Keep Your Best Self Out of My Gathering

 

Six

Keep Your Best Self Out of My Gathering

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We have spoken so far of gathering with purpose, and of making practical choices that flow from that purpose. You have absorbed my pleas to own your power as a host, but to rule generously. You have encountered examples of people spicing up their gatherings with rules and fleeting formats. You’ve been instructed what not to do in your opening, and what to do once you stop doing those things—and how to ready guests before it even starts.

Now your event is under way. The tracks are laid. Things are rolling. Your thoughts may turn to where many of my friends’ and clients’ thoughts do: the question of how to get those you gather to be more authentic. How do you keep people real? I have some suggestions. Fifteen, in fact.

15 WAYS TO MAKE A CONFERENCE—OR ANY KIND OF GATHERING—SUCK LESS

Nowhere is puffed-up phoniness more palpable than at conferences. Nowhere else is the chance to have conversations across borders, identities, and professions so often wasted. Nowhere else are so many people with the influence to change things so frequently brought together, only for the resulting conversations to remain on the surface. They lurk there because everyone is presenting the best self they think others expect to meet.

If you had to pick the setting where this “conference self” is at its worst, you might well choose the meetings of the World Economic Forum, an organization that convenes the world’s rich and powerful several times a year, most famously in Davos, Switzerland. Which is why, a few years ago, a colleague and I set out to see if we could hack the WEF. Could we create an anti-WEF on the sidelines of a WEF event? Could we induce people trained to present themselves as perfectly baked loaves to bring dough worth sharing instead? Might we have better conversations about what the world actually needs when people drawn from a dazzling array of backgrounds share their full selves, not just their puffery?

The event we decided to infect with our gathering ideas was an annual WEF conclave in the United Arab Emirates, a couple of months before the major event in Davos. The purpose of this earlier conference is, in part, to surface ideas and agendas for Davos. The WEF organizes dozens of “global agenda councils” on issues ranging from artificial intelligence to the future of the oceans. Each council is instructed to “provide innovative thinking on critical global issues and incubate projects, events, and campaigns for the public good.” Nine hundred council members meet in the UAE for three days of meetings to discuss the work they have been doing throughout the year on their topics and to suggest new directions.

The people chosen to join these councils are invited because of their accomplishments and their strengths, not because of their vulnerability. For this reason, the meetings, and even the dinners and coffee breaks, can become like show-off sessions, with round after round of one-upmanship. Even when they were not competitive, the conversations I was part of often remained superficially intellectual, with little realness or emotional risk. It was like many conferences I have attended: you go, try to impress people with how smart you are, perhaps come away with a few new work opportunities. But it was difficult to have any authentic engagement. Everyone tended to behave like his or her own brand ambassador and press secretary. Given that this wasn’t an insurance industry conference but an event about addressing the biggest problems of humanity, this superficiality seemed to interfere with our chances of doing so.

I had been invited that year to join the WEF Global Agenda Council on New Models of Leadership. According to a past report by that council, its focus was to understand and create an in-depth dialogue about the “profound shift in the context in which leadership takes place and in what it takes to flourish as a leader.” Specifically, the council felt that changes in the world were “opening up a new leadership space.” It said that space was defined by, among other things, “the emotional capacity of the leader (values, courage, self-awareness, authenticity)” as well as “the extent and depth of their social relationships and networks.” Perhaps because of this focus, many of us on the council were struck by how the WEF’s culture made it hard for leaders to develop along these dimensions. A colleague of mine on the council, a German marketing executive named Tim Leberecht, and I wondered if an experiment could change that.

Our experiment, perhaps not surprisingly, involved gathering differently. We suggested throwing a small dinner the night before the conference began, with members from various other WEF councils. Our goal was both simple and very complicated: to get people to turn off their networking engines and elevator pitches and get them to connect—humanly, authentically.

But how do you create an intimate dinner at a networking event? How do you get people to be vulnerable when they show up invulnerable? How do you create a work dinner that feels more like a rehearsal dinner? How do you take people who have come to hawk one idea or organization and restore them, for a night, into the complex, multifaceted human beings they actually are? How do you allow for weakness and doubt in people who normally exude certainty and confidence?

At first, we focused on the normal preparations: We booked a private room in a restaurant. We invited fifteen guests from various councils, many of whom we did not know but who intrigued us. To help focus the evening, we chose a theme: “a good life.” We had used that theme previously on another project we had worked on and knew it was a rich topic—and one we were well prepared to moderate as a result. It was also purposefully a good life (as in, what do we think makes for a good life?), not the good life.

The night before the dinner, I had trouble sleeping. Why did we invite all these people? What if it doesn’t go well? What if no one speaks? What if the theme doesn’t work? I was worried about the actual conversation, the one part I assumed I could not shape ahead of time. I felt there was too much riding on our ability to facilitate a complicated conversation among fifteen strangers. And while we had spent so much time mastering every other detail down to choosing the opening welcome drink, we hadn’t given much thought to the actual structure of the conversation. We were winging it. I wanted to make something intimate. But I had not actually designed for intimacy.

