Nov 28, 2023 | Podcast

Creating Transformational Group Containers with Kerry Dobson

Listen Now:

Watch a Clip:


About the episode:

Have you been thinking of adding a group program to your business offerings (or even investing in one)? This episode of The Prosperous Empath is for you! I’m honored to have Kerry Dobson, a coach who supports authors, coaches, and other thought leaders in crafting & leading their own group certification programs, on the show. After hosting over 100 professional groups in her career, Kerry has so much insight into what makes a group course successful for the leader and the participants via igniting passion and creating long lasting & impactful connections. Just by listening, you can hear the care and expertise she brings to this work. Your programs can be just as transformational as your 1:1 offerings, consider today’s episode as a resource to help you get started on creating your own!


Topics discussed:

  • The origin story of Kerry’s business after being stranded during the pandemic 
  • The dangers that can come from pedestaling your leaders and the way Kerry intentionally creates group coaching containers 
  • Knowing when it may be time to create a group program in your business and the biggest differences between group and 1:1 coaching 
  • How group programs can be especially beneficial for empaths as they lean into community and receiving 
  • Some best practices to instill and to avoid as you create your group program and invite people in 
  • The different ways you can open the doors for deeper transformations in your group container 
  • The importance of understanding the struggle points that your clients will have so you can strategically serve them


Connect with Kerry:


Episode Resources:


Connect with Catherine:

  • Website
  • LinkedIn
  • Instagram
  • YouTube
  • Sign up to receive my weekly digest on empathic entrepreneurship and hear from voices committed to spreading this message, sent straight to your inbox every Friday since 2016, here


Work with Catherine:

  • Interested in working 1:1 with Catherine or a certified coach on her team, or joining one of her premium mastermind programs? Schedule a low-pressure call to begin the conversation here.


Click here for a raw, unedited transcript of this episode



Catherine A. Wood  00:00

Yeah. Hey, Carrie, welcome to the podcast.



Thank you so much for having me.


Catherine A. Wood  00:07

I was thinking about how we connected and Jen Corcoran was the first one to introduce us.



Yeah, yep. I have so many different connections to Jen right. She’s just such a super connector. Like, literally, that’s her tagline. But it’s she lives in.


Catherine A. Wood  00:23

She, I think she was our first guest on the podcast. And I think that may be the title of her episode. She’s certainly the super connector. Well, I am thrilled to have you. And by way of kicking us off, I would love to invite you to share your pronouns, and then a little bit of your story, and you can start and wherever you seem, you see fit.



Perfect. So Carrie Dobson, and it’s she her the, the way that I’ll start my story is that, you know, I’m one of those people that feels really lucky that I get to talk about something that’s so important to me, and that I’m so passionate about. And it’s really about groups, and it’s about the power that happens and the magic that happens when people come together in order to learn and grow and transform and just connect and celebrate each other. And so that’s really all that I got to talk about. And all that I’m about because I just find those environments, so amazing. And so my kind of way that I came here was, I was in learning and development in the corporate world for over 15 years. And, you know, I loved what I was doing, right, I was bringing groups together, but it was all very corporate, they didn’t, you know, leadership development programs that were amazing. But it was all still kind of within this work container. And I ended up moving from Canada, where I’m located to the US for my job. And I joke, like I got on the plane, February 3 2020, which, you know, punch line is coming. So by March 13, I was in lockdown. And by the end of May, I was had gotten COVID layoff notice. And it was such a unique experience, first time being laid off. But also, I was in a country where I only had the ability to work at that one company in a global pandemic, when there was literally an executive order that said, I couldn’t transfer my visa anywhere. And I had 60 days to get out of the country. And I know for a fact that if it had happened in any other way, I would have just got another job because I was enjoying what I was doing. But in that 60 days of kind of packing up this newly created life and experience and driving my foster fail cats on the east coast of the US to like the midwest of Canada, which was a lot of windshield time. I asked myself for the first time in a really long time, what is it that I wanted to do? And what I realized is even though I loved what I was doing, and I loved bringing people together and loved leading in the leadership development area, I didn’t love who I was doing it for anymore. And what I mean by that is I was working with executives who had great ideas of what they thought their employees needed. But then when you would actually go bring those employees together. Turns out maybe it wasn’t so accurate. Not everybody wanted to be there. And so it’s just a very different vibe, if you will. And so during that windshield time, I kind of thought, Well, how do I continue to do what I love to do, but serve people that I really want to serve and work with? And that’s where I kind of said, Okay, I’ve got my coaching background? How can I help coaches? And how can I help authors to create these group programs where people do come together, and they’re open to learning, and they’re open to connecting with other people, so that they can kind of truly experience the magic that happens in a group. And so that’s what I get to do now.


