You Winning Life Podcast Ep. 182: Unleashing Team Potential with Kendall Wallace

In this episode, host Jason Wasser, LMFT, interviews Kendall Wallace, founder of Executive Offsites, about the power of intentional team‑building offsites and retreats. Kendall shares her career pivot from a decade in tech to creating immersive, purpose‑driven experiences that boost employee morale, trust, and ROI. The conversation covers why many companies settle for superficial perks (foosball tables, pizza days) instead of deep, human‑centered design, and how to move from “just getting together” to measurable outcomes. Kendall outlines her practical framework – pre‑offsite surveys to define purpose, a BART (Boundaries, Authority, Role, Task) lens for structuring groups, and tools such as Enneagram, love‑language exercises, conflict‑style identification, and embodied leadership practices. Both hosts stress the importance of regular check‑ins, monthly team health reviews, and integrating family‑systems concepts (Bowen theory, ART) to surface hidden dynamics. They also discuss cost‑effective venue ideas (sleep‑away camps, outdoor settings) and the need for leaders to model the behavior they expect. The episode ends with actionable resources: Kendall’s playbook of 100+ exercises, her LinkedIn/Instagram, and the executiveoffsites.com website.
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Welcome back to another episode of the You Winning Life podcast. I am Jason Wasser, but you already knew that. Before we get started and I tell you a little bit about our guest today, I wanted to invite you to first, if you haven't already, subscribe on the podcast platform that you're listening to this on. We are getting closer and closer to hitting episode 200. And I'm really excited about the number of guests that are coming up. And as well as if you are getting any benefit out of that, please go to Apple Podcasts. And even if you don't have an account there, but to leave us a positive review, that helps us obviously get found by more people and shares the wisdom with all the guests that they're sharing with us. And also just, you know, helps us out. And of course, we'd always appreciate that. And if you have any questions, or you're looking for therapy services, entrepreneur coaching, please send me an email or a message, which you can easily find on all of our social media. But today's guest is Kendall Wallace, and she's a dynamic leader in the field of marketing and team development. And she's the founder of Executive Offsites, where she specializes in creating impactful team building exercises, enhancing employee satisfaction, team cohesion, and communication. She focuses on fostering deep human connections and facilitating breakthrough results through these strategic offsite events. Her expertise lies in maximizing the ROI for the team members and ensuring that the stronger bonds and aligning teams better are towards all the common goals of the company. And she has done some really cool stuff. And I love the idea that we're going to get into talking about neurology and relationships. So I hope you all enjoy. And again, Thank you for listening to us and giving us your time. I know that there's so many incredible podcasts out there and YouTube videos and books and everything. But it really does mean a lot to us that you've joined us on our journey. And really, really, really, I would love to hear from you. I'd love to know who out there is listening. So please send us a message. All right, so as promised, Kendall, thank you for hanging out with us today.
Oh, thanks so much for having me, Jason Wasser. It's awesome to be here.
Yeah, I'm so excited because, you know, as you all know who are listening to me over 180-something episodes, I guess at this point a lot of the magic happens in the pregame conversation with the guests and I. And it's always the debate of like, do we even record the pregame conversations? But it might be a little disjointed for the listeners because, you know, you're jumping into something. But we're going to try to recreate some of the awesome stuff that we already just started getting into and, you know, repackage that for everybody. Buddy, uh, in the few minutes that we had already. But, um, you know, you, you're one of the people that I love talking to because you've had a career pivot and where you were already invested in, in, in a certain trajectory and you found something that you saw missing in a niche, in an industry, and you went after that. But, uh, before we tell them what that is, even though they heard a little bit about that in your bio— not enough, but a little bit— uh, let's start off with like, you know, where you started in the professional journey and then as that took you into seeing what you saw that allowed you to pivot.
Sure thing. Yeah. Well, and I'll just say one thing too, is Gary Vee always says to people when he's giving advice, right? He's like, spend your 20s like figuring out what you want to do and your, your 30s like finally getting going with that selected path that really calls to you. And I feel like that was my trajectory on all honesty, you know, like, um, I have worked in tech for about 10 years in different companies. And really, that experience of working remotely at a satellite office where— or actually working at a satellite office where the headquarters was elsewhere before this was a remote work world, and that was just challenging in and of itself, to working in office, to working remotely, basically I've been able to work with different teams. And so now I help organizations really create connection and better team dynamics so that they can really improve their output and ultimately make more money. And—
yeah, go on.
And so what I— how I do that is by creating either in-person or virtual experiences that are really team gatherings. The best version, in my opinion, is the multiple-day corporate retreat all the way to You know, if a company just needs an hour workshop, we can also do that. But you're, you know, you're going to get your results a little bit different than when we're able to spend a few days together. But ultimately, it's really, I mean, let's be honest, right now there is a morale issue in companies. You know, you get these employees like with all these layoffs that are not motivated, or it's really like the detachment that happens when you see hundreds of people go out the door and when it's this survival kind of method or kind of mode that people need to be in. And that creates this kind of environment where everybody's out for themselves in this competitive, like, just looking out for number one. And ultimately, that's not— then employee engagement scores and employee satisfaction tank. And you wonder why when you're not doing any outs of team building or team, like, actual cohesion investments to address the elephants in the room. So what I do in my experiences is really to create, um, to create connection and then ultimately resolve team dynamic challenges. And, and I'll tell you why that's so important to me is because when I worked at a big tech company, I was actually, um, in a situation where there was this, uh, I didn't get along with a teammate and it exacerbated into a minor misalignment into the strategic direction we wanted to take the particular product we were working on into me getting fired for not being a good teammate. And, you know, the funny thing about that is like some teams are like, ah, you know, it's, it's all right, like whatever. But when you At the end of the day, these layoffs, firings, they happen. Like, livelihoods can be very impacted when you don't— when you have these little cracks in kind of the team dynamics that aren't resolved. Right. And so that's what I— that's what I care about doing is making sure that people's livelihoods aren't impacted in the way it was for me. And that's through investing in, you know, healthier team dynamics.
