866: The Power of In-Person: A Peek Into the Magic of Our Team Building Retreat

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2:02Let me tell you as a boss and a leader, having a strong connection throughout your team will change the way that you do business. It'll change the way that you work. It will change your attitude around work. It will change the way that you communicate with your peers in the company. And so it was just amazing. I'm Jenna Kutcher, your host of the Goal Digger podcast. I escaped the corporate world at the age of 23 with nothing more than a$300 camera from Craigslist and a dream. Now I'm running a seven figure online business that feels even better than it looks all from my house in small town, Minnesota with my family.

2:37Here we value time as our currency. We mix the woo and the work, and we are in the pursuit of building businesses that give us the freedom to live lives that we love. I've always loved turning big goals into reality, and I'm here to help you do the same. This isn't just a peek behind the curtain. Come along with me and my guests as we tear the whole curtain down. Every week, we tackle practical, no-fluff marketing strategies and host honest discussions on what works and what doesn't. Join me and my expert guests for actionable insights to help you grow your dream business with confidence. Pull up a seat and get ready to be challenged, inspired, and empowered.

3:16This is the Gold Digger Podcast. First, let's talk about the intentionality behind a retreat. So I have been hosting team retreats for the last few years, and I've had a few different styles. So my first team retreat that we ever did, it was full relaxation. We did not do a darn thing for work. I mean, naturally work would come up in a few of the conversations, but there was like literally nothing planned that was about work. It was a celebration relaxation trip. We've also done our team retreat where we are working. So it was during a huge launch. We were all sprawled out at this table, all on our laptops, working together, collaborating.

3:59and it was amazing. It was like this unbeatable energy that we just don't get when we're working remote. So when I was planning this year's team retreat, I wanted it to be a mix of both. I wanted it to be celebration and relaxation, but I also wanted to take advantage of this face-to-face time and the ability to just communicate without calendar restrictions, without internet interruptions. And so this year's team retreat was kind of a mix of work and play. It felt like this natural ebb and flow between business and life. And I would smile because most of the time as we were all hanging out, we were just talking about life.

4:37We're talking about relationships, marriage, kids, politics, religion. I mean, we went across the board when it came to conversations, but then we also had these beautiful sessions where we were all in on work. The main goal of this retreat wasn't to solve a huge problem or to plan a big launch. It really was to vision cast for the future, to really make sure that as we continue to grow and evolve as humans and as I continue to grow and evolve as a leader, that we stay in alignment. And the last big goal of this retreat was just reconnecting, like making sure that the team leans on each other's strengths and that they reconnect to me as a leader.

5:19Well, let's dive on in. Let's talk team retreats. So let me just preface this and say that I was nearly a decade into entrepreneurship before I ever had a team retreat. In fact, I didn't even really know what a team retreat would be. And so I have been doing team retreats for about five years. We've had four team retreats in the last five years. And we've had a few different styles of retreats. So a few of our retreats were literally like full relaxation, no work. It was basically like a gathering and a celebration. We used to tease that it was like a bachelorette party, but there was nobody getting married.

5:56That's what it felt like. We've also done a team retreat in the past where it was a working retreat. And we like picture us in this hotel restaurant sprawled out across this huge banquet table, all with our laptops out collaborating, working together. We would literally like set timers and work on something. And then we'd come together. And so we've had both styles of retreats. And this year for the retreat, I wanted it to be a mix of work and play. So I wanted it to have this like natural ebb and flow between business and life, because in reality, we haven't seen each other in two years in the flesh.

6:31And so we have a lot to catch up on that isn't always possible to catch up on via Slack. But I also wanted to take advantage of the fact that like we are all together. We don't get to do this often. We don't get to really focus in on something and go deep on something. And so the main goal of this retreat was really vision casting, alignment, and reconnection. The goal here for me wasn't to like solve a huge problem or to plan a big promotion. it was really to just reconnect the team to each other. So reconnect with each other's strengths, but then also reconnect the team to me as their leader.

7:07So team retreats, one thing to note is that they often have a lot of logistics and I have to give a shout out to Marissa. She is my right hand. But as soon as we decided, okay, we're going to do a team retreat, she ran with the logistics and we have gone to the same place every single time, which has been so helpful because it's familiar. It's easy to get to from the airport. It's central for all of the places we're flying in from. We have people from Canada, Ohio, Minnesota, California, Oregon, like we're all over the map. And so we have gone to the same place. We know what to expect. We know the lay of the land.

