612. Gather with Purpose: 5 Steps to Better Meetings & Events

6:54PM Mar 28, 2025

Speakers:

Jonathan McCoy

Becky Endicott

Tes Cohen

Keywords:

Intentional gatherings

belonging

continuous learning

community

curiosity

Peace Corps

nonprofit

corporate philanthropy

radical reset

rest

impact measurement

reflective leadership

facilitation

debriefing

peak moments.

What's happening be Hey, Jon, I am very excited about today's conversation, and we have an incredible guest on who is coming in to talk to us about how to design intentional gatherings that are one gonna help you feel great. Help you feel this sense of belonging, but Hello, it's going to help you scale your impact internally and externally. We are so excited to have Tess Cohen on the podcast. She's the Chief gathering officer at gather better. And Tess just has this amazing life story, and she really drills it down into this life purpose she has to foster belonging and continuous learning by creating spaces that center community and curiosity. You know, we're here for that, so here for that. And so, you know, she started on the front lines, and she started her career serving as a Peace Corps volunteer in rural Costa Rica Jon, it's like your home away from her. Yeah,

totally. And

she also spent a lot of years in the nonprofit world, as well as five years in corporate philanthropy at Gap. She is also the co founder of radical reset, which is creating this movement of rested leaders and a world in which rest is democratized, normalized and celebrated. Hello, that is what I want in this lifetime, too. In her spare time, she enjoys biking, rock climbing, teaching yoga and traveling. She's hot on your tails. Jon, 30 states in 30 countries visited and counted. So good. We are excited to talk to test and really start to talk about how we gather is going to not only help us scale our impact, but help our well being too. Tess, welcome to the We Are For Good podcast. We're so excited you're here.

Thanks, Becky, Thanks Jon, thanks for having me. Well,

I feel like the only We Are For Good member who has not met you in person, Julie has met you in the middle of Central Park. Jon has met you and your mother. And so take us back to tiny Tess, probably the heartwired Empath like, what is she? What is she like growing up? And give us kind of a little bit of background into your early story and what led you to today. What

feels resonant from growing up is that I moved around a lot. So for the first until I was in eighth grade, my family moved every three or four years. And on the one hand, it was so hard at the time of doing it, and then it's been kind of wild that then as an adult, I have also moved around to New York, and then I was in Chicago for a summer, and then five years ago, moved to Denver, Colorado. And I think that that moving around really helped me to be adaptable and flexible. And then the other thing that comes to mind, especially as I think about impact, is growing up Jewish and how the spirit of giving back is very much in the ethos and I'm sure all religions, but Judaism in particular. And I think probably the first time that I can remember being more keenly aware of philanthropy was when I was 13 years old and obtaining my bat mitzvah, and you have to do as part of that project. And so I worked like a community service kind of project. And so I worked at a local school. I think it was actually a not an elementary school. It was more of like a early childhood ECE school and for young people. And that definitely sent me on a path to and a passion for serving particularly young people. That's been very much a through line of my career.

I love it. I mean, your story, your beginnings, definitely connect with whenever you came into the We Are For Good world. I gotta give a shout out to Lauren Atherton, who first made the connection, fellow Denver lover out there best such the best. And she, you know, when we launched impact up last summer, we didn't know what we were doing. Y'all, we knew that the community wanted to get together, but we've never put something together like that event. And following the first meetup, Lauren was like, You guys, this was a great infrastructure, but you have to meet Tess because this, she can help you really understand how this can go to the next level. And that's the first time we get to sit down and get to chat Tess. And I mean, you do intentional gathering so dang well, and that's what we wanted to bring you in the podcast today to really talk about that. And so could you kind of set the stage, because everyone listening wants to get people together in a meaningful way, whether it's to grow their mission, or maybe it's to launch their brand, or whatever it may be, what are the some of those key elements to make a gathering impactful? Yeah,