Everything you said is what I'm constantly hearing from my clients that are in the entrepreneur space, or they're intrapreneurs, right? They're maybe C-suite or maybe even a team leadership level. And they're constantly saying there's so much— not unfairness as a complaint of like, oh, that's so unfair, and like pouting, but just the direction of leadership not properly guiding the teams or not investing in the teams or seeing one person kind of like legitimately getting away with like there's some favoritism. And then I hear on the other side, company culture, right? It was big in the last 10, 15 years. Put a foosball table and an espresso machine in your office and unlimited snacks and you have company culture. And you're like, I don't really care. Like, that doesn't make like it less of a toxic environment when it still comes to personalities and self-awareness and actual training of leadership. And I found by interviewing some leaders where I'll say, oh, well, what books are you reading? Who are you listening to on leadership? Like, you know, I throw out like John Maxwell or even like Gary Vee, like you said, Gary Vaynerchuk, right? Stuff like that. And like, yeah, no, we don't, we don't have time for that, you know. And it's so interesting. I see this in all fields and all levels of just not investing in each other and not investing in your team. But I think that trickle-down effect of what's happening and why what you're talking about is so important and so missed is that the first thing is they'll say, well, we don't have time for this, we don't have a budget for it, or, you know, we saw something like that somewhere else or maybe at a conference and it's not a fit for us, right? There's always some type of like first-stage excuse to that growth. What have you— like, so when you were— when, you know, when you started seeing these, these, these holes and, and what you were doing and working around and what you needed for yourself, when did you start realizing you're like, okay, So I'm not getting— this teammate and I are not getting along. No one's kind of like facilitating. It's not an HR thing, but it could be an HR thing, but HR doesn't really know how to— they don't really know how to do conflict resolution, most of them. When did you start seeing like the writing is on the wall and start brainstorming, right? Because you're, you're doing this job, you eventually, like you said, you eventually left. But when did like the wheels start turning as like, okay, I'm doing this, I'm navigating this, but I also think I might want to create this?
Yeah, great question. So I picked myself up by my bootstraps, you know, traded in digital experiences for in-person ones. We were really, you know, coming out of the pandemic as well. And so I created retreats. I had moved to Hawaii at the time and created retreats to bring people back to life after the pandemic, have these mind, body, soul nourishing experiences for entrepreneurs and remote professionals. And the level of bonding that occurred was mind-blowing. I thought, just by the way I designed it, you know, in a, in a way I designed, uh, activities again to nourish the mind, ones to nourish the body where we would do group workouts and ice baths, ones to nourish the soul where I would bring in Hawaiian healers to teach us about Hawaiian culture, and we'd you know, learn how to do hula and make flower crowns. And people ended up connecting so deeply that many lived together, like, for many months afterwards. At some people, there was actually just a wedding, and here we are years later, where a bunch of people that met at this experience all went to this person's wedding literally 2 weeks ago. So The level of connection really surprised me. And then I thought, you know what? There is— there can be a better way. There can be a better way than what I experienced, you know, of like the investments in our team building was like, let's have a carnival or pizza day. Right, right.
Pizza straight out of The Office TV show.
Right, right. Well, and the funny thing, to your point, you know, the foosball table. I think the thing that can be a little tricky around that is that those things are actually better than nothing because nothing will get you absolutely nothing. So that's, that's a, that's a markup on, on nothing, but it's not as good as what it could be. And what it could be is actually investing in people's growth and development as human beings, as teammates with one another, and as employees. And that happens like the one of the magic or special sauces of how I structured my, my retreats that I still do now is I give an opportunity for each person to shine, i.e., stand out in some way, but also each person to be humbled. So I've incorporated different presentations, but then also that's kind of the beauty of of having such a dynamic experience during the offsites is because you can have, you know, some people are going to be good at the sports or more physical related things and other people are not. And so it really can be a humbling experience. And thing is, is that trust is built in humbling experiences.
100%. Yeah, it's, I see it with you know, I started offering family retreats. And it's not— it's funny how many people have reached out to me over the years for it being an intervention. And it's not created for it to be an intervention, right? Like kind of like an MTV, you know, come in, like, person's doing right, that type of thing. And it's more for those that are on the self-aware ladder They're those that realize that we can take advantage of doing a vacation and add some extra value to the vacation by doing some workshops together, some family team building or whatever it may be— parent-child, parent-parent, um, additional family members, whatever it may be— and adding in like just 2 hours a day while away on vacation somewhere. And no joke, I constantly like, you know, it's that low ball versus like that low frequency versus high frequency. How many people are looking for to get away, to get out of their norm, not to be in right in office somewhere, whether it's for therapy or like you're saying for like a leadership training event, but just to get out, but to be away from that situation or the environment that they're used to, to just go to a hotel, doesn't even have to be a nice hotel or a nice resort, but they just want to be somewhere else to do some type of personal work than what they're used to in the Menani. And this is what I love about retreats. I'm doing one in August. It's like a TED Talk-y type of conference. But it's at a sleepaway camp. The best. So instead of it being like you're sitting in a workshop hall and being lectured, right? It's a full immersive, like you're saying, mind, body, spirit type of thing. I'm teaching a workshop on core values, but it's, it's in nature and there's gonna be hikes and there's gonna be learning how to make certain types of food and what, right? So I see that, that's such an important environment for— it's even not the foosball, it's not the coffee, it's not the— it's the It's environment, but it's the self-awareness of that.
Yeah. I have a question for you. When you've done these family ones, because I haven't done family ones before, but an intact team is a different experience than when you have strangers. Yeah, for sure. So, well, what I mean is that you have strangers who sign up. I've found that they can go to a level of depth that people who already know each other, it's— you got these intact relationships. So I'm I'm curious, like, how deep did the families go in what you've structured?
