Transforming Team Dynamics Through Retreats

What if you could transform your team’s productivity and cohesion with just one well-planned retreat? On this episode, I’m pulling back the curtain on our upcoming team retreat in Boise, Idaho. You’ll hear about the magic of retreats in fostering deeper connections within remote and distributed teams.

From the balancing act of coordinating logistics to the joy of shared experiences, I share personal anecdotes and practical tips that will guide you through the chaos of planning a transformative event, even amidst personal and professional hurdles.

Topics covered in this episode:

• Importance of retreats for building a connected and cohesive team.
• Positive impact of retreats on team productivity and connectivity.
• Steps for planning a successful retreat.
• Importance of informing clients in advance for transparency and trust.
• Having a variety and choice of planned activities.

RESOURCES FROM ALYSON:

The Kid-Proof Business Checklist
https://alysoncaffrey.com/checklist

Maternity Leave Planning Guide
https://www.mastermaternityleave.com/guide

Transcript

Speaker 1: 0:06

Are you juggling the challenges of running a business while raising your little ones? Do you crave more ease in balancing your professional ambitions with the demands of parenthood? Well, sit tight, you're in the right place. I'm your host, alison Caffrey, and I understand the growing pains that come with building a business while nurturing a growing household. Think of this as a soft spot to land when you feel like your ambitions are starting to become just a little overwhelming. Welcome to Growing Pains.

Speaker 1: 0:37

Welcome to another episode of the Growing Pains podcast. I'm your host, alison Caffrey, and I am going to actually unpack a really cool topic on the show today. It's all about how I am preparing for and running my upcoming team retreat. Our team voted at the end of Q1 for our annual retreat this year and they voted to go to Boise, idaho, and we had a couple of places in the running. But I am so excited to give you a really kind of logistics packed and kind of behind the scenes. Look at why retreats are so important, what we are doing on our retreat and how kind of I am planning this to be the next level accelerator for our team growth and connectivity and all of the things. So I hope that you enjoy this episode and I think that this will be really great for folks who are either growing a team already and maybe we're looking for more ways to become more connected.

Speaker 1: 1:35

If you are remote and distributed, or if you guys work in a professional setting, in person together, but rarely have time to really connect and really have some time together, that's outside of work, and this is a really great thing to consider doing. I have done a couple of retreats in my time, both for myself at operations agency and as part of a team when I was employed almost 10 years ago, which is so crazy, to even say out loud. And the biggest thing that we need to acknowledge when we start talking about team retreats or getting the team together outside of the office setting, outside of the work setting, is that, number one, it's required. It's necessary to grow a connected team, something that I think a lot of remote, distributed companies do, especially if you are hiring lots of contractors, if you're really working to grow the business and the team doesn't feel like it's fully fleshed out or that you've got a lot of people who are supporting you, it might feel really challenging to get everybody together, and ignoring this can actually create a little bit of a revolving door inside of your company, meaning that people are going to interact with your business or your brand and they're not going to stay, because it's going to be just like every other business that they have interacted with, whether they're finding freelancing jobs on Upwork or whether they're applying to open sales positions or anything that you may throw at them growing your small company. The fact of the matter is is that having a plan in place to get folks together and really connect with them and show them the heart behind the business that you are running and that you are actually a human being who also makes mistakes and has a pulse, is going to be so incredibly impactful. And I know so many companies that tell me, after walking away from a team retreat or an event for their clients where they are able to bring their entire team in, that the team productivity after the fact skyrockets and everybody's on the same page, because it's really hard to look somebody in the eye and spend a couple of days with them and not be in a position to leave with a stronger bond than you had before.

Speaker 1: 3:47

Now I want to go ahead and move to the next section, which is really the big elephant in the room right, so retreats are required. This is the first thing I need to say. The second is that there is no convenient time to host a team retreat. Whether, from a revenue perspective, you're looking at reinvesting into the business and into growing your team, whether you guys are trying to find space in a super busy client calendar, or if you're throwing lots of events or doing lots of speaking gigs, there's never going to be a time where you're going to say, hmm, look at this week, this feels like exactly the right time where nothing's happening in our personal lives or in our business. If you're wondering why on earth I am sitting in horrible lighting in an empty home office, it's because right now, as we speak, I am planning our team retreat. It's happening next week. My lovely assistant, kelsey, has really taken the brunt of a lot of the logistics, but we are really planning to get together, get the team on the same page, really be in a position where we can look forward into the second half of the year and our buyers of our house pulled out the day before we hit the closing table.

