10 Ways to Dominate Your Company Retreat

Planning an overnight offsite for your team can be one of the most daunting and challenging tasks on your plate for the year. The worst part, it probably wasn't even listed in the job responsibilities when you applied.

planning company retreats

It's so common for a first-time founder to be hot off a funding round and to look over at an OM, EA or HR rep and say, "Hey, can you get put together a company retreat for us?" She has NO IDEA what the roadmap looks like for you between this statement and a finalized venue with a full itinerary of food, activities, work session content, transportation etc.

Here's our roadmap to help streamline and simplify the next steps in this retreat planning process for you:

  1. Get The Budget: Your boss, at this point, will probably throw out a completely random number. "Let's keep it under $10k." That's not going to work so let's take a step back.

  2. Vision, Goals and Requirements from Leadership: To get started, meet with your leadership team and get a really idea of what they envision for this retreat? Starting with the basics-> Who is going?, what are we doing?, where are doing it?, when are going?, and the most important, WHY are we investing in this? A typical scope of a project might look something like this: Who: All employees(office+remote). What: One night retreat with company-wide work sessions, mixed team breakout sessions, a team building activity, a nice dinner party and some karaoke and other fun organic bonding opportunities. Where: driving distance from office (within 2 hrs of office). When: Ideal Date One(+back-up dates). Why: We have a lot of new hires and hope that people can connect in an out of office setting. Get everyone on the same page with the current state of the company and have a shared understanding of where we are going. Create unique bonds and a strengthened community around the culture in the company.

  3. Back to the Budget: Now you have a good idea of the vision, goals and requirements for the offsite from your team. Break it down per night based on the following categories and start allocating a dollar amount per required activity for the retreat. Transportation, Lodging/Venue, Workspace, Food and Drink, Team Building and Activities. We call this "Bones of the Experience" with our clients. Our recommendation for teams planning their first overnight retreat is to allocate at least $500/night/person for all-inclusive retreat experience. If your leadership is still stuck on that random low-budget number they came up with in their head, our recommendation is to focus on eliminating some of the goals and requirements and plan a single day experience without transportation or venue costs.

  4. Budget Allocation: Whatever your budget is, in the beginning of a new project, we work in terms of percentages to help find the perfect venue for your upcoming offsite. Our goal is to have the venue cost land between 28%-35% of your total budget for the experience. Let's say you have $600/night/person for the offsite and your team has decided on offering shared rooms for the attendees. Focus on venues that land well-under $360/room/night for an "out the door" rate. The lower you can go on the venue costs, the more budget you're going to have to invest in the WHY your team has decided to plan and execute this retreat for your team. Other Budget Allocation: Food + Drink(25%), Team Building & Activities(30%), Workspace(5%), Transportation(5%), Other(5%).

  5. Find The Perfect Venue: If one of the goals is to inspire a more cohesive and connected team, we always recommend starting with sourcing a buy-out option for offsite venue. You have your cap number based on the percentages above so it's time to hit the interwebs. Gather a list of destinations based on your leaderships vison, goals and requirements and start making a more condensed list of properties of interest. Once you have 5-8 seemingly PERFECT properties, boil that down to the top 3 and get in touch with them. Remember that you have very strong negotiating power here. These venues, most often, will be willing to provide steep discounts to get your team on-site, especially mid-week!

  6. Outline The Itinerary: Once you have a venue locked-in, build a sample itinerary that hits on all of things you want to accomplish on this offsite. Don't be afraid to dream big here, we can always dial it back once we cross-off a few essential items. A typical sample itinerary would have transportation, check-in, team bonding activities, a structured team building event, work sessions and meals.

  7. Planning for Team Building: No one knows your team or the inner-workings of your company culture better than you do. Use this to design team building events that allow everyone to showcase their individual skills, personality and expertise as part of a small group within your team. For teams of less than 40 people, we recommend structure activities like a a Kayak Tour, a Ropes Course, The Offsite's Wilderness Survival Training, GoKart Racing etc. For teams of 40+ people, we will typically design a customized collection of events like scavenger hunts, the team olympics, relay races etc.

  8. Bonding In The Seems: Most of the phone calls I have throughout the week revolve on understanding the goals of our potential clients. You won't be surprised to hear that almost every single retreat has a goal of team bonding and cohesion among the people. When you're designing the retreat, look in-between the major experiences for some super impactful, easy to manage organic bonding opportunities. This is especially important if you're working on a less-than-opportune budget.

  9. Pre-Retreat Hype: We always invite our clients to open the conversation to more people internally regarding the retreat. This can build the momentum and excitement for the retreat. We also encourage setting up a simple landing page with a high-level idea of the activities, the work that's going to get done and the experience to expect.

  10. The Retreat Overview: Thirty days prior to our clients departure, we provide a detailed overview of every elements of the retreat. This includes everything from contact numbers, additional vendors, menu's for each meal, room assignments and packing lists. This document will be your compass leading up to and while on-site the event. We also recommend having key vendors sign the document in agreement of the terms, timeline and deliverable expected before the event.

For some, planning this annual event is one of the highlights of their role within the company. Many OM's share the exact opposite sentiment. Whatever the case is for you, take it one day at a time and remember that the more up-front work you do with your leadership to have a clear understanding of the goals, vision and budget; the simpler and more streamlined the experience will be.