EP 184 – Dr. Sherry Walling – A Guide to Planning a Successful Company Retreat
Some people hear “Company Retreat” and they may think of trust falls. Others may think perhaps a fun outing at a park, an experience for bonding with people we don’t talk to every day, but overall, a potential time sink.
A well-executed company retreat can be a great way to get clarity on many company initiatives and goals in a relatively short period of time.
In the following podcast, Dr. Sherry Walling guides us through what makes the company dynamic in an external setting so valuable. Just the very “change of scenery”, away from our day-to-day distractions, can be enough to have highly meaningful conversations that may just change the trajectory of our companies forever.
The following interview has been transcribed for our readers from rev.com. Please excuse any discrepancies from the transcription.
Chase Williams:
Today on the Legal Mastermind Podcast we have Sherry Walling, PhD. She’s the author of two terrific books, Touching Two Worlds and Keeping Your Sh*t Together. Welcome to Legal Mastermind Podcast.
Sherry Walling:
Hey, it’s good to be with you. Thanks for having me.
Chase Williams:
And I gave a brief introduction to that book, but the actual full name of the book is The Entrepreneur’s Guide to Keeping Your Sh*t Together: How to Run Your Business Without Letting It Run You.
Sherry Walling:
That is true. That is the title. The title was suggested by my then 11-year-old child. And I was like, “Where did you hear that language?” And then I was like, “Really good title. We’re using it.” So yeah, it’s for kids, too.
Chase Williams:
It’s a kids’ book.
Sherry Walling:
It’s not a kids’ book. But it is all things that people who are running a business find helpful to think about when it comes to their own internal well-being.
Chase Williams:
And I’m sure as entrepreneurs we act like kids a lot of times, especially when we don’t know how to handle emotions or tough situations.
Sherry Walling:
And also sometimes in the best possible ways when we’re being creative and playful and thinking about different approaches to sort of old problems. So I don’t think acting like a kid is an insult. I think sometimes it can be a great amplifier of our inner well-being and can make us feel free and happy.
Chase Williams:
I love that insight, and that’s why you’re a doctor and have a PhD.
Sherry Walling:
That’s what I learned in PhD school, how to act like a kid and rationalize it with big words.
Chase Williams:
No, I love that. So today, Ryan, we’re going to talk about company retreats and kind of taking that break that you kind of need to reset, get back to the basics of human connection. And the reason we want to talk about this today, and we came to this podcast kind of with an open book, really just, “Hey, what can we talk to you about today?”
And we just left a retreat for our company. We had about 30 of our employees there and it was just a really great time for everybody to get together. And a lot of our team is remote and have never met anybody before. So just having that experience was really unique and special. And not many people are talking about that or really focusing on retreats, but we really made it a priority. And we just got back. So let’s talk about it.
Sherry Walling:
Let’s talk about it. What did you like about the experience? What really stood out to you, because obviously company retreats are really expensive, right? It’s taking everybody away from the day-to-day. It’s the investment of travel and lodging and food and all of that. But it sounds like there were things about it that made it feel like it was worth the investment. So I have my perspective, but I’d love to hear what felt like it for you all.
Ryan Klein:
Yeah, absolutely. It’d be easy just to say, “Oh, the money isn’t a thing. It’s an invaluable experience.” But you really do have to weigh the actual cost and then also the time away from the office, being productive and hoping that the takeaways are going to pay over time.
So the first thing is just people all over the place that see each other face to face on Zoom, talk on Slack, there really is, I’ll use invaluable once for that, that they’re meeting for the first time and having those dynamic interactions does go a long way. They are kids. Some of them are actually practically kids. But there’s activities. But we kind of go back and forth between having conversations about goals and values but then switch it up and segue into an activity that involved marbles and one that involved dice and one that involved probably a lot of drawing. So those are kids’ games. But really seeing the interactions and seeing the value with people that may have never thought they’d meet in person and having conversations that they would literally never have over Slack or Zoom, I think, was one of the bigger takeaways.