I just think there's so much opportunity, especially in the social impact philanthropic space and in corporate America as well, for sure, and so I, over the last year or so, kind of coalesced this for. Five step process to gather better and so I'll just walk through it. So step one is all about being really clear on your why. And truly, I think this is one of the places where people get really tripped up. So often it's like, oh, we just, you know, we always do the every year, staff retreat, every year, board retreat, our fundraising event, right? And it's just very check the box versus and I will bring up one of my biggest inspirations in this work is Priya Parker, who's written a book called The Art of gathering. And so she talks about how saying it's a board retreat like that is not the why, that's the what. And this past fall, I worked with a team. It was a corporate team for their leadership off site. And usually when I think of a team annual retreat thing, it's like part looking back at the last year, kind of hindsighting What went well, what are the areas of opportunity? Part looking ahead, planning out, you know, the year ahead, three years ahead, whatever the time horizon, and then part community building. But I don't make that assumption right, like that's just kind of generally what it could be. But for for these folks, they're like, no, no, we've already got the debrief stuff with all we have our team structure, we really want to drill down on getting a really solid road map for our 2025 game plan again. So first step is why? Getting really clear on goals, getting really clear on outcomes. And I like to think of goals as what happens during the gathering, and then outcomes are what happens as a result of a really impactful gathering. And I really like to think about what do we want people to think, feel and do as a result of an impactful gathering that can be a helpful way as kind of like the North Star, to then map out what you do during the gathering. Step two is crafting an intentional agenda, so thinking about how people have diverse personality styles and diverse learning styles, right? Like, I'm a really visual person, but other people are much more auditory. They need to hear things. So you need to acknowledge that people come with all these different styles. So you it's incumbent on us as gatherers to create spaces that are welcoming for all, and that means a combination of kind of introducing a topic of some sort, having time for solo reflection, having time for small group connection, and then bringing things back to the to the group as a whole. Step three is really fun, sprinkling in special ingredients, so things like opening and closing rituals, things like group agreements, things that really bring really bring, if you have a theme to your gathering, things that really bring that theme to life. And then four is actually the facilitation, the doing the thing. And I like to think about and encourage folks when they're when they actually are doing their gathering, to think, you know, there's a million things that we can be thinking about it, it can be really stressful, right? And just think of like one thing you want to start, stop or continue doing in that gathering, I think can be a helpful, a helpful framing. And then lastly is the debrief. In my time in the nonprofit world, we never did. It was always like, we don't have time for that, right? Like full speed ahead. Of course, people like on to the next thing, on to the next program cycle. And it wasn't actually until my time incorporate in in philanthropy for Ed gap, Inc, the clothing company, that the team was really into debriefing. And it was, to me, it's such an unlock of, you know, there, it's actually part of what set me on this path together better was we would do this annual summit of bringing together all of these nonprofit partners and business leaders. And it was so impactful. Of course, we'd get survey feedback, and then it was what went well, and what were the areas of opportunity? And I think, and I'm almost done here, I'm hanging on to every word keep Okay, okay. So the biggest thing about the debrief, I mean, number one, I think most people don't make time for it. But then the other biggest thing is that should be your starting place the next time you're doing a similar event, right? So when y'all do impact up, and then afterwards, hopefully, like the week after, when it's still fresh, you say, okay, What? What? Well, what are the areas of opportunity? Then when you're going to, and I think you're doing it quarterly, is that, right? That? Julie said, Oh, my goodness, wow. Y'all like that. The first place you should start when you are beginning to plan that next time is, let's incorporate, how do we fold in these learnings? And again, take one or two things that you want to start, stop, continue doing and and that is how then we have that continuous improvement. And are always. Doing better in service to having the impact that we want to have in the world. Here's

something that I keep thinking as you're speaking, and we've said this many times on the podcast, a podcast episode is not just a podcast episode. A gala is not just a gala. A board retreat is not just a board retreat, and I want to talk about just the power of intentional gathering, because you kind of hinted at this a little bit. We are so in that space, in the social impact sector, specifically a nonprofit, where it's like, go, go, go, check things off the list, but when we sit down and create pause and intentionality and rhythms to this gathering, something shifts. And so I want you to talk about the unlock that this is going to give to leaders, to re imagine how they're going to gather, whether that's with their teams or externally.

