Tips on Planning a Successful Company Retreat

Kicksaw is a 100% remote company, and we’ve written a lot about what it takes to succeed as a remote company, as well as how to build a thriving company culture that provides your business with everything it needs to succeed. As company culture enthusiasts, we love sharing what we’ve learned with others. 

A topic that comes up pretty frequently, especially for remote companies such as ourselves, is company retreats. Should you do them? How often? Why? What does it take to put one together? What about the burden on employees?

To answer that first question: yes. You should absolutely do them, particularly if you are a remote company. We recommend a retreat once per year — not only is this a nice tidy rule for simplicity’s sake, but meeting more frequently than this can put what feels like an undue burden on families (not to mention undue pressure on your company finances), while gaps of greater than one year between retreats can stretch those interpersonal bonds within your team a bit thin. 

As far as what it takes to put one together? A lot. If you can designate at least one person on your team to, for part of the year anyway, be devoted to planning the retreat in a nearly full time capacity, do it. If you can’t (which is totally understandable), create a core team that meets regularly throughout the year to make sure everything is on track — a successful company retreat boils down to planning, planning, planning, and then planning some more. 

Part of that planning should absolutely involve research — research the locations you are interested in, available accommodations in that location, restaurants, etc. And don’t forget to look into what other companies have done for their retreats. What lessons can you learn from what other companies are willing to share about their retreat experiences?

Fresh off the heels of our third all-hands company retreat, we’ve put together the following guide on pulling off a successful company retreat. Retreats are wildly complicated, of course, and this is not meant to be a comprehensive guide — far from it. Think of the following recommendations as little trail markers we’ve dropped for you. We think you’ll find these insider tips helpful as you do the tricky work of plotting out the ideal bonding experience for your team. 

Have contingency plans for factors that are beyond your control.

This is event planning 101, and a great reminder for retreat planning committees everywhere. Mother Nature doesn’t care how many months it took to plan your retreat or how much money you spent on the venue — the weather will always be a wild card. Don’t forget to make backup plans, and not just for events that are weather-dependent. What are you going to do if your indoor event is canceled for reasons beyond your control, or your keynote speaker calls in sick? Plan B is a must, and Plan C is advised. Plan D…well, we’ll leave that one up to you.

Along these lines…you are not crazy if you are considering hiring an event planner for your retreat. It is an event, just as a conference is, and there’s a reason this industry exists. Don’t be afraid to reach out for help if you feel like you need it. 

Land on a budget early, and stick to it.

When attempting to stay on budget, we’ve found that setting a per-person cap is the best way to stay on track. For example, for our last retreat, we budgeted ~$2k per person. This included airfare, hotels, meals, per diem, ride shares, swag, team activities, photographers, and conference space fees, as well as AV costs. There are a lot of factors to consider when determining the dollar amount for your per-person cap, of course, but setting a clear budget up front creates restraints that will keep your relationship with the Finance team intact and fuel creativity for your planning committee.

Find ways to give your team members new experiences during the retreat.

This will probably require some hardcore brainstorming, but do your best to give your employees at least one (hopefully) unique experience during the retreat. New experiences are, of course, far more memorable than their counterparts. Pushing your team to try something new is also a great way to exercise teamwork, strengthen communication skills, and foster a spirit of camaraderie — this is why you are hosting the retreat in the first place, after all. 

For Kicksaw’s most recent retreat, this looked like a songwriting exercise led by a team of outside facilitators. Over the course of a morning, our team split into four groups, and each group worked to write a song about one of Kicksaw’s core values. This forced people out of their comfort zones in a completely safe and welcoming way, to much laughter and applause. 

When the retreat was over, we received quite a bit of feedback that, while many of our teammates were apprehensive about this exercise going into it, not only did they really enjoy the experience, but they considered it the highlight of the entire retreat. 

Save high-energy activities for the afternoon or evening.

Retreats take a lot of energy. Traveling is tiring, and most likely, your teammates are not accustomed to being in the company of, well, the entire company, which means they are probably going to become socially drained more quickly. So, don’t add to the load by scheduling the most high-energy activities for early in the day. Give your teammates the morning to complete more relaxing activities, such as mingling or listening to a keynote address, and then cap off the day with your more exciting agenda items. This helps folks stay energized throughout the day, and it’s of course always a good idea to end on a high note (or cruise right into happy hour on that high). 

A lesson learned from our last retreat was that we should’ve scheduled our “fireside chats”  with teammates (which are pretty low energy) early in the day and saved the big songwriting exercise (which was very high energy) for the end of the day. Because we started with our high-energy songwriting activity, our fireside chats were a little sleepier than we’d have preferred. Lesson learned!

Don’t overdo it with the schedule.

This is really important — don’t plan out every last minute of your team members’ time during the retreat. Not only do people need time to reset after agenda items, but they need time to simply enjoy each others’ company. Some of the most memorable conversations happen when folks are in limbo, so don’t crowd out that limbo. Bear in mind, too, that the more you have scheduled, the easier it is for the entire schedule to go off the rails. A ten minute delay waiting for brunch to be served can quickly escalate to a missed afternoon event if there is no wiggle room built in. As Kicksaw Co-founder Kyle Morris likes to quip, “Do half as many things twice as well.”

Additionally, make sure you schedule in some more low-key times, such as casual roundtable discussions with management. Make it a priority to create space for genuine, honest conversations during your company retreat — it will very likely end up being some of the most special time you and your teammates share together. 

Let employees make the retreat their own.

Don’t make the mistake of crowding out opportunities for team members to create the retreat they want for themselves. Building that wiggle room into the schedule helps here, but there’s more you can do to ensure that folks are able to personalize their experience. Give them a budget and let them spend it how they want! Go the extra mile by scouting out opportunities for them — what are local attractions that you don’t want to bring the entire company to, but would likely be interesting to a handful of your team members? Make a list. Some people like to tour historic markers or nature preserves, while others are shoppers or thrill seekers. Make those lists too, and give folks enough free time to customize their experience. 

Ask for help!

Don’t be shy — let folks know you’re coming and that you’re ready to be pitched to. Contact local resources, such as city governments, travel bureaus, museums and popular tourist destinations, event venues, or even Facebook groups, and ask for their recommendations or advice. Googling will only get you so far — it’s the locals who can really show you a good time. 

And don’t limit your ask to the locals. Ask companies similar to yours for their advice — you might be surprised at the candid responses you get back. Get in touch with the team here at Kicksaw — we love advising folks on more than just Salesforce (although we’re pretty darn good at that too). 

Above all, though: relax. Have fun. Let loose, plan an event that suits your team, and make those incredible memories. All the hard work and expense are absolutely worth it. Best of luck to you, and don’t forget to pack your camera!