That day I had lunch with my mother and husband, who were with me on the trip. As we ate in a badly lit mall in Abu Dhabi, I shared my anxieties. Why would people share authentically? How was I going to decide who goes when? I put my facilitator hat on and started to think about potential structures. The most basic, and easily forgotten, gathering principle returned to me: We needed to design for what we wanted.

What if, instead of just introducing the theme of “a good life,” we asked each guest, at some point in the night, to give a toast to “a good life,” whatever that phrase means to them? OK, that was good. But what if people just waxed on and on about some grandiose idea of theirs?

Another idea: What if we asked them to start their toasts with a personal story or experience from their own life? We were making progress. But this was a lot to ask of people.

What if no one wanted to toast? What if everyone waited in long silences between toasts?

Then came the clincher: What if we made the last person sing their toast? I laughed when my husband proposed this, but he was serious. It would set a brisk pace for the evening and add some nice risk.

That evening, the guests arrived, not knowing what to expect, but people seemed intrigued and excited to be there. They were senior advisers to presidents, CEO types, journalists, entrepreneurs, and activists. We were split relatively equally by gender. The ages ranged from our early twenties to our eighties. People hailed from half a dozen different countries. We stood at the entrance of the room and handed each guest a welcome cocktail, warmly introducing them to one another. They saw their names written on cards and realized that there would be a seating order.

When we sat down, I raised my glass and thanked everyone for coming. I introduced myself and Leberecht. We described the theme and our reasons for wanting to hold this dinner. We explained the rules, including the singing rule and the Chatham House Rule (borrowed from the Royal Institute of International Affairs) that we had adopted, which allows people to talk about their experience of a private meeting and share the stories that emerge, but forbids specific attributions to any of the participants. We also instructed people to begin each toast by telling a story, and to signal when they were done by raising a glass to the value or lesson behind that story. And, at last, we began.

The first three toasts went quickly: The first toaster drew from the well of her own story to talk about a good life as a life with choices. (“To choice!”) The second toaster spoke of her work in disaster-relief efforts and, as she did, became emotional. Her toast showed the group that it was acceptable to be human when you care deeply about something. In the third toast, a man talked about three elements he thought made a good life: to work for oneself, to work for others, and to have fun. He ended his toast by saying, “Two out of three ain’t bad.” Someone then burst into song, singing: “Two out of three ain’t bad!” Everyone started laughing. (“To two out of three!”) The group was starting to relax.

At that point there was a lull, and we took a break to eat and chat with the people around us. I began to think about what I was going to say. I had a distinct advantage going into the dinner, as I had known the theme in advance. I had a toast idea in mind. In that moment, though, I realized that I wasn’t really taking a risk with that toast. An image came to mind of a good life, and it was a moment from when I was eleven. Then I thought: I can’t share that with thisgroup. My heart started pounding, a sign that I tend to interpret as saying, Do it. I took a breath, hands shaking, and clinked my glass. People seemed surprised that I was going to go so early in the evening.

I began with the idea that a good life is about seeing and being seen, and launched into a very personal story about a time when I had felt seen. This is roughly what I can remember of what I shared:

When I was eleven years old, I got my period. I was sleeping over at a friend’s house in Maryland and wasn’t sure how to react. I didn’t tell my friend, but went home the next day and told my mother. I was at an age where a lot of my beliefs and judgments about things came from other people’s reactions, and I watched hers closely. When she heard, she hooted and hollered and lifted me up and swung me around, laughing with joy. She then danced all over the house celebrating. I learned that day, from her reaction, that being a woman was something to be celebrated. But she didn’t stop there. Two weeks later, my mother threw me a period party.

People at the table began to laugh and clap in delight. Even the men, to my great relief. I continued. I shared the story of my period party as I could remember it:

She invited her female friends rather than mine, all older women who had passed through this important transition of womanhood themselves. I received presents from each woman. One guest gave me my first pair of pink lace underwear, because one of her favorite things about being a woman was “opening the underwear drawer and seeing a splash of color.” They sang me songs, including my mother’s favorite two songs: “On Children,” by Sweet Honey in the Rock, and Crosby, Stills, Nash & Young’s “Teach Your Children.” That day, I knew I mattered. I was seeing, and I was being seen. I was being witnessed. And to me, that was a good life. And a small surprise for you all: My mother is here with us, sitting right over there.

My mother happened to be on another council at the forum. Because we have different last names, no one knew we were related. Everyone was stunned to realize that a woman who was sitting at the table, someone they might have known only as a World Bank expert on poverty, was also a mother who had designed a period party for her daughter. I was still shaking from telling such a vulnerable story, but I thought, What the hell, hoping it would crack others open.

The wine flowed and the toasts continued. One woman shared her mother’s words on her deathbed: “I spent 90 percent of my time worrying about things that didn’t matter. Don’t do that.” Once the topic of death was introduced, I noticed it showing up in several other toasts. After all, thinking about what makes a good life implies thinking about life ending, about it being of limited quantity. Another person now said in her toast that she was going to tell us something “weird” she does every morning, something she’s never told others about. Every morning, she does a “death meditation,” in which she imagines she has died, sees all the people she loves and all she’s left behind in this world, and just hovers over the scene, watching. She then wiggles her fingers and toes and comes back, deeply grateful to be alive, perhaps a little more aware of what she values. It turned out that, for her, part of having and savoring a good life was keeping aware of death. She then raised her glass and toasted something like “To death!,” signaling she was done. “To death!” we replied, glasses in the air.

