Enabling Deep, Meaningful Conversations Through Hospitality - Margaret Lefton, Yours Truly Hotel

Josiah: Deep, meaningful conversations are the foundation of hospitality. So, how do you enable these? We've learned from Margaret Lefton, Creative Director at Yours Truly, a Washington, D.C. area lifestyle hotel, about community building. And since that episode was so popular, I'm bringing her back on for an encore episode about something practical we can all get better at to improve our ability to provide hospitality professionally and in our personal lives as well.

Margaret: A friend of mine who is a journalist and reporter, who at the time was producing at CNN, and I had been having these conversations about what it means to have a better conversation. We got into running this discussion group called "DMC" - Deep Meaningful Conversations - where we were just bringing friends together in a living room to talk about interpersonal topics.

Josiah: I would love to follow up on this DMC concept because I'm really curious: how do you create those environments that are conducive to great conversations?

Margaret: Yeah, that's been a great journey of my last decade, honestly. So I, you know, we didn't quite get to it, and I'll get there later. But I actually studied clinical mental health counseling at one point as well, and really got quite into the depth on psychology and all that sort of, as a result of these earlier moments, I think the first self-help book I ever read, which now to me is kind of funny, but How to Win Friends and Influence People, which I legitimately, the only reason I knew it existed was sitting on a subway in New York on my way to work one day and somebody across from me was holding the physical book and I saw the title and I was like, that speaks to me. I too would like to know this.

Josiah: It's an old book, which is kind of an interesting thing. I was talking to Victoria Taylor, who's an experience designer, a couple of days ago, and she was saying, yeah, it comes back to the basics, right? It doesn't need to be super new stuff. It doesn't need to be a book that was published in the last couple of years. That book's probably a hundred years old.

Margaret: It has such, you know, and I don't know if I reread it now, a decade later, how I would feel about it, if I would resonate with it the same level or not, I'd be curious to and actually experiment with that. But it really, it launched me on this, like, oh my god, it never occurred to me that I could have these meta conversations about what does it mean to have a conversation and what makes the other person feel. So all of that to say, I think in the background, I was looking into that stuff independently. And with the DMC concepts, like, We sort of were lucky initially where my co-founder and I, Adam, like we met on this local to DC retreat that we went on. And so everyone who was on the retreat lived in DC. And so our first batch of people, so we kind of initially already had a group that were interested in this, were just people from that retreat who were like, yeah, we'll show up because we all want to get together again and hang out. So like, let's do this. And from there, like, you know, the first session, of course, we had everyone. It was like 30 people. Second session cut down to probably like 10. But 10 is a great number. And from there, it just kind of fluctuated in and out of friends of friends, or you tell people about it, and they'd be like, Oh, that's so interesting. I want to do something like that. And it was such a learning process of these small community dynamic moments of like, you know, initially, I started this when I was working at the restaurants. And so we would host them at the restaurants, they would donate the backspace to us and give us a happy hour deal. And so it was us bringing business in as well. And what we discovered quickly was like, no one actually wants to drink during these. Everyone's like too involved in the conversation that they're not trying to like, so we're like, huh, that doesn't really work. And then it was like, actually, I don't know if the restaurant environment works because it doesn't really feel that intimate. And there's like background noise. And then we're like, okay, what happens if we host it in a living room? Oh, suddenly it feels like such a warm container and people are way more open, like in a subtle subconscious way, people are just opening up more.

Josiah: Why is that? Is it the size of the space?

Margaret: I believe in like containers make all the difference, right? So you're building a physical container in this space. So like small things around the room are indicating what energy you're in. So for me, like even as the facilitator, if I'm in the restaurant, there's a small part of my brain where my work brain is on because I'm in a work environment. Versus like, as the facilitator at home, I'm at home. So there's more of my personal side that's just present. And I don't have to have any of my work brain on or any thoughts around like, Oh, someone from the restaurant going to peek in and see what's going on. And then from the participant side, it's like, oh, we're in a restaurant, which also brings a certain vibe to what you're thinking about. It's a happy hour or whatever versus, oh, we're in my friend's living room or this person's living room. And there's like cozy couches. And I can kind of like hold a pillow if I'm sharing something a little bit more intimate. And we always kind of joked it was basically like book club without the book. We were like, show up, don't RSVP like we want the most millennial thing on the planet. Don't RSVP. Don't read anything. Come as you are. Share whatever you want. You can sit there quietly and share nothing and just listen like It's fine. So it was very just like, be who you are, show up, do the things.

Josiah: I'm inspired because I'm trying to get little groups of people together here in San Francisco and all of those challenges. So I'm inspired to make it easier.

Margaret: You know, we found I this is so funny because it's such small turnkey moments that I think make an impact. And as we were developing the programming, which was very simple the way that we ran it. But there was like one piece that I think set up the whole thing for success, which was whenever we started a conversation, one of us would give a mini intro. So let's say the topic was we did defining the concept of home or friendship breakups. We would talk about like I would give an intro of like, here's what I'm thinking about related to this topic. Here's why it's front of mind for me. This is what's going on in my life. Whatever. And then we would go around the room once and every person would say, I'm curious about blank related to the topic, open umbrella. You can pass if you want, but just getting everyone in the room to, again, the container setting, everyone in the room to speak once, also putting a curiosity out. So you're framing it from this like observation perspective of like, this is the thing I'm curious about versus I feel angry about it. I feel whatever, like it's just putting all these thoughts in the middle of the room and like the middle of us sitting in a circle. And then all of us looking at the thoughts and being like, cool, which threads do we want to jump in?

Josiah: The container concept's really fascinating. I'm curious, as a hotelier, it's tricky because it's a semi-public space. Are there any things hoteliers can do to create environments that are a little more conducive, a little more kind of welcoming, that would facilitate these conversations? To get the answer to this question, listen to our episode with Margaret on community building. You can find a link to this in the show notes.