Top Six Things to Avoid When Planning Your Company Retreat

We’ve explored how to plan a company retreat AND the steps for setting a budget. But here’s a list of what NOT to do when organizing your team’s offsite. Below are some common mistakes that people often make when planning a company retreat….avoid these pitfalls and you’ll set yourself up for a positive experience all around. 

1. Overplanning

The old saying “less is more” still applies here. Yes, your company retreat needs a framework. People like structure. You’ll most likely be spending a bit of money to bring your team together, thus you’ll want an overall plan with scheduled events. Team members appreciate an overview so they can plan accordingly (e.g. what to wear hiking vs. cocktail lounge). However, jam packing the schedule can be stressful on everyone and leave your team feeling exhausted. It’s tempting to plan something to fill every hour in order to maximize the trip, but we don’t recommend this for two reasons:

  1. Things can run behind schedule, especially in a group setting. If one tour takes a bit longer than planned and starts to bleed into the next activity, it can create a domino effect for the rest of the day. It’s not enjoyable for the team members and can be unfair to the vendors. Plus, you’ll most likely save a little money by not choosing every activity the destination has to offer. 

  2. Leave room for magic to happen. Providing a bit of unstructured time allows your team members to gather organically — they may stumble upon a funky coffee shop that would have not happened otherwise, or gather leisurely by the pool. Some team members may have introverted tendencies and need some time alone to decompress. Not having a jam-packed schedule gives your team a bit of freedom to connect on their own and provides time to rest…..it IS a retreat after all. 

2. Not asking for input from your colleagues 

Whether you’re running the company or have a role in workplace management, you may think you know what your team members want. You may also not want to bother them and keep some elements a surprise. This is reasonable, but we don’t recommend it. No one wants too many cooks in the kitchen, but we highly recommend gathering feedback from your team members prior to planning. It may help shape the intention of the retreat, or at the very least, refine it. 

Your team members may have some excellent ideas that may not have been on your radar otherwise. An activity you believe to be a hit may not resonate with the group. If you’re going to spend the time and money on a company retreat, make sure you’re giving them what they want. Plus, they’ll be more invested and excited if they’re included in the planning process. It doesn’t have to be a fully democratic operation, but having your colleagues weigh in on their interests will almost guarantee a worthwhile retreat. 

Use Google Forms or Survey Monkey to assess interests, or simply have a brainstorming session to get the ball rolling. Whether or not your group is the most vocal, you’ll start to understand where their interests lie and put together a killer itinerary.

3. Not taking a day trip prior to the retreat

It’s amazing how much you can learn online, but NOT taking a day trip prior to the destination itself is risky. Yes, you can do your homework comparing hotels, scouring TripAdvisor, and mapping out travel plans, but you’re taking a gamble if you don’t assess the destination in real life. You’ll want to be confident in the location and the quality of the accommodations. Plus, you’ll have a better understanding of how to navigate the city whether it’s by foot, Uber, or public transportation (traffic can be a buzzkill and put you behind schedule). 

You’ll want to feel the space before bringing your group to the destination. You’ll have the chance to meet your vendors and make any changes if they’re not up to par. A pre-retreat trip to the destination may seem frivolous, but it’s highly recommended before sending your group sight unseen. The last thing you want is to realize that you missed the mark in real time. If you can’t commit to a night or two, opt for a day trip. 

It’s amazing what you can achieve with proper planning in a single day. Depending on the flights, you can meet with a surprising amount of vendors AND gain a decent understanding of a location. Even if you’re on a budget, don’t skip this part of the equation. It’s a small price to pay to feel confident in the planning process. 

4. Booking airfare without consulting your team

You may be tempted to book airfare for your team for a few reasons: 

  1. You have control over the arrival/departure times 

  2. You’re aware of the cost 

  3. You’re providing ‘concierge’ service. 

We used to to believe this, too (and still offer this service), but we don’t recommend it. Here’s why: booking airfare without consulting your team can be a giant headache. People prefer certain airlines over others because of allergies, loyalty points, and more. 

Some people have an aversion to flying and would prefer another method. People’s plans change and it’s extremely difficult to change a flight on someone else’s behalf. If people need to change their flight, they can do it on their own time. 

There’s often an additional cost that can be subject to the employee’s expense if the change is for personal reasons. If you want control over arrival times and costs, we highly recommend spending 15 minutes with each participating team member. With a one-on-one consultation, you’ll be able to review the most affordable and efficient travel options together. That way, there are no surprises and you can make sure that airfare is being purchased at an optimal time (e.g. approx. 45 days in advance for domestic flights, Wednesday AM, etc). 

If it’s in your budget to hire a full-fledged travel agency that specializes in group bookings, go for it. But in our experience, having people book their travel and then be reimbursed is the most efficient method. 

5. Not starting with a general budget

A quick way to sour the intention of a retreat is to be anxious about the cost. Start with a budget and plan to go over about 10-15%. This will serve as a baseline for what you can and cannot do. Perhaps there are no financial limitations and you’ll opt for luxury all the way (good for you!). 

If there are financial limitations (most of us), then it’s time to get creative and do the best with what you have. You can still have an amazing experience within a budget, but it’s best for all parties to be on the same page from the beginning. Have an approved number in mind, view the retreat as an investment in your team, and let yourself enjoy the experience. 

6. Not setting an intention

Before you even begin choosing the destination or start diving into planning activities, start with the intention. This will be your north star for designing the entire experience. It provides a roadmap and reminds your team WHY they’re gathering in the first place. Is the purpose of this trip to recharge? Or perhaps it’s to try new things and get out of one’s comfort zone? These two intentions aren’t necessarily exclusive, but the mindset may lend itself to different activities. 

If your team is fully remote and they’re gathering to meet in person, opt for activities that strengthen personal bonds. Or maybe you’re organizing a retreat for a group of company veterans to celebrate their years of hard work. In the words of Simon Sinek, start with why. It will serve as the foundation for the entire retreat and help solidify the purpose of the gathering.

We hope this provides some insight when it comes to planning your next company retreat. Whether you’re remote or hybrid, gathering in-person is crucial for relationship building. Treating your team to a destination in which they can experience something new together cements professional ties and helps stir creativity. If you ever need guidance on where to begin, or just don’t have the bandwidth to plan, we’re here to help. Feel free to reach out to danielle@thetrianglesessions.com. Travel safely, folks, and gather with intention! 

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When Should You Start Planning Your Company Retreat?

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How to Set the Right Corporate Retreat Budget