Yeah, I think so much of the time what happens in gatherings is it's so talking at like, it's very unidirectional, right? You think of like an all stat, like an all hands meeting, and it's like, report out, and what are, you know? And, yeah, that could have been an email, right? Like you can send it. I would think that a better use of time is more like, what's problem solving that could only happen with this group of humans. And then again, what's the why? Like, what is the need? And seeing the need in whatever that is. So whether it be for your board retreat, whether it be a training for your volunteers, right? Is it? I'm kind of harkening back to me being a volunteer in a couple of different instances in the last couple of years, where, actually, you know, certainly there's an aspect of obviously learning the content that you need to be an effective volunteer. But I've often felt this missed opportunity for connection between the volunteers. So like these, people also care about, you know, whatever the topic is at hand. For me, it's often around youth or immigration are kind of my two topics that are very dear to my heart. And these are people in my community that care about the same things that I do. I want to know these people, and I want to meet these people. And so I think it is getting really clear on that need. And my other biggest inspiration is a woman named Adrien Marie Brown. She has written many amazing books that I have over here, emergent strategy, pleasure activism and then holding change is all about bringing her kind of pillars to a facilitation perspective. And she talks about how, you know, we have so this crunch for time and that, like, actually we have exactly the amount of time that we need to do, the things that we need to do, and so it's like, what's the best and highest use of that hour and a half of that board meeting? I

definitely think what you're lifting are some themes that just stream through the conversations we have, because we wanted to start this podcast five years ago, oh my gosh, to have some of the conversations we didn't feel like we're having in the limelight. And it does start with like asking better questions, like, why do we keep doing the same things? And we're recording this live in 2025 the same old things clearly are not going to work. That even maybe worked last year. So it's like we have to get dialed into the why. And people are looking for that. We're itching for purpose. We're itching for what matters in this moment. And we have an opportunity to show up with our, you know, believers, the people that really believe in what we're doing with something that can cut through the noise. So I'm going to give you this stage for a minute of just what are some of the limitations. You know, traditional nonprofit events maybe lean into what are some of those limitations, and how could infusing more of your intentionality provide, just like a meaningful alternative, I think, especially in this moment right now, when we're looking for more connection and engagement.

Jon, like, how much time do you have?

40 minutes, according to Julie totally,

I mean to me, the number one limitation certainly the check the box thing. Of course, budget, right? Is always something, and I think something that I want to underline or lift up is I mentioned the unidirectional Ness that often happens in our gatherings, right? I think about conferences where it's just like, speaker, speaker, speaker, panel, which I like, can get on my high horse about how I just think transformation doesn't happen via panel, right? Like I mentioned that I was at a conference last week. Y'all, the most impactful part of that entire conference was 30 minutes that I spent with two other people where I got to workshop. Each of us got to go around and workshop a challenge that we had and then get feedback from other people. I just am a really big believer. Favor in the role of facilitator, as bringing out the wisdom that is in the room, right? That That doesn't happen with a panel, because the wisdom is only up here, right? The three you can't see me or people,

all of us, listening

to the people that are in the front of the room, in stark contrast that it's actually a what's called liberatory structures. It's an activity called Troika that is bringing out the wisdom that is in the room. And that's what happens also when you introduce a topic, but then you have time for me, to the attendees, the participants, to be like, how does this relate to me? So even in the middle of the panel, we're gonna pause, and you're gonna turn to the person next to you and talk about what's coming up, what questions, how might you relate this to your organization's context, right? And what questions are coming up for the panelists. And then at the end, we're going to take three minutes to debrie to do a solo reflection of what's one action I want to take in the next week, to bring the learnings from this panel to my organization's context. What's one thing I want to do in the next week? One thing in the next month, one thing, you know, whatever, in the next quarter, end of year, like I want it to be tangible. I want it to be action oriented. I just think so often we go to these things, and then it's like speeding on to the next thing, versus gatherings as a catalyst for the impact that we want to have in the world. And if your gathering isn't going to do that, then don't have it

hard. Stop. Yes, keep going.