Catherine A. Wood  04:05

I mean, I love hearing your story. You know, on the podcast, we talk with so many creators who have transitioned from corporate, or the federal government as I did into entrepreneurship. And most of those journeys start from a place of burnout, or not really loving what they do. And what I’m hearing is that you you actually already loved what you do, and you made it even better.



Yes, yeah. And I that was such an important part for me in that transition of trying to figure out what I wanted to do because, I mean, not only that, I put a lot of time into it and done a lot of education in it. I did love it. And it’s just something that like when when we talk about being in flow state, that’s what happens when I think about groups and I’m designing groups like it just it’s even as I said, it’s like full body goosebumps, just that experience and you know, trying to figure out do I do this for Mr. Do I do this first, you know, how many people are in the room? How does that impact what we’re doing? Or we’re online now. So how do we keep that engagement going? It’s, it’s just, it’s my flow state.


Catherine A. Wood  05:12

I love that terminology. Like I often say that when I’m facilitating my mastermind calls that I feel like a conductor, where I get to conduct the meeting, and, you know, speak to this person in this person, do you see how you do that, and how this is reflected of your experience and like calling people as they see fit. And it just feels, yeah, flow state is such a good term for it.



When it’s, you know, I love the imagery of a conductor, the one that I’ve been playing with when I’ve been talking to people is a guide, right? So there’s times where you’re a guide, and you’re at the front of the group, and you’re telling them and showing them where to go right, and you’re really leading the way. And then as the group connects, and as they get more comfortable with each other, and with what you’re talking about, you’re able to kind of go to the back of the group and kind of watch what’s happening and just make sure everybody kind of stays where they need to. And then there’s these beautiful times where you get to be really in the group. And, you know, anyone looking at the group wouldn’t necessarily know that you’re the guide of the group, because you’re immersed in it, and you’re really part of it. And so it’s that same thing of being able to conduct as you said, you know, those times where you’re bringing this person forward and this person forward, and then suddenly they see something that they just never would have seen without that group connection.


Catherine A. Wood  06:33

Maybe we could jump in there, because I, I love that metaphor of shifting roles during the kind of the cycles of group development. And I think that can be really hard to do well, and I’m even thinking about some of the groups that I was a part of, in my, in my beginning journey, like I had such admiration and reverence for the leaders that I put them on such a high pedestal, that I always related to myself as different and less than, and I always kind of revered them, right. Like I felt like I needed to build my business exactly the way that they did talk the way they did sell the way they did have the confidence in the way they did. And mind you, they were both two men. With 40 years of experience, you know, and I was so different than then in all the ways. And now in my mastermind, I always try to kind of level myself down and bring my own humanity into the space like, share my own faux pas. Like, I always try to humanize myself, because I don’t want people pedestal in me as I did my own leaders and coaches and mentors. So how do you from a group design program? How can you intentionally create a group container to facilitate that experience?



So I think first and foremost, especially when we’re talking about like US, and Canada, we have to acknowledge the fact that most of us were brought up in a school system where the person leading was given to like was was shown to be the person with all the answers, the person who marked you and told you if you’ve got to move forward. And so for so many of us, our inclination as we enter these groups, is to look to a leader. So you’re actually having to work against years and years of that belief that the person at the front of the room and air quotes, it has all the answers and is there to kind of tell you what to do. And so you want to be really intentional about how do I start breaking that down. So people recognize, hey, this isn’t the same. And one of the easiest ways to do that, is when when you first bring the group together and you do introductions, don’t talk first, don’t introduce yourself first, go last. And it’s this subtle way of saying to people, it’s not about me, I’m not the most important person, and I’m not going to have all the answers. And so that’s such a quick, easy way to model it. And then I also think it’s an important conversation to have when you’re setting up the whether you call them rules of engagement or you know, the way we act together or that we agree to, to kind of talk about the fact that the role that you’re going to play and how sometimes you’re going to be at the front and you’re going to be sharing something and there’s tools or tactics or strategies, but that so much of the time in the group is really about reflecting towards each other and mirroring things and celebrating together and it’s not so much here. Let me tell you what to do.


Catherine A. Wood  09:54

So, you work with coaches, consultants and authors.



Yeah. Yeah, so, yeah.


Catherine A. Wood  10:01

So I’m just imagining, when, when would a client? When would one of your clients consider a group container? And what should they be thinking about as they want to design a group? Yeah.



