

a) go according to plan? Or

b) when the unexpected happens?

Me? I’m a planner. I like lists. I print out calendars. I guess it’s what comes with being a Virgo perfectionist. ๐Ÿคท๐Ÿผ

Most people pick control and predictability.

If you are a planner, you are not alone. Our brains are hard-wired to seek out predictability. We scan for patterns and build habits around them.

And yet we crave surprise.

Think about it – what really sticks in your memory? It’s not usually the humdrum stuff that happens every day. It’s the surprises that capture our attention.

There is a science to engineering surprises.

When it comes to leading live online sessions, it can be tempting to always play it safe. After all, you don’t want your participants to feel awkward or send people into their panic zones.

You can harness the element of surprise.

There is an art and science to engineering the unexpected. When you learn to harness the element of surprise in your live sessions, you’ll transform your sessions from ordinary to extraordinary.

So how do you engineer surprise in your live sessions? That’s our quest for this week. ๐Ÿ”Ž

๐Ÿ‘‰Surprise: Embrace the Unpredictable and Engineer the Unexpected

๐Ÿ‘‰5 Strategic Ways to Weave Surprise into Your Session


๐Ÿ‘‰This Week’s Top Picks for Facilitators

Let’s jump right in!

๐Ÿ“™Surprise – the book

For a deep dive into the science of surprise, I highly recommend the book Surprise: Embrace the Unpredictable and Engineer the Unexpected.

It’s written by Tania Luna and LeeAnn Renninger, two PhDs who engineer surprises for a living.

It’s one of the most fascinating books I’ve read in a while. It’s not a “facilitation” book per se, but it made me re-think how to engineer surprises in live online sessions.

Here’s what they say๐Ÿ‘‡

“We feel most comfortable when things are certain, but we feel most alive when they’re not.”

Surprise, they say, is the little-known key to growth, attention, and connection.

This book is packed with surprising insights on how to get attention, keep interest, handle ambiguity, boost creativity, and more.

When it comes to live sessions, here are my top 3 takeaways:

1/ ๐Ÿ‘‰ Master the “Surprise See-saw”. Too much surprise can cause stress. Too little leads to boredom. The goal is to find the sweet spot where surprise enhances the experience.

2/ ๐Ÿ‘‰ Reduce surprise to produce surprise. Setting stable ground first gives us the confidence that we can handle surprises and use them to our advantage. Establish a sense of psychological safety and trust first.

3/ ๐Ÿ‘‰ The smallest surprises matter most. You can weave small surprises into everyday things – gifts, stories, compliments, events, meals, and conversations to spark more delight and connection.

๐ŸŽ‰5 Ways to Engineer Surprise in Your Session

Engineering surprise in your sessions isn’t about manipulation; it’s about enriching the experience and sparking genuine engagement.

Here are five ways to embed surprise in your live sessions, complete with why it matters and practical ideas you can use straight away:

1/ Prepare for surprise.

Surprises are best received when participants feel secure. Building psychological safety ensures that surprises foster innovation rather than discomfort.

How? Send a pre-session email outlining the session’s purpose and a glimpse of what to expect, setting a comfortable stage for the unexpected.

2/ Design small surprises.

Small surprises can break monotony, capture attention, and encourage creative thinking.


  • Share an intriguing quote in your waiting room.
  • Play welcoming music when participants join.
  • Invite participants to unmute and say hi on the count of 3

3/ Move from the comfort to the stretch zone.

Gradually introducing surprises encourages participants to embrace challenges without feeling overwhelmed.


  • Begin with an easy question like, “What’s one thing that has surprised you lately?”
  • Organize an initial breakout session with the prompt, “What’s one thing people may be surprised to learn about you?”

4/ Facilitate the discovery of surprise.

So often in live sessions, surprises and insights are lurking just below the surface. It’s your job to help people uncover surprises.


  • Be flexible in your session plan, allowing space for the unexpected
  • Ask reflective questions like “What’s one thing that surprised you?”

5/ Close with a surprise.

The end of every live session is a moment that’s ripe for surprise. It’s often what people remember most.


  • Replay the opening music again at the end
  • End with a prompt question “One thing that surprised you in this session”
  • Invite participants to unmute and say goodbye

Surprise doesn’t just happen; it’s a creative, thoughtful process.

What unique twists do you bring to your sessions? I’m eager to hear your strategies and experiences. Hit reply to this email to let me know.

Turn on your mics and say goodbye

๐Ÿ’ชFacilitator Finds

1/ Jan Keck’s Top 5 List of Facilitation Resources(LinkedIn Post). Jan produces brilliant content about turning meetings into inclusive, engaging, memorable experiences. Check out his recommended books, podcasts, YouTube channels, LinkedIn accounts, and honorary mention for The Quest. ๐Ÿ˜ƒ

2/ 2024 Black History Month Playlist (h/t John Chen). 128 songs curated by the CHORUS Las Vegas with some of their favorite songs from the past and present in celebration of Black History Month.๐Ÿ™Œ There’s a whole lot of inspiration for opening session songs on this list.

โœ๏ธ Quote of the Week

“Our brightest blazes of gladness are commonly kindled by unexpected sparks.”

Samuel Johnson, English Writer

๐Ÿ’Œ Thanks for reading The Quest

I always love hearing your feedback and suggestions. Just hit reply to share your thoughts and ideas.

If you were forwarded this email, you can subscribe to The Quest ๐Ÿ‘‰here.โ€‹

If you enjoy The Quest, I’d appreciate it if you shared it with anyone you think might like it.

Creatively yours,

Whenever you are ready there are 2 more ways I can help you:

๐Ÿ‘‰Custom coaching & team training. Book a free 15-minute zero-commitment call with me to see how I can support you and your team.

๐Ÿ‘‰5-week Live Online Course. The Breakthrough Facilitation course gives you tools, personalized feedback, and a proven framework for designing and leading high-engagement live sessions. Join the interest list and be the first to get the next cohort dates and discounts.

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