I was just gonna say I have this vision of going to companies or teams and doing like a gathering audit to say, let's look at every time you bring your team members together, and let's get really clear on that purpose. And it's my straw. I haven't yet done this. We'll see if it ever happens, or like, somebody else can do it, I'd be so happy that to happen,

putting that out in the world. So yes, yes, I'll,

like, be your guide and coach and doing it. And it would be my strong hypothesis that you could probably get rid of, like, let's call it, at least a third of the team meetings. And when we talk, you know, anybody I know talks about back to back meetings, it's like, okay, let's not do that. Like, what does the world look like where that is not the case?

Well, I just, I think you're expanding our mind about why we do the things that we do, how we do the things that we do. And thank you for putting the activation component on it, because to me, this is the beauty of true and authentic team building that leads to belonging, that leads to believers, that leads to rabid fans, leads to retention in businesses where people want to stay because they're seen. And so I want you to help us and our listeners right now like rethink how we can make our gatherings more personal, whether it's personal or professional. What advice would you give us for how we can reimagine gatherings that lead to action, that lead to community growth that lead to belonging. Because in my mind, Jon, this is like our core value number four, it is, it is never and never will be about the donor. It will always be about the belief the believer. And if you can cultivate someone who believes in what you're doing, and they are bought in, then what comes from that is going to be so much deeper than just the financial offering. It's going to be so much more scale. So talk to us about how we can elevate those gatherings. Tess,

yeah, start small, right? So what comes to mind with this question, Becky, is the step three of my process of this sprinkling in of these special ingredients. So even something as small as an opening or closing ritual, which my you, you talked about, I have this kind of side hustle, passion project, radical reset, that's all about building a movement of rested leaders. And in our weekly team meetings, we start by taking a minute. One of my co founders puts a minute on her phone just to breathe and to land and right because, because we are in those back to aforementioned, back to back meetings, right the three of us a minute to arrive, and it doesn't. It's all it's only a minute. But I when I have a workshop that's called nurturing your inner rested leader, and I started by saying, I think the smallest intentional form of rest is a single breath, and so even just take right like, if we just do it right now together and. Invitation to listeners to do the same, just take a minute, or take a moment to let the air out of your lungs, and then a deep inhale and exhale and like it's pretty powerful ground.