Speaker 1: 4:51

And so, of course, I couldn't have expected that. Of course, there are so many moving parts in my life personally and, of course, as the leader of the business. But there is never going to be a convenient time. We need to remember the things that are important about growing our business, which is growing a connected team, a team that's on the same page, a team that respects each other, that works really well together and ultimately holds your customer and your client's needs and the deliverables of your projects and your services and all those things and keeps them really really close to their heart. So there's never a convenient time to take a retreat.

Speaker 1: 5:26

I always say that if you can't afford to take a retreat, you want to do something special for your team that can get them together in some capacity. Sometimes that can be really challenging, especially if everybody is remote and distributed. We have some team members who are overseas and so they're just doing something different to be part of the retreat. They're going to be doing some activities together with us that will be virtual and they'll be receiving some gifts and some things like that that actually make them feel really connected. And so you can choose to do something totally combining and really bring everybody together and go to a location and do things a little bit out of the ordinary, or you can really go to a happy hour or go do an activity together and take everybody bowling or something like that and I know it seems really cheesy and sometimes, especially as you are growing an online business right, you wanna be in a position where you're like I don't do things like corporate does it, or I don't have to get our team together to really get everybody on the same page. I don't think to get our team together to really get everybody on the same page. I don't think that retreats ever should be a substitute for really great communication processes or really incredible connected systems inside of the business. However, there are just some things that Zoom cannot recreate. There are some things that we can't tell each other just on Slack or on Zoom, and my opinion on this is that, even if it's a small budget, create a budget, create a continuing mental health or a continuing education budget and put it toward getting together with your team, even if you want to bring an expert in or bring somebody in who's going to support you guys.

Speaker 1: 7:01

We've done tons of different types of retreats at Operations Agency and I wanted to talk through how I'm planning for this one. So the third thing I want to talk about is how to plan for a retreat. So the first thing that we typically do is I'll typically set an intention right. So what is the big thing or the big reason for why we can get together and make the most out of our time? So oftentimes it'll be connecting right. So, like we want to just be more connected we. The last time we did a team retreat, it was really about making sure that we had a good quarterly planning and annual planning process in place and I felt like getting everybody together in person was really helpful. We actually invited some of our clients to do that and, of course, over the years of COVID and all of those different things, we had to kind of get creative and get crafty for how we got together and got connected. Um, I saw a couple of our teammates kind of one-off while I was traveling or in other cities doing, you know, workshops and speaking engagements and that kind of stuff. So you can kind of create little mini pockets of time to be able to connect with folks.

Speaker 1: 8:04

Our really big why for getting together, of course, other than just connecting, is to rethink, you know, our client journey and really rethink the core deliverable of what we do at Operations Agency. Nothing is changing per se, but what we want to do is we want to package things up in a way and really line out our customer experience, inviting some new folks to the team. We have three open positions right now, one of which actually just got staffed as of yesterday, and then a couple are in their second and third rounds of interviews. So we're so excited about the new folks that are coming onto the team. We're really excited about the new way that we're going to approach and really share the load of being able to help our clients continue to win, and so client journey for us is something that we're going to talk about.

Speaker 1: 8:50

Right, kind of like a relay team. When I was in high school, I used to run the distance medley relay, and so the distance medley relay had four separate runners and each of them ran a different length of time in a different order. So it was like the mile would go first, and then the 200, and then the 400 and then the 800. And so you would basically have and I might've messed up the order on that to be totally fair but what you would do is you would basically tell each of the runners okay, this is the portion of the you know the race that you are running. Um, and they were all different and we needed to understand when the baton was being passed off, right. So we need to be paying attention because all of the lengths of time were just slightly different, and I think that that is a really incredible way to kind of think about what we plan to tackle at operations agency at our retreat, because, at the end of the day, what's going to end up happening is things are going to shift right. I'm not going to have as much responsibility, lauren's not going to have as much responsibility, and we're going to kind of share things a little bit more with some of the incoming folks on our team, and it's going to be really incredible because it'll help us kind of redefine and rally behind this new version of what operations agency is going to look like, and so I'm actually super excited about that.