So, you know, I joke, but it’s serious. So many times the conversations I’m having with people, that desire to have a group is coming from this pressure to believe that they have to have one. So first and foremost, it’s like this, you know, who might give the permission, but permission to everybody to say, you don’t have to have a group program, that’s not the only way you can grow your business, that’s not the only way you can have impact. What what I look for is, you know, have you worked with enough clients that you have, you’re really confident in kind of your structure and your strategy and your tools, and they give you kind of this repeated outcome of some sort, right, you can really rely on the tools that you have. Because if you’re not at that point, it becomes really challenging to build a group around that, because the biggest difference between working kind of one on one with someone, and working in a group is one on one, you can kind of pivot, right, if someone brings something up, you can quickly go down whatever rabbit hole or path that they need to go down at that moment. But when you have a group, one of the things you have to do is you’ve promised this whole group that everybody’s gonna get to what I call the program promise, right? There’s going to be experiences and accomplishments that everybody’s going to kind of have. And so it’s a lot harder to kind of go down those pathways for each person, because you’ve got this responsibility for the whole group. And so, you know, it’s one of the reasons why I encourage people with groups to kind of think about, can I insert some one on ones here, so that we can still go down some of those random pathways, because there’s such insight that can come from that. But it really is about knowing that I’ve got this structure, I’ve got these strategies, I’ve got these tools that consistently deliver results. And that’s when it starts to be like, Okay, how can I do this in a group setting? The other thing that happens is people ask for it. So they say I love working with you, but I’m really missing a community. This would mean so much more to me if I could learn this with other people. Or if I could hear what other people are doing, or what are your other clients do? How did they how are they successful with this? And so those kinds of questions start to say, okay, maybe it’s time to bring some people together in some format.


Catherine A. Wood  12:30

I can, I had that exact same experience with my long term coach, I worked with him for five years and nearing, actually, in the middle, I was like, What are you talking about with your other clients? You know, like, what did they bring to coaching calls as requests? How can you coach them differently than me work for sessions? Are they having differently than we get to have, you know, like, just wanting more like wanting different? And, yeah, so that’s such a good example.



Yeah. And, you know, it’s, it speaks to the curiosity that you have, right. And it’s also, so much of what we do feel so lonely until we start talking to people. And then we discover, there’s so much more in common in our human experience, and there isn’t right. And so being able to do some of this work in a way that allows us to kind of see, like, I’m not alone, I’m literally not alone. But also, you know, maybe they’re a little further ahead than us. So they give you hope, like real hope that it’s possible. Or maybe they’re a little bit more behind on something. And now suddenly, you’re able to help someone and realize I was there six months ago, and now I’m helping someone like that. That’s


Catherine A. Wood  13:42

something that I share when we’re setting the foundations and all my mastermind is this idea that, you know, we all experience terminal uniqueness. The idea that we think we are the only ones who feel this, that we are the only ones who experience impostor syndrome or doubting our confidence when in reality, like it’s that self othering that prevents our growth and our acceptance. And when we can see ourselves reflected in other people’s experiences and journey, it creates another creates another entry point to accepting ourselves our own our own gaps.



Yes, absolutely. And it takes the bite out of them because you see them in someone else and you’re like, that’s not as bad as I thought it was for me. Or if sometimes when you see it in somebody’s in a good way, you’re like, oh, like that’s a great reframe of that, that I’ve been kind of being mean to myself and saying this is a bad thing, and only I do it but look at how it comes out here. Like maybe this is something that’s helping me move forward.


Catherine A. Wood  14:46

Well, I I would love to talk about why you love group programs so much and I think I asked this maybe even selfishly because I want to know your perspective because that it’s something I talk about here. on the podcast a lot the importance of having a values aligned community to support you, and particularly for empaths. Because I think empaths like we just, we self other ourselves so much we we give to others at the expense of our own success and our own well being so deeply, so fully, so open heartedly, that I think we particularly can benefit from being part of a, of a real values aligned community. So and I know we share this belief, so you know, why, why, why do you think they’re so effective? So,



