Magical Questions to Spark Connection

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My guest: Priya Parker is a master facilitator, conflict resolution expert, and author of the bestselling book The Art of Gathering: How We Meet and Why It Matters. Priya has spent decades facilitating difficult conversations in boardrooms, communities, and conflict zones. In this conversation, she reveals the mechanics of meaningful gathering and why most of us are doing it wrong.

A facilitator is interested in the life of a group. I think of facilitation as working with people who are interested in the infrastructure of three or more people who need to come together and are ideally changed for the better by what transpires between them. A facilitator thinks deeply about how to set up the conditions to increase the likelihood that transformation happens.

Great facilitators are obsessed with language. There's listening to make someone feel heard, but the difference between green facilitators and seasoned ones is an obsession and ability to hear, recall, and play with language. You have to understand what people are actually saying and be able to reflect it back in ways that unlock new meaning.

Understanding power is essential to facilitation. You need to know how decisions are being made, who is talking more than others, when to allow for that, and what your own relationship is to holding the group. When do you shut up? When do you pull people out? When do you push back? All of this is fundamentally about understanding power dynamics.

I'm a third-generation ostrich. On both sides of my family, when conflict arises, we stick our heads in the sand. Nothing to see here, folks. But I've cultivated the ability to hold heat. Even now, when facilitating a reckoning and the heat rises, my palms still get sweaty, I can feel my heart racing, blood rushing to my cheeks. But I've learned how to stay present with that discomfort. Counterintuitively, having deep empathy for people who want to flee makes me more effective.

"90% of the success of what happens in the room, and as a facilitator, happens before anybody arrives." This is what my mentor Randa Slim taught me, and it's absolutely true. The construction of the house happens before anyone gets there.

Dr. Hal Saunders changed everything for me. He was an American diplomat who served five presidential administrations and was part of the Camp David Accords. After leaving government, he realized that while governments can create peace treaties, people's perceptions of each other on the ground haven't necessarily changed. He trained me as a teenager in sustained dialogue, and I learned facilitation the way it should be learned—through apprenticeship. Even in his seventies and eighties, he always believed he had something to learn.

The first questions people ask you signify what they value. When I arrived at the University of Virginia, people kept asking, "What are you?" I learned quickly that they meant racially. My mother, an anthropologist, had taught me that the first questions a community asks reveal what matters most to them. Race was clearly very important there.

I made myself a conflict resolution facilitator. Growing up between two vastly different households—toggling every two weeks between a vegetarian, Buddhist home where the word "God" was never mentioned and an evangelical Christian home where we never ate before saying Grace. I became deeply interested in when and why and how people come together, what they think of as normal, how they create and change cultures, and how they come apart.

Your highest real estate is when people are together in the same place at the same time. Wasting time in the room figuring out what to say or do is actually wasting everyone's time. A huge part of preparing for any gathering is figuring out what the right conversation is for this group to have, and how to equip them to have it well.

Think of military pre-mission briefs. They're really good at setting mission objectives. This is the goal, this is what we're striving for. Then they debrief afterward to learn and do better next time. That same discipline applies to any gathering, whether it's a leadership retreat or hosting dinner at your house.

Every gathering is a social contract. You're creating a temporary constitution. At a dinner party, there's an implicit rule: bring a bottle of wine. People find out they've broken the constitution when someone says, "Wow, they didn't even bring a housewarming gift." We have all these implicit norms, and in diverse groups... Which is every group, not just racially, but people with different assumptions about how things work—you need to make the contract explicit.

Elizabeth Stewart ran a startup networking organization and wanted it to be a true community, not just a shark tank for pitches. She created a pop-up rule: you can't talk about what you're selling. No pitches. Super counterintuitive for a networking night, but it created exactly what she wanted... Trust and long-lasting relationships rather than transactional encounters. The rule signified what she was trying to create.

Using your power as a host means protecting your guests. You're temporarily equalizing people so they can coordinate group life. Gathering is fundamentally a coordination problem: helping people understand what the rules are, protecting them, and connecting them.

There are moments when you should surprise people. If a team is stuck in a 50-year-old institution that's always done things the same way, and they'll die institutionally if they don't change, maybe the purpose is to build their skills for discomfort and navigating uncertainty. In that case, maybe you don't tell them the full roadmap because the practice itself is learning to navigate the unknown.

Making things explicit and transparent equalizes the room. Showing the roadmap is deeply beneficial, particularly to people with less power and knowledge. For newer people who don't know how things work, for people with other obligations like tending to an elderly parent or being a student athlete with fixed schedules, transparency helps level the playing field. But it may not always be your purpose.

