Planning and executing a flawless corporate retreat can be a real bear.
This is an extensive Step-by-Step Company Retreat and Offsite Planning Guide. Follow this guide to streamline and simplify the planning process and set yourself up for a smooth and amazing retreat for your team.
This is the exact formula we use to save our own team dozens of hours for every step of the planning process.
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Here are the steps to streamline and simplify planning your next Company Retreat. Click a link to jump to that section.
Before we get to the good stuff, we should probably address the elephant in the room: Ms. Rona. From venue to safety and everything else, we’ve got you covered with everything you need to plan your next employee retreat!
To be remote or not to be remote, that is the question. The biggest thing to consider when debating whether to hold your company retreat in-person, aside from state guidelines, is employee preferences. While the vaccine may ease some minds, others who are immunocompromise, or leave with those who are, may still be uncomfortable with an in-person employee retreat. Before getting to far into the planning process, take a poll to gage your employees preferences. You can also ensure that everyone must test negative ahead of time to help ease some people’s worries.
Venues
If you do decide to host your company retreat in-person, consider having into outdoors to optimize safety and cut-back anxieties. Some great ideas for outdoor retreats are:
After a year in lockdown, the thought of a social event can sound magical and daunting all at the same time. The key to easing anxieties: finding the sweet spot for time. First and foremast, establish an agenda. What are you going to be discussing at your company retreat. No one likes feeling like they wasted their time so making sure the itinerary is intentional is a must! While the sweet spot for a retreat is anywhere between one to three days, the exact time depends on your itinerary, as well as travel time.
Flexibility
It’s been a long year for everyone. As much as we’d love to pick back up where we started, things are different. People are working from home, their kids my be taking classes from home, their financial means may have changed. When planning be considerate of everyone’s boundaries. Make sure they know this is a fun opportunity for productive team-bonding and not another hassle.
Cleaning
Whether you decide to host your retreat in a park or a luxury hotel, make sure to prioritize safety. Bring hand sanitizer, wipes, masks, and have everyone get tested ahead of time!
This is going to be the foundation of any successful retreat. While we’re working on 10+ company retreats and offsites per month with our clients, it’s vital to have a clear understanding of these elements before really diving into any project.
We always recommend working in a collaborative environment when trying to define the goals and the vision. Most often, the budget is assembled along the way but it is important to have a rough idea from finance or leadership on what they are ok with spending on the retreat.
Identifying The Goals: Is this all work, all play or a mix between the two? Are there specific work sessions you want to tackle while away on the retreat? Do you want to see increased communication among new team members? Do you want people to create new connections and have a better understanding of how each role is essential within the growth and sustainability of the business? These are some of the questions we dig into while trying to identify the goals of the retreat with our clients.
Identifying the Vision: We like to ask our clients to describe a rough itinerary outline of the employee retreat at this point. If you build a rough itinerary on paper, this can give you a really good starting-off point in the next phases of the retreat planning process. For starters, we use blocks of time with key elements from the goals section to fill in a rough itinerary. Some key elements are typically as follows: Transportation, Meals and Drinks, Team Building, Local Experiences, Work Sessions and Downtime.
Identifying The Budget: Work with your leadership to identify a targeted price per person for your retreat. Once you have a target number here, we can reverse engineer the experience based on your goals and vision as described above.
We use forms for much our planning process with our clients. Start with your leadership team and find a window of dates that work the absolute “must attend” people. Typically, we will walk away with 3-4 ideal date windows that work for the company from here.
This is where we see a lot of our first-time clients engage our services. Don’t get overwhelmed but also know that if you’re really looking for that perfect venue, it can become a time consuming process.
Here’s a roundup of our top destinations and venues for Bay Area Corporate Retreats, New York, and Austin!
For venue research, you have to have a good idea of about how many people will be attending. Don’t get to hung-up on the number but make sure have a good realistic estimate.
Take your budget per person and multiple it by 35%. This is your rough venue/lodging cost target for your company retreat. If you have $1,000/person for a 2 night retreat. You should target for $175/night/person for the venue/lodging, maximum. If your team is sharing rooms and you’re looking at a typical hotel stay, your are looking at hotels up-to $350/night/room.
Let your vision and goals help direct the region you start looking in first. We always try to get a sense of destination style from a client. We break it down as follows: coastal/beach, Mountain, River/Lake, Glamping/Camping, or City/Urban.