As the night went on, tears welled more and more in the eyes of people speaking and the eyes of people listening. Not because they were sad, but because they were moved. Over the course of the evening, people stood up, one after another, and over and over again we heard some version of “I have no idea what I’m going to say” or “I hadn’t planned on saying this” or “I’ve never said this out loud before.” People dropped their scripts.

One man pointed out that certain superheroes wear their underwear outside their costumes. We laughed. It was a perfect metaphor for what we attempted that night—and what I am challenging you to cultivate in your gatherings. And, yes, at last, the final person sang. He closed his toast with a Leonard Cohen song. A line about cracks allowing for light shimmered over a room that had, for one moment, practiced letting go of that most consuming of worries.

It was a moving, beautiful night. All these people whose titles usually enter the room before they do left their egos at the door. They showed us fresh, raw, honest sides of themselves. The dinner pointed to what was possible at gatherings like this.

REALNESS CAN BE DESIGNED

After that moving evening in Abu Dhabi, we decided to take our format on the road. We called it 15 Toasts, after the number of people around that inaugural table, and we scouted for other stuffy gatherings that could use an injection of human feeling. One or both of us, and even some former attendees who felt comfortable facilitating, went on to host 15 Toasts dinners on the sidelines of events in South Carolina, Denmark, South Africa, Canada, and elsewhere. Everywhere it went, the format worked wonders. So I began to test it out on another type of gathering: ones where people did know one another, through work or family or otherwise. To my surprise, it still worked. And after hosting many of these dinners, and seeing groups of various kinds being authentic with one another in remarkable ways, I began to detect certain patterns in what helped the real and the revelatory to surface. In addition to setting the right environment (we always try to do it in private spaces, with low lighting, flickering candles, comforting food, and flowing wine), I have found there are certain approaches the thoughtful gatherer can take to encourage people to jettison the phony and the polished for the true.

SPROUT SPEECHES, NOT STUMP SPEECHES

One of these approaches is to seek out and design for what I call the “sprout speech,” as distinguished from its tedious better-known cousin the stump speech. The stump speech is the pre-planned, baked spiel that people have given a thousand times. We all have stump speeches, and at many of the more formal and important gatherings we attend, it is our stump speeches that come out to play.

If the term “stump speech” evokes the strongest, most durable part of the tree, the part that is firmly in the ground, the sprout is, by contrast, the newest and weakest part of the tree. It is the part still forming. What I learned from 15 Toasts is that while we tend to give stump speeches at so many gatherings of consequence, it is people’s sprouts that are most interesting—and perhaps most prone to making a group feel closely connected enough to attempt big things together.

So much in our culture still tells us to present our stump speeches when we are anywhere in the vicinity of opportunity, especially at something like a conference. But I keep stumbling on interesting experiments doing just the opposite, inviting people with impressive stump speeches to leave them at home and bring their sprout speeches instead.

One of these more forward-thinking gatherings is called House of Genius. (You may recall encountering it briefly in the chapter on pop-up rules—and, yes, some of the more interesting gatherings of our time may need better names.) House of Genius was founded by two entrepreneurs, Toma Bedolla and Tim Williams. The pair had gotten tired of networking events where everybody shared puffed-up sermons about what was working with their companies or jobs and few people shared what wasn’t. They decided to experiment with a new format of business get-together—a format that would eventually be replicated around the world.

The format was this: A group of strangers would gather in a room. Two or three of them would be entrepreneurs or other professionals with a problem. To get into the room, they had to apply for the chance to present their problem to the others. The others were people from varied fields who had applied to volunteer their time to solve someone’s problem. A moderator would guide and tightly orchestrate the proceedings.

In both House of Genius gatherings I attended, I was struck by the moderators’ ability to get people to share their challenges openly with strangers and to let the rest of us look under the hood. By inviting people to share their problems, House of Genius elevates authenticity over selling. They, too, have organized a gathering around our incomplete selves (and companies).

Both events I saw took place in conference rooms in coworking spaces in New York City. There was some time to mingle near the office kitchen before the event formally began. As people walked in, we were encouraged to meet one another but told that we couldn’t discuss anything related to work. On one occasion, I started talking to a youngish man with blond hair wearing cargo shorts, and we both immediately realized we had to stretch a bit not to ask each other about work. We tried to chitchat. He asked whether I had taken any vacations recently. I think I asked him whether he had any pets. We both started laughing when we realized how bad we were at talking to each other about topics other than work. A number of questions kept accidentally bumping into the topic: “Have you been to one of these before?” “Yes,” I said, “because I . . .” I stopped myself because I realized I couldn’t tell him that I was studying gatherings, since it broke the no-work-talk rule. “When did you move to New York?” I asked. “Five years ago.” “What brought you here?” “Uh, I can’t tell you the real reason.” More laughter. But we improved as the night progressed.

Later, I met the moderator for the evening. “Have you moderated before?” I asked.

“Yes, a few times.”

“How did you get involved?”

“Um, we’ll leave that for later.”

