The Retreat Roadmap | Retreat Planning Guide

What if your only responsibility, every year, was to plan, manage and design your company’s annual retreat? Life would be grand.

Unfortunately, that is NEVER the case with our clients. Typically, we’re working with a point-person that has a full-plate of deliverables to attend to throughout the year.

Aside from the monumental amount of time that can go into planning a company retreat, there’s a lot of pressure to deliver a super fun experience for your colleagues.

We know this because it’s all that we do and we’re here to help. In an effort to help you wherever you are in your retreat planning process, we’re outlining the Retreat Roadmap that we work on with every single client. Here’s a step by process for organizing your retreat.

We’d also recommend checking out Retreat Planning 101: Finding the perfect venue.

Step 1: Create a spreadsheet that will be your master roadmap for all things retreat. We use Google Drive so we can share and work off of a live document both internally and with our clients. We’ve found it more customizable and easy to work through with our clients than other project management tools out there.

Step 2: Organizing the tab structure on your spreadsheet.

Tab 1: Vision / Goals / Budget

If you’ve been following along with The Ultimate Retreat Planning Guide or any of our other guide content, you will know that we consider this the absolute most important first step to help you manage your time and your leadership teams expectations.

Here is an except from The Ultimate Retreat Planning Guide in regards to Vision, Goals and Budget:

Now is the time to put pen to paper and make a list of your company’s specific Goals and Requirements for a successful retreat unique to your group. Go wild and wordy here, because you can always refine your list in the future. Here’s a few great ideas to get the ball rolling:

Goals:

  • Create an organic way for team members to bond outside of work

  • Engage in fun, friendly competition to uncover your team members’ hidden talents

  • Announce the launch of a new internal program

  • Connect new hires with colleagues outside of their department

  • Inspire everyone to understand the importance of their specific role in the new direction and functionality of the new company

Requirements:

  • Meals must include vegetarian options

  • Everyone needs their own room

  • Must be 3 hours or less from the office

  • Workspace needed for 100 people

  • Rooms needed for breakout sessions

  • Venue must be a full buyout

  • Transportation from office is needed

  • Venue must allow hard alcohol

Getting away on a company retreat with your team, you open up Pandora’s Box of new goal crushing opportunities between the leadership team and your employees. Not only does getting out of your current environment spark inspiration, new ideas, and promote strong company culture, it becomes an invaluable journey by creating bonds through a mutual experience that you bring back to the office at the end of your retreat.

On this tab of the document, you want a very clear and agreed upon list of Goals and Requirements from your leadership team. Of course, these might shift and change and you can take note of that along the way of planning the retreat.

Now we want to focus on VISION.

The vision for the retreat can include themes from your Goals and Requirements but we really like to use this as an opportunity to start to talk-out a high-level itinerary. What does the flow of the retreat look like? How many nights do are you thinking? What do the work sessions look like and about how much time do we want to spend working?

Here is your opportunity to ask a ton of open ended questions to your leadership team. Another way we like to frame a question here is as follows:

This retreat is a significant investment, why are we making this investment? What do we want to walk away with?

Finally, let’s explore the BUDGET.

Below is an excerpt from Retreat Planning 101: Vision, Goals and Budget

The goals and vision of your retreat are critical, but often times the most difficult topic to address with your team is simply how much to budget for an offsite experience. When meeting with leadership to discuss the financials of planning a retreat, we have found that it is most helpful to have a targeted price per person. Our recommendation for a starting number, for an all-inclusive experience, is $500/night per person.

Once you have the ideal spend in mind, we can reverse engineer your experience based on the goals and vision above. Remember that every dollar saved per person in one area can directly go to fund another more important part of your retreat. Below is some food for thought to further develop your ideal in-budget retreat:

Budgeting with your Team:

  • How much is your team wanting to spend per person?

  • What locations will allow our dollar to go the furthest?

  • Will transportation be handled individually or as a group?

    • Tip: If you plan to travel 2 hours or less from your office, carpooling is a great way to save of transportation

  • Is your team comfortable with single or double occupation?

    • Tip: There are lots of amazing properties with condo-style accommodations that are great on the budget, but provide each guest with their own private room and bathroom, while sharing a kitchen and common space.

  • What meals will be central to the group experience?

    • We have found that a lighter lunch is a great way to splurge on an amazing Happy Hour and Dinner experience!  

Know that even with a smaller budget, there are many ways you can organize an activity-packed retreat that aligns with your goals and vision, and also won’t hit too hard on the wallet such as utilizing local parks, beaches, or hiking trails for an afternoon adventure that are often free or only ask for a small donation to keep up the land.

The main items that drive the cost of a retreat are lodging, transportation, meals, and alcohol. If you find the perfect venue or the ideal team building experience that would be central to your retreat, you can always find ways to cut costs around the next corner. If you are sold on an afternoon kayaking adventure, you can alter your meal plan and save by doing casual boxed lunches to allocate more dollars towards your activities that day.

That is it for TAB 1! We have a well defined, for now at least - Vision, Goals and Budget for the offsite.

Tab 2: Retreat Planning Roadmap

Here we wan’t to look at a roadmap for the actual planning stages. This helps us commit to deliverables with a team. It can become tempting to procrastinate decision making for a variety of reasons and this tab reminds us that we need to make decisions today so we stay on track for the decisions we need to make next week.

A well planned and executed retreat is built like a house - starting with the foundation. And then each brick is laid up on the previous one set.

This page, on our Roadmap, is set-up in blocks of major decisions that need to be made. As an example, we have the following sequence to get to a Venue Decision:

  1. Venue Research and Proposal Gathering

  2. Venue Proposal Deck (to leadership)

  3. Venue Decision

This process keeps us on track with required meetings with the client on each step of the process.

Tab 3: Itinerary

With each new client, this is a blank canvas with the dates on-site clearly marked at the top of the page. We also find this REALLY HELPFUL to start filling this out sooner than later. A high-level itinerary can help your team dial into what the venue looks like.

This tab is continuously being updated throughout the entire retreat planning process.

Tab 4: Master Budget

Important One. We’re tracking the actual budget but also the estimated budget every step of the way. Once we have a venue decision - we have the Out The Door rate added to the Master Budget. At this stage, we might have estimates for things like swag, team building event and any other special events. We want to be making strategic decisions at every step and making sure we’re staying tight on the budget allocation.

Tab 5: Venues

Here is a list of every venue our team reaches out to for a specific project for pricing, availability etc. Even a venue that doesn’t have enough rooms or is way over budget goes in here. Who knows, a client might love it anyway or we might use it for another client.

Tab 6: Rooming List

At the beginning of the planning process, this is a blank page. Once you have a venue, ask them for a rooming list outline and upload it into this tab. You can start filling this out once you have that venue locked-in.

*it’s not uncommon for us to be working with forms to send to everyone at a clients organization to help organize rooming list preferences, F&B allergies and preferences and activity options.

Tab 7: Activities

If you’re offering a window of time for what we call 'a la carte’ activity options you will want this tab here. We also include any vendors or information regarding activity so that all lives in one place. In here should be a concise list of everyone who has signed up for that activity.

Tab 8: Vendors

Every single vendor you’re using for the offsite. This might include some of the following: Venue/Hotel, AV, Activities, F&B, Transport and more.

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