for the empath thing, you know, for me, what comes up with that is, you know, it’s the space that I get to receive what I give, right, if I’m in a group with others, I can’t always be the one giving like, it’s, it’s impossible, but it also is an invitation to not always be the giver. And to really practice that receiving, and to kind of say, like, what, you know, what can someone else help me with? So for me, there’s part of that is to receive what I sometimes am always the giver of, but for me, I, there’s a calling for me, in this moment in time, because I think, especially post pandemic, we are all experiencing loneliness, like the Surgeon General of the US has said, It’s like one of the biggest problems right now, this, this idea of loneliness. And fundamentally, I know, we’re all connected, I know that that’s a knowing deep within, but how we live our lives isn’t that way. And we are so disconnected. And I think so many people are looking for, and hoping for community. But we have all these really clunky ways of having community that aren’t really feeling that need. And so for me, that’s where the power of groups come in. And so for me, it’s, it’s a group, when it has kind of a start date and an end date it can go on, you can have another iteration of it. But there’s this commitment to this time together. And there’s this opening of the group that happens, where we really start to connect, and it becomes almost this other entity, this container, if you will, that we get to be part of. And so for me, I think there’s such a need and a desire for it right now. And unfortunately, I think we have, we don’t have enough examples of where it works really well. So we have a lot of people who are trying it, but it’s not filling that need, just because it hasn’t been set up in a way that will fill that need and will make it safe for people to connect in that way.


Catherine A. Wood  17:38

But I just feel that so deeply. Like I think the the loneliness piece is so it’s so deeply true, you know, and even for me, like when I launched my mastermind in 2019, I launched it because I couldn’t find the community that I felt like I belonged. Yes. So I literally created the thing to heal the experience of loneliness that that I felt personally. And yeah, and the piece about empaths like that rings. So true for me, like having places to practice receiving. It impacts every aspect of an empaths life, from their marriage to their parenthood, to their intimate family and friend relationships. Like we all need places to practice in a safe container where there is consent and permission to lean in. Yeah, there’s


Kerry Dobson  18:35

that permission. And then there’s this, this communal kind of agreement, but also this communal commitment to doing it together. Right? That I think especially when it comes to the entrepreneurial world, we’re we’re alone and so much of what we do, right, especially if we’re a solopreneur, we’re kind of working on our own, that to be able to go into an environment where yes, we all have our own businesses, but we’re also working towards a different way of being together and for showing up for each other. To me, it’s so what I say is, you know, if I make a promise to myself, I will easily break. If I make a promise to a coach, someone that I’m paying, they can hold me accountable a little bit more, but at the end of the day, I’m paying so if I show up and have a story, you know, we just kind of keep going. But when I have a responsibility to a group and others are relying on me and expecting me to have it done, I’m not showing up without it done unless something really big happens. But then that’s what I need to help you know, processing right. So the level of commitment that comes with groups without pressure necessarily, it’s not this pressure filled thing. It’s this I want to serve in this community and I hold this community sacred and my responsibility in this community sacred so I’m going to show up for myself and for them. Absolutely.


Catherine A. Wood  19:59

I mean, I always joke that whenever I’m in a group fitness class, I work out the hardest because I’m trying to motivate everyone else as much as I’m trying to motivate myself. And I think the same is true and group containers, right? Like when we are leveraging a group in order to make a powerful declaration. And we know that we have 10 voices, rather than just one counting on us holding us to account checking in on us how it’s going, like hopping on a call to virtually co work together, like wanting to celebrate our progress and ground taken, like, there’s just so many positive levels of accountability. And I think positive is really important, because in my experience, as a coach, so many more people are naturally motivated by a stick than by a carrot. And in a group container, it can really kind of rewrite the script on what holds us accountable and really incentivize us and reward us positively in a self honoring self encouraging way, versus a self loathing, self detrimental way.



Yeah. And I will say that that is dependent on how you set the group up, right? Because you can just as easily have a stick based group where it’s competitive, and you’re, you know, ranking each other. And it’s like, so it’s about saying, Hold on a second, what is it that I want this group to be? And CO creating that together? And I think most people who say they want to be part of a group want that positive piece of it. But if we as the guides are not leading the path of that different way, we can very easily become kind of that stick based group.


Catherine A. Wood  21:41

Thanks for naming that. Because honestly, I would have never even considered that possibility. And it’s absolutely true. Like there are certainly groups that that have that energy. Well, I mean, I think that’s a really good segue, because you’ve made several references to ways in which we can set a group up well, or ways in which groups kind of suffer or can fall apart. So what are some of the best practices to instill and to avoid?