Retreat Planning Pro-Tip: Always negotiate with the venue for inclusions once you have decided where you want to go.
Retreat Planning Pro-Tip: Ask the venue for a rooming list template. They will typically provide a sample rooming list you can easily fill-out and return to them to simplify the check-in process.
The earlier you can get the Save The Date out for your next company retreat, the better. Use an internal calendar or use a site like Paperless Post.
Transportation can open up a whole new can of worms if you try to approach the subject too early in the game.
Remember, our goal here is to simplify and streamline the retreat planning process.
What we know about your next company retreat: The approximate number of people attending, where you’re going, the dates of the retreat and the targeted budget allocation.
First off, if you are already tight on budget, our first recommendation is going to be to look at arranging carpool options for your team. Make sure the venue has enough parking spaces for your group and, if they do charge for parking, you’re going to need to negotiate to get that comp’d.
Most often, for our clients, we’re looking at booking private transportation. This is executed in one of two ways.
Transportation Planning A: Full-time transportation throughout the retreat
Transportation Planning B: Two-way transportation. This means that the bus will pick your group up at specific locations and drop everyone off at the venue. On check-out day, the bus will be back and take everyone home. Typically, we like to keep it to 2 total stops per bus but certain cities provide various options in this regard.
All-in-all, the venue, the number of people and the itinerary will be the best indicator of the transportation option you will need. If your group is more than 50 people and you’re investing in multiple off-venue experiences, we’re going to recommend hiring transportation for the entire duration of your company retreat.
Retreat Planning Pro-Tip: The Offsite Co. has a partnership with a U.S. transportation company serving 33 cities throughout the country. Our pricing is typically 30% below group quoted rates.
Retreat Planning Pro-Tip: The venue you’re working with might have a great resource for transportation.
Retreat Planning Pro-Tip: If you’re looking at 50+ person charter buses, make sure to confirm with the venue that a large bus can easily access the front-door or check-in area of the property.
The food and drink on a company retreat, when handled correctly, can really be presented as a highlight experience for all. We focus on designing at least one meal as an elevated time for people to connect over food. Here’s our process for organizing the food and drink of a company retreat:
Another important thing to consider when making your retreat as epic as possible is balancing work and fun. While including breaks in between work sessions is essential in preventing burnout, you also need to make sure you're scheduling the work time efficiently. Blending sessions, speakers, and ad-hoc syncs will help to break up the work sessions and prevent them from feeling like another day in the office. Consider adapting Zapier’s method of designating themes for each workday. This allows each day to be productive, while also preventing it from feeling too repetitive. Some themes to choose from are marketing, team-building, and product management.
Depending on the goals of your employee retreat, this will be an action item on your list or you can skip it. Most times though, we want to have at least one area where people can get together to get work done. If you’re like us, we want that workspace to be an inspiring place for people to meet.
Work with your venue to negotiate inclusion for a workspace inside of your quote. For smaller teams looking to get more work done, we use sites like Breather and Splacer.
There are lots of ways to make the most of your work session.
Two common goals we hear everyday for our clients when we ask…why are you investing in this company retreat for your team.
A) Get everyone aligned on the mission and vision of our company
B) Build real human connections between colleagues.
A strategic and fun approach to the work sessions on your next company retreat can actually help check the box on both goals mentioned above.
From our perspective, the goal around work sessions is to do two things:
a) Inspire the collective team on the Mission and Vision of the Company.
What we want to do here is have everyone feeling like they are all-in on the mission when they fly home. We want everyone to feel like..hey, I’m on this rocket ship with this community of people. I
Let’s start by focusing on some fantastic All-Hands meetings at your next in-person company retreat.
1) Where we have come from
We like to do this in a very casual way on the first night or the at breakfast on the first morning of the retreat. Have leadership get-up in a casual environment and share some anecdotal stories about where the company has come from. What we want to do is HUMANIZE the history and ethos of this fast-growing company and the leadership.
If you can help the team see that this was, at one point, just an idea. It took incredible amount of hustle and build to get it to where we are today. Share some fun stories of those early days.
2) Where we are Today
This is a great session to use an all-hands meeting for. Build a simple PowerPoint outlining where the business is today. It’s important to be vulnerable, both from a leadership perspective and on-behalf of the business as a whole. We all know it’s not all Roses around here. Make a point to outline the good, bad and ugly that’s going on.
One way to do this is to outline a Competitive Analysis for the business. You don’t have to go into deep deep detail but it shows that we HAVE MOMENTUM and WE HAVE HOLES to fill in the business.
3) Where are we going:
Let’s sell the vision now. This is where we have the opportunity to go. If we can all execute on our strategy; the big carrot is out there for us.
Remember, we want people leaving feeling like they are a part of the biggest opportunity in your space out there!
Breakout Small Team Meetings:
Now that we have told this story of where we came from, where we are today, and where we have the opportunity to go; let’s figure out how we are going to get there.
1) Split the teams up at random and have them tackle different elements of your growth plan. This can be tactical strategies or it can just be a thought experiment with small teams getting together and poking holes in the strategies around where we are going.
2) Split into teams by function.
This is a fantastic time to let various team functions simply work together, in the same room. Team leads can either develop a conversation or project for the group to tackle OR, they can just decide the team will benefit to work on their own but in the same room.
Closing out Work Session Content on Your Company Retreat:
1) Pre-Assembled Question and Answer:
Send out survey to the entire team. Ask them, if you could ask one question to leadership entirely anonymously; what would it be?
Comb through those questions submitted and cherry pick 7-12 of them.
Give them to leadership before the event so they can be aligned on the answers to these questions.
Set-up a Fireside Chat environment and have someone from your team ask the questions to leadership.
Now we’re onto the most exciting and, in our opinion, the most crucial element of any company retreat or team offsite; The Experience! Going back to your goals, vision, sample itinerary budget; you can create a good idea of what the activities and experiences look like for your team. Planning activities for your group doesn’t have to be a stressful job and you just have to remember that know one knows your company, your culture and your people like you do.
Company Retreat Group Activities: For team building activities, we always recommend running a specific event focused around getting people to connect in new ways. Most of our clients opt for us to design a team olympics, fun run or a scavenge hunt. There is no boiler plate itinerary inside of these activities and each can be highly customized to pull unique things from your company culture to drive better engagement among colleagues.
Company Retreat A-La-Carte Activities: For any size company retreat, we typically offer some time for people to choose what kind of experience they are excited about in the specific destination you have chosen. These include things like white water rafting, kayak tours, hiking, bike tours, survival workshops, crafting, poker tournaments and much much more.
Planning for experiences and activities on a employee retreat is where our process extends beyond any event planner or hotelier. The magic is in the process of truly identifying and understand your leadership goals and vision for the retreat. If you’re stuck here, go back to that first itinerary you built and think about the high-level goals you set out. If everyone walked away with one highlight feeling from this retreat, what would it be?
Retreat Planning Pro-Tip: Giving your people a window of time to pick their own experience, from a list provided by you, is a great way to show them that the retreat is truly meant for them. To be able to express and explore their own fit inside of the company and the culture.
Team building can be such a scary thing to approach. A healthy and diverse company will see colleagues from all different paths in life, different skill sets, different goals and different interests. Your goal in designing the team building experience is to connect people in new ways. So that when they are back in the office next week, they might have an inside joke or an inspiring moment between them to talk about.
We believe this can happen at various levels and times throughout even a single day retreat and that is why we separate team building time on company retreats into two categories; Structure vs Unstructured.
Structure Company Retreat Team Building:
The Team Olympics: We’ve been running these for years. 40-90 minute event where you will organize everyone into random teams. We do the team organization as an ice breaker event so that off-the-bat, people are connecting in a new way. Once you have team, ask each team to name their team and design a flag. Now we go into a series of 10-20 highly customized events. Each team member has to choose an event to take part in.
Scavenger Hunt: Not your granny’s scavenger hunt here. 90+ minute event that is specific to the destination and venue of your choosing. Split people into teams in the same way as the team olympics. Work with the local area and inside of the vibe of your culture to design various stops for your team collect things. We like the end the scavenger hunt at one location for happy hour or party.
Going back to that initial itinerary you created, we can now fill in each item with a specific Name, Description, Time and Location. We build out these itineraries in a google spreadsheet with our clients. We also color code experiences differently based on the following: Transportation, Meals, Activities, Workspace, Downtime.
Trust us when we tell you that we know what you’re trying to tackle here. If you follow the steps above, we hope your planning process will be much more streamlined. The more you can solidify before the retreat starts, the more you will be able to enjoy the retreat.