Sherry Walling:
As a psychologist, I can really nerd out on a lot of the things that you said. On one hand it’s really, really helpful for us to be in person together. Even though we can have really meaningful relationships in a remote work setting and some of my best friends I like haven’t actually met in person or seen in person very often, but that sense of being embodied in the same place, the way that our brains work, we have a deeper sense of attachment to people that we’ve met in person, when we have a sense of how they work in physical space and what it feels like for our body to be next to their body in physical space. So that does help to sort of weave together relational connection in a different way than our sort of digital or remote work environments.
I think the other thing that you talked about is this playfulness, the marbles and the drawing and those kinds of activities. Those things are actually really, really important in non-linear thinking. They seem like silly kids’ games and we were joking about entrepreneurs acting like kids, but they are ways for our brains to rest from the day-to-day kinds of tasks that most of us do while we’re looking at a computer, where we’re reading, where we’re writing. So when we get down and we’re playing with a three-dimensional object or we’re drawing or we’re doing something else, we’re actually using our brains in a super different way, which is very, very good for our neurological health. So taking some time out from the structures and the consistency that we have in our day-to-day job and doing something totally different helps to reset and rest our brains. It’s actually really helpful in preventing burnout.
Chase Williams:
I love that insight and I think my biggest takeaway from the retreat was getting to connect people and actually seeing them come out of their shells. A lot of people are very reserved, especially on a Zoom call, kind of have to call them out, ask them the question or one or two-word answers. But the second you get in a room with them you’re like, “Oh, wow, this person’s got a huge personality.” Like, whoa, if you compared two sheets of paper, it’s a whole different person on a Zoom call versus an in-person meeting. So I thought that was very interesting. I think it probably just has to do with, I mean you know better than I would, but just the differences in being cooped up in a room and just not having that real human connection that naturally you do when you just see somebody in person.
Sherry Walling:
I kind of think of the way that you’re describing coming out of your shell is actually our different forms of intelligence. When we’re sitting together on the Zoom call looking at each other face to face, we’re really leveraging our verbal intelligence. We’re using our words, we’re using some of our interpersonal intelligence in the sense that I can see your face and you can see mine. We can anticipate how each other are feeling, but really we’re highly leveraging only one part of us.
But when we get together in person, again there’s this sense of kinesthetic intelligence of how we move our bodies and how we crack jokes and how we interact in a different way that allows us to bring our full self to the relationship. I also think that sense of coming out of your shell when we have shared experiences as people, even if it’s something as silly as Ryan knocking over the pitcher at lunch and we can sort of laugh at him about that, but we have a joke now and we have this shared experience and that shared story is what weaves our relational threads to be stronger and more connected. So I think that that kind of investment, if you have a team that requires interdependent working, if they have to rely on each other, if they have to trust each other, if they have to work together through emotionally difficult content sometimes, the investment in helping them to really connect in a multidimensional way tends to be a really good investment for the business.
Ryan Klein:
For the record, I didn’t spill the pitcher, but I almost tripped over the power cable to the projector. That thing was sticking out pretty hard. That would’ve been pretty embarrassing.
So I have a question for you. We’ve done two company-wide retreats and so the people moving it along were Chase, myself, operations manager, and it’s been a long time, but I did go to a retreat where it was a kind of neutral third-party facilitator. How do you think that changes the dynamic? What are the benefits of having someone on the outside moving things along?
Sherry Walling:
And probably I should come clean and say this is something that I do for companies, so what I’m about to say may be biased by my own, well it is biased by my own perspective. So I think that when you have an outside facilitator, it does a couple different things. One is I think it allows the leaders of the company to participate more fully. You get to be in the group discussions, you get to be kind of part of the goings on of the retreat without the burden of being the person who’s moving everyone from point A to point B, whether that’s in a discussion or just in the logistics of the day. So I think that’s a nice investment for the leaders is they get to play too. They don’t have to be the one who’s hosting every different element of the retreat.