“For the end?”

“For the Big Reveal.”

“Oh.”

Eventually a young woman, apparently the organizer, invited us to enter the room and take our seats. “First names only,” we were reminded. As we wandered in, we were asked to take a name tag, grab a seat, and not talk about work. “You can talk about Disney World, but not work,” she said. We started talking about Disney World. After the final stragglers came in, we were officially constituted as a “House.”

The organizer welcomed us, gave us some background on the House of Genius, and reminded us of the purpose of the gathering and the rules, which were also posted on the wall. “Even in giving feedback, you can offer suggestions, but please don’t talk about what you do,” she told us.

That evening there would be two presenters, and each would get a roughly forty-five-minute session with the House. For the first five minutes, each one would make a presentation to the room about a challenge. We would then have two or three minutes to ask clarifying questions about the challenge, and the entrepreneur would answer them. Then everyone would have one minute to give their “first thoughts.” (You can ask questions during this period, but the entrepreneur can’t answer them.) And the rest of the time is a dialogue between the House and the entrepreneur. The moderator makes sure that everyone has a chance to talk and guides us on what makes good feedback: examples of past successes and failures, contacts because “we want to extend tonight into the future,” and books and articles. At the end of the evening, we would have the Reveal, in which we would each share who we are and what we actually do for a living.

The first challenge-bearer was a woman running a social enterprise that was trying to build more inclusive workplaces. She wanted our help figuring out how to create true partnerships with employers and influence them to “think outside the box” when hiring. The second was a young man starting a travel app that would let people create and share their own guides with a larger community. He wanted our ideas on how to cultivate “loyal and rabidly engaged early users in this city with little budget and some connections.”

In each of the conversations, I observed as the dozen or so of us began to figure out how we could help. In both cases, we needed to know more about each idea. But as we asked more questions, it made each entrepreneur more vulnerable. They had to give us more information: “So how many companies have you spoken with?” Not as many as they should have, maybe. Or our suggestions created more work for them: “Have you thought about partnering with job-training programs?” Or we pointed out their blind spots: “I’m not sure if your basic assumptions about why companies aren’t hiring these populations are right.” Yet if they could remain open to it, they would receive valuable help from smart people.

It was an interesting dynamic, and the more we got into the weeds of each company, the more I felt a desire to help these entrepreneurs. Had they come up to me at a networking event and pitched their idea with the usual puffiness, I may have been interested, but I doubt it would have tugged at my heartstrings. But seeing them there in the hot seat, knowing they had volunteered for this, to expose themselves and their ideas to strangers, made me feel compassion for them and made me want to use my brain and resources to push them forward. And in the rare moments when one of the problem-bearers would get testy or defensive, or withhold information, it was obvious to everyone, and it caused the helpers to pull back. It was like watching a group dance in vulnerability. The more the entrepreneurs shared, the more I could relate and the more I wanted to help. The stronger they seemed, the less they needed me and the less I could connect with their travails.

In some ways, this should be obvious. Being vulnerable with people makes them feel for you. Scholars like Brené Brown have been telling us this for years. But if it’s obvious as a description of human behavior, it doesn’t seem obvious to most of our gatherers. A gatherer is bringing people together. Sometimes, as at the House of Genius, the explicit goal is for people to help one another. But every time people gather, they are being brought into the opportunity to help one another, to do what they couldn’t do or think up or heal alone. And yet so often when we gather, we are gathered in ways that hide our need for help and portray us in the strongest and least heart-stirring light. It is in gathering that we meet those who could help us, and it is in gathering that we pretend not to need them, because we have it all figured out.

A graduate school program I attended epitomized this paradox. At the Harvard Kennedy School, legions of brilliant, passionate students arrived with real questions and real fears and real wonderings about how to solve the problems of the world. All too often, however, they ended up intimidating rather than helping one another. In the classrooms where we were supposed to learn what we didn’t already know, the culture taught us to avoid sounding stupid in front of one another. It didn’t make sense to try ideas out loud, because these were your potential future bosses and partners and employees, and it was important to show your strength. In the early days of the semester, when people asked, “How are you?” we answered with smiling, and often false, positivity, falling into the terrible habits of politicians on the campaign trail: Never voice the truth; always be sparklingly upbeat. When we spoke of our pasts, we often spun like flacks on Capitol Hill: The up-and-down facts of our lives were smoothed into ascending narratives, our accomplishments were humble-bragged, and our personal brands were promoted.

Lisa Lazarus, a student one year ahead of me, had the gall to suggest that this was a lonely, miserable way to learn. She revolted by creating a small group called CAN, or Change Agents Now. The idea was simple: groups of six interested Kennedy School students would agree to meet every other week, for 3 hours at a time, and do the opposite of what they were doing for the other 333 hours of that fortnight. Against all odds, they—we—would be honest.

We would skip over all the parts that were working and dive straight into sharing what was not. We would tell authentic, painful stories—about parents who had abandoned us, about bullies who had taunted us, about poverty that had shamed us. We showed frailty, vulnerability, and fear; in fact, in an inversion of Kennedy School norms, weakness became more valued than strength.

