Retreat Planning 101

Ashley Ross
July 9, 2018

As companies grow and offer a greater variety of cool office perks, expectations may rise concerning company retreats. Events that take employees out of the office and into a new environment—whether for a night of laser tag or a weekend of skiing—provide loads of opportunities. The primary reason for a retreat could be to boost morale, reminding employees that they’re appreciated and giving them space to mingle with teams. Retreats also give companies and employees space away from desks and computer screens to brainstorm and plan for new projects, next year’s goals, and beyond.

It takes skill to plan a great retreat, it is even harder to pull one off without a hitch. Whether you’re planning your first or fifteenth retreat, here are some tips to make sure your company has a blast—and you do, too.

1. Gauge what people want to do

If you’re starting with a blank slate, talk to people in your office about what they actually want to do. Some people dread spending time with colleagues outside the office, particularly for an extended period of time. While that might not be the case everywhere, keep in mind that your company’s retreat should be as engaging as possible for everyone. Talk to everyone in your office, or poll them with a Google form, and then plan what seems like the most fun, all while keeping your company objective in mind. If you’re taking direction from an executive on what to plan but you know a majority of employees won’t enjoy it, speak up with your concerns. Use the data collected from the surveys to showcase your employees’ desires. The last thing any executive (or employee) wants is a retreat where few people have a good time.

2. Set expectations

Let everyone know exactly what to expect for the event. Public itineraries are a great way to provide this kind of intel, listing addresses, phone numbers, hyperlinked Google maps, addresses, Wifi passwords, rules, safety precautions, menus—you name it. If the bar is only going to have beer and wine, give people a heads up. If the hotel doesn’t have air conditioning, let everyone know. These sorts of things will not only make people feel ready for what they’re attending but should keep them from complaining if they’re surprised by something.

3. Sort out finances ahead of time

Before you enter your credit card number on anything, clear your spending with the powers that be. Make sure you know exactly how paying for things will work, whether you’re using a company card or your own card to be reimbursed later—get the details in writing. Then follow protocol, save receipts, and submit any expense reports as soon as possible.

4. Know what you are signing up for

Be sure you’re clear on cancellation policies, late policies, options if weather gets in the way, you name it. If you know exactly what you’re getting into, it’ll minimize any potential surprises if things need to be changed.

5. Have a contingency plan

It’s rare for any event to occur with zero problems. Work with your executives to prepare for potential disasters and have a solid Plan B ready. For example, in case your catering company bails last minute have a few quotes lined up for a different vendor to take its place. Be ready for things that can happen overnight, too, like people getting sick or drinking too much, and have a plan in place for how to handle (and even prevent) things like this.

Retreat Planner Checklist

  • Poll attendees on what they want to do / where they want to go, etc.
  • Get approval from executives
  • Get finance plan in place (i.e., how to pay for and expense everything)
  • Create a detailed itinerary and share it with attendees
  • Clear any cancellation policies with vendors you are using (be sure to ask about weather cancellations as well as last-minute drop outs)
  • Create Plan B options for everything

While there are many great options for company retreats all over the world, we chose to highlight examples near San Francisco and New York City.

San Francisco Bay Area

1) Lake Tahoe

Lake Tahoe is an equally great option for both the winter or summer months. In the summer, enjoy boating on the expansive mountain lake, going to the beach, or if you’re feeling lucky, head to the casinos in South Lake Tahoe across the Nevada border. In the winter, you’ll have access to world-class skiing and winter sports, plus those casinos.

2) Wine Country

Team bonding paired with delicious wine equals a winning combo. There are plenty of bus and limo rental options for team tastings to ensure you have a designated driver. Napa and Sonoma are both known for their great wine and fine dining options that would make any team forget the stress of impending goals and deadlines (at least for the day!).

3) Big Sur

For teams who are feeling a bit more outdoorsy, Big Sur is one of the most beautiful stretches of coastline in the world. Located south of San Francisco, this is the perfect location for camping or renting a scenic cabin overlooking the Pacific Ocean.

New York Metropolitan Area

1) The Catskill Mountains

When New Yorkers want to escape the concrete jungle, they often head up to The Catskills. These famed mountains have long been a refuge for artists, musicians, and writers. There are plenty of quaint lodges to rent and take in the fresh Appalachian air.  

2) Beacon, NY

Beacon is unofficially known as the hippest city in the Hudson Valley. Whether it’s shopping, museums, restaurants, or incredible views, there is no shortage of things for your company to do there. Plus, it’s only a short hour and a half drive from New York City.

3) Hudson, NY

Hudson, NY is located on the east side of the Hudson River. Originally settled as a whaling town, Hudson is quaint and has a rich history to explore. Your company can enjoy getting to know each other better while wandering Main Street, visiting a craft brewery, touring a farm, or taking a hike in the mountains. As an added bonus, you can easily get there via Amtrak.

Whether you’re looking to celebrate a company milestone, counteract employee fatigue, or just want an excuse to get everyone together, company retreats are a great way to boost employee morale and strengthen relationships.

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