inline image

Rob Bellenfant is the Founder and chief strategy officer of TechnologyAdvice, a B2B demand generation company based in Nashville, TN. He is also a serial entrepreneur, investor, and public speaker with specializations in IT, sales, marketing, and talent development.

As summer approaches, many execs are setting their sights on the annual company retreat.

Retreats are fun, but they're also a practical way to boost morale, strengthen collaboration and introduce new business objectives. Getting on board with the idea of a retreat isn't usually the challenge: the challenge is planning and executing a retreat that proves to be enjoyable, rewarding and cost-effective for everyone involved.

As previous CEO and now Chief Strategy Officer at TechnologyAdvice, I've seen the way retreats can bring employees together. Employees get to have fun, make new connections and see their co-workers in a different light.

Over the years, we've taken trips to Gatlinburg, Holiday World and New Orleans. We've gone canoeing and rafting together, sung karaoke and pummeled each other in bubble ball.

Our annual company retreat has become a mainstay of our growth and culture; something the team anticipates every year and remembers for years to come.  How do we pull it off? Here are five tips to help you plan a "workcation" that everyone enjoys:

Set a Budget

Decide how much money you want to spend up front per person. Instead of picking an arbitrary number, set your budget based on how the company is performing against goals for the current fiscal year. Think of the amount you spend as a capitalized investment in your company culture.You want your team to have fun without breaking the bank, so look for ways to cut costs as you book travel, accommodations and events. If you're planning to fly, for example, pick an airline that offers a discounted group rate, as this can make a difference in cost. If you're interested in a particular tourist destination or attraction, consider going off-season to get tickets at a lower price.

Choose Your Destination Wisely

The destination can make or break a company retreat, so choose yours wisely. Propose three or four options that fit your budget, and then take a vote among your executive team.There are several important factors to consider here:

  • Attractions. Try to pick a city that offers a good variety of culture, food, music and attractions. You want enough to keep everyone entertained for a day or two and to elicit their interest in the destination.
  • Time of year. Depending on the destination you choose, the season may have an impact on the climate and what activities are available. This year, we held our retreat in January, so we headed south to avoid cold and snow.
  • Transportation. Moving from place to place with even a few dozen people can be logistically challenging. To mitigate this challenge, select a city with good "walkability" or low-cost public transportation. San Francisco, New Orleans, Boston, Miami, Washington D.C. and Seattle are a few of the most walkable U.S. cities.
  • Accommodations. Your hotel will serve as a forward operating base for the duration of the trip, so pick one with helpful staff and all of the amenities your team will need. Conference rooms? Shuttle service? Wi-Fi? Business center? Double rooms? An ill-suited hotel can easily ruin a company retreat, so don't skimp.  
  • Company culture. Pick a destination that aligns with your company culture. You know your team best, so you'll know what type of setting is appropriate. For us, something edgy and adventurous made sense, so we chose New Orleans.

Put Your Team First

It shouldn't be too difficult to get your team on board with an all-expenses paid trip that gets them away from the office for a couple days. Still, consider their needs and do everything possible to make the experience a positive one. Once you've decided on a destination, get people excited. You can plan various activities leading up to the departure date to build anticipation. For our New Orleans trip, we passed out goodie bags with Mardi Gras beads, masks and company-branded luggage tags.You should also make sure to communicate the trip itinerary, accommodations and travel plans clearly. This will make it easy for your employees to keep their families informed and prepare accordingly. We distributed a one-page agenda with addresses, contact information and daily schedules to keep everyone in the loop.

Make Time for Business

Let your employees have fun, but don't lose sight of important business goals and the mission that brought you together in the first place. Try to set aside one day to focus on business objectives. That could mean unveiling a new product, problem-solving an issue that you're facing or reviewing performance against goals.

Leave a Day to Decompress

Although it can be tempting to plan a trip outside of business hours, don't take up an entire weekend of your team's time. Leave at least one day (Saturday or Sunday) to let everyone decompress at home. In some ways, a company retreat can be more exhausting than the work week itself. You want your employees to thank you for the break in routine, not resent you for stealing their weekend. With the right approach, your company retreat can add real, qualitative value to the business. It can also be a strong selling point for attracting new talent. The key is to know your team, know your budget and plan a trip that is enjoyable and productive for everyone.