Well, it's interesting because I kind of created a menu of different activities and they get to choose, right? So it's a pre-qual, you know, pre-qualification and pre-conversations. We kind of set up a menu, uh, of what we're going to do. There's— and we get to pick and choose, right? And I have like, you know, let's say 15 different activities, and I hear what they need and I hear what they want to work on, and I get everybody's input, and then I come up with, based on those on that menu, kind of like, you know, it's not one size fits all, we're going to do everything. It's like, oh, it sounds like you need more of, uh, talking about and experiencing everybody's love language and how to practice and start changing engagement styles through love languages. And even though it's like anybody can read a book and watch a few YouTube videos on it, but I think like putting it into play and doing a 30 to 45 minute full-on immersive just on that— it doesn't have to be 3 hours, right? It could be a 45 minute thing. What's your love language? Okay, now let's practice what that would look like with each person based on theirs and making it really like in that way hands-on. A lot of times in general, I always use the Enneagram personality styles as an index just to communicate and engage and understand why the other person is acting a certain way or responding a certain way, right? So it's self-awareness about not just about ourself, but about, oh, no matter what I say, this person will respond this way because I don't understand the lens in which they're seeing the world through, and it's not right. So I love looking at it from perspective as well. But I think like what you're saying, like when you're doing, like on your program, a curated experience, it's really profound because it's exact— it's what does this company need? What does this family need? Versus we're just lockstep, everybody comes, gets the same thing, it's the same curriculum. It's like, it's not a cruise, right? It's not— we stop off at this port and on this day we're going to this port and you have no choice. And you either like the itinerary or you go on a different cruise. Very different.
Yeah. Have you read Priya Parker's book, The Art of Gathering? No. She has a great line in there where she says, you know, bringing— the purpose of bringing people together is not a purpose. Like, that's a vehicle to accomplish a purpose, right? So, and it's so funny because I was actually just in a call with the potential client and who wants to create an offsite and bring his team together. And I had to deliver that exact news. He was just like, I want to bring the team together. I'm like, yeah, but like, don't you want an ROI for bringing the team together? Like, do you want to build more trust? Do you want to enhance connection? Do you want to have them resolve conflict more effectively? Do you want two people to have a better working relationship? Like, do you want everybody to figure out how to align. Like, those are all purposes that is going to give you a much better return on your investment for bringing people together. So when I plan— before I plan any offsite, I actually send out a survey to every single participant to know what they want to get out of this. Like, i.e., what's the thing that if you spend 2 or 3 days of your time that if you got would make this 100% worth it to you? Because that's my North Star. That's where I'm going when I facilitate these offsites is so that as much of the team as humanly possible can get that true desire of what they want to get out. Because coming together for, like, to just get to know one another, You know, even that is a slight purpose. That's— but it could be course-corrected to something a little bit more profound. You know, that'll move the needle.
It's—
sorry, just one more thing. That'll move the needle on working relationships to 2 weeks down the road. Like, I, I literally hated walking out of an experience, and I think to, to a degree, this is why I do what I do. I hate walking out of an experience to be like, what was the point of that? Like, I would feel like such, such a failure if people came to my offsites and said that. Like, no, no, you better know the point because you just shifted a lot of stuff, you know? So that's, that's what I keep in mind.
Yeah, I was thinking when you were saying that, when you're talking about ROI, return on investment, I find in a similar, similar concept, but I use it in a different language, is that a lot of people create— what they think is their goal is really just an action step. So they're solving for the wrong x variable, right? So they're making the thing that they think they want to solve as the end goal, but I'm like, no, no, no, no, that's just an action step because you're not thinking big enough about what— like you said, what's the real thing you want to solve? And they end up like getting stuck by their old way of thinking, and that's only what they come up with, right?
It's—
it doesn't allow them to think or see anything differently because they can't solve the problem from the place in which the problem was created, which is where, right, we come in to say like, oh, it sounds like this is actually what needs to be solved. Like, oh yeah, right. So I see that. And it's funny, a buddy of mine, shout out Pablo Gonzalez, he was a good buddy of mine, also earlier guest. He was— he's an emcee for conferences and business conferences. And he basically— I think he facilitated it with one of the big hosts was instead of just having someone present to them, all day, right? Speaker after speaker after speaker, as we've, you know, seen those things. He— they split up the guests into team— gave them a problem and then split them up into teams for the first hour. And then each team had to present their idea to the rest of the conference. So it's a good— right, so one, you're thinking about, right, you have different people with different personalities and different traits and different skill sets. And team 8 may have never thought of that because maybe they're all a bunch of engineers and this team is a bunch of whatever it is, right? There's an HR person on your team or there's just the systemic thinker who can just think differently or a psychologist or— and it just was a good for all. But you actually solve something within the first of being at a conference and that just sets the momentum for, for sure. Right.
So I think it's worth it. Just nothing's worse than having a CTO up there. You got a room full of highly paid engineers and all of them are staring at their phones. I've seen it. I've seen it. It's like, and then they call that a success. I don't really think so, guys. So when, mind you, then those engineers who don't feel seen, heard, and valued will just switch teams or Irish goodbye to another company because they've been treated like mercenaries instead of like human beings.
It's hired help, right? The whole idea of like, are you an employee or are you just hired help, right? Are you, do you realize, are you being told and shared and rewarded for the value you bring to the company? Or do you, that's why I left working for nonprofit programs before I became a therapist is that at the end of the day, I realized I was hired help and there was just a round robin of professionals going around the same, like every few years it would just be the same people moving to the other comparative nonprofit. But we're all like, we've all known each other for like God knows how many years. It's just who's ending up where with the roll, with the shake of the dice, right? And we all did the same stuff. We're all very talented and gifted. It's just that was the BS of that system. And when I left it to be a therapist full time, finally, it was such a relief to not have to be hired help anymore, knowing that, you know, I'm no different, unfortunately, than the janitor because I'm replaceable, which is true. But also, if they fire me or let me go at the end of my contract and they bring in someone else, we're really not that much different. They think on the outside we're different, but it's really— we're doing the same programs, we're doing the same events, we're doing the same fundraising, we're doing the same admin skills. So it's really, really challenging. But, um, just to go back to the point of what you were saying about if you have your, your team sitting at the conference being on their phones. I was watching— I'm a big fan of Jesse Itzler. And yeah, yeah, he's a good guy. Yeah, he's a fabulous human being and really authentically genuine. And it popped up the other day when I was on break that he was doing a backstage at one of the speaking events that he was doing, and it was for some insurance company or whatever. You know, a couple thousand people there, and people were on the Instagram Live commenting that they were sitting in the audience while someone else was also a big speaker, but on the Instagram Live of Jesse preparing for the speech behind the scenes saying, 'We can't wait for you to come on, we're here, we're in this conference,' which goes exactly to your point. They're literally right. So whoever was on the stage— I mean, obviously Jesse might have been like the highlight of that morning, but They're literally not just like on the Facebook or on TikTok or whatever. They're literally on an Instagram Live while they're at a live presentation of the event of the future guest that's coming on because there's not just like— but it was, it was like, oh, well, this person reached this level of award and sales and then it, and like, it was like, yeah, I would have shot myself if I was there. It seems like it was just because you can see clips of what was going on from So I think that just proves your point for people out there who are listening or running conferences and workshops and team leading events, that that's just like, just because you have someone held hostage within your event doesn't mean they're getting the value that you think they want out of it.
