How to Plan a Company Retreat Without Losing Your Sanity

Updated on September 4, 2020
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How To Plan a Company Retreat

Planning a company retreat can be stressful. Figuring out the right date, location, and people to invite can sometimes get the best of you.

While retreat planning may seem intimidating, there are many benefits for your company when the event is well executed. Not only can getting out of the office with your team give everyone time to relax and reflect, but it’s also been shown to increase employee motivation and provide time for you to get to know your team better.

To help get over the stressful planning stage, we created an easy step-by-step guide to plan your company retreat without completely losing your sanity. Skip to the benefits of having a company retreat.

Also, jump to our infographic for an easy roadmap on how to plan a successful company retreat, or keep reading for a more detailed look.

Step 1: Define Your Goals and Objectives 

You wouldn’t attend a meeting if you didn’t have a goal in mind—same goes for company retreats. If you’re planning to host a company retreat without a purpose, you should use your resources for other business goals instead.

Brainstorm on your own or with your team to figure out what everyone would like to accomplish. Helping team members overcome their fears, encouraging collaboration, and exposing coworkers’ hidden talents are just a few goal examples. Whatever goal you have in mind, create a plan with actionable tips to produce a positive outcome.

Make this even more powerful by writing down each goal and keeping them in mind during your planning process. Discuss these goals with your team and make sure everyone’s on the same page before making your way to the company retreat.

Step 2: Schedule During Your Slow Season

When planning a two to 10 day company retreat, consider when your business is at its busiest. Avoid adding to your employees’ stress loads during these times. Schedule such an event during your slow season, and far in advance, to increase participation and the overall success of the retreat.

When figuring out the specific date of the event, consider how long you would like it to last. Sending out an anonymous questionnaire to your team with options such as dates of interest, retreat duration, and locations can help during the planning process.

For instance, if you run a retail business, gather dates of interest for the following year during the spring when schedules are usually lighter. Sending out dates a year in advance will ensure there is no way your team will have another event going on at the same time!

Step 3: Ensure the Presence of Leaders

To optimize your team bonding experience, make sure the leaders of your company attend. Not only does this encourage employee involvement, but it can show different sides of your whole team and learn how individuals handle different situations outside the workplace.

Check everyone’s calendars to see what dates work best for this event. From there, nail down the exact date that works for your team and put it on the calendar.

Step 4: Pick the Perfect Location

Location is often the hard part as many people will have opinions of where this event should be held. Yet, picking the right spot is crucial to helping encourage participation on your team. Locations for retreats should be held in an area that has more than enough open space for activities, conference rooms to come together, and dining areas for open conversations over meals.

Speak with your company leaders and employees to strategically pick which location the majority of your employees recommend. Take into consideration the weather conditions during this time frame and the accessibility to restaurants, wifi, and any other necessities needed during this event.

Research event locations that have large open areas for team building activities and meeting rooms for closer events. Once you have narrowed down your selection, figure out which best fits your team’s needs, and request a price quote for that location.

Step 5: Choose a Stress-Free Transportation Method

Now that you know the date, location, and an approximate number of attendees, it’s time to brainstorm transportation methods. Having the right transportation can alleviate the stress of making scheduled activities on time and helps everyone avoid navigation mishaps.

Depending on your group size, you might choose a bus (or a few buses), employee vehicles, or rideshares to ensure your team makes it to their destination safely and on time.

Step 6: Negotiate Pricing 

Go into this with your hard hat on. Ask business owners if they’re able to provide a discount since you’re bringing an exponential amount of business their way. Wait until you have your final quote for catering, transportation, and the venue before bringing up the idea of a discount.

Start the negotiating process with small talk, and work your way up using questions such as “Is that the best you can do?” If discounted pricing is out of the question, consider asking for free delivery for catering or tips being included with the quoted price.

Always be respectful and put yourself in the other business owner’s shoes when negotiating pricing. Even though you may want to save a couple pennies, other business owners need to make a profit too.

Step 7: Brainstorm Team Bonding Exercises

Now on to the fun part! Start brainstorming exercises and activities that can help your team grow and connect. Depending on the purpose of your retreat, there are numerous activities you can explore for your event.

To encourage team bonding, you might want to incorporate activities like a scavenger hunt, team Olympics, or cooking classes. If you want to focus more on personal development, consider having your team speak about opportunities in their lives or plan team building activities that encourage problem solving.

Step 8: Provide Internal Networking Opportunities

Internal networking involves reaching out interdepartmentally for one-on-one conversations to grow workplace connections. While hosting a company retreat, this is the perfect time to foster such opportunities.

Most employees forget they have a strong network to help answer any questions they may have. Not only can connecting with those around you help with complicated tasks, it can also increase employee motivation, engagement, and productivity.

Hosting a dinner party, team mixer, or one-on-one meetings are great ways for your team to connect with co-workers. Knowing team members that are there to help can increase productivity by 21%.[1]

Step 9: Reconnect and Reflect

After the event has run its course, come together and speak about the highs and lows as a team. Not only can this spark gratitude, it can also uncover what could be done better for the next company retreat.

Book an office boardroom after the event and provide lunch for your team to come together and reflect on the great time they had collaborating with each other. Encourage your team to share their favorite and least favorite parts of this retreat. Not only goes this spark thankfulness for your team, but it also provides constructive criticism for next year’s planning.

5 Benefits of Taking a Company Retreat

Now you might be thinking—is a company retreat actually beneficial? Some employers say getting out of the office with their team increases their drive, while others might say it’s a waste of time. Read on to learn five benefits of planning a company retreat for your team.

1.Destress and Refocus

No matter how encouraging and comfortable your office might be, there are always going to be stressors in everyone’s career. Encouraging time to unplug and get out of the office with your team can help reduce stress. In fact, 80% of employees find their work more stressful than not, so take this opportunity to refresh as a team.[2]

2. Get to Know Your Team Outside the Office

Over 76% of employees admit they’re more productive and have more compassion outside of the office.[3] To solve this problem, get out of the office and into an environment that encourages collaboration on the team without revenue in mind. This can open the door to gratitude and motivation for everyone on the team.

3. Explore New Places to Spark Inspiration

While getting out with your team increases motivation and inspiration, so does traveling. Enjoying time away from the office with your team can allow you to reconnect your coworkers, increase collaboration, and reflect on the recent projects you and your coworkers have worked on together. Hit that reset button by traveling to a different destination and allocate time for team bonding to gain new perspectives and drive.

4. Provide Time for Reflection

Reflecting on the good and bad can help your team learn from past mistakes. When done as a team, this can help everyone put their best selves forward every day. Schedule time for your team to reflect on the good and bad to help improve meetings, workplace structure, and the short- and long-term goals of your establishment.

5. Increase Empathy and Gratitude 

Creating memories with your team can show how much you value their hard work and dedication. Coming together at the end of this event to point out the good times can uncover what you’re truly grateful for and encourage more gratitude in the workplace.

How To Plan a Company Retreat

Infographic Sources: 

CPA | 10KTEN | Working Knowledge | Positive Adventures | Positive Psychology | Entrepreneur | HBR |

Article Sources:

  1. “10 Timely Statistics About the Connection Between Employee Engagement and Wellness
  2. “Workplace Stress
  3. “76 Percent of Employees Are More Productive When They Leave the Office
Meredith Wood
GM, New Markets at NerdWallet

Meredith Wood

Meredith Wood is the founding editor of the Fundera Ledger and a GM at NerdWallet.

Meredith launched the Fundera Ledger in 2014. She has specialized in financial advice for small business owners for almost a decade. Meredith is frequently sought out for her expertise in small business lending and financial management.

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