Speaker 1: 10:01

So I know I promised y'all logistics. I'm going to tell you a little bit about what we have planned and frankly, I don't even know everything, because my wonderful assistant, kelsey, has taken on most of the planning side of these events. So what we're going to do is we got together, specifically decided to do three full days, so we've got a really fun time plan. We're going to eat lots of really great meals. So that's something that I firmly believe. I mean, whether that's with my family or with our team or our friends, if we're always getting together around the table, we're always trying to have delicious food. We're going to also do some experiences and we have some options for those. So that's kind of like a how do I put it? A tip, a trick, a hack.

Speaker 1: 10:44

When I was first doing retreats when I was employed, we would all do the same thing and then some folks would be like super into the activity, and then some folks would kind of check out, and so I believe in having a variety of options that folks can choose from and that they can say hey, listen, this feels like it's for me and this other thing kind of doesn't, and so they can kind of pick and choose what they want to do. So we are doing some activities together. Also really, really important and this goes either way, whatever you guys want to do For me it's super important that we share the same roof. So we got a really beautiful Airbnb. Everybody's got their own room, their own bathroom, they've got their own space.

Speaker 1: 11:25

But there's something about like those early morning chats, like over coffee, when like nobody else maybe is up yet, or being able to just like snag some time and like go out for a walk with somebody, like ad hoc, or sitting out on the deck or out on the patio and just shooting the breeze about something. Um. So I actually really believe in if I was going on a family vacation or sharing time with friends, often what we would do is we would look for a big house, and so that's what we've always done. We've always shared the same roof and we've really tried to make sure that that feels comfortable for all. We do extensive surveys and things before. Um, you know, we go on our retreats and that is super, duper fun.

Speaker 1: 12:05

Um, next big thing is making sure that everybody has a good heads up about what is going on. Um, some folks like me are huge planners and we got to know, like, do I need to buy a bathing suit? What do I need to do? And so I think it's super helpful to be able to plan out in advance. But I think, at the end of the day, you always want to surprise and delight your team. You always want to give them some options. You want to be able to share this time with them and be able to be fully present. So making sure to have like one person dedicated to logistics and communicating all of the things that somebody might need is going to be so, so, so helpful. So I, we go out on a retreat, so I leave next week on Monday and it's super exciting. I know the team is all very excited.

Speaker 1: 12:55

One last logistic I will share about our retreat because, again, I don't know all of the nitty gritty details. Thankfully, I can kind of show up and be present and have a great time with our team, but tell your clients way in advance. We told our clients hey, listen, operations agency is going to be closed. We're going to be out on our retreat and that's going to be something that's going to give your clients and your customers and things a peace of mind. And I think, at the end of the day, too, you want to be forthcoming with them. You want them to understand that they have not been forgotten or they are not going to wait three days without notice to have an email response from you, but that you're spending this time to become more connected. And, frankly, I was actually preparing for this podcast and I was going to mention to Lauren, our account director. I really do think that even sharing with our clients, like what the intention is for our retreat because I think that especially solidifying and improving our client journey is something that's directly going to affect them Like the moment that we hit our desks back after retreat is over and so I think actually sharing the intention and that we're all really committed to growth and we're all really committed to their success and we want to be able to share that, I think, is going to be super fun.

Speaker 1: 14:15

Okay, a couple of bonus things, if you know time, if a budget and all those different things allow. So first we got new swag. I know it sounds so silly, but we haven't gotten swag in years. I kind of don't super care what I look like. If you guys are watching this right now, you're probably like you definitely don't care what you look like, but at the end of the day, I want folks to be super proud about our brand and what we're building together, because it's not just me. We've been at this for almost seven years, which is so exciting. Lauren on my team has been with me for five years. A lot of our teammates have been with us a year plus and it's so fun to think about what we've built together and how far we've come.

Speaker 1: 14:57

So we went through maybe Kelsey will not remember it as fondly, but we went through kind of an extensive and exciting process of choosing our merch and really being intentional about, like, what people were excited to wear. And I know like we didn't just get like branded coffee mugs because we were like, oh yeah, this is going to be the easiest and the cheapest. Like we really thought about it, we really asked our team, we were super excited about it. So number one is everybody's getting new merch, which I'm super pumped about because you're going to be seeing, especially as clients, you're going to be seeing lots more of the operations agency team around, which is like so exciting for me. I can't believe, um, like how wonderful the people that uh support me, you know, growing this company, starting this company and, um, our clients have have been so, so pumped about that. So, merch, get some stuff, get some t-shirts, get something fun that connects everybody and you can all wear it together.

