Why Hosting An Annual Team Retreat Is Essential For Remote Businesses



November 11, 2019

Something amazing happens when a group of people come together in one place and truly get to know one another: unity. Unity brings better relationship dynamics and productivity in your workplace. If you are the owner of a remote business or you work for a remote business, then you understand the feeling of isolation that comes in waves. Even though you may be emailing, using Slack, or having weekly Zoom calls, it may not feel like you are really getting to know your employees or co-workers. Do you want to know our simple fix to this? An annual team retreat. This is a trip that our company does once a year to gather all of our team together in one central location to meet one another, build relationships, and cast vision for where we are going as a company. This trip is meant to be FUN. Get your team involved, ask them their dream team retreat location, and see what fits your companies budget! We believe that hosting a team retreat is essential for remote businesses. We are going to be sharing our process, where we have been, what we are learning, and the positive outcomes of hosting a team retreat.

Why is a team retreat important?

“If you can laugh together, you can work together” – Robert Orben 

I love this quote because it is so true. Here at Steadfast Bookkeeping we love to have a good time and share both our personal and work lives with one another. This kind of culture is something that has to be allowed, created, and implemented. Team retreats take the pressure off. Your employees and co-workers don’t feel the need to perform or only be “professional.” They simply get to be themselves. You will start to see that certain personalities cannot be understood through a Zoom call or through other social programs. You will find that some of those ‘quiet” employees or coworkers are actually some of the wittiest people you will encounter. Team retreats allow for this growth process to begin in your team if it has not already taken place in your company. 

What activities do you do at team retreats?

The goal of our team retreats is to find a good balance of both team activities and learning. We not only want to have a fun experience but want to create space for building our knowledge. Depending on where you are holding your team retreat, the facilities may have activities on site. If not, then this is where your creativity comes in. Your team activities do not have to be anything extreme like skydiving, they could be as simple as a team bike ride. The goal is not quantity but quality. The big picture is to have everyone in the same place doing the same thing and creating memories. For example, on our first team retreat in 2018, we went to Watersound, Florida and stayed at an Airbnb. A couple of our team activities were a bike ride to dinner and sitting by a fire chatting with one another. At our most recent team retreat at the Biltmore Estate, our activities included a winery tour and clay shooting. Crazy enough, we were all nervous about the sporting clays, but it ended up being one of our favorite activities we did together. If you can do a team activity a little bit out of your comfort zone, we found it to be a great learning experience. You see how each person analyzes, rises to the occasion, and how we as a team encourage one another in our weaknesses. 

What do the meetings look like at a team retreat?

This leads us to another important part of a team retreat: team meetings. These are the moments that are set out in a schedule to go over what is successful in the company, what needs improvement, how we can improve these areas and what is in store for the future. Consider starting off your meeting with an icebreaker to rid of any nerves or awkwardness your team may be feeling in a new environment. This year, we started our meetings with an icebreaker. This was so much fun! The day we arrived at the Biltmore our day started with a “get to know you meeting.” In this meeting, we played two games to get to know our co-workers a little bit better. What better way is there to get to know someone than by playing Two Truths and a Lie? This was a hilarious way of getting to know more about your co-worker’s lives that seem too crazy to be true. The other icebreaker game we played together was Shark Tank. We had two teams that had to create a product and try to get the Sharks (Stephanie, our Founder and CEO, and Noel, our Operations Manager at Steadfast) convinced of investing in their product. This allowed us as team members to think outside of the box, work together with new people, and try to achieve the same goal. For Stephanie, this allowed her to see her employees spark creativity, show teamwork skills, and show their knowledge. 

As for the bulk of information in our meetings, we decided to send out an email before our team retreat to all of our current clients asking for feedback on how their service has been with us so far. Can we say, we are so grateful we sent this email out. The response rates were great and our clients provided us with a lot of valuable information. If you are the owner of a company, you understand that it can be difficult to get feedback from your clients. The responses can be vague such as “good” or “there are some things that could be improved.” When we sent out this email, we were overjoyed to get detailed responses from individual clients. If things needed to improved, we knew where the disconnect was and we started brainstorming on how to implement change. We also loved celebrating the emails that were full of praise saying how great of a job each bookkeeper was doing! This feedback was not only beneficial to our clients but also to our team. If you own a company or are a part of a team, do not be afraid of feedback, it is the very thing that propels you forward. Our team was happy to see the personal feedback of clients they work with on a weekly basis and to start implementing their new ideas. Other meeting content ideas for your company may look like reevaluating your processes as a team or creating breakouts to increase your team’s knowledge of certain subjects. Here is a tip: whatever your meeting content looks like, make sure your team feels secure and excited about the future of your company leaving the meeting. Always end your meeting with a “win” or a high note. 

How have team retreats changed our team and company for the better?

We are a firm believer that team retreats have helped us grow as a team. We left our team retreat at the Biltmore this year already excited for the next one. We were sad to leave one another because we had all become so close over those few days. Something changes in your work dynamic when you have met your co-workers in person. You know how everyone reacts and responds to certain things. You learn each other’s strengths and weaknesses. This is not to exploit each other’s weaknesses but to come alongside them and help each other grow in certain areas. As a team, we work together to accomplish the same goal. We now are using the information and feedback we have gathered from our clients to start implementing change in our company. Our team meetings are now less awkward because you know your co-workers and can crack jokes with them. As a whole team, we understand our companies mission, vision, and values better. We understand the goals and vision that Stephanie has for our company and we are excited to help her grow her dream! If you have been on the fence about doing a team retreat, just do it. Start small and do something a little more advanced every year. Team retreats will help grow your employees, co-workers, and your company. 

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