7:42We know what the food's going to be like, like it's very easy. And so Marissa handled all the logistics. That part's not easy, but she handled it like a boss in terms of booking hotel rooms, getting reservations, figuring out dinner plans. And then I also always book a spa appointment for every team member, which I am a spa girly. I like love a good robe and a good spa treatment. And so every single year that we've done a team retreat, I get my team members a spa appointment. And so Marissa handled all of those logistics, which was amazing. And so, like I said, it was a total mix of like relaxation and celebration along with some focused work and inspiration and ideation is what I would say.

8:26And that was the intention. And one thing that I think is important to talk about is it's an expense, right? Like you have to invest in flights, hotels, taxis, food, like it is not necessarily cheap to host something like this, especially if you have a team like I do, where we had 12 people flying in from all over the world and spending the night for a few nights. And so it is an investment. But for me, it is such a worthy investment because we get a lot done remote. But when people can reconnect to me and who I am right now at this stage of my life and where I see the business going, and if they can reconnect to one another and be reminded of the genius that we have amongst ourselves and the special gifts that we all contain, it will make my life ultimately easier in the long run.

9:17And it'll make us so much more anchored in the vision of where we are and where we're headed. And so when I look at legitimizing the expense of a team retreat, I'm like, this is absolutely worth it because even if a retreat would help maybe reconnect somebody and retain them as a team member, like that's going to save you a lot of money in the long run, or if it helps people collaborate better, or if it brings up one idea that could make you more money as a company. Again, all of those things are absolutely possible on a retreat and they all make it absolutely worth it. So here's kind of how we structured it.

9:53So we flew in on a Tuesday. I booked the stupid early flight, like the like 5am flight, which meant I had to wake up at like 4am, which meant I didn't sleep at all and got up at 3am, which meant my kids were already anxious about me leaving at 2 a.m., which meant I basically just didn't sleep. So I had this stupid early flight, which put me in to Arizona at 9 a.m. And I was so excited when I got to the hotel and my room was ready because I just needed to take a cat nap. But essentially, everybody flew in on Tuesday and we all kind of arrived mid-morning to early afternoon and we just met by the pool.

10:29And so we all had our suits on. We were all ordering poolside food and drinks and just chatting and catching up. And then that night we were going to go out to dinner. And as we were planning the retreat, I was like, you know what guys, after everybody's flying in and a travel day, what do you think if we just ordered takeout and we all hung out in somebody's hotel room and just like relax? Like that to me is like the dream. It might not be someone else's dream, but like, I love takeout in a hotel room and like not having to get dressed step. And so it was so much fun. We met up at one of our rooms.

11:02We were like inside and outside until it started raining, which was so ironic in Arizona. And we all scooted into one hotel room and we're all like sharing food. Some people got sushi, some people got pizza. Like we all ordered whatever we wanted. And this was a really awesome night because it was super intimate, mostly because of the space. But we talked a ton about brand positioning and messaging and just who it is that we serve and why we love to serve them. And so it was really just a simple and honest conversation of like, who are we right now? Why do we do what we do? And who is it that we're creating for?

11:40And I will never forget this moment where I kind of like stepped up on a metaphorical soapbox, but like, I love serving beginners. Like I absolutely love serving that niche of the market. People that are bold enough to take their first step in, to try something new, to launch their business or put out their first offer, like helping somebody get their first win is my absolute favorite thing. And so I talked about this to my team for a while. Like I have such a heart for beginners because I know what it feels like to bet on yourself. And I know how scary it is. And there are so many other people in the market who are now like, I'm done with beginners.

12:20I'm over it. I want to teach more elevated strategies. And I'm like, I love this segment. Like I want to be there for every first step. That's it. I love it. And so we talked a lot about how do we continue to serve that area of our audience? How do we simplify the journey for our audience? And how do we kind of consolidate all of the information we have out there? Like we have thousands of blog posts and hundreds of podcast episodes. How do we help people find exactly what they need and how do we do it faster? And so that night it was super informal. Nobody was taking notes. Nobody had laptops out.

