How To Plan A Corporate Retreat: A Step-by-Step Guide

By: Flok
Last updated: November 01, 2023

Whether you’re looking to boost morale and company culture with an offsite team building experience, provide training in an unstructured environment, or simply get your entire team together after one too many months apart, a corporate retreat is the way to go. But here’s the thing: deciding to take the plunge and invest in a getaway is the easy part. Then comes the planning. From selecting a destination to sorting out logistics, building an itinerary to finding catering, the process can be overwhelming — not to mention time-consuming.

Below, we break down the nuts and bolts of planning a corporate retreat that fits your budget and team goals.

First things first, define the goals of your corporate retreat

Why are you bringing your team on a retreat? That’s the first question you should be asking yourself. From a work perspective, teams often use corporate retreats to reflect on past performance, plan for the future, and hammer home the company's vision. It's also great to be able to host brainstorming sessions with everyone in the same room. In addition to work, companies try to foster team building and psychological safety among team members. Retreats are meant to be fun and social! Whatever the case, be clear about the objectives from the outset because that is what will inform the remainder of the planning process.

From there, begin thinking about retreat location

There are multiple considerations that come into play when deciding where to bring your team.

• Retreat goals
  If team building is high on your list, it’s important to consider locations with ample activities either in the resort/hotel or in the surrounding area (think hiking, boating, skiing, water sports, yoga, etc). If you’re hoping to have the team work in the morning and enjoy downtime later in the afternoon, locations with work-friendly venues (fast wifi, suitable table space, etc) are critical...more on that below.
• Budget
  Unsurprisingly, price is typically the biggest determinant of location. If you’re budgeting $2000/person, for example, European locations would be off the table since an average flight from the U.S. would run you around $1200, give or take depending on what coast you’re on. However, domestic flights can come in at under $500, meaning there’s more room for upgraded lodging and additional activities.
• Duration
  Even if your budget allows for an international trip, your allocated retreat duration may not. As a rule of thumb, we recommend stays of at least one week for international trips to account for travel time, jet lag, etc. For domestic trips, 3 nights/4 days can work well.
  
  If the trip is domestic but select team members are coming from overseas, Flok recommends flying them in a day or two early to allow them time to settle in. This way, you don’t have to increase the trip length for everyone (which will up your costs).
• Time of year
  Once you define whether you want warm weather (for beaches, hiking, etc) or cold weather (for skiing), then it’s important to think through time of year in order to identify peak/off-seasons. Traveling to Vail, Colorado in February will cost you a whole lot more than July. The same goes for tropical locations like Jamaica, whose airfare and hotel prices surge during the winter months in the U.S.

Be smart with your choice of venue

Keep in mind that the goal here is to strip away the “corporate” elements of the workplace to allow space for more fluid, informal bonding. So when you’re selecting a venue, prioritize spaces that have a more homey, “fun” feel rather than the more traditional conference halls.

For small teams under 10, well-designed Airbnbs or villas are a great option. Between 10 and 50, boutique hotels tend to work well. Above 50 team members, companies typically rent out a section or even an entire hotel or resort.

A shortlist of things to look for when selecting a venue include:

• Fast Wifi
• Workspace and meeting rooms with suitable tables and outlets
• AV setup in case you’re hosting all-hands or C-level presentations throughout the retreat

Looking for help planning your next corporate retreat? Turn to Flok. We’ll save you weeks of planning and months of stress by coordinating everything down to the last detail.

When selecting a retreat venue, ask about their food and beverage programs

Oftentimes, hotels will provide a food and beverage minimum for large groups. The bigger the minimum, the cheaper the rates. While that sounds like a no-brainer, keep in mind that your team will likely not want to eat every single meal at the hotel, especially if you’re in a location with a vibrant food scene. If you do decide to plan off-site dining experiences, select when and where you’ll be eating early so you can secure reservations for the group (or have Flok do it for you).

Looking for more guidance on venue selection during the planning process? Our friends at The Vendry have some great tips.

Plan retreat activities, but leave room for flexibility

Depending on your company goals, you may have allocated unstructured free time as part of the retreat agenda. However, if you’re hoping to plan a few fun activities or excursions, here’s what we recommend:

• Select team building activities that you can split off into smaller teams to do, such as cooking classes or scavenger hunts
• Provide options for more active opportunities (e.g., hiking, yoga, water sports) as well as laid-back ones (e.g., board games) to accommodate for people’s preferences and comfort levels when it comes to icebreakers
• Consider hosting “un-conference” talks where team members volunteer to give chats about specific areas of expertise
• Get (a little) personal by hosting sessions where team members share a bit about themselves outside of work (about their family, where they grew up, where they went to school, etc)

A note on timing...

• Plan early!!
  When you should start planning depends more on your team size than on the destination. As a rule of thumb, we recommend kicking off the process at least one year out for teams of 100+ people, otherwise it’ll be difficult to find venues, transportation, and dining to accommodate the large group. For teams of 50 people, 6 months is best, and smaller groups of 10 can get away with 3 months.
  
  
• Flexibility is key
  Odds are you may be hiring between the time you start planning and the date of your retreat...especially if you’re a startup. If possible, try to project your future headcount (easier said than done, we know) and be flexible in the planning process in case you need to find a last-minute flight or book a room for a new team member.

Looking for some help planning your next company retreat? Flok’s got you covered. Whether you’re a startup, small business, or large company, we’ll do the heavy lifting to find your ideal destination, book your work-optimized venue, plan team-building exercises for the ultimate bonding experience, and coordinate flights. All you have to do is enjoy (finally) getting your remote team together. Safely and efficiently.