So first and foremost, the most important piece that you do is deciding who’s in your group. And it’s, you know, as I often see kind of messaging around groups about scaling your business and making all this money and you don’t have to work and I see it the opposite way, I see the group as is even more responsibility because you’ve got this additional entity. But the first and foremost is having conversations with people to know who’s coming into your group, right? To make sure that it’s the right fit. And I I get it, and I have so much understanding when you’re trying to fill a group and you just know you want 10 people, both for the financials, but also for the way that it works better, you know that number, but if you let in somebody who’s not prepared, who’s not ready, who isn’t interested in that same kind of container, one can make it all go all over the place. So the first and foremost is being really clear, in kind of your intake process, the enrollment process and making sure hey, it’s a right fit. So that first and foremost, the second one is, is to go really slow, when you’re building it, what I say is at least 10% of your total program time should be spent in that opening of the group and creating those connections and creating the container and creating the ways in which you all agree to work. It, it sometimes feels a little slow for people, right? They want to kind of get in and just get going. But the best thing you can do is set such a solid foundation for that group, because then you can go further later on. And then the other important part of that is how you end your group and the research on it. And the area is sacred endings. And it’s, it’s really about saying, we’ve put so much into this group. And there’s a grieving process that comes with it. And even if we’re going to start another group, two months down the road, there’s still a grieving process. There’s an ending here. And so being able to give people the opportunity to have conversations and share with each other. You know, this is what happened because of you or this is how you helped me or this was the role you played in the group and ending it in such a way that yeah, we’re still sad that it’s over. There’s still some grief, but we’ve also given names to it and we’ve given opportunity to celebrate and, and have that ending kind of actually happen versus Oh, we’ve run out of time. That’s it. You’ll see an email soon, you know, like, there is the sacredness that’s required once you create a container like that.


Catherine A. Wood  24:56

I mean, I’m really here kind of the call forth around boundaries. Having a kind of reverence for the beginning, the middle and the ending of a group container. And I really love the way you started your answer, because you started with the who, like, Who do you invite in the room? And how do you ensure they’re a great fit? And what happens if they’re not like, that’s been a huge learning for me over the years, because I’ve certainly had people in my group who it just wasn’t the right fit for them for some reason. And I actually had to change my contractual terms over the years, because, you know, it takes many hands to form a group, and it only takes one, one bad fit in order to really cause harm in a group and, and take away that safety, which which takes time to build that safety and that vulnerability and that willingness to be intimate. And not only and I’m curious, your thoughts on this, but not only between the group members, but also with the facilitator, because the the facilitator, the mentor, the guides, willingness to be vulnerable and intimate is what models and leads the way for everyone else to lean in as well.



Absolutely. Right. If you’re up there just pretending away and you’re asking people to be vulnerable. It doesn’t work, right. So it’s that modeling piece, but it’s also about, you know, those clear agreements around, how are we going to work? And what does that look like? And, you know, one of the things people always kind of ask is like, what do I do if I’ve got a problem group member? And I’m like, Well, you know, that’s something you have to fix, right. And usually, it’s about getting them out of the group in such a way that they’re still okay. But also that the group recognizes that you’re dealing with what’s going on and you’re aware of it. One of the things I say frequently is like, as a guide, you need clear eyes, you need a full heart. And so the idea here is and strong arm so clear eyes is that you know where you’re going. And you know what that program promises. But you also have clarity, as you’re looking around and seeing how people are reacting, interacting, reflecting. So you’re always kind of scanning the full heart is that you are showing up fully that you are connected to this, you are being vulnerable, you’re sharing your experience, but you’re showing up fully, and you’re holding space for that heart for everybody else. And then the strong arms, which I think is the one that is often forgotten, is really about those boundaries and saying, I will hold those boundaries so strong so that you all can be safe in the container.


Catherine A. Wood  27:41

Well, that’s lovely. Well, so let’s talk a little bit about transformation. Because I think as a, there’s so much possibility for facilitating transformation in a group container. Like it’s really magical. And And I’m curious, what you’ve noticed, even even kind of going back from your corporate experience to what you’re doing now, in your own business, like, what are what are the ways in which we can open the doors for deeper transformation in our group containers?



So first and foremost, I think you have to be honest about how long it’s going to take. And so so many times we have people saying, well, I, I can’t commit to six months, I can’t commit to a year, right? I maybe six weeks, maybe eight weeks, and it’s, I would say you get to choose either, you know, do you have the resources? So that you’re kind of saying, Hey, this is what we’re going to do? Or do you have the timeframe? Right, the expectation? So what it is, is it’s being honest about how long is this really going to take and transformation takes time, because we’re our brains are literally wired to have us do exactly what we did yesterday, and the day before that, and the day before that. So transformation requires a change in how we show up and how we do things. So making sure that you’re giving enough time for people to actually learn what they need to learn, grow, but then transform. And so for me, it’s about the duration of how long you’re going to keep them and being honest about what that means and what’s needed. But then it’s also about kind of saying, This is what’s really possible, right and breaking it up for people. So it’s not this big overwhelming thing that’s going to take them five years, but instead is something they could accomplish and experience in six months or a year.