Speaker 1: 15:53

The second really really cool thing that we have done over the years is we created a company book club and we do that every other month and so in person this time we're going to get our new books, which feels super exciting, and we're going to be able to take those home and, you know, of course, chat about them and all of our reading when we get back. Third thing again, if budget allows and if it feels like you is, we have a photographer and videographer coming to the retreat this time and I thought that was important because oftentimes, when our clients interact with our brand, they see lots of me, you guys see lots of me, and I want them to feel really comfortable and I want everyone to feel really comfortable interacting with our team, because we've got a huge, incredible supportive team and it's going to be so important that, as we kind of embrace and grow our brand and we serve more clients, that our clients know that these folks are incredibly trained and have a lot of experience and can really, really support them, and so we're getting this opportunity to take some photos together, to do a little bit of content together, which is so exciting, like guys, so, so, so exciting. Um, I can't believe that. Um, honestly, even the other day and Lauren might, um might be embarrassed that I'm sharing this, but she um had her very first like self-led client onboarding call and she's starting to like move more into um doing some some client facing stuff on calls and I'm so excited about it. I'm sad actually that we kept her best kept secret. I think she's a little nervous about coming into client calls but I do think that everybody always loves whenever they get to interact with Lauren, and so being able to share more of our team's personality, our culture and have that be a little bit more forward facing is just a treat that I'm really excited. To share more of our team's personality, our culture and have that be a little bit more forward-facing is just a treat that I'm really excited to share. So to wrap up one team retreats or getting together in some fashion outside of work, it's required. So please do that.

Speaker 1: 17:55

Second, that there's never a convenient time and if you don't already plan this inside of your budget, it's not going to feel great in the very beginning to start to allocate resources, time, money, any of those things to this experience, but it's so crucial if you want to grow a team. The third is I absolutely want you to remember to set an intention and communicate that intention to your team If you, of course, want to connect with them. Of course we want to share experiences and we all kind of really want to connect with them. Of course we want to share experiences and we all kind of really want to take some time to digest or even have a conversation about what the next steps or what the future looks like you know for your company. And then the fourth is make sure they know all the logistics. Create some time to break bread together, to actually do some activities together. Present, you know, a variety of options. Connect people with cool swag if you can create some memories by inviting a photo and video team and do something special that feels just like your brands, like what we're doing with our company book club.

Speaker 1: 18:57

I personally haven't seen a lot of information about team retreats outside of those major corporate ones that do all the crazy things and everybody's on an episode of Top Chef or they're kind of like recreating Wheel of Fortune. So I feel like this is a nice light and exciting type of thing. Make sure that you are telling your clients ahead of time or your customers, that you guys are going to be out on team retreat and if it feels exciting and confident for you make sure to share your intention and why. Getting your team together and being off grid or um, you know what whatever works for you guys for a couple of days is going to be incredibly impactful to them. So thank you, guys so much for joining me on today's episode.

Speaker 1: 19:46

If you have a second which I hope you do, and you're enjoying the content you're enjoying the guests please, please, leave us a rating on iTunes or Spotify or wherever it is that you're listening to the podcast. It really does make a huge difference for how we reach other moms who are growing businesses and growing families, giving them these incredible interviews and really bringing out um. You know just some of the things that we're all thinking about, um, as we're growing businesses and growing families. So if you can leave me a rating, I would super duper appreciate it. Um, I also understand if you're like Ellie. I'm totally not cool with these uh, these empty office videos. But hopefully next time I come to y'all with a solo, I will be in a much more exciting area in Colorado in my new office. So thank you, guys again for joining Growing Pains and I'll see you next time.

Speaker 1: 20:36

Thank you so much for tuning into today's episode of Growing Pains. I know that you have so many things vying for your attention right now, so I am so grateful that you just spent the last hour or so with me. So I hear all the time from mompreneurs Allie, allie, what systems do I need to have in place in order to thrive in business and in parenthood? If you go over to alisoncaffreycom checklist, you can grab my kid-proof checklist and it will get you started in the right direction around making sure that you build a business that doesn't steal all of the time away from your family. If you loved today's episode, I would be so, so, so honored if you would leave a review on the podcast. It helps us reach even more incredible mompreneurs just like you and give them the resources they need to be wildly successful in business and wildly present at home with their families. Thanks so much again and I'll see you next time.