We followed a loose curriculum that focused on sharing “crucible moments,” a concept borrowed from Bill George, a professor of leadership at Harvard Business School and the author of True North. Crucible moments, according to George, are challenging moments in our lives that shape us in some deep way and shift our lens on the world. They are stories that define us in our own minds—and that, nevertheless, seldom come up in the ordinary course of conversation.

My CAN group met every other Wednesday, and for our early meetings, we shared our life stories, focusing primarily on these crucible moments. We knew what we were signing up for, and we were curious about one another. I didn’t know the students in my CAN group well, and the stories they shared—about their own childhoods, difficult decisions they’d made, relationships with their parents, hometowns, religious beliefs—made me see them in an entirely new light. It also made me feel safe showing my own different sides, sharing my own demons.

This series of gatherings, simple in their design, purposeful in their conception, transformed my experience of graduate school. The school became a different kind of place for me. Armor fell off; ears widened and mouths shrank; we learned to love one another for our flaws. The navy officer whose father was once homeless. The entrepreneur who grew up poor. The executive director who, in light of an absent father, became a second parent to her siblings. I began to see their behavior through a different lens. And rather than feel jealous or intimidated by their accomplishments, I began to feel empathy for them, because I understood their stories, just as they understood mine. Experiencing a different way of being in my CAN group led me to take similar risks with some of my peers outside of the group.

Lazarus had an insight about her peers: that we all wear masks, and that while masks have uses, taking them off can allow for deeper connection, shared growth, and more fruitful collaboration. More than a decade after she started it, Lazarus’s CAN group still meets.

NO IDEAS, PLEASE. WE’RE GATHERING

Another tactic that helps to undam realness in gatherings is a push for people’s experiences over their ideas.

That evening in Abu Dhabi we had asked guests to give their toasts in the form of a story, but we had done so mainly as a form of quality control. We figured that anyone can tell a story from their life, and that such stories might be better than riffs on a theme people hadn’t thought about. As it turned out, though, the emphasis on stories did something else as well, something we hadn’t necessarily planned: It helped us feel connected. And it worked because we were explicit about it. We got stories because we asked for stories—we made a clear distinction in the prompt between people’s concrete experiences and their abstract ideas.

Many gatherings would be improved if people were simply asked for their stories. And there are few institutions that have done more to demonstrate the power of this principle than The Moth, a series of gatherings that promote the idea and practice of storytelling as social glue.

The Moth was founded in the late 1990s by a Southerner named George Dawes Green who had grown tired of poetry slams. A novelist himself, he attended poetry slams to try to meet other writers and artists. But rather than feeling transported by the poetry, he would leave feeling irritated. “I felt something was wrong with them,” he told me. Every poem, he said, “was told in this singsong voice. As soon as the poet stood up there, he’d begin to speak in this poetic language, and this wall would come down.” That barrier, in his view, came from a prevailing idea of the poet as an ethereal and distant figure: “You were part of this deep tradition, and you gather your ideas from some connection that you had with God or with the powers of the universe. You were a shaman, and you were pulling this information down, and through you would come this exalted language—an almost nonhuman language.” This may sound great to you. But to Green, at least, it was off-putting.

Despite his contempt for the slam scene, Green noticed when the poets did wow him. It was often during the preamble, an unscripted backstory poets would tell about the roots of their shamanic creation. “My grandpa would go fishing upstate,” Green imagines one of the poets saying all these years later. “I remember having to get up so early.” What struck him about the language in the preambles was that it consisted of “perfectly natural phrases,” Green said, “and the audience would immediately perk up and be with the poet, because there was no longer a sense of artifice, a wall. And I was always fascinated by that.” He started experimenting with a gathering format designed exactly around that moment, and The Moth was born. Two decades later, The Moth has ongoing programs in twenty-five cities and has presented eighteen thousand stories, often to standing-room-only crowds.

I told him about my experiences running 15 Toasts and asked him why, and when, he thought story works in a gathering.

“A moment a story works is usually a moment of vulnerability,” he said. “You can’t tell a story that’s any good about how successful you are. Trump tries to do that.” But when you touch this vulnerability, he said, “people feel this utter comfort. I went through that. I know exactly what that person is saying.” Green has spent years studying the art and craft of storytelling. He explained some of the elements of a good story told simply:

Story is about a decision that you made. It’s not about what happens to you. And if you hit that and you get your vulnerability and you understand the stakes, and a few other things, people will intuitively find great stories to tell, and as soon as they do, we know them. We know them as human beings. This is no longer my boss’s colleague. This is a real person who had heartbreak. Oh, I know that.

THE DARK THEME

If guests often bring their stump rather than sprout speeches to events, if they often talk of their theories rather than their experiences, then organizers can succumb to their own kind of phoniness. They insist on keeping gatherings positive, especially when choosing themes. The meaningful gatherer doesn’t fear negativity, though, and in fact creates space for the dark and the dangerous.

If you recall that first 15 Toasts dinner, the theme we had chosen was highly positive: “a good life.” Looking back, I don’t think it was a great theme, and our guests evidently agreed. After all, it wasn’t just one person who shifted the terms and tone of the conversation by bringing up death. We hadn’t explicitly asked about death, nor did either of us introduce it ourselves. But as we spoke of the joy of life, there seemed to be a need to bring in the flip side of life. As we did, the conversation took on a new depth. People began to lean in more, no doubt thinking of their own mortality or that of those they loved. It made the evening richer and rawer.