Catherine A. Wood  29:47

I really appreciate the setting of expectations and how being really clear about your expectations in a group creates that that permission that willingness to lean in, to trust the process, something we talked about, in the beginning of any of our group containers is just presencing people to the hero or the heroines journey, and just what that transformational experience is like, and really presencing them to the roller coaster that is transformation and inviting them to stay on the roller coaster, all the way through, to learn how to find joy along the way, and, and lean into the journey. Right? It’s like, we all know that if we’re suffering our way through a roller coaster ride, taking ourselves way too seriously, like, Soul holding in our belly, like we’re really gonna, you know, have a stomachache, or throw up by the time it’s over. Versus like, maybe we just need to throw our hands up and surrender and



scream, you know, or laughs with the person next to us. Yeah, and just say we’re in it, right, we’re in this, you know, one of the things I talked about is understanding the struggle points that people will have, right, and this is where you need to have, you know, done a lot of research or worked with a lot of clients, like you need to know your stuff to know, where are the points where people are going to struggle the most. And then really being strategic about how do I add additional support, whether that’s an activity or partnering up, whatever that is, either just before the struggle point in preparation for it, or as it’s happening, or right at the end of it, so that they’re getting that extra support. I was trained as advanced Grief Recovery specialist. And, you know, there’s, there’s two weeks of, of the program where it’s horrible, it’s, it sucks. But you need to work through it and come through it. And so that’s the week that people are going to cancel. That’s the week that people are gonna show up. But it’s about having that conversation and saying, listen, when you don’t want to do the homework, and you don’t want to work through this come anyway, come to the group anyway, we’ll hold the space for you, and we will help you through it.


Catherine A. Wood  32:04

I love that like it’s like anticipating the break down points, and putting the structures in to meet them there and to make them feel held truly, really held



and that it’s normal, like normalizing it because again, this, this othering that we do, it’s like, well, everybody else is having a good time No, no, like, come let’s talk about it. That’s why we have an extra session, or that’s why we do the one on one now, because this is this is the hard point.


Catherine A. Wood  32:31

So I would love to talk about the quality of a group container, and how you can facilitate more intimacy more kind of really like that locked arms energy, because I noticed both as a facilitator, leading groups for many, many years now and also being being part of communities, you know, like I was a Peace Corps volunteer. And I always say that, like my experience of belonging and feeling part of something larger than myself. I’ve never had a greater model than being a Peace Corps volunteer, because I created just such such a deep sense of community and lifelong friends. And, and I think it’s really extraordinary. And I think that there is an art in creating that experience of really belonging to a community belonging to something larger than yourself. And I’m wondering, like, how can we as container holders and cultivators, how can we set ourselves up for success there? Yeah.



So it goes back again to making sure you’ve got the right people in the room, right and, and that you also have a program promise that you can deliver on that you’re setting people up for success that you’re actually going to do what you say you’re going to do. So there’s all these expectations. And then it’s an invitation because you cannot force that type of connection, you cannot force that type of belonging. So you want to have those conversations before you let someone in. But then it’s about the invitation. And then it’s about a slow ramp up to it right, like expecting that the first time everybody gets together that suddenly everybody’s best friends is unrealistic, right? So it’s about saying, Okay, where were where can we take them for that first session? What about the second session? So for example, you know, the first session, we’re not going to talk about like, the biggest frustration I have or like my biggest fear, but maybe we’re going to talk about what’s going on around me one of my this silly, but one of my favorite introductions is what’s outside your window. And the idea behind that is please invite us into your surroundings beyond just this little square that I see you through. And so it’s slowly these these little invitations to bring your whole self and to just show us who you are. And again, you can’t force someone to do it. But it’s these invitations and if you’ve selected the right people They’re gonna grab on to those invitations.


Catherine A. Wood  35:02

And my version of that question is, what are your favorite pair of your of shoes? And what do they say about who you are? Right?



Yeah. And like, the risk on that is so low, but yet what, what, what great information we get from people with those kinds of questions, right? And it’s, it’s, it’s really those simple little things. And then it’s, it’s setting up the expectations and CO creating them. So, you know, you have all this experience in groups, you could go into a group and say, This is what makes a group successful. But then those are your rules, and you’re holding them to it, versus if you invite people, and then you say, what do you need, in order for this to be what you need it to be? They will tell you, they know. And then you co create it, and then you get everybody to agree to it. And suddenly, they’ve their voices already part of this, and they hold each other accountable. Because it’s the rules they’ve created together.


Catherine A. Wood  36:03

There’s so much more buy in that way. I completely agree. I mean, I think, you know, facilitating transformation, holding groups, like we all have these experiences that, that leave a mark, you know, for better and worse. And, and we learn from them. And I’m wondering, like, what, what’s that experience for you? Like, what is the group that you’ve either curated or, or trained or belong to that had the made the greatest impact? And what did you learn from it?