I do think that having an external observer or an external question-asker can also disrupt some of the consistent patterns in your company. Companies are like families. We all have roles that we play or systems that we adhere to. We have unwritten rules, we have written rules. So someone who comes from the outside who doesn’t know the rules or doesn’t feel bound to follow them can ask questions or can think about relationships in a different way. So, I think there’s some value in that if some of what you’re doing in a retreat is really helping to get out of the stuck points or the sort of well-practiced patterns and begin to be more flexible and more creative.
How did it compare for you? Because you’ve done it with an external support at times and then sometimes you’ve done it yourselves.
Ryan Klein:
We haven’t done it with an external. I did it at a different company way back in the day and it was interesting because the person pretty much didn’t have any preconceived notion about anyone, didn’t really know much about their background, personality, even really what their day-to-day role looked like. And pretty much just asked very neutral, straightforward questions and got people thinking about, “You’re right. Why is that person doing that thing?” And the facilitator didn’t have any knowledge to have any bias. They just asked a question that was very straightforward based off the conversation and made a pretty intense point that changed the way people thought about how they were doing things.
Sherry Walling:
So it can add maybe some complexity. So I often work in the tech space, not exclusively but that just tends to be the community that I work with. And so I work with a lot of companies where they have a lot of developers and, if you’ll forgive me or at least permit me to make a generalization, often developers are quite introverted. They sort of see code in their head, they’re builders, and to put a bunch of them in a room together can be sometimes a little bit sort of socially a heavy load for folks. And so the other benefit of bringing in an external person is that part of their role is to do some of that sort of group dynamic heavy lifting, which facilitates and allows people to find the pathways to come out of their shell without relying again on the leaders of the company to be both excellent CEOs and also, of course, people who are excellent social massagers of relationships as well. Not everybody has that skillset.
Chase Williams:
So jumping a bit back into the benefits, I know one of the things you briefly mentioned was avoiding burnout. So that’d be a benefit of throwing a retreat. But I guess a lot of these benefits are intangible, like intangible. But what are some other benefits that you think our listeners and/or people you’ve worked with in the past could benefit from?
Sherry Walling:
Yeah, I think, so to make it not intangible but tangible, one of the measurable metrics that you can kind of keep an eye on is just how much turnover you have. Turnover is obviously really expensive to companies. You got to train people, hire people, it takes a lot of time.
But I do think that retreats can be an investment in people feeling connected to the company and people working well together. And they’re fun. I mean hopefully they’re fun. Every once in a while I talk with a company where all they do is sort of get together in a different location and just work in the same way. And I’m like, “That doesn’t make sense. That’s not a good investment of your time and money.” But if you can have an event that helps people feel happier at work and more connected to the people they work with, then that tends to be something that contributes to people staying. So I think that that turnover is one metric that you could look at as it relates to retreats.
So I did mention burnout, I did mention just sort of overall job satisfaction. I do think that retreats can be a place where people problem solve and they can look at the system of their interactions differently. So it can be more efficient hopefully for a company in the long run.
Chase Williams:
Where are some of your favorite places to recommend companies go on retreats?
Sherry Walling:
Oh, I really like warm places. I live in Minnesota, of course, so I’m very biased. But I’ve gotten to help support company retreats in Breckenridge, Colorado, which is a great option. Punta Cana in the Dominican Republic. I think places that feel kind of vacation-y are really lovely. It’s lovely when companies have the opportunity to get together and sort of play outside, but also it needs to be affordable and reasonable for the company. So if going to the Dominican Republic seems like a heavy lift, there’s definitely some lovely, I would say, kind of ranch experience that you could go to in Arizona that would be much less expensive if you have a US-based team, for example.
So I think it’s helpful to have a place that feels recreation-y and where people can be outside easily. But it’s certainly not necessary to fly everyone first class to some fancy five-star resort. I mean, if you have the money to do that, I would be happy to facilitate. But it is not necessary to have a good retreat for your company.
Ryan Klein:
Chase is really good at proposing destinations for retreats. He makes lists.
Sherry Walling:
Ooh, what do you got Chase?