Totally. And this is where something we talked about before we started recording, but is around embodied leadership comes into play. You know, you can create those rules around, hey, put your phones away when it's kind of bought in as a group. But it also has to be demonstrated from the top. You know, one of the hardest things, I was consulting this team where bigwig, like VP PM at this, at a big company you would know. And had basically, whenever they had a real challenge of trying to engage younger, younger employees. But here's the thing, the, what the Chief of Staff didn't point out to the PM was that, but pointed out to me, was that every time those young 20-somethings had the opportunity to, to present to this 40-something person He was on his phone the whole time. And so all those young whippersnappers, just because that's the first term that's coming to mind right now, but you were just like eager to, you know, they're hungry for that validation, especially coming fresh out of school, just get so disenchanted because somebody else is on their phone when it's their big shot to present in front of, you know, and it's just, that's one of those things where we had to work on that, as that had to be pointed out and then worked on. Um, because that's how you're gonna fix it, is when you fix it in an embodied way from the top.
And I love that, that— what's that whole thing, like, if you're out, what, like, we naturally, those of us who— well, I don't know if everybody does this, but I know that there's a set of people who do this— they may still have their phone out, but it's flipped face down, right? So the screen's not up, But it's still on the table. And it's still face down. But that's still like, like, I'm trying to be very, very, very mindful of like, you know, if I'm in the middle of like, I had a networking friend of mine who also does some nonprofit stuff, we caught up this morning for coffee. But we like, you know, it's very casual. We've been friends forever. But you know, both of our phones are on the thing. But it was funny, but I realized like my phone was like on the counter at the coffee shop, but face down. And I'm like, right, so rote. That's so like, and this person would not be offended in any way, shape, or form if I like had him like, oh, hold on, this is a client that I've been playing phone tag with, wouldn't care. But I want that person not only just as a friend, but as a, you know, professional in the community to know that I'm 100% theirs for the time that we blocked out. Right. Well, it's that difference of just being mindful, not just being— but like, yeah, we have to— we have to talk about this. As mundane as this sounds, I think like this is like we have to talk about this. We have to like kind of be self-aware enough to even say, oh, crap, I'm doing that. Can I just keep it in my pocket or my purse or my— right? And not— right? The time is the time.
Yes. Well, and I've seen individual teams also, how you can create that buy-in is when they set parameters themselves. And that just can take a little bit of time, not not, you know, not more than an hour to really be able to say, hey, in our meetings, how do we want to— what are the rules we want to live by on this team? And that can also create identity and belonging, you know. But like, like, for example, things like cameras off, I just don't recommend whatsoever. Um, and yeah, I mean, there's things like that. There's also one of the things I work on with teams is to try and come up with a conflict style, like identify people's conflict styles and And then, hey, when our team has conflict, how do we want to work through it? It's really, really important to have rules for the road because ultimately, we're humans and those things do come up. It really does. And it's like, I think as we get more and more technological in this AI world too, it's about really making— still making the investments though in the humanizing because at the end of the day, we are humans on this human experience in this world. And not every relationship in the workplace needs to be transactional. No. If you want to keep losing, you know, good quality people and have people switch teams and all that stuff and have, you know, that underperformance kind of pattern, then sure, okay, make everything transactional. Yeah. But if you want to, you want to have people rally around each other and support one another, and guess what? Yeah, one person got passed up for promotion. How's that person doing? Because you heard for freaking 3 months that all they wanted was that promotion, and then the performance cycle came up, you didn't hear anything, but instead we just leave them alone. Now what do you think they're gonna do? They're gonna freaking disappear.
Like, correct, they're already looking for other ways. Oh, I advise my clients all the time, like, oh well, my, my promotion, my, um, my annual review is not till— so we're now, right, we're in July 31st was the date of this recording. So they're like, oh, my, my My bonus review is not till March. I'm like, okay, so what's part of the protocol leading up to that? Or is it only you have to do whatever you think you can do and, and just hope and pray that they're going to acknowledge your KPIs, or if there even is KPIs, right, about what you're doing? Are you— can you push yourself to have a meeting with whoever is in charge of advocating for your bonus once a month? To make sure, like, what's going— because, you know, also then a business might say, oh, well, we didn't have this, we didn't have money this year for the bonuses. Well, you didn't tell us that 6 months ago, so I would have left. And, you know, I'm doing all this output and I'm working extra hours and you kept dangling it. That I find I'm hearing so often from employees, that all of a sudden the company doesn't have money for bonuses after— but your bonus will be right, but we have a review in this, this many months away. But no one has ever updated them to say, oh yeah, we're not doing bonuses this year, right? It's, it's, it's, it's That's really frustrating for me as a therapist working with passionate professionals who are committed. Like, this goes exactly to your point. These people are committed to these companies slash organizations. They may have been there for 5 years. Some of them may have been there for 15, 20 years. They don't want to go anywhere else. And these companies still pull this crap.
Mm-hmm. Well, yeah. And it's really important. I interviewed actually this amazing mindset coach who was the mindset coach for the Yankees when they won 3 out of 5 years. It was like Joe Torre era. And he told me, I asked him what happens when, you know, what happened when people screwed up like that, that level of detachment, i.e., passed up for promotion, somebody missed a play, whatever. He said, yeah. The trajectory usually is to detach. But the best coaches and the best leaders leaned in. Yeah, they leaned in in those moments and didn't kind of like rid their, you know, hands, but actually like, how can we work together to get you back re-engaged? Because the most likely trajectory is you just continue to check out, right? So like, it's kind of these like normal humanizing conversation that like, for some reason we tiptoe around versus like, you know, there are opportunities. That's what creates connection is just to be real with one another. The highest performing teams actually have the highest trust. And one of the key, one of the key traits of having high trust is being able to talk straight with one another.