As Leberecht and I began to spread 15 Toasts to other venues, we varied the themes: 15 Toasts to the stranger, to faith, to happiness, to collateral damage, to escapes, to borders, to Them, to fear, to risk, to rebellion, to romance, to dignity, to the self, to education, to the story that changed my life, to the end of work, to beauty, to conflict, to tinkering, to the truth, to America, to local, to the fellow traveler, to origins, to the right problem, to the disrupted, to the fourth industrial revolution, to courage, to borders, to risk, and, yes, to vulnerability. What we came to find over time was that the best themes were not the sweet ones, like happiness or romance, but rather the ones that had darker sides to them: fear, Them, borders, strangers. The ones that allowed for many interpretations. The ones that let people show sides of themselves that were weak, that were confused and unprocessed, that were morally complicated.

Sadly, themes like these are exiled from so many of our gatherings. Far too many of them, especially more professionally oriented ones, are run on a cult of positivity. Everything has to be about what’s going well, about collaboration, about hope and the future. There is no space for what our guests were telling us they wanted at the dinners: a chance to pause and consider what is not uplifting but thought- and heart-provoking.

When I push this idea of darkening the theme on clients and friends, they often resist more fiercely than they do with most of my advice. So I am resorting to extreme measures to convince them, and you, of why it isn’t just acceptable but also essential to create a space in your gatherings for the darkness to come in: I am outsourcing the job to a dominatrix.

I originally learned of Stefanie Zoe Warncke from a German DJ. He suggested that I meet a dominatrix he knew, as she was an expert in creating environments and scenes. I imagined some covert meeting at night in a parking lot. Much to my relief (or maybe dismay?), we ended up meeting for tea at a French patisserie in New York City.

Warncke, who goes by Zoe, trained as a lawyer and for years worked as a partner at a firm in Düsseldorf by day and as a dominatrix at one of the larger dungeons in Europe by night. She eventually left Germany and the law and moved to New York, where she still practices as a dominatrix. She sees her job as helping clients explore their darker fantasies in a safe space.

“I want to help people explore parts of themselves in a safe way,” she told me. She said her interest in the work probably traced back to her own family environment growing up, a place where she “wasn’t allowed to explore parts” of herself.

Why, I asked, was it important for people to probe their darkness? “I think it makes the world a better place,” she said with a laugh. That sounded too simplistic. Why did letting people be dark make the world a better place?

She thought for a moment. “Because I think if they know who they really are, they don’t have to compensate with anger or self-hatred or all those things,” she said.

Warncke was touching on a concept that psychologists call the “integration of the shadow.” I contacted Dr. David M. Ortmann, a psychotherapist and the coauthor of Sexual Outsiders: Understanding BDSM Sexualities and Communities. I described Warncke’s work to him and asked him about it. He explained in an email that “integration of the shadow” is “a Jungian term that identifies that we all have shadow material (aggression, violence, nonconsensual fantasies, etc.). Disowning these parts of ourselves is not an effective way to deal with them, as what is disowned or ignored tends to grow (and often grow unconsciously). BDSM offers a way for shadow material to be integrated consciously.” Of Warncke in particular, he offered: “I would say your dominatrix friend knows her work very well and would go further to say that she’s doing something therapeutic.”

At this point, you may be wondering what a dominatrix has to do with your next staff meeting or family reunion. I’m not suggesting you hire Warncke, but rather you heed Warncke. What she does in concentration you can do with an appropriate level of dilution in your gathering. The lesson she offers is that darkness is better inside the tent than outside of it. We all have it. It’s going to be at your gathering. And if you bar it from the formal proceedings, it doesn’t disappear. It shows up in ways that do your gatherings no favors.

THE STRANGER SPIRIT

One of the more improbable secrets of unleashing honesty and vulnerability in a gathering is raising the stranger quotient. Though it seems counterintuitive, it is often easier to get people to share when many in the room are unknown to them—or when they are helped to see those they do know with fresh eyes.

After one 15 Toasts dinner in New York, a guest was upset that a close friend of hers, whom she had brought to the gathering, had spoken openly of his depression. She pulled me aside afterward, feeling confused and betrayed that he would share with several strangers something he had never told her. Yet the man was making the same choice that many of us do in similar situations. It is often easier to confess parts of our lives with strangers, who have no stake in our lives, than with intimates who do.

The power of the stranger lies in what they bring out in us. With strangers, there is a temporary reordering of a balancing act that each of us is constantly attempting: between our past selves and our future selves, between who we have been and who we are becoming. Your friends and family know who you have been, and they often make it harder to try out who you might become. But you’re not the singing type! Why would you want to be a doctor when you hated biology in school? I guess I just don’t see you doing stand-up. Strangers, unconnected to our pasts and, in most cases, to our futures, are easier to experiment around. They create a temporary freedom to pilot-test what we might become, however untethered that identity is to what we have been. They allow us to try out new sides. In front of a stranger, we are free to choose what we want to show, hide, or even invent.