12:59It was just this like very heartfelt discussion about what we love, who we love, who we're serving and like, how do we make this process easier for them? Because when you are just starting out, there is so much information everywhere. It's information overload. It's hard to know what step to take first and what is the right method and where you should begin. And so we just had this like very beautiful conversation. And it felt like one of those like popcorn conversations where one person would go and then somebody would riff off of that. And then somebody would have a different perspective. And it was just really beautiful.

13:33And so that was our first night. And honestly, I loved it. I couldn't believe I made it up to like 930 or 10 o 'clock because I barely slept a wink the night before. And so I was just so proud, but it was just so nice to be in the energy with the team. hey hey it's marissa vp of ops on team jk and co-host of this retreat alongside jenna and we thought it would be so fun for you to hear from me and several other members of our team about our personal experiences throughout this episode so let me start by pinning the picture behind a few of my favorite retreat moments now envision 12 women scattered about a spacious hotel room, some sitting on the bed, some spattered on the floor, a few on a cozy couch.

14:18We're eating takeout, totally relaxed, yet vibrating in this togetherness. I mean, it was truly a vibe. And as we sit and munch, we start casually chatting about the brand mission and messaging, the way we want to connect with humans and support their success so deeply. We shared ideas and you could truly feel like the brain bubble sparks as we worked our way around the room. I mean, cue the strong head nods and brain bumping as thoughts popcorned about. And you know we love a little woo and work intersection and with so many different energies on one team. This in-person time had and absolutely has the power to unlock and fuel just really cool creativity and strategy and even gap sightings.

15:04It deepens trust and camaraderie in such a way that Slack messages, Loom videos, I mean, Zoom just never will or could. And after we hive minded, one of our team members, Shannon, then kicked off a prompt. And it was, if you could do anyone else's job on the team, what would it be? And from a leadership and ops perspective, I loved this cue because it gave me a little behind the scenes insight into where unspoken interest or talents may lie. And that then speaks to me as future cross-training opportunities or role expansion possibilities, none of which need immediate action, but are good to have when thinking about how to develop and retain your talent down the road.

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17:40And give them the best shot at success with Shopify. Sign up for your$1 per month trial and start selling today at shopify.com slash gold digger. Go to shopify.com slash gold digger. Shopify.com slash gold digger. Then the following day we did breakfast. And so we were all kind of meeting up. We did later start times because people are from different time zones. We had moms who were nursing, so they were pumping. Like we were just trying to make it really ease filled, not super busy. So we met up after breakfast and we sat outside of the restaurant and we did a couple hour session. So before we left for the team retreat, I was brainstorming just different questions for the team to help them really think through and come to the retreat prepared to answer a few questions.

18:33So here were the three questions that I asked the team to show up to the retreat with thoughts. So the first question was, what is one creative or strategic idea you've been itching to try either in your area or in the business as a whole? And what, if anything, has held you back from trying it? The second one was, what is working really well in your area right now? What is one thing that feels like a roadblock? And could the team help you clear it? And then the last one is, if there were no limitations, budget or time, what is one bold strategy you would love to see us try to drive big results this year?

19:08So those were the three questions that the team showed up as. And what was interesting is, is during our second day, we had already kind of covered a lot of these ideas in our just casual session the night before. And so we sat down and every single team member shared just a different idea that they had. And then we as a team kind of doubled down on a few of our favorites. So we had like 12 different ideas. And then we were like, okay, let's go deeper on like two or three of these. And the goal was not to leave feeling overwhelmed. The goal was to leave just feeling centered. And so it was a really nice approach.

19:42And there were certain ideas where like two of our team members were sharing a hotel room and they were like, okay, last night we had this idea. We were going back and forth. We were like so excited about it. And it was just like awesome because you could feel the energy that is just not happening over Zoom or Slack. And so just like those conversations were so rich. So we did the brainstorming session. Then we went to the spa. We all hung out by the spa pool, continued conversations, got our spa appointments. And then we went out to this like wonderful, wonderful dinner. It was so much fun. One of my team members.