It's so funny that you're saying that just to go back to the Yankees for a second before you go forward, right? The Yankees right now, have a pitcher that majority of the time when they bring him out as a relief pitcher, he has tanked the games for him and they keep bringing him out because now a lot of the rules have changed in Major League Baseball. I just got a whole update on this because one of my best friends is like diehard, right? Loves the Yankees. It's all he wants to talk about. But then he also like wishes they would all just like, you know, go down in a plane because they're doing so bad on those days. And it's like there's this pitcher who is just like has tanked games for them. And one, what's the remediation? What's the right— are they just like avoiding it? Are they talking to him about it? Is the whole team getting together and cheering this person on and saying, hey man, do you— after practice next week, do you want to sit with us and we're going to go through that? Like, we want you to pitch batting practice for the next week. You're the guy and you're going to come, right? Like, what's— it's not just from above, but most— a lot of companies don't have permission to allow the people that are potentially amazing leaders to step into that role because they don't want to get crapped on or feel like they're overstepping and getting then a negative point of view from the team leader. Oh, this guy's gunning for my job. This woman's coming after me, right? No, no, no. It's not about the— it's again, it's that investment. But a lot of the structures don't allow that to show up.
Well, I'm glad you started talking about like role because, uh, I've— if any of your listeners want to have a crash course in self-awareness of their own patterns and proclivity to, you know, with authority and role, I highly recommend getting yourself to a group relations conference. So I recently attended one and I'm about to attend my second, and there is a framework that I think is really tremendous. It's called ART. So the B stands for boundaries, the A stands for authority, the R stands for role, and the T stands for task. And basically, when any of the— like, for me, when I went, it was a real interesting understanding of— you have these small groups and large groups, and for some reason, in our large group, whenever anybody tried to We weren't given a task or anything to do. And so whenever anybody tried to kind of lead the group, because they didn't have the designated authority or role, it just kind of was anarchy, actually. Like, everybody— nobody— like, we couldn't even go through introductions and icebreakers. Like, I— like, it was that— it was that pathetic. And it's just an interesting— it's an interesting study in self-awareness of, like, You know, for me, right, as a facilitator, here I am, I'm putting on my facilitator hat. I'm like, guys, can we just do like basic things? And it was so fascinating for me because even that in small groups or large groups, people didn't react positively to it. And I was just absolutely, you know, was like, what is going on with my leadership? And so it really creates these self-awareness opportunities that it's funny because I Obviously, in my offsites, create self-awareness opportunities, but I'm trying to integrate more and more of what I experience in this social experiment into what I offer because it's really tremendous, really tremendous.
Yeah. And I love that there's these offshoots of different modalities, right? The Conscious Capitalism community, right? And they talk about how can you really just do good and even though we're still making a lot of money. And be like, you know, how can we take care of the world? And it still goes back to everything you're saying, which is the relationships. At the end of the day, there's no relationship, there's no business. And sales, whether our people are doing multi-million dollars, $100 million a year, or they're a therapist and they're doing, you know, a bare minimum of six-figure practice, still all about the relationship. And how to talk to your colleagues. And because it's not just like selling the idea of what you want to do with your team, it's closing the idea with your team, getting people to be stakeholders in that idea. I had this conversation with one of my colleagues. I'm like her go-to for consulting on like business stuff, and she's done some really amazing things over the last couple of years evolving in her private practice. And we had this whole conversation and she's like, oh, okay, but if I put my, you know, change my profile and someone calls, well, that's great, right? I'm like, yeah, yeah, but you still have to close the deal, right? You getting them there is one thing. And I see that like companies have— people are getting people. You're— they're always going to hire, they're always going to let go, there's always going to be new people wanting to come in. But in a way, you're talking about closing the deal, not just the day that you sign them to work with your company, me. But closing the deal every day, closing the deal every week, it's like, it's like a couple. Like, just because you convince the person to get engaged to you or get married to you or be in a relationship with you, 6 months later you can't rely on the day that you said, do you want to be my, my, my whatever developmental relationship partner? Like, you have to constantly reinforce, like, I still want you to be this. What do we need to do today that's different about our relationship than where we first started? Which is, right, most of the sessions that I have with my clients have been married for over 15 to 20 years, is that they're still doing the stuff that they did when they first started dating in, you know, 1992. They think that they're doing in 2024 that same stuff and it's still going to work.
No.
Entire culture and life has changed. So, right, so I think that's so applicable to that corporate structure, what you did to get that employee money to woo them and bonuses and incentives. And right, what, what's, what's the next— what's the conversation 6 months from now? What's the conversation 12 months from now?
Right.
And in between.
And one of the healthiest things I think, uh, for teams honestly is to have a team check-in once a month. How are we operating as a team? Like, what's— like, that's where it's work is off the table, but it's What is working about our team dynamic? What is not working about our team dynamic? What would we like to try next month to see how we can improve? And then it's like these moments to just take a gut check because it doesn't have to— you don't have to wait until it's feedback time, you know, and it's going to go in this black box of the internet, come back on your report, all official, like, That's, again, we're trying to integrate the human aspect, right, in a more technological world. And the human aspect is just, yeah, having straight conversation, you know, legit conversation.
Yeah, I do that. I have a weekly accountability group I'm in through a business mentorship program, and this is the stuff we do every week, right? There happens to be another therapist in it, but the other two people are not in any, you know, one's in a, um, a home maintenance type of field. The other one does business brokerage. But we get real. We get on what's going on in your life that's helping, that's holding you back from what you want to accomplish from our, you know, the stuff that we're working on in our accountability group for your own individual thing, both personally and professionally. What, based on what you know about anybody in the group, can we as a group collectively brainstorm idea with you? Or is there something that we can talk about that one of us that maybe we can have an additional call during the week to help you sort through some stuff that might be helpful? Or do you need resources from our Rolodex outside of what we're talking about, of someone we might know outside of that who might be able to help you? And, you know, those questions are million-dollar questions that companies like, I don't want to talk about their personal life, I don't want to be therapy session, I don't want to dump, I don't want to try— you have to be quick, like you said, boundaries, right? Which is the first thing, right, in the BART. But But it's such like when people show that they care more or a leader asks, is there anything going on in your personal or professional life that will help, that will hold you back from accomplishing this KPI? It's such an easy, simple question.
