planning retreat

Planning Retreat the Right Way: A step-by step Guide for your Team Offsite

Before you start reading this, know that when we say “planning retreat the RIGHT way”, we are using tips from our own experience of conducting two offsites and not just mere facts. Here’s our team standing together at a beach in Goa in our recent offsite (January’23)

We bet that the moment you start talking about planning a retreat, the environment in your workspace is going to light up.

It becomes more of a necessity in a remote company. An offsite is the only time where employees get to know each other beyond work talks and G-Meets. That’s not it! Periodical offsites fosters collaboration and team-bonding among employees and increases productivity thus leading towards better business and employee retention.

But as fun as this looks and sounds, conducting an offsite is no piece of cake. It requires months of planning, checking out logistics, coordinating with vendors, and so on. So let’s begin with a step by step guide to planning an exciting retreat for your company and fulfilling the team building agenda through it.

Why should you do a company retreat?

Employer branding – ✅

Happy employees – ✅

Especially if you’re a remote company, team bonding – ✅

If this is a work offsite, these retreats and change of place can help you brainstorm better together with your colleagues. You and your teammates can develop a more collaborative approach and welcome more ideas and opinions.

If this a fun offsite, well, make sure you steer clear of any work-related discussions because things need to get happening. Company offsites have doubled in numbers because companies understand its value in terms of team-building and collaboration. Post the pandemic, these offsites have become a necessity, your employees might love remote work but they also want to meet their colleagues face to face atleast once a year. It creates a sense of belongingness and team-growth among them. So you don’t have to overthink the need for this and simply go for it.

How to choose a suitable place for your company offsite?

The kind of place you go for naturally matters. And that doesn’t need to be measured by how fancy the place is but on the following factors:

  • The nature of your offsite (is it a fun trip, go for a beach vacation. Beaches might not be suitable for work- related events. You can go for a resort outside the city in such a scenario.)
  • For a more adventurous or nature-oriented offsite, consider the unique and flexible option of RV rentals, allowing your team to explore remote areas without the hassle of tight hotel bookings.
  • What is the most accessible place from all different cities? Check through all modes of conveyance ~ trains, flights, and even by road.
  • Which place would require the least transportation? That is just an unnecessary, extra hassle and a lot of coordination to bring up.

Steps to conduct a team offsite effectively

Why are you really doing an offsite? Find the purpose for planning a retreat

Why are you conducting this offsite? For better team-bonding? To have fun? Or to discuss business (work offsite)? Depending on that you will also get a picture of what kind of a place would be suitable and how the itinerary would look like. If you want to simply enjoy, a beach place would be perfect. But in case of work offsite, you might want to consider someplace else.

Money matters! Set a budget for the team offsite

Well, no questions asked here. It is obvious that your offsite budget is one of the most significant things among the list to decide the further steps of your retreat planning. It is important to note how much you want to spend overall and also per person. Set your budget accordingly and make sure that it doesn’t hamper your business goals. 

Fun part’s here! Find the ideal place and date

This is the most fun yet hectic part of the planning process. But the clue is to ask your employees for their opinion. Imagine spending months planning an offsite just to see your employees not enjoying the place. 

To avoid confusion, list down a few ideal places based on your budget and goal of the offsite. The next step is to ask employees to vote for one and the one with the majority votes is the place your next team offsite happens.

If you’re a larger team specifically, chances are that you might not be able to accommodate everyone on a specific date. Go with the same procedure- ask your employees to vote among a few options and pick the one with the most votes.

Find the best vendor based on your offsite planning

With the basics all cleared, now is the showtime. Retreat planning is best done with the help of a vendor as they take care of all the things for you ~ from flights and hotel bookings, transportation, all logistics are handled well by them. They have better knowledge about getting you great deals and preparing your itinerary.

What to look for while picking a good vendor? The one who can provide you the best solution within your budget. 

Tip: Go for one vendor for all requirements instead of separate vendors for each of them. Having multiple vendors can confuse you and increase your workload.

Start prepping your itinerary for the team offsite

Place and dates are decided, logistics are getting taken care of. Now is the time to prepare your itinerary (ideally, your team building plan). Ask yourself these questions:

  1. What are the activities your employees would like to participate in? What are the goals behind these activities?
  2. Who can you reach out to for fun team-building activities?
  3. What are the places you can plan for your outing?
  4. Will these places be convenient in terms of transportation?
  5. Will all the activities fit inside the budget?
  6. Is there enough free time for employees where they can just do their own thing for a while?

Prepare a schedule for all activities along with their duration and dates. Share these ideas with your employees to create excitement.

It’s go time – Bring your offsite ideas into action

And you’re done with the planning part of things. Now the execution starts. Make sure you have enough volunteers who will help make this offsite a success. It is ideal that all the people who are closely involved in conducting the offsite reach the place a day earlier to ensure that the trip happens smoothly.

Talk to the hotel a few days in advance for confirmation of details. Have regular calls with them updating them with any sort of changes. Make sure that everyone stays in loop.