So I’m gonna tell you, the one that made the biggest impact, but not in a good way. Because sometimes, sometimes it is those those bad experiences that really light up for us like, this is somewhere I need to go. So my husband and I, were attending a class for potential foster and adoption parents. So heightened group, right, people are coming in, considering this life choices, huge impact. And so we all kind of come into this room, and it was set up with a half circle, but there was different rows. And it turned out that all of us ended up in the last row. Because we were all uncomfortable. And the facilitator came in late, zoom to the front of the room and said, Why are you guys sitting at the back move forward. And I I remember, first of all, just the feeling of vulnerability that I’m already uncomfortable being here, this is already really tender for me. And now you’re forcing me to sit in a place that I’m not comfortable, you’re forcing me to come front and center. And I remember saying to my husband and I had had some training already in this past, like she can’t do that she’s risking everything with this move. And I, I know what she was trying to do, like she was trying to make it good for her because no one wants to talk to people who are back in the room. But she also wanted to bring us together. But in that choice, she made it about her and she made us move, versus all she had to do was move one table and come to us. And it was in that moment that I realized the decisions we make when we’re guiding groups completely impact the outcome and the experience that people have.


Catherine A. Wood  38:25

Gosh, I love that. You know, something I have practiced over the years is when I noticed myself in one of those choice points. I put it on loudspeaker. And I let the group choose versus me choose for them.



And that choice is so important, especially when we’re dealing with transformation. But I think it’s always important. But when you’re asking people to transform, you want to give them choice wherever possible. I have a framework that I call design with ease. And it’s about making sure your program is engaging, actionable, supportive, but the last one is ease. And it’s that idea of how do I make this easy through giving them choices and making things that don’t have to be hard? Easy, right? Because there’s some part of this, it’s going to be hard. And so how can I make it easy for them by giving them choice, giving them control over whatever it is? And as long as you get them to the program promise. It doesn’t matter what your plan was?


Catherine A. Wood  39:28

Well, you know, now now you have me super curious. I’m going to do something I don’t think I’ve ever done before on the podcast. But maybe you could just live workshop with me something. Absolutely. So this weekend, myself and my mastermind partner, we’re hosting our first ever retreat for our unbounded mastermind. We were going to host one in 2020 in my parents bed and breakfast because my parents only been b&b for 30 years and it got indefinitely canceled. So this is our first in person experience. And we have people coming alumni from all the years. So there’ll be 10 of us in total. And most of these people know each other, some extremely well. And I notice, I have all of these emotions coming up about hosting this retreat, like I have great pride in the relationships that have been cultivated between one another great pride in the community. And also it feels so like, there’s such an opportunity here, you know, like just such an opportunity to make an impact. And it’s feels like, like very, this is going to be a significant defining moment in my business, like, I know, I’m going to be deeply touched by this experience. And so all my empathic tendencies are kind of, really front and center for me. So what questions should I be thinking about, as I gear up to facilitate a powerful experience? Well, I’m



curious about when you offered this to them, what was kind of the experience that you were sharing with them? And what what what might you say is the program promise for this weekend together?


Catherine A. Wood  41:16

So we feed back to it and invited them to share what they wanted it to be rather than generated for them. So I think I did that well, based on your responses. And what they shared was that they wanted opportunity and time to to be together, spaciousness to kind of deepen relationship and have fun. And they wanted support around leveling up the next stage in their business. Yeah,



yeah. So I just want it like first and foremost that you asked is so beautiful, because I think sometimes we need to tell people where to go, right. Like, we need to help them with that clarity. But because you’re dealing with people who are already in your program, and your alumni, there’s already this built in trust, there’s already this level of knowledge that everybody has. So those are those perfect opportunities to say, let’s get some feedback and see where they want to go. The thing that I think is so important to pay attention to is that connection request, right? Because you could go into this with all your knowledge and all your abilities. And like just bang topics out do these great activities. But when it’s about connection, we actually want to slow it down. We want to give people free time, which I know seems crazy when we think about retreats, but allowing people to fill some space with what they want to do and giving them that choice, especially as empaths. Like, sometimes we need to just go back to our room, or go for a walk, right. And so giving some space where that connection can happen. And doing some of it in a really kind of tactical way, if you will, so that everybody does get the opportunity to connect with each other, but then also just trusting in the group to ask for what they need and to connect with who they need to connect with, and giving them the space to do that. Oh my gosh, I was so glad I asked you.