Some extreme gatherers so believe in this stranger spirit that they organize gatherings entirely for and of strangers—like the seventy-sixth birthday celebration of the Oxford professor Theodore Zeldin. Zeldin—a renowned historian of France and a famed philosopher, with a wild white mane—decided that year that he would hold a birthday party for people he didn’t know. He issued a public invitation through the BBC for everyone who was interested to join him in Regent’s Park in London at a particular date and time, and to celebrate his birthday by talking to someone they didn’t know.

Hundreds of people showed up. Each of them was tasked with having a one-on-one conversation with a stranger. In lieu of food, at each setting was a Zeldin invention called the “Conversation Menu” that led the pairs through six “courses” of talk. Under the heading of “Starters” were questions like “How have your priorities changed over the years?” and “How have your background and experience limited or favoured you?” Under “Soups” was an invitation to ask, “Which parts of your life have been a waste of time?” Under “Fish”: “What have you rebelled against in the past and what are you rebelling against now?” Under “Salads”: “What are the limits of your compassion?”

FRESH EYES

The reality is, you don’t have to invite the entire United Kingdom to your birthday party to raise the stranger quotient among your guests. If you host consciously, you can bring the stranger spirit to a gathering of people familiar with one another. When I have tried to do this with family dinners and team get-togethers, I have found that choosing the right question and structure can help people long acquainted see one another with fresh eyes.

A few years ago, my husband and I were going to India to visit our grandparents and extended family. We decided to gather both sides of our family for a dinner. There would be seventeen of us in total. Being well acquainted with large family dinners, I knew that if we didn’t do anything to design the evening, cousins would gravitate to their own cousins, grandparents would talk among themselves, and most of the conversation would be small talk. We would eat, drink, get sleepy, and call it a night. Not necessarily a bad evening, but we wanted to make it special.

We decided to borrow from the 15 Toasts model, but with some changes. Because there were multiple members of our families who had no problem singing in public, we scrapped the singing rule and instead had each toaster choose the next toaster. Borrowing from my CAN group’s use of “crucible moments,” we asked the group to share a story, a moment, or an experience from their life that “changed the way you view the world.” Then we added the clincher: It had to be a story that no one else at the gathering knew. This was, in a sense, a rather wild requirement for a gathering of family members in a tight-knit society in which relatives are a bigger part of life than friends. But we thought it might give the dinner a shot at getting people who thought they knew everything about one another to see one another with fresh eyes.

A cousin began by saying something like “The birth of my children.” But now the group, having already absorbed the rules and their purpose, immediately protested: We already know that! That false start and correction laid the groundwork for the others. People began to share stories that even their nearest and dearest had never heard before. Even if one or two people present did know a particular story, it was told that night in a way that revealed impacts or implications that no one had known. One aunt, a geneticist, spoke of being told as a teenager that she couldn’t be a doctor because she was a woman. It shocked her into studying harder. Another aunt, a civil servant, talked about passing the Indian Administrative Service test, completing officer training, only to be put in a district magistrate’s office for months on end, never being let into the field. She finally went out on her own in a truck one day because she couldn’t understand why they weren’t letting her do her rounds, and a local government official told her that she would always be treated differently, no matter how smart she was, because she was a woman.

As the toasts went on, I began to realize that something remarkable was happening. Our original goal had been to get our relatives to continue the weaving of families that had begun with our wedding. But now something even more interesting was going on: Fathers and mothers and sons and nieces were learning about their own family members in ways they’d never expected. When a family elder, now in his nineties, shared his story, he recalled a time fifty years prior when he was working at a large company and realized that the advertisement reels he was sending out to movie theaters were often not making it there or, if they were, not being played. He told us how he solved the problem. Suddenly, in this aging man who often stays quiet, in part because he is hard of hearing, the table saw a young, sprightly, inventive businessman. My grandmother, shy to speak in English, asked me to share her story, which I had learned only a few days earlier. It was the story of how she became one of the first women in her caste in the conservative city of Varanasi to attend Banaras Hindu University. She was the eldest of seven children, and her father adored her. He told her to go register for university and begin attending classes. Then he left town for a relative’s wedding on her first day of school. When his neighbors complained that he was letting his daughter attend university and violating gender norms, he wasn’t there to hear the complaints. When he returned, she was well into her classes, and he asked the same neighbors if they really wanted him to pull her out of school. Even if it was wrong for her to have started, should education ever be interrupted? The moment changed her perception of her father and educated her in how change happens (slowly and with people in privilege as protectors).

What was striking about the evening was everyone’s willingness to embrace it. And to try something new. We began to see parts of one another with fresh eyes. A grandmother as a daredevil college student. A grandfather as an innovative young executive. Aunts, who in Indian family gatherings are often relegated to the role of silent nurturers, as pioneers in their fields. It reminded me of how much there was left to know about people I thought I knew well. We weren’t “strangers” by any stretch, but we found a way to design for the stranger spirit.

THE INVITATION MATTERS

If you want to try this type of gathering, centered on people’s real selves rather than their best selves, you need to warn them. One of the insights we learned from 15 Toasts is that, in keeping with my approach to openings, you should tell people as explicitly as possible and at the beginning what you want in the room and what you want to be left at the door.

When I host 15 Toasts on the sidelines of a conference or another high-powered gathering, I tend to say in my welcome words that there is a typical dynamic to such events that we are hoping to avoid—the dynamic of showiness and puffery. Given our desire to counteract that, I invite people to leave outside the door those parts of their lives and work that are going great. We’re interested in the half-baked parts. We’re interested in the parts they’re still figuring out. We’re not interested in their preplanned speeches but rather in the words and thoughts still forming.

In the very different situation of the 15 Toasts format applied to family gatherings, a different kind of invitation was required. Normally at such dinners, no one reveals anything fresh or surprising. If we wanted to change up the kind of family dinner we were having, it required guiding people. So I told them to leave their familiar stories about themselves at the door and bring into the room those parts of themselves that might surprise even their kids.

When I work with business teams and do a 15 Toasts before a big meeting, there is another set of problematic dynamics to fend off. Teams often interact in well-worn ways, with the same people playing the same roles. So in my welcome I name that and tell the group that the whole point of this dinner is to try out another way of being together, to create space for everyone to show different sides of themselves and play different roles. By naming the way I anticipate they will be, and asking them to set that aside and try something else, I often get through to them. Often, but not always.

This cueing of people in the welcome doesn’t have to be elaborate. Just a strong and suggestive hint. At the first 15 Toasts dinner, I said something about how we hoped the evening would feel more like a wedding than a conference. Someone joked, “Who’s getting married?” Another guest said, “We’ll vote at the end of the night!” People laughed, and I knew the night was taking off.

At each 15 Toasts since, I almost always say something like “Tell us something that would surprise us,” or “Leave your successes at the door,” or “There’s no need to slip in an accomplishment.”

I have also found that this leaving of things at the door is easier when people are seen for their virtues. People are still people, and, particularly in professional contexts, no one wants to look weak. But I have discovered that if I, the host, acknowledge and broadcast their strength, as individuals and collectively well in advance, it relieves some of the pressure people feel to flex during the event itself. I say something up front like “You’re all here because you’re remarkable.” I acknowledge their remarkableness and then I add, “That said, we don’t want to hear about your résumé or how great you are. We already know that.”

HOST, REVEAL THYSELF

It isn’t enough to signal what you want and don’t want from your guests when it comes to sharing more honestly and authentically. Early in the gathering, you, the host, need to go there yourself. You need to show them how.

If you are hoping to help your guests be more real, you need to be real yourself. When I host these dinners, I make sure that every toaster has my full attention throughout the dinner. I listen deeply and show the kind of self that I am asking them to show me.

This is what I was doing when I spoke about my period party. In contexts in which I am at a disadvantage, I typically try to tell stories against type. I could emphasize other details about me so as to be taken seriously: studying at an engineering school or not knowing how to cook. Why on earth would I tell a story not only from when I was eleven years old but also about getting my period? Because few stories could have more clearly communicated to my guests that I was willing to be genuine and to connect with them—and that they might do the same.

The period story sort of just came to me, but a Dutch colleague of mine, Bernardus Holtrop, actually follows a principle about sharing in this way. I saw it in action when he and I (and many others) co-facilitated a meeting of a few hundred business leaders who had come together to create trusted circles of support with one another. Holtrop shared one of his pro-tips with us: To get the group to be vulnerable, he said, we facilitators needed to share an even more personal story than we expected our clients to. We would set the depth of the group by whatever level we were willing to go to; however much we shared, they would share a little less. We had to become, in effect, participants.

RISK MANAGEMENT

When you’re asking people to go deeper, to share what they don’t usually share, you must manage the risk-taking you are encouraging. Sometimes that means prodding people to take more risk; other times, it means soothing people afraid of taking risk.

The singing rule we established with 15 Toasts was a way of nudging people toward risk-taking. By creating a risk in not coming forward with a toast, we evened out the risk calculus. People had to decide which was worse: giving a toast early or singing. The singing rule also creates some playful drama toward the end of the night, when all of a sudden three or four people, realizing the risk of having to sing, start clinking their glasses desperately after each toast, making sure they are not last.

It is also important as a host to be attentive to the needs of different personalities. No one, however extroverted, wants to feel like they have no choice but to share a deeply personal story. One of the reasons choosing a general theme works so well is because there is a lot of freedom within that theme to choose the level of depth one wants to take. While we do ask that everyone present participate, we let people decide what and how much they want to share. And this level of choice is the difference between people being game for the evening and people resenting it.

Leng Lim, a fellow facilitator and an Episcopalian minister, uses the analogy of a swimming pool to talk about people’s different comfort levels. He hosts a range of gatherings, some at business schools, some at his farm, and he told me that he invites intimacy in all of them. But he is explicit about letting every participant choose their desired level of depth.

“I draw a swimming pool,” he said. “There is a deep end and a shallow end. You can choose whatever end you want to enter. If you want to tell us your deepest secrets, you can. Or you can be superficial, and getting wet means being real, so bring something that is real for you.” It is important, Lim said, to offer an “invitation to intimacy, but depth is a complete choice.” Allowing each person to choose what and how much they want to expose was vital to making 15 Toasts intimate without being pushy.

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