Absolutely. Yeah. And to be honest with you, like the people who are just so, I guess the wrong, maybe that's the wrong word, stiff, but so, attached to these old kind of rules of like, we will not budge. Well, that's fine. I'm just not interested in working with you.
Yeah.
If you're open-minded and want to create a better human experience for your team, I'm your gal. If you're just not, and I get it, some companies are not, I'm just not for Exactly.
Well, when I was looking at your website, you know, I was already excited to, to have you. And then when I was going through your website and I saw on the bottom of one of your pages, which is 100% what I literally— this is verbatim the conversation I had with this friend. It's what you do and what you do not, who you see and who you absolutely don't see, who, who, what are the prequalifications of the people reaching out to you? Like, so for me it was, are you a person who reads personal development books, listen to podcasts? And believe that lifelong learning and personal growth is incredibly important even outside of going to therapy? Right? Do you believe in integrative mind-body medicine as a support to, you know, eating well, working out, right, nutrition, blah, blah, blah, right? I had 5 or 6 prequalifications. But if you're this, this, and this, right, don't call us, right? If someone is telling you, you need to go and you're going to appease a partner or a family member, right? If you're in this stage of like addiction, and you're not already in recovery, right? It was such a like, it's such an easy, clean way. And I saw you have that on your website. Yeah, right.
I do.
Yeah, this type of company, right? These bullet points.
HR reps that fear any, anything unconventional, I'm like, don't call me, right? Because, well, what was super interesting, I will, I will share with you. I, I worked with a client that, um, with an athletic company, so there's a ton of athletes on the team. And I had, um, an HR person actually reject some— me bringing in Wim Hof. Mm-hmm. Wim Hof's basically right-hand person to come and lead breathwork while we did an ice bath. And the person, the HR person, was also so rejected, said no way, no how, because people might be scared, might be scared to see each other in swimsuits. So here's— now here's the two things I'll add. This particular person was not attending, and this particular person was overweight.
So projecting their own stuff onto the team. Yeah, yeah, it's a self-awareness factor, right?
I'd say it is.
Yeah.
And it's a, it's a tricky thing when, um, that's— it's why we have to create these self-awareness experiences. And I think ultimately the people who are really going to be most drawn to what I have to offer are those that, you know, are already in personal development and growth and are leaders, and you want to create something for your team that is not too woo-woo that it's going to scare them, but is enough to create these moments of real connection and real team dynamic enhancement, uh, that is something that they will also remember. Like, my whole goal is I really do a lot of stuff outside too engage with sunsets and sunrise hikes as part of the programming. Because you want to be able to have an experience where people are like, wow, this is awesome. And then, oh, by the way, they're with their teammates. It's like an afterthought. That's what I strive for, you know.
But that's where the memories are made. And it does add so much. The beauty of it, these are like, it's so funny, because this is how we operated before the Industrial Revolution, right? This is just— we were sitting outside, we were doing these things, we were, you know, it's so interesting. Like REI, just to, you know, tie this in together, like REI, which is right, the great out— I joke that it's, you know, Bass Pro Shops. You have Bass Pro Shops and REI, right? The REI is the Democrat, the Democratic, like, you know, like I've never heard of REI. I'm like, do you know like Bass Pro Shops? Yeah, yeah. Okay, so imagine a Democratic ver— a Democrat version of our Bass Pro shops, although it's not necessarily true. I'm just like, you know, for people who've never, you know, for context, because not every— we only have one like 45 minutes away from me here in South Florida before you start going further north, uh, finally. But, um, REI created this massive corporate thing at the beginning of the pandemic. They were like moving new headquarters, right? Full tech, digital, whatever. And they ended up not even moving in there and keeping everybody remote because the pandemic kicked It was like, you know, top-of-the-line tech, and they're gonna do, right, all these cool things. It was a beautiful campus, LEED certified, in the right nature around you. And they ended up not even moving into this place, and they ended up selling it at a loss, which tells you that, like— and they still kept most of the jobs remote, and just, you know, some people can, you know, the idea of just being together in ways that, you know, are not forced by having to be in the office is still, is still so important.
And it's, it's funny too, people assume that bringing people together has to be expensive, and it really doesn't. Uh, you know, there, you know, I think when you're— there are so many different creative ways to save on costs of bringing people together. You can take time to be outside. You can, um, not stay at a $300 a night per room hotel, you know? Like, it's— I, it's— I can't tell you the number of companies that are like, we, we don't have budget. And then I'm like, okay, give— let me help you. And then I magically find budget because I find a place that's still— it's not, it's not a crappy hotel by any means, but it'll be less than $200 a night. Like, we can figure it out, guys.
Yeah, or even sometimes outside the box, you know, said— go ahead. Yeah, no, you're talking about a sleepaway camp that you did, right?
Yeah, absolutely.
Yeah. And I think like people are okay, like, oh, it's so cool. Like we're going to bunk together. Like, yeah, I think like, yeah, super making like $200,000, $300,000, you know, $400,000 a year. Like they would— some people are like, that'll be so much fun for a weekend to be like super rustic. It's not like tents, but like, you know, you're sleeping on like, you know, twin beds. But I've done retreats like that where like the one I'm going to in August, I had a choice. It's a, it's a sleepaway camp. It's, it's winterized. They do have like hotel rooms. Condos and the retreat center. I'm like, I am doing the bunk situation because like I want to hang out with more people. I don't want to be like, you know, by myself, even though I do know people that are going and I am going to be speaking. But like, I want to meet people that I wouldn't typically meet and put myself in a more uncomfortable situation. And, you know, yeah, with like 3 or 4 other people in the entire bunk.