And

in other opening and closing rituals, I love a check in or check out and just a couple word. And I actually you could do just one word of, how are you feeling entering the space and then also exiting. And I like to do two words because I think it gives a little more opportunity for nuance of like I could, you know, like I could be feeling excited and nervous or deflated and also cautiously optimistic, right? Like, so things can be true, yes, dualities, very it's been my big theme of mine for the start of 2025. Is holding duality. So, so that's one thing that, again, really small, and you can look up a million opening and closing rituals, and it can be something really fun to do, to co create with your team, and actually to bring back my team at Gap, for a moment, we had an awesome team meeting structure where opening ritual was for we would rotate around the team for someone to share an impact story. So we were the team that was running this first jobs program all across the US and Canada, but we were not working directly with any of the young people, right that were getting the jobs. So this impact story was this like grounding, like, what is the impact? Like, reminder of the work that we were doing and the impact it was having on the ground. And that was really powerful. And then we'd end each meeting with Team shout outs to say, Thanks Jon for giving me that pep talk when I had that big challenge. Thanks Becky for sending me a letter in the mail, I don't know, whatever, whatever. Becky, um, so that's one piece. Another piece is around peak moments. So I, if you haven't all picked up on already, I'm just a really big I really nerd out on resource sharing. And so another one of my favorite books is called the power of moments. It's the Heath brothers, Chip and Dan Heath, and they have this concept of peak moments, kind of like surprise and delight moments. And there's, there's an acronym called Epic. So it's elevate pride, insight and connection. Again, to go back to that team at gap. We had one time, an in person team meeting, where as a closing ritual, we got these puzzle pieces. And actually, I still have mine. This was like eight years ago. I have mine, everybody wrote down what is one or two words of the impact that you have on this team, right? So we're all parts of this puzzle that all fit together to have the impact that we want to have. So again, this is, like the elevation, like I'm elevating you as a member of this team. Then I have this little it's, there's a there's an aspect of insight, right? Of like, I'm taking a moment to reflect on the impact that you have. Then it certainly is a very connective kind of thing, right? There's like, A, you go around and everybody shares with fundraising events. The biggest opportunity is to think about, how do I get your potential donors, or donors really connected to the story of the mission? And that's by connecting their stories. And so I could imagine, one of my favorite things to do, this is a from Priya Parker. It's called 15 toasts. You have a theme for the evening. So I did one a couple years ago, actually, with the nonprofit that I was just mentioning, where their focus is on immigration. And so over the course of dinner, everybody gave a toast to their immigration story. And so I shared the story of my great grandfather who came. My grandma always used to say, the bottom of the boat, you know, with no money. And then he moved to New York City and dug the subway tunnels, which I lived in New York for about a decade. So often I would think about that. And so everybody gives a toast to that, to that theme. And if you really want to do it, well, the last person has to sing part of their toast, which in my one, that person was actually a musician. So they were, it was meant to incentivize you to be like, I'm gonna do it quicker. Quickly. This person was, you know, like, mic drop, amazing that he incorporated music into his but I just would think that would be so powerful to do something like that, where then you're. My story, and then I'm connecting my story to this mission. Yeah, what's the peak moment? Okay,

you and Becky are very tethered in this I feel like I'm having a conversation with Becky right now about just the power of our collective stories. So many of us leave that off the table when we're designing these moments, and it's like it's what pulls us together, and it's what can break through the noise of not just having another talking at US event. Nobody needs that. But, you know, I want to thread this together with the series that we just came out of, the social impact trends that matter. You know, we feel like there's a reckoning happening that impact measurement has to be redefined. It's not just about the dollars we raise. How do you think about measuring success at gatherings? I mean, it's something that so many intangibles are coming together. What does success measurement look like for you? There's

definitely intangibles for for gatherings, and I really think about it in two primary dimensions. I think surveying participants is super important. Like, if nothing else, do three questions on a scale of one to 10, how likely are you to recommend this gathering to somebody else, to a colleague or peer? And then what was the best part, and what would be the area of improvement? And always, things come up. So, so that's the one dimension of the day of and then the the other one is more of the long term impact, and this is so dependent on the context, right? But like thinking about like a team retreat that then you're setting the strategy for that year. What are then the checkpoints to say at this gathering? We defined our goals. Now we're going to have, for example, quarterly check ins to say, how are we doing? Where are we, you know, Is it some kind of like a dashboard of some sort, where we're referring back to, how are things going? Where are we on track? Where do we need to readjust? So, yeah, so that's kind of, those are kind of the two dimensions that, for me, I think about, how do we ensure that the gathering is actually having the impact and kind of having the best and highest purpose and role, and really is serving as that catalyst for the impact that we want to

have? I just think it's so relatable on so many levels, and one of our other trends this year is fuel young generosity. And I have to tell you that there is a commonality I'm finding in the two questions. I have found that if you ask children about their involvement in generosity and philanthropy, it is so similar to what you're saying, because the two questions I ask are, what did you notice and how did it make you feel? And when you get to the and I feel what you're saying is very, very similar, what did you notice about our gathering? How did it make you feel? And asking those questions allows someone to come in so honestly. And I just think we as missions have such an opportunity to take care of that, to foster it, to use it, and that is what our expansion is built on. And I don't just mean the expansion of our mission, but I think it's the expansion of our humanity, the way that we are connected to each other. And so I adore you. I am so jazzed that there is this level of focus in the world on gathering, because I do think it is a balm to a hurting, hurting society. I think it is so much deeper than business, than missions. So I and I'm excited to ask you this question, because I know how much you value story. So take us back to a moment of kindness, a member a moment of generosity or philanthropy in your life, where you felt changed by it.