Catherine A. Wood  43:15

And here’s why like everything you just shared, I was intuitively feeling this real desire to create so much spaciousness in our itinerary. And that being at odds with the part of me that used to have a second business, curating international retreats. And it’s so right, like, sometimes we just need to give people exactly what they asked for and stop making it about ourselves and our need to perform. And, and on that note, one of our last retreats that we hosted in the Dominican Republic, it was just a women’s retreat. And they had probably, it was one of the most impactful retreats because of the level of relationship that was built. And it was because of exactly what you just said, because there was sufficient spaciousness in the itinerary in order for them to connect and have fun and laugh together. I have never talked more about sex and poop in my



in public and you know that it’s a good retreat when sex and poop


Catherine A. Wood  44:23

oh my gosh, Haley, do not put this in the show notes.



The other thing is, is one of the things I think about is if someone says to me, oh, like I have a new best friend or I was talking to someone like that they keep that relationship going. That’s the indication that you’ve got something going with that group when when they move the relationships forward without it being kind of forced. Yes,


Catherine A. Wood  44:53

I could not agree more like absolutely that is one of for me, that is one of my KPIs. have an effective mastermind, if I know that lasting relationships are formed. Yeah, yeah. Oh, wow, what a beautiful episode, I guess I just want to open the floor is there anything that I haven’t asked you that you want to talk about or you want to share?



The only thing that I think is still kind of on my heart is just this idea of, you know, there’s so much more potential in groups than what we see and what we’ve probably experienced ourselves. And so really opening up to this idea of you are an expert in helping people to get to where they need to go. And that doesn’t change in a group. But what changes is there is this other entity, and there’s so much magic, and there’s so much power, and there’s so much presence in that other entity, that I really encourage people to slow down their process. Usually what happens is we think I want to have a group and we start, they’re going to do this, this, this, this slow down and get really clear about what is your program promise. And the way that I love to do this is imagine that it’s like the next day after your groups finished, and your phone rings out of nowhere. And it’s a participant, and they’re telling you this was the best program they’ve ever been part of. And then you ask them why? And what is the answer that you hear? And that will help you to figure out what’s most important with this group? What is that program promise?


Catherine A. Wood  46:36

What a beautiful practice to leave with. Wow, Carrie, thank you so much. This has been so affirming and permission giving for me and yeah, I’ve just you’ve really, like shared so many drops so many pearls for our listeners. So as we wrap up, I’d love to invite you to really share what I ask all my guests, which is what is supported you and becoming a prosperous and Beth. So it’s



community, which is not surprising, based on what I talked about. But it really is. You know, when I was in corporate, you know, I didn’t recognize how much guarding was going right for survival and for success. And as I got into this entrepreneurial world, I started kind of recreating that because it was all that I knew. And it was through my community and through the connections and through the amazing people that I’ve met, that I’ve really been able to open up and say no, the whole point of this is to be me in what I’m doing, to bring my passion to bring my happiness to bring my sensitivities into this. And so for me, it’s about that connection, that community, don’t do it alone. Don’t do anything alone. Find people to help you with it.


Catherine A. Wood  47:55

Yes, yes, yes. Thank you so much for today. It’s been an absolute joy having you on the podcast.



Thank you for having me.



Get the Essential Reading List for Ambitious Empaths

Snag a copy of our favorite confidence-building + intuition-honing business, money mindset, and leadership books to help you embrace a holistic approach to your success. Grab a cup of tea and let's reverse engineer your life, removing the hustle and grind and replacing it with more joy and leisure.

Exploring Sensitive Leadership with Nina Khoo

On this week’s episode of the Prosperous Empath®, we’ll explore how to effectively lead as a Highly Sensitive Person (HSP), mitigate challenges, and work with your strengths. I’m thrilled to sit down with Nina Khoo, a Sensitive Leadership Coach and a Master NLP Coach who helps HSPs understand and embrace their unique wiring so they can become confident and empathetic leaders. It’s common for Highly Sensitive People to believe that they’re not capable of effective leadership and struggle with overwhelm, perfectionism, and second-guessing. Nina and I uncover how our greatest strengths can sometimes be the traits we feel most self-conscious about and pose a central question: How does a Highly Sensitive Person protect their gifts as a leader? As an empath and an HSP, your brain is physiologically wired to take more information in and process it more deeply, which can be an incredibly powerful leadership skill. Yet, it can also lead to overwhelm and self-criticism. Through our conversation, you’ll learn how to approach leadership in a more sensitive, empathetic, and compassionate way so you can own your gifts and make a bigger difference in the world  

Visit this episode’s show notes page here.

The Prosperous Empath® Podcast is produced by Heart Centered Podcasting.

Check out this episode!


Download The Book List Now