events, 6 lessons in hosting a transformational live event

What six events taught me about great facilitation

At 4am tomorrow morning I’ll wake up and head to Buffalo airport for the last stop on my Fall tour—a business retreat with Maegan Megginson in Portland, Oregon.

This is event #6 in as many weeks, and I may be the world’s smartest person for booking it as my final stop. My phone will be in a basket. All my meals will be provided. It’ll be exactly the kind of full-service retreat I just delivered to my Power Mastermind members last week.

Inspecting the outdoor dinner setup at our Power Retreat

Maegan’s retreat will be a 5-day reprieve from watching the news, from answering emails, from cooking meals, from serving clients and writing promotions, from doing anything at all to impress, please anyone, or move anything forward.

I plan to abandon half-drunk mugs of tea wherever I please, sleep through at least one session, and wander the woods alone singing to the trees. It’ll be about getting quiet and seeing what emerges from the stillness. 

Can you imagine? I can’t wait.

This Fall has been a real season of learning what makes an event great—as a participant, a facilitator, a human learning to art of holding space, and a human who needs holding. After completing a certification on how to lead transformational group experiences (affiliate link) less than a month ago, I’ve been seeing everything through that lens: what makes people open up, what helps them relax, what quietly shuts them down, and how can events be truly supportive, rather than just overload people with more information.

Here are a few things I’ve noticed, in no particular order:

Comfort is the foundation

The physical environment is the event. If the chairs are uncomfortable, the lighting is harsh, or the dining experience isn’t quite right, participants can’t fully land. Comfort isn’t extra, it’s the ground on which everything else stands.

You can tell how well an event is going just by watching people—are they hiding out in their rooms, or are they lingering at the table long after the dishes have been cleared, or sprawled out on the couch delaying bedtime “just five more minutes so we can finish this conversation”?

The right brand of oat milk matters

People remember the ways you made them feel important. Care lives in the smallest details: remembering someone’s favorite oat milk from last year, preparing a traditional Yom Kippur breakfast for the one participant who would otherwise be observing this holy day, seeing an opportunity to let someone lead who might otherwise be hiding out in the background.

Transformation becomes possible only when people feel a deep level of safety. Those gestures tell the room, “You belong here, and we are thinking deeply about how to care for you.” 

Moments of tension should be welcomed, not avoided

When people feel present and safe, a lot can bubble to the surface—emotions and ideas that we do not have space to explore in our daily lives. Saltiness, anger, fear, unexpected imposter syndrome, whatever. 

These aren’t failures of facilitation, they’re signs people are sinking in deep enough to access parts of themselves that were there all along. The work of facilitation is to create a space strong enough to hold everything that wants to emerge. Sometimes the biggest ideas and a-ha moments are preceded by frustration and internal collapse. 

People remember the peaks and the ending.

Best case scenario, you create a high point that everyone remembers—a collective moment of joy, laughter, or awe. At my Power event we hosted a homegrown talent show with guest judges (my team), a moment of laughter and playfulness I bet we’ll joke about for years! (“OMG, remember when Suzy performed The Lorax?! It went on for 15 minutes and she fully committed to EVERY PAGE!!”)

Worst case scenario, the moment that sticks is the trough—that time the bus broke down and we all stood in the beating hot sun for half an hour, milling around awkwardly waiting to be rescued! That becomes the story people tell.

Almost anything can be forgiven if you’re able to end on a high note (in our case, everyone singing and crying in each other’s arms). 

The event starts way before the event starts

A great event starts long before the opening session. Having space for people to meet each other, go over communication agreements, set expectations for the event (including what could go “wrong”), and give everyone a chance to get their jitters out—those things help people drop in much faster and be fully present for an event. 

I believe what people need most right now is connection and holding. And business strategy, OF COURSE! But even the best strategies are useless if we’re too freaked out, tired and overwhelmed to process them, let alone implement when we get home. 

A common theme at our retreat last week was, “I can’t believe how much I needed this.”

OH MY GOD, yes  

We need each other more than ever right now—true communities where we can be held, where there’s space for all our parts to be seen and acknowledged. The scared parts, the cautiously optimistic parts, the “is it okay to feel joy right now?” parts, the parts that think it’s their job to single-handedly free Palestine, the parts that wonder if receiving care is indulgent. All the parts. 

We all need this. 

But you especially need it if you’re a community worker, a leader, a politically engaged person, a caregiver, a new mother, a person in a healing profession, and I’m sure a whole bunch that I missed. Feel free to add yourself to that list. Your support and well-being matters. Community, connection and healing needs to be a line item on the budget, as important as your Meta Ads manager or your many software subscriptions. 

…and now I will step off my soapbox because it’s 7:34pm and I haven’t even packed yet. 

But I’d love to hear from you:

What do you require from a live event in order for it to be worth the travel? Which parts do you have that need more support right now? What would your dream scenario support system look like? 

Looking forward to your replies.

A very tired T-Boss

Tarzan Kalryzian [she/they]
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