Before you default to a dinner party, ask what you actually need. If the goal is to laugh hysterically and create memories with friends you don't see enough, a dinner party might not be the best form. Maybe you should play kickball in the park, stage a made-up pickleball championship, go to a morning rave, or take a party bus to a concert. We're so boxed into thinking about how adults must hang out.

When hosting dinner parties, keep the menu relatively simple. Increase the meaning dial and it decreases the pressure on food quality. Think about food that tells a story.

The invitation matters deeply. I could send an invitation: "Come enjoy my best attempts at Ruth's BLTs." My grandmother's recipe that takes me back to childhood. I tell the story in the email, narrow the expectations, and create a social contract. This is for BLTs. If you're a vegetarian, you can take out the bacon. And please don't bring your mushroom penne, not in this context. Then I ask: bring a story of a dish that takes you back to childhood. The whole night plays itself.

Magical questions are questions everyone in the group is interested in answering, and everyone would be interested in hearing each other's answers. It's a magical equation. It's subjective and relative to each group. My seven-year-old daughter once asked at dinner: "What's the naughtiest thing you've ever done that was worth it?" We laughed and shared for two hours. My son asked my elderly father: "What's the meanest thing you ever did to anybody before the age of 15?" That caveat, before age 15, temporarily equalized everyone at the table.

Testing and practicing are how you develop the muscle. I test questions on my team, I think through social arithmetic: what do these specific people have in common, what don't they have in common, what's the right level of vulnerability? I ask my community on Instagram and Substack to share their magical questions. Someone from Brazil sent me: "Would you rather spend 10 minutes on the moon or one year traveling through Europe?" It inspires heated debates in his friend group.

My favorite question for virtual groups: "What was the first concert you ever went to, and who took you?" People pause, then you see a waterfall of answers—Bonnie Raitt, Madonna, New Kids on the Block. Everyone's interested in seeing everyone else's answers. You realize who's here, you see there's someone behind everyone (my sister, my mother, my college girlfriend), and you increase the likelihood that people realize these are real humans.

Creating psychological togetherness on Zoom is my single most important skill. During the pandemic, I lost all my physical facilitation tools. I couldn't chase someone into the bathroom to convince them to come back, couldn't use my body to signal it's time to quiet down. I was just a little green square. Magical questions became my most powerful tool for creating psychological togetherness when people aren't in the same room.

Ryan's champagne question works because it's visceral and emotional. "We're meeting exactly one year from today and popping bottles, what are we celebrating?" That's not "what's your goal for the year." That's boring. You pop champagne for something that matters emotionally. It's a somatic, physical question that forces people to think big because you're not popping champagne about something boring.

The responsibility of gathering is about both connection and power. Particularly in work contexts, you can ask questions that are too vulnerable or that aren't appropriate. You need to protect your guests by ensuring questions relate to the purpose of the convening. Asking "what's a core experience from your early life that connects to why you do the work you do today?" helps people understand motivations without crossing lines.

Questions can open up the world. They're a sequence of words that, if you ask them in a specific way, can fundamentally change what's possible. Being genuinely curious and fascinated about people and their stories and life experiences will change your life. Full stop.

Writing The Art of Gathering let me articulate what deeply frustrated me about gatherings and try to convince other people it should frustrate them too. What's been beautiful is that people are starting to get fed up with mediocre gatherings and expect better of how we spend our time together. They're realizing we can change it with some thought, some temerity, some bumping around.

The pandemic made the book even more relevant. The paperback came out in April 2020, when gathering was banned, which was super awkward. But by taking gathering from us, we began to see it. We began to see that this thing we took for granted shapes our lives—how we wed, fight battles in court, host funerals, host galas. People started asking first-order questions: when and where and why should we meet, and who decides? That's a powerful question to be asking.

Anyone can gather. Many of the hundred gatherers I interviewed for the book identified as introverts, loners, people on the outside of things, people with social anxiety. As one person said, "I create the gatherings I wish existed in the world. And other people seem to like it."

• What gathering in your life, whether a team meeting, family dinner, or community event, would be transformed if you paused to clearly define its purpose before diving into logistics and form?
• Think about a group you're part of where people come from different backgrounds and assumptions. What explicit "social contract" or ground rules could you create to help everyone understand how to show up and what's expected?
• What's a magical question you could ask in your next gathering that everyone would be interested in answering and everyone would want to hear each other's responses to?

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