But yeah, yeah, it's fun. Yeah. I did lead this offsite at a sleepaway camp and it was just people actually were in tents because HR did get involved that didn't want people to sleep in the same bunk. And so we problem solved around it by having everybody in tents. But nonetheless, being outside, hearing the grasshoppers at night, being under the stars, roasting marshmallows together, like that That's, you know, it, it, it, there's a level of, of like, there's something that happens neuroscientifically when you're just embracing your inner child, you know? And it's nostalgic. Oh my God. Yeah, it's this nostalgic thing. And guess what? It's freaking better than a conference room, let me tell you that much. Like, this is why people are like, we can't afford it. I'm like, think outside the box. You could do it.
You can.
And it's just like, we had glow sticks and a silent disco and just—
Color war or whatever, right?
Anything. And these are the quote unquote fun things, right? Quote unquote fun things. And we balance that out with healthy exercises also to evaluate how the team— who are the leaders that come up in the key exercise? Then one of my favorite things to do with different teams, especially when there's that natural kind of competitiveness that can happen. So then I love to do this orienteering exercise. Have you ever done orienteering?
Basically, but tell me, yeah, give me your definition.
So use a, um, use a compass, a map and compass to go find certain locations. And then we would have little Easter eggs hidden there with like clues specifically about straight out of scouting.
Yeah. Straight out of scouting. Yeah.
Straight out of their organization. Yeah. And so that may sound very escape-room-esque or scavenger hunt, which kind of is. However, the way to then ground that in how it relates to work is then you have a rich debrief afterwards. Like, what came up during this exercise that related to how you guys work together and how you have this innate competition? And just gut-checking that with discussion afterwards.
Was the person trustworthy when they said, I know the difference? Directions? Did you— who followed? Who led? Who stepped up? Who, who did you notice going to the back and just like not being silent and just going along with it? Right? These are all amazing, amazing, amazing. I want to call it bait and switch in a negative way. I would say bait and switch in the most positive way, because you're setting up a scenario in a way they don't even realize that this is— yes, practicing interpersonal dynamics. And that's what's so—
exactly, exactly. And it's like And it's not just the fun, but then it relates to how they'll work together. And because at the end of the day, I care so much about moving the needle on how people work more effectively together 2 weeks down the road.
Correct.
You know, I want to always move the needle on that stuff because it wasn't moved for me. And like to have it not moved, like, for example, to have a communication workshop, which I went to when I was in a tech company. But we never did the communication workshop with the people we actually worked with, right? Like, you guys, this is a layup.
Half-assed. Yeah.
Like, this is, this is missing a layup, you know? Um, and it's just like, this isn't a 3-pointer. Like, this is a layup. Come on.
And I see the same thing in therapy, right? It's kind of like people talk about— where this is why I love Family Therapy Systems so much is there's so many times where all work I'm working with someone wonderful, amazing, self-aware, invested in personal growth, ex-military, just a wonderful, wonderful, wonderful human. And I'm like, by the way, did you know that you can invite your child? Because the child lives in a state I'm licensed in. I'm like, if you wanted to, you can invite your child to join us, not because something's wrong, but because we want to enhance something. And the person was like, we're allowed to do that? It's just like, it's like non, like, you know, but, but, well, this is my therapy. I'm like, okay, right, but it's not about— you're not here because something is necessarily wrong. You're, you're here because you're going from good to great, right? That great book that you and I are, right, the business world's familiar with. But I use that metaphor all the time with my clients. Like, I don't take people who are going from absolute shit show to mediocre, right? I want people who are like going, right, already things are going well, and I want to amplify all that. Like, you already have a great relationship with this person, with this child. Let's— what can we do to make it even better?
Right?
Why not invite them? But we're talking about how you can be a better father. We were talking about how you can be— well, why don't we invite them for the conversation and hear their feedback in real time and come up with a game plan together? And it's like, that's what I love about systems approaches, right?
Wait, so you must— do you involve Murray Bowen theory?
Well, that's one of the foundations of— yeah, Bowenian therapy is one of the family therapy premier I ever—
okay, so 2 years ago, yeah, I just knew that, um, the scenario I went over a little bit earlier, I knew that, um, the reason that it was so triggering for me actually at the end of the day was here I had this other teammate who was telling me what to do and it was her way or the highway and I didn't feel seen or valued. And then someone posed question to me. They said, where else in your life did you have that relationship with someone like that? And I was like, oh my God, was I just playing out mother shit in the workplace? Are you kidding me? And so, and so since then I have become such a student of Bowen theory. In fact, I have taken two courses at the Bowen Center.
Oh, that's awesome. That's amazing.
One, yeah, including one specifically around work. Work because I love to identify the patterns. Oh my gosh, people's family, and you see it playing out. Yeah, it's like clockwork. And so right now, the way I kind of integrate that in, in my work is to create these journaling opportunities, you know, because I can't necessarily force like, who here wants to tell me about your family tree? Let's go through.
So one day, one day.
Yeah, one day. But for now, it's like journaling, and even that, you know, creating these self-awareness opportunities that weren't there before.
There's a book that I'm looking at on my shelf. It's a workbook. It's, I think it's called Family Ties That Bind. And it's kind of like going through some of that intergenerational stuff. But I just had this with one of my clients the other day. It's so funny. Like, I literally, like, I love my clients. And like, that's the only type of people I want to work with at this point, who is like, if I know that I'm like, really gonna have fun working with them, sorry that they're going through whatever they're going through. But like, I want our time to be enjoyable. And I want it to be enjoyable for me too. So Like, I can't remember who said it, was probably some TikTok video I saw pop up. It's like, people, you don't have a, you don't have a type, you have a pattern. I'm like, well, that succinctly explains it. And that goes hand in hand with what you were saying, right? Especially in that Bowen theory about like developing communication between family members to develop autonomy, right? And like differentiation and enmeshment and triangles and all those different things, right? And, you know, position. Like, I love like hierarchy of like siblings and positions, right, of birth order stuff. And right, I'm the oldest, and my brother— I was born in 1978, my brother was born in 1984, right? He's as if he's his own firstborn. He has a lot of the firstborn traits, way more than I do, right? So it's so interesting to see developmental stages, uh, of generational stuff, right? Just within— yeah, between me and my siblings. Um, but I love the Bowen. Yeah, all the family therapy systems, relational stuff.