What came to mind, speaking of fueling youth generosity, is, when I lived in New York, I was on the junior board of a nonprofit called Global glimpse. They work with young people in cities across the US about, how do you how do you grow as a global citizen? And so they have after school workshops that are focused on things like globalization and poverty. And then the young people get to go abroad to Latin America, and they get to really see how different people live in the world. So I had been on the board for many years. I got to go to the DR just for a weekend one time. But then it had always been a dream of mine to to lead a trip like this, week and a half long trip. And so I got to do that. Think it was 2021 and got to lead a group of high school students to Costa Rica. And it was just so impactful for them to see the world in different eyes. And I'm thinking of this one moment the students really got to then meet other students, local students. They the the local students would come and that, you know, a lot of the. Didn't speak Spanish the the American students. And so then they would, um, they would dance, and then they were teaching them to dance and just have it, you know, like university language Exactly, exactly. And I just like remembering the students, yeah, dancing with their with their friends, and having such a ball. And I just think about, for me, spending time abroad has been tremendously transformative. And I think I would like to imagine a world in which all young people have the chance to experience what is it like and like walk a day in somebody else's shoes? And yeah, I really believe in that, in that work and global glimpses work and set the work of so many others. Gosh,

I love that story, and have had transformational experiences like that too, that just like, stick with you when we get out of our bubble, and I feel like that's what this conversation keeps coming back to. Like, same, all, same, all is not working for anybody. So how can we create moments that do stick with each other, you know that can help shape us and change us. And so friend, as we round this out, we got to think about a one good thing. What's a piece of advice? Maybe a mantra that is really resonant for you today, that's lifting for this conversation.

What I want to share is, is, it is a practice that I do on a weekly basis, which is having a meeting with myself once a week on Mondays. And it is this time. You know how I feel so strongly about the debriefs. I feel really strongly about this concept of what does it mean to be a reflective leader? And I think the world needs more reflective leaders, and so that is time for me to look back at the last week and say, What were my wins, what were my challenges, what were my learnings? And then look ahead at the week ahead and really narrow in on what are my focus areas. And I just find it to be really a grounding presence of, like, what am I going towards? And then I do and then I take time on a monthly basis, on a yearly basis. You know, it build. It builds. From there. One of Adrienne Maree Brown's emergent strategy pillars is a concept of fractals. And so small is all how we do anything, is how we do everything. And so this is, like the small unit of this weekly time. So, you know, use it anything that I share right, like adapt it to your to your individual context. But yeah, just invitation to take that time to connect with yourself, to then be really clear and how you want to show up in the world.

I like you so much. Tess Cohen, I mean, I just think you you come in and you talk about the art of the gathering and help us reimagine that. But I feel there is such deep humility and commitment to the to your self evolution in what you're saying and to grow and to help others grow. And I tell you, Jon, the only time I'm in my head is like at midnight when I'm about ready to go to bed. That's my reflective space, and that is not a healthy practice. So really feel like we're taking a lot from this conversation. People are gonna wanna meet and get to know you. They're gonna wanna connect with you. So tell us, like, how they can connect with you, with gather better. Where do you hang out, on socials or online? Yeah,

I would say LinkedIn is the best place for from from in the socials. And My full name is to Sandra, so I'm in there. And then it's gather better.co. CEO, so not.com and yeah, with that, I have a monthly newsletter where I share, I provide a gathering experiment. So you can, like inspiration to say, try this out. Try an opening ritual, try closing ritual. Try experimenting with group agreements. I really like to think about this like being in the experimentation. And then you take what works, leave what doesn't behind. So yeah, would love people. Would love, love to hear from folks in in the We Are For Good community. I

mean, Thank you friend so much. Here I feel so buoyed. It's always good to be in your presence. Thanks for being on the podcast. Thanks for having me.