I’m pressing send on edition #200 of The Quest! 🎉
And wow—what a journey it’s been!
Before I share 19 of the biggest insights I’ve learned along the way, I want to revisit what this newsletter is really about.
“In the word question, there is a beautiful word – quest. I love that word.” – Elie Wiesel
When I led my first live online training five years ago, I was a nervous wreck.
Every bone in my body told me this wouldn’t work.
But to my big surprise, it did.
And it sent me on a quest to answer one big question:
👉 What makes an online session truly engaging and meaningful?
I didn’t have a roadmap—just a deep curiosity and a hunch:
If I kept showing up—writing, reflecting, sharing—I’d start to figure it out.
Since then, here’s what this quest has looked like:
✨ 200 editions
📝 180,000+ words (about 3 books!)
🔧 600+ tools, frameworks, and resources
💬 Countless conversations, ideas, and collaborations sparked
What started as an email to a few supportive friends and family is now a weekly letter to over 1,700+ facilitators, trainers, coaches, and creators around the world—including you.
“The essential questions have no answers.” – Elie Wiesel
There is no perfect formula when it comes to designing and leading live online sessions.
There’s a lot of experimenting. A lot of figuring it out as we go.
But here’s what I do know:
Live online sessions—courses, workshops, webinars—don’t have to be draining or dull.
They can be designed to be meaningful, memorable, and even magical.🪄
💡19 Big Insights from 200 Editions of The Quest
Here are 19 things I’ve learned about creating powerful live online experiences on this journey.
(And I’d love for you to share #20!)
1/ Prep your participants
🧠 When people know what to expect, they show up more confidently and ready to engage.
2/ Create an inviting virtual space
💻 People feel more comfortable when the space feels warm, human, and well-held.
3/ Up your enthusiasm
⚡ Your energy gets dialed down online—so turn it up. Bring the spark, and they’ll feel it too.
4/ Reduce distractions
🔕 Cognitive overload is real. The simpler the screen, the more people can focus on the moment.
5/ Engage from the get-go
👋 The first 5 minutes matter. A prompt, poll, or quick chat check-in gets people involved right away.
6/ Connect early and often
💬 Spontaneous connection doesn’t just happen virtually. You have to intentionally design them in.
7/ Cut your content
✂️ Less is more. Especially online. Give people space to think, respond, and apply.
8/ Increase interaction
🙋♀️ In virtual rooms, it’s easy to tune out. Frequent interactions pull people back in and keep them engaged.
9/ Design for virtual
🌐 What works in person doesn’t work online. Tighter timing, bite-sized segments, built-in pauses, and digital tools fuel engagement.
10/ Mix up your methods
🎨 Variety keeps attention. Switching formats—chat, breakout rooms, solo reflection, visuals—keeps energy and attention high.
11/ Give people options
🎛️ Not everyone engages the same way. Use polls, chat, breakout rooms, silence, or drawing to meet people where they are.
12/ Tame your tech
🧰 Glitchy tools kill momentum. Keep your setup simple, test in advance, and have a backup plan ready.
13/ Movement is your secret weapon
💃 Screens zap energy. A stretch, a gesture, or even changing posture can quickly bring focus and vitality back.
14/ Check in often
👀 Online, you lose the body language cues. Use chat, reactions, or a quick poll to see how it’s landing and adjust in real time.
15/ Take breaks
🧘 Zoom fatigue is real. Breaks boost retention and goodwill.
16/ Keep it simple
🚦Clarity matters more online. Fewer instructions, one clear goal, and simple slides go a long way.
17/ Live time is sacred
⏳ Don’t use live time to deliver what could be a video or handout. Use it for connection, co-creation, and real-time insight.
18/ Have fun
🎈Joy is contagious—even online. A little playfulness helps people open up, connect, and stay present.
19/ Keep learning
🧭Every online session teaches you something. Reflect, tweak, and keep evolving your approach.
20/ …is yours 👇
🎤 What’s one insight you’ve learned about leading live online sessions?
Leave a comment below and let me know. I’d love to share a few in a future edition.
💌 Thanks for reading The Quest
Whether you’ve been here since issue #1 or just subscribed earlier today, I want to say
Thank you.
For reading.
For replying.
For joining me on this 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 👉here.
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:
👉Custom coaching & team training. Book a free 15-minute zero-commitment call with me to see how I can support you and your team.
👉 Live Session Design Video Course. Live Session Magic gives you a proven system for designing consistently high-quality online sessions. Join the interest list here and be the first to get access.
👉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.