Oh my goodness.
As it applies to entrepreneurship and businesses is basically where I'm coming from as a therapist.
Well, I have a real hunch around this is that from what I've seen, specifically managers and leaders, I think one of the big mistakes they make is if there is conflict between two of their reports, two of their employees, is basically getting involved and making one of those employees on the outside of the triangle.
Correct.
I think that's a huge, huge thing that I encourage all managers is like, when there's conflict, don't you let yourself get in there. Don't you, don't you get on the inside of that. You got to maintain a coach frame.
Correct.
And help correct it from the outside.
Right. Without getting pulled in because of your— again, that goes back to the self-awareness of getting pulled in from your own triggers. Rand Stegen, I'm not sure if he's— he's big, big in the conscious leadership world. I remember him being at a presentation of his and he was showing different types of triangles. And different types of things. And I'm like, this is literally systemic family therapy, right? But that's what they're using in his— in his— in the— in the Stagen leadership program, which you're talking about, like, top, top, top CEOs and, like, top leaders in, like, Fortune 500 companies and, like, you know, millionaires and billionaires and whatever, like, capital venture funds, right? This is part of that training that he has in their teams. And I'm like— I was just, like, salivating during the presentation. I'm like, you basically, like, just, you know, this is just a model in a marriage and family therapy graduate program. Like, I mean, it's great. I mean, I was— that's how excited I was because I didn't see it applied. That was the first time I really saw it applied in entrepreneurship. And it was so exciting for me to see how cross-denominational these ideas are, right? And where that self-awareness of like, oh, so this person unconsciously has the traits of my father, and this one is my sibling, and I can see how it's like, you know, and now I'm like here to navigate and be the mediator, just like I was pulled into during parents' divorce and like, you know, all that stuff. Or here's the type of personalities I really connect better with unconsciously. So now I have an unconscious favorite of those two employees, right? All of that stuff to bring that. And I love, love, love, love doing that. And with this— with that client, that was just like, oh man, like, so you're doing this at your company with your boss, you're doing it at your company with this team that's, that's your team leader, and you're doing this also with someone that was a contractor. And tell me which one of your parents does that thing that you inherited this from, right? Yeah, it's— damn it, right? So, and it was accurate, right? It's— this is exactly honoring that parent by continuing that, because that parent is so loving in that way. But it wasn't about the boundaries, and it wasn't about the assertiveness, and it wasn't about like, you know, it was always like, but we want to be good people. And we don't do this if we want to be a good person. And, well, but can you be a good person and still be assertive? Can you be a great person and a loving person and a loyal person and still be assertive, right? It's the both/and theory, which is very much part of that dynamic. Yeah.
And now it's coming full circle with when you ask managers, "What are you reading?" And they're like, "I don't have time to read." And I'm like, "But this could help you. This one. This, like, learning Bowen theory could help you." help you, yeah, exponentially to understand the dynamics at play on the teams you're managing and your role in them. Just incredibly.
Yeah, yeah, yeah. And I saw that with my— when I was back in the day when I had my practice and I was trying to bring on an associate, I'll be like, I'm gonna ask you to read some stuff. You're not getting paid for it, but this will help you even if you don't work with me in the future. And then we will come back for our next monthly meeting. I'm like, so what did you read? Or what learn? Oh, I didn't get around to it. Those people ended up very quickly being dismissed. Yeah, right, right. Because it's not— that's not who I want on my team. And if I don't want that for my client, I don't want that from the therapist or the practitioners. Because I had an allied practitioner group of different practitioners, um, but they didn't even last a month after— because that hire fast, fire fast type of thing.
Oh yeah, right, right.
And I really embodied that very quick. I'm like, yeah, this is I'm not, you know, I'm not the right place. Like, I want to help you and I want to invest in you, but like, you have to show up. And they would not do— that's it— for 2, 3 hours over lunch and take them for lunch, give them a curriculum that I would charge someone hundreds of dollars for, and they come back with nothing. And I'm like, yeah, that's not gonna work. So I love what you're doing. I love what this is. So where can they go? Let's, let's, you know—
oh, thanks, Jason.
Yeah, where are they going to find you? Where are they going to connect with you?
Well, everybody can find me on LinkedIn or Instagram, and specifically, if you are looking to create an offsite or just really looking for some exercises that you can potentially implement with your team, please DM me, uh, playbook plus Jason Wasser, and I'll be happy to send you my playbook, which includes a lot— over 100 exercises that I use, um, to basically facilitate create team connection, or depends on— it actually depends. It's listed based on what it helps to create. But really, my whole goal is to help teams just have better team dynamics and really ultimately, like, create those workplaces that people love because they're enjoying it. And it's not this, this kind of, you know, it's not subpar when it can be better.
And it's not that difficult to make it It's really not.
Yeah. So thank you so much for having me. Yeah. My Instagram is KendallWallace123.
Oh, super easy. And right, and executiveoffsites.com is the website.
Exactly.
Catch that before. But Kendall, thank you. Thank you. Thank you. Right. Again, like when I knew, I was already excited, like I said, but then when I saw, I'm like, she does what I do with this, like, you're this. And literally, and I have, if any of my colleagues, when they hear me talk about like, what do I do for my private practice, get like the clients and be really clear, and I'm not sure with my niche. Well, you have to break it down to if you're this, this, and this, do this, right? You can reach— call me. But if you're not, don't call me, right? And it just wastes up— wasting so much time for who you are. So that's when I knew if this was going to be an even better conversation than what I was even expecting. So thank you. And for everybody else, please, please, you know, if there's anything that you specifically took away from this conversation, send us a message. Let us know that you got something from it, right? Reach out to Kendall, as you— as you heard her Instagram, or you can send her on LinkedIn. In. Send me a message. Let us know who you are that are listening. We— there's so many, you know, up over 180-something episodes. We want to know who you are. And, you know, just, just give us a thumbs up and let us know that we're, we're on the right path with what we're talking about here. And look forward to checking more out from Kendall for hearing all your more successes in the future. And we hope everybody keeps joining us for the ride.
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