20:16It was her birthday the next day. So we sang happy birthday. And it was just a great, great day. And then the last day of the retreat was when everybody was flying out, but most people didn't have flights until the afternoon. And so we just hung out at the restaurant and we were kind of a revolving door between the pool and the restaurant, just connecting, getting back into work and enjoying the last few minutes of the retreat. So it was very simple. There wasn't a lot of structure. It was wonderful. And it had just this beautiful rhythm of like being restful since most of the people on my team are mothers and leaving their children behind, but also just having this creative energy.

20:54And so I loved it. Hi, my name is Christy, the Gold Digger podcast producer. And this was my second retreat with this amazing team. And I just have to say, I absolutely love the simple structure that Jenna and Marissa prioritize for the time that we have together. I mean, we had dinner reservations and massage appointments booked. And we also had like a team brainstorming session on Wednesday morning. But besides those, the few days we spent at the resort were really free flowing. We could choose when and where we ate our other meals, when we went to the pool or worked out or napped. Or if you're like me, I honestly spent my days sipping a pina colada by the pool and chatting about my favorite books with my coworkers.

21:37It was so relaxing to just be together and not be tied to a mandatory agenda of meetings and breakout sessions and lectures. So yeah, that's definitely my favorite part. So here we're kind of the heart of the conversations. So again, thinking about creative and strategic ideas that we've been itching to try, really discerning, okay, this has been working really well and this is where I need more help. And then we kind of positioned the last one instead of saying like, what is a bold strategy? we positioned it as this prompt of like, wouldn't it be crazy if, and you like fill in the blank, like, wouldn't it be crazy to just try this sort of launch?

22:19Or wouldn't it be crazy to hire a video team for the next launch? And so it was just really fun conversations and certain things I was like, okay, I probably don't necessarily want to pursue that, but I love that idea. So like, what would that look like? Or let's table a few of these brilliant ideas and revisit them during a slower season in the business like summer. So I also had during this retreat, just a lot of reflections on leadership and growth. You know, it's so interesting because for so many entrepreneurs, we start out as solopreneurs. So we were joking at one point of like, I have played everybody else's position in the room at some point in my business.

23:02And I was telling them stories of like a few of my first launches where it was literally like me, myself and I, like I would do the webinar, then I'd get off of the webinar and I'd edit the webinar. Then I'd send the email for the replay of the webinar. And we were just like laughing so hard because it's hard to believe that one person was managing all of it. And let me tell you, it wasn't half as good as it is now, but it was also just interesting to like look around the table and recognize that like I have built a business that supports 12 people and their families, their kids, that they are reliant on this business and the success of it for their livelihood.

23:41Like it was both beautiful and also like, holy crap, this is wild. We also have a few team members that have been with me for nearly eight years. And so if you think about that, in internet years, that's like a hundred years, right? And so we have walked through so much life. Like some of my team members have been with me through my pregnancy losses, through becoming a mom, through moving back to Minnesota, like all of these huge life transitions and all those life transitions for me, but they've also had their own life transitions. And so when I think about like the depth of our relationships, not just working relationships, but like real relationships, it's honestly so beautiful because if you're going to build something and you're going to have people be a part of it, like do it with people that you actually love and enjoy being with.

24:31Hello, this is Keri Swetman and I am the Team Jenna Kutcher Ads Manager. Jenna and I have been working together since 2016, which is wild to say, so eight and a half years together. As a mom, I tend to think of things in kid years and my youngest was two when I started working with Jenna and he is 10 going on 11 now. So you can imagine all of the life that has been lived in those years and some really crazy ones around 2020. Everything that we have done together, not only in life, but as business owners and to grow the brand, it has just been absolutely incredible to watch and to watch the team grow.

25:16The retreat that we just did was pure magic. It's very classically Jenna. and I think that that's why we've been able to work so well together for so long. It's the perfect mix of smart and thoughtful business with good food and sunshine. And if you know Jenna, that is just her. There is a high level of respect and trust for each other's skills and I just really, really appreciate that. In fact, when her team says that they're thinking about doing a retreat, literally none of us hesitate. It's a no brainer. It is so incredibly good for the soul. We genuinely love to be together. And it was funny because on the last day we were sitting by the pool and we were all just like laughing and having a great time and all like, isn't it weird to think that like a lot of us would choose to go on a trip with each other?