Chase Williams:
So our next retreat for our leadership is in Playa del Carmen, Mexico.
Sherry Walling:
Excellent.
Chase Williams:
So, it just made sense because you can stay at an all-inclusive resort and then there’s co-working spaces there that are very affordable and we have some warriors on our team that like to enjoy themselves sometimes. So it’s good to-
Ryan Klein:
You’re not looking at them right now.
Chase Williams:
You’re not looking at them. Maybe once a year but-
Sherry Walling:
Some warriors in quotes.
Chase Williams:
So the all-inclusive aspect is, we’ve never done this before. So it’s always been like we just did our retreat in Vegas, so that was a little different. But it was cool because half the team never visited Las Vegas before. But before that it was we did a retreat in Austin, Texas on a ranch and then in Orlando, downtown vibe, and then also Chicago, so.
Sherry Walling:
Those are all great settings. I think with something like Vegas, you really have to think through how much play is part of your retreat. What proportion of play to focused reflection or work time do you want for your team? So it sounds like Vegas can be super fun. I would tend to stay away from a place like Vegas just because it in itself can be so distracting. And so to find a spot where there’s definitely something to do, something to engage you, but it doesn’t feel like a waste of time to be having a retreat conversation when it’s Vegas. It’s right outside that door.
Chase Williams:
No, that’s a good point.
Sherry Walling:
How did that work? Was your team able to buckle down and do some of the things that you were hoping?
Chase Williams:
Yeah, I mean we had a pretty solid agenda with not too many breaks and we got pretty positive feedback so far from the team. We sent out an anonymous survey and asked what we could do better. Yeah, I mean it was just to kind of preface a little bit, we went to Vegas because we had a conference there and we’re like, “Half the team’s going to be there already. Why don’t we just bring the other half there?” And so that’s what we chose-
Sherry Walling:
That makes sense.
Chase Williams:
… Vegas, but I don’t know if I’d recommend it, but it worked out fine I think. But I think there’s probably a definite feeling when we’re behind those doors. Hey, Vegas is all right here and we’re stuck in this room playing these games, but.
Sherry Walling:
I think it does also raise a question that’s sometimes tricky for leaders to sort through, which is questions around alcohol, how much partying happens at a retreat, how much you’re comfortable with, and then how much potential sort of bad behavior and headaches does that create a risk for that really can distract from the point of the retreat.
So I do think it’s helpful for companies, you don’t have to have sort of a punitive like, don’t do this, don’t do that. But I do think setting a tone and setting an expectation to conduct yourself in a way where you can be fully present and all of our normal standards around how we treat each other and how we operate within our business are still at place during a retreat. Because obviously a worst sort of nightmare scenario is people drink too much, they behave in ways that create significant problems for trust and for ongoing relationships together at work.
Chase Williams:
We had our red-screen FBI warning before the retreat. You know, like the movies when they used to put that before you’d rent the movie?
Sherry Walling:
Nice.
Chase Williams:
We had that, but it was much more subtle, so.
Sherry Walling:
And it’s important, you can make it playful, but it does need to be said, and I think it needs to be accounted for.
Ryan Klein:
So we’re talking about burnout and being aware of where people are mentally. And it seems like psychologically that all the day-to-day business problems and issues originate within the business, that being able to talk them out and work through them shouldn’t actually happen there too. It’s in the same environment almost. So that’s why working them out sometimes offsite seems to make sense. For anyone that’s not thinking about flying or booking tickets or going somewhere else, have you worked with clients on creative options that are maybe a drive away or something that’s more within a vicinity but still feels like a retreat?
Sherry Walling:
Yeah, I think what I would advocate for and what maybe underlies this question is some periodic practice of getting out of the typical patterns and interactions and interacting in a different way. And I would say that one of the best ways to do that is through play. So I love it when companies do an escape room together or take the day out and go to the fair or there’s lots of different things that companies can do. I actually personally really love the circus, so I’ve brought companies that work with me up to Minneapolis and we’ve done a day at the Flying Trapeze rig. So everybody gets up on the trapeze and is scared together.
So even companies that are distributed, there are some interesting and creative ways to do those kinds of things remotely now. There’s a company called JAM, which helps companies play. So whether they’re doing quiz games or a cooking experience, just something that helps people interact in a different way can be really helpful. And they don’t have to go on a plane. They can either drive somewhere or even do it digitally.
Chase Williams:
That’s great. I’m just looking at their website right now. Very cool. I think we talked about one time doing a cooking class with everybody, but it just fell through.
Sherry Walling:
Yeah.
Ryan Klein:
We talked about doing, what, the Second City acting class in Chicago and, at the time, it was pretty expensive, but then I was listening to an audiobook and they’re like, “And then the executives love doing Second City.” And I’m like, “Crap. That was maybe something that would’ve been a great idea.”
Sherry Walling:
You were on to something.
Chase Williams:
But there’s always next time.
Ryan Klein:
Yeah, yeah.
Sherry Walling:
One thing that I like to encourage people to do is actually that entrepreneurs regularly take their own retreats. So not with their company, but to go on a founder retreat or a leader retreat. And I think it’s actually really helpful when people do that by themselves and do it a couple times a year and really spend time in sort of this deep dive personal reflection of is my life going the way that I want it to? Is my business thriving in the ways that I want? What am I satisfied with? What am I looking to change? And that kind of extended time for internal reflection can be really, really helpful in helping you kind of stay focused on your North Star and in helping you show up in your workplace the way that you want to.
Chase Williams:
That’s really interesting. I’ve never heard of that before. Have you, Ryan?
Ryan Klein:
Is that not something that we did before? Are you saying with other entrepreneurs and other owners, or are you saying just by yourself?
Sherry Walling:
I’m saying by yourself. I mean with other entrepreneurs is cool too, but a solo retreat I think is extraordinarily helpful for people. I wrote a little guide called The Zen Founder Guide to Founders’ Retreats. It should be easy to find, but it’s sort of like, what kinds of questions do you ask yourself when you are alone and away from all of the distractions and busyness of your world?
Chase Williams:
Why am I so tired?
Ryan Klein:
That’s every day. I can ask myself that at home.
Chase Williams:
Yeah, we’ll-
Sherry Walling:
You don’t have to go away for that.
Chase Williams:
We’ll put that in the show notes, we’ll find it so our listeners can just click on it and jump in. And then, like I mentioned before, you do have two books that are available on Amazon. So if our listeners want to get in contact with you, Sherry, what’s the best way to reach out?
Sherry Walling:
Yeah, so I am at sherrywalling.com. I also host a podcast called Zen Founder, Z-E-N founder. I’m on Instagram and Twitter @SherryWalling and generally fairly easy to stalk on the internet, so.
Chase Williams:
Are there any other parting words that you wanted to leave with our listener, Sherry?
Sherry Walling:
Yeah, I mean, I guess I might mention a little bit of what I’ve been working on a lot most recently, which is a pretty deep dive in the subject of grief, which may seem like a really weird thing to mention on a business-oriented podcast or on a lawyer-oriented podcast. But of course, grief is a human universal. All of us experience grief, whether it’s through the death of someone that we care about or the loss of something that we hoped for: the loss of a relationship, the loss of a marriage, the loss of a business.
And I think the ways that we pay attention to our grief can be really core to how much we grow from those experiences, how tender they make us, how human they make us, versus the other option, which is to sort of suppress and run, which I definitely don’t recommend. So my new book Touching Two Worlds is sort of this dive into how do we honor those darker, more difficult parts of our experiences and also let ourselves be fully present in the aliveness of our work, the things that we’re building, the ambitious, alive parts of us that we can be both at once.
Speaker:
Thanks for listening to the Legal Mastermind podcast. If you’re interested in working with Ryan and Chase, please email mastermind@marketmymarket.com. Make sure to join the free mastermind group for growing and managing your firm at lawfirmmastermind.com. Ryan Klein and Chase Williams are the managing partners at Market My Market, one of the top legal marketing companies in the United States.
