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Live life more alive

5 Lessons from hosting 500+ strangers for dinner

(how to become a better facilitator)


I’ve hosted 500+ strangers in Denver for Dynamic Dinner over the last 21 months.

What are they all seeking?

Meaningful connection.

Here are five things I’ve learned about creating real connection for groups of 10 to 50 people—without booze, hypnosis, or free pizza:

The last one is really important if you’re leading a community in your personal or professional life already.

1. Influencer ≠ Facilitator

Influencers aren’t just on Instagram. They’re anyone with a big audience—like your favorite musician, the CEO of a huge company, or a famous actor.

→ Musicians (J. Cole, Taylor Swift, East Forest)

→ Leaders (CEO, President, Manager, Pastor)

→ Actors (Will Smith, Matthew McConaughey, Emma Stone)

→ Social Media Creators (Yes Theory, Dan Koe, Gerrain Jones)

I love that influencers are trying to bridge the gap between followers and community, but the word community gets thrown around like a soggy chew toy.

Attracting people to you, and gathering them effectively are different skill sets.

In brief, two people won’t develop a deep relationship just because they both cheer for the same team.

The common interest is a common thread together. You have to pull on it to cultivate deeper connection.

An example would be sports. Have you ever been on a team where you felt like you didn’t belong?

The sport brought you together, but doesn’t cultivate the sense of belonging itself.

The leader does. (If they’re a skilled facilitator)

2. Spectrum of Connection

There’s a reason why events go hand in hand with alcohol.

Alcohol makes money.

Super Bowl x Bud Light

Coachella x Heineken

Even your local bars and restaurants host music because it attracts people so they can buy alcohol.

Alcohol makes money because it numbs you. You don’t have to feel awkward. You can walk right up to that person you’ve never met and start a conversation without being paralyzed by fear.

You may still be awkward, but you don’t feel awkward.

“Have a few beers and you’ll loosin up a bit.”

It’s easier to have a few drinks and enjoy yourself than to confront the fact that you’re terrified of other people’s judgements, and that’s the real reason why you don’t know how to interact with them.

Alcohol hijacks the spectrum of connection. It takes you from level 1 to level 7 by altering how safe you feel in yourself.

Skillful facilitation takes a group through the spectrum of connection without alcohol. Taking people from level 1 to level 7 with mindful questions, playful fun, allowed awkwardness, and by reminding the group that they’re safe to take risks.

Let me be clear, a “safe space” doesn’t exist. The concept of “judgement-free zone” is bull shit.

A beautiful ideal. But, we’re all human.

However, there is a spectrum of safety.

At Dynamic Dinner we’ve created a structure for cultivating a wild amount of authentic safety and connection in one night, without substances.

Here’s the flow:

1. Bridging

Everyone gets a warm welcome right away. If you don’t get a hug, call me up—I owe you a free dinner!

2. Pattern Interrupt

You need to equalize the room. Everyone walks in with different baggage and different defaults. We interrupt those default patterns as quickly as possible.

3. Group Gathering

We create glue by bringing everyone into a circle and having one conversation together.

4. Clarity & Main Intention

The group wants a reminder for why they came. What are they getting out of this experience?

5. Level 1

Activity 1: Get the group to speak to one another. Allow this to be simple. Most people are meeting for the first time.

6. Level 2

Activity 2: Dig under the surface. Ask a deeper question. Do something weird or funny together.

7. Level 3

Activity 3: Lean into the yellow light. Prompt the group to be more vulnerable with one another.

8. Small Groups

Dinners cap at 40 attendees. That size is way past having an intimate, natural conversation. After the large group (facilitated) conversation, we break up into groups of four to allow space for exploration.

9. Honoring

This is crucial! End the experience on a high note. We take 10–15 minutes to offer positive affirmations around the circle to finish the night.

“Criticize generally, praise specifically.” – Warren Buffet

10. Group Closing

I call this a group gratitude moment. It looks like prayer. Hold hands and remember we’re all in this crazy human experience together.

3. Healthy Hardship

Unpopular opinion:

Connecting over challenges doesn’t equal trauma bonding.

Hard things bring people together. It’s not about wallowing in sad stories; it’s about growing closer by climbing the same mountain—literally or figuratively.

Go hike a 14,000 ft. tall mountain in Colorado with people you’ve never met, I bet you end up feeling like best friends at the top.

Share what’s truly on your heart with a stranger at the next networking event you go to. They’ll either walk away because you didn’t take their business card or remember you forever.

I believe the most effective way to create deeper connection–fast, is through challenge.

As a facilitator (or group leader) you have to create this healthy hardship for the group.

You can plan a trip to hike that mountain together, or you can facilitate a group conversation towards vulnerability.

*tip – do this gradually. it’s an art and science. the hike starts by getting out of the car, not scrambling boulders.

If you want good questions to ask, here’s a free download of the question cards I created for Dynamic Dinner.

Example:

4. Destroy Etiquette

  • Etiquette: Salad fork. Dessert fork. Don’t F it up.
  • Temporary Rule: You can’t talk about work.

Gathering with unspoken etiquette creates a divide immediately. Some people (who’ve been before) will understand what they’re supposed to do.

They’ll know to eat with the salad fork first, then put the fork on top of their salad plate turned left to right in order to signify they’re complete with that dish.

If you didn’t grow up eating dinner with 8 pieces of silverware this scene feels like an escape game setup.

Priya Parker is the queen of gathering in the new age. She says intentional experiences should offer temporary rules instead of etiquette.

Creating temporary rules creates a new universe for attendees. That’s what we want when we go to an event, experience, or even meeting.

You want the feeling of group flow state.

The other challenge with etiquette is you put pressure on people who understand the etiquette to teach the people who don’t.

That takes both of their attention away from the experience, event, or facilitation itself.

5. Community is a Byproduct (and should be)

If you’ve read this far I can almost guarantee you lead groups of people, have a community of your own, or desire to be in a position of leadership.

I can also, nearly guarantee that if you open up Instagram right now, it would take less than 10 swipes on your feed to find a video of a massive influencer telling you how important it is to create a community and monetize them.

Honestly, I agree.

But, I believe that the community is always a byproduct of what you offer.

Take Dynamic Dinner for example.

We don’t offer community.

What we offer is a set of values and a way of being that attracts a certain type of person.

Those specific types of people typically want to be around others like them.

Similar life experience creates a felt sense of safety.

That’s human behavior.

If you want to live life more alive, care about meaningful connection, personal development, and spiritual growth – then the Dynamic Crew is for you.

You’ll find community through the offering.


Side note:

Setting up a community for community’s sake creates more management than you’re aware of. That management doesn’t make any money.

If you want a guaranteed way to burn out, build a community for community’s sake.