Planning a company retreat can be a monumental undertaking. Don’t stress. We got this.

There’s really nothing sweeter than being on-site and looking around and knowing you dominated this years company retreat!

Below is a step-by-step guide that anybody planning a retreat for any size team with any budget in any destination can follow to simplify and streamline the entire process. We use it for executive retreats of 15 people and company-wide retreats of 200+.

If you’re not investing in your employee experience, how much can you expect your employees to invest in your client experience? Leading by action is not an idea; it’s’ a business model.”
-Offsite Co. Founder - Mat MacDonell

With over 5 years of planning company-wide and executive offsites; we’ve picked up a few processes that not only save our clients time but, most importantly for us, save our event producers and coordinators time. But hey, we don’t want to wave any false flags. It hasn’t always been like this. We’ve made every mistake you can imagine over the years and it took us a lot of work to get our service to place it is today for our clients.

Hopefully this guide can help minimize some of those mistakes and, most importantly, streamline and simplify your time and effort on this project for your team.

15 Steps to Planning Your Next Company Retreat

1. Vision, Goals and Budget

Sorry for to those of you who have read through the Ultimate Retreat Planning Guide ebook but we’re not going to stop beating this drum.

Always start by identifying the Vision, Goals and Budget with your leadership team. Starting here will save you so so much time at every step of the process moving forward.

Setting the VISION means having an keen understanding of what the experience might actually look like for any employee while on-site. What does a rough itinerary look like? What is the lodging situation look like? Single rooms, shared rooms, are bunk-beds ok, how about glamping? Are we looking to offer just beer and wine or do we wan’t a full-bar? How much space do we need for an all-hands session? How important is Wifi, Cell Service or a VPN?

The more specific you can get on the VISION, the easier your job will be in the next step.

Identify the GOALS your team has in putting this retreat together? A great question to ask your team is, “why are we investing in this experience for our team?”

A common goal for more distributed clients is to introduce team-members that have not met before and get everyone in the same room to share the vision and goals of the company going forward. We’d recommend have a list of 2-3 goals, maximum, for your retreat.

The BUDGET conversation needs to happen to here? Based on the vision and goals; how much are we ready to spend for this experience. If you need some fire power for a budget conversation, check-out the Vision, Goals and Budget workbook and article.

2: Date Windows

Don’t let your leadership off-the-hook yet! We need date-windows from the VIP’s to make sure we’re researching dates that work for everyone that absolutely has to be there. Ideally, we would have 2-3 windows that can work before we get into the venue research phase.

3. Budget Estimates

Now, we want you to create a target budget for your venue research. This is going to save you TONS of time here! Here is the way you can calculate your target budget for venues.

Total Out-The-Door Retreat Budget: $120,000 for 100 people for 2 nights

Let’s say that 20 people have to fly-in. We will give them all a $400/person budget right now.

Final Budget Minus Flights: $112,000 for 100 for 2 nights

112,000 / 120 / 2 = $466.66/night/person

$466.66 x 30%(lodging budget): $140.00/night/person

We have a lodging per night per person target! Let’s Go! Wait, keep in mind that this is just a compass for ourselves as we dive into venue research. We know that hotel rooms for $300/night w/ 2 beds in them will work for your group. We also know that a buy-out ranch or camp needs to land under $150/night/person just for the lodging element.
This is a healthy budget and we shouldn’t have an issue here!

4. Find The Perfect Venue

Strap in because if you’re going this on your own and it’s your first time planning a retreat, you will most likely hire us next year.

With a good idea of the budget estimate, # of attendee’s, date windows, vision for lodging and venue, goals and requirements for a venue; you’re going to be able to cross a lot of venues off the list without dialing a group sales office or submitting an RFP. (For new planner - this is a good thing)

Hit your favorite search engine and focus in on 3 areas that you believe are great based on the vision component you worked with your leadership team. Try to find 2 great venues that fit inside of your scope in each area. Once you have 6-10 venues that you think are solid, then start to reach-out and check availability and pricing. If you think the venue is over budget - we like to send them a budget in the initial email and say - if you can make this work at your property for this price, let me know.

Once you have 4-5 venues that are great for your vision and goals and fit in or around your budget - we recommend putting together a presentation for your leadership so you can get feedback. Also, make sure your leadership knows - we need to pick one of these venues because there are not a lot of other options out there. Make sure they know how much research you did.

5. Rough Itinerary

Congratulations, you have a venue for your next company offsite! Wahoo. it’s (mostly) fun stuff from here.

Now that you have a venue contract - work with the venue to design a rough itinerary for your retreat. We use google sheets and even build deck presentations here - whatever works for you and your team.

6. Food and Drink

Most likely, your venue comes with F&B or you have an F&B minimum in your contract. We recommend starting to work with your venue contact or catering contact to design basic menu’s for each of the meals. Keep in mind you will be coming back to them to take care of all of your people with allergies and preferences.

7. Workspace and Work Session Content

We’re seeing an increasing trend in a decrease of work on our retreats but we’re not complaining. If you do have worksessions planned, make sure you have a clear understanding of the set-up in the room(s) and the AV equipment included or that needs to be rented to execute your meeting sessions.

Work with various department heads to inquire about who needs and wants to run a meeting.

This should all go into that Rough Itinerary we talked about before.

8. Team Building and A La Carte Activities

Now for the fun part. We always recommend at least one structured team building event and an array of options for A La Carte Activities for people to partake in. Either run the team building yourself or, if you’re working with us here at The Offsite, we work with you to design and execute a customized event.

Next, take a couple hours out of the itinerary and hold it for A La Carte Activities. Find fun, bucket-list style activities in the local area or on-site and open it up to interested based activities to your team. *We’ll come back to this in our Survey’s section.

9. Special Events

At this point, you have a pretty clear understanding of the retreat and it’s time through some WOW factor in there. Special events can be elevated dinners, a happy hour with lawn games, a karaoke and bar night, a talent show etc. Work with your venue and any additional vendors you need to get something on the itinerary that brings that WOW.

10. 2nd Itinerary

Now we’re really cranking. Let’s take a step back and look at the itinerary. How is the flow of the retreat. Is there enough room for every activity to be a bit late? Because, everything is always a bit late.

11. Surveys

We really try to keep the maximum # of surveys we send to a team at 2. It’s possible but really depends on the venue, the group, the itinerary and more.

Typically, we want the following information

Confirmed Headcount; Rooming List; Meal Preferences; Physical, Religious or Spiritual restriction from partaking in anything, Activity Option Choices.

12. Transport + Swag

You have your headcount, your venue and your dates. Time to book transportation. We wait a bit later for this because headcount change so much from a client engages us to when we actually need to book.

We might recommend getting a quote once you get a venue and then putting that as an estimate in your master budget tracker.

Swag - Let us know what you need. We’ve done everything from custom tee’s and stickers to custom sleeping bags.

13. Retreat Overview + Weekly Calls with Key Vendors

Open up a blank document and type out every elements of the retreat. Include all vendor contact information and every bit of the retreat. Aside from making sure all of your vendors where they need to be and what they need to do - we also want to make sure someone else can run the event if you’re sick or even just decide -
I’m gonna have some fun.

14. Landing Page + Communication Channel

We like to build custom landing pages for each retreat so our clients can have their team access those before, during and after the retreat.

Also make sure you have everyone on one communication channel! When things run late or meeting locations change - we wan’t everyone to know.

15. Enjoy!

You put a Sh*T load of time into this. Don’t forget to take a breathe and enjoy the process. Even more important, take a moment while on-site to take it all in. You did an amazing job.

Thanks so much for your doing what you do! Culture curators around the country are designing these high-impact events to keep engagement high and to motivate a more connected culture. You don’t get enough praise for tackling this project and so many others!

Let us know however we can help.

If you’d like to download the Ultimate Retreat Planning Guide. Click here.

To learn more about The Offsite Co., you can check-out our About Us page.

How to Plan a Company Retreat: 15 Steps to Getting Started Today