planning your small business retreat
My small team had regularly traveled together over the course of a couple of years (we were a team of Travel Advisors, after all)... but at the end of 2021 I decided to host my first true company retreat. Not just any kind of a trip, but a real retreat.
I wanted it all — maxed out and fully-loaded. This retreat had been something I’d dreamt of doing for years! I’d imagine how it would all come together long before I even had a team big enough to host a retreat for… Is that embarrassing?
But finally, after months and months of planning, my team headed to Arizona for the big event.
It was everything and more. But was it perfect? No way.
I learned so much about hosting a company retreat and since then, I’ve been asked thousands of questions around the occasion. All of those questions, of course, inspired this post. Ready to dive in?! Me too.
The Dos & Don’ts of Planning Your Small Business’ Company Retreat:
DO: SOMETHING CHALLENGING TOGETHER.
For us, it was hiking allllll the way to the top of Camelback Mountain. For me, it was doing it 5 months postpartum - phew! At the risk of sounding completely cliche, doing something this challenging together was extremely bonding. Good old fashioned team building, you might call it.
We laughed so we wouldn’t cry, we sweated our faces off, we stumbled and fell, we encouraged one another, and eventually we took cute photos at the top to prove we made it up all 2,706 feet.
It was glorious!
DON’T: PUT IT ALL ON YOURSELF TO PLAN EVERY DETAIL.
In the beginning stages of planning, I took it upon myself to ‘do it all’ because I falsely assumed no one could do it right but me (a trending mistake in entrepreneurship).
Halfway through planning, I looped in my right hand woman and travel coordinator to help me research things like activities and restaurants, create a survey to see what the rest of the team was most interested in doing, and more.
Thank God I did!
Teamwork makes the dream work! Make the planning process collaborative where you can. People love to feel like they’re a part of something!
DO: INCORPORATE SPEAKERS, TEACHERS, AND MOTIVATION.
No one wants to spend a weekend watching 30+ speakers give presentations, but working a healthy amount of motivation into the itinerary is a staple.
We had two speakers during our retreat. One came IRL to speak on sales, work-life flow, growing your client list, and more. The other came to us virtually and taught on social media, online marketing, and building your own brand.
Incorporating speakers, teachers, and motivation was my personal favorite part of the retreat!
In fact, I was so inspired by how impactful the retreat speakers were that I’ve began putting together a few presentation ideas myself! If you want to talk about possible collaborations for your small business’ company retreat, please reach out!
DON’T: PACK YOUR SCHEDULE TOO TIGHT.
This was a big fat fail of mine.
Because I wanted to make every detail of my dream retreat a reality, I didn’t leave any ideas on the cutting room floor. From the second we landed PHX until the end of the retreat, we were on the go. It was too much, and I suspected it by the end of the first day. Oops.
Then, that anonymous feedback survey confirmed my suspicions. People were exhausted after the trip! My team kindly brought me back down to reality and reminded me that you’re supposed to feel rested after a retreat. Why didn’t I work in an afternoon spent at a spa?!
DO: SPLURGE ON SOMETHING MEMORABLE.
For us, it was a hot air balloon ride. And as a bonus tip: we did this at the very end of the retreat to go out with a bang! We loved doing this together, and it was worth every penny.
DON’T: FEEL LIKE YOU NEED TO PAY FOR EVERYTHING.
Speaking of being worth every penny, one of the most frequently asked questions about planning your small business’ company retreat is, “What all do I need to pay for?”
The answer is, not everything. But if you’re going to do this, you should take financial responsibility for a lot of components of the trip!
At the time, my business had experienced a lot of growth, but we weren’t at a place where we could pay for absolutely everything. We covered accommodations, the hot air balloon ride, a branding photoshoot, speaker presentations, and an award ceremony. I also made sure to work in several free components of the trip like our hike and touring top hotels in the area (since this was a travel industry retreat, we also had a few meals covered by our generous supplier partners).
Some pieces of the event were not covered, like airfare, meals, drinks, and Uber rides. We used Splitwise to make it easy to pay for group dinners and keep track of Uber receipts.
DO: PROPERLY DOCUMENT THE EVENT.
Whether you pay to have a company branding photoshoot (c’mon, what better excuse to update your website with fresh photos or get your Christmas card squared away?!) or are intentional about capturing photo/video on your iPhones, make sure to document the retreat! These are great memories and they definitely should be kept forever.
DON’T: MAKE THE TRIP A REQUIREMENT.
Even if you are paying for every single piece of the retreat, you still shouldn’t make it a requirement. No one wants to feel like their work retreat is just another thing on their to-do list! The retreat should be intriguing enough that everyone will have FOMO if they aren’t there, anyways! ;)
DO: PUBLICLY PRAISE YOUR TEAM.
On the anonymous feedback survey from our retreat, almost everyone said that our “award ceremony” was one of their top two favorite memories of the entire weekend. I was so glad that I did this!
During our last dinner together, I made sure we had a private room at a restaurant for the little surprise ceremony. Once everyone had their drinks, I stood up and gave a toast to how much I loved my team (easy to do!) and then awarded two awards. I even had small custom awards made at a local trophy shop in my town!
This ended up being a really special moment. I’ll never forget this night!
DON’T: FORGET THAT TEAM BONDING IS THE PRIORITY.
Since I was so wrapped up in making this retreat absolutely perfect, at times I lost sight of this truth. Remember when I said our anonymous feedback survey had a “favorite memory” question?
Next to the award ceremony, the other favorite memory was actually when my husband (who is a constant supporter of all that I do and tagged along to help me that weekend!) stayed up late playing drinking games with all the girls.
First of all, this definitely wasn’t on my perfectly crafted itinerary. And if I’m being honest, I was mad at my husband for doing this at the time - how inappropriate! I am supposed to be a professional, after all!
And, I felt left out. I was too tired and too dehydrated to join in on the fun. I had totally exhausted myself leading the trip and forgot to drink enough water in that Arizona desert heat. I missed out on what I heard was a crazy fun night.
When I got the feedback survey results and saw that every single person said how much fun they had letting loose with the team that night, it hit me that I should have never been upset in the first place. Team bonding (yes - even late night, silly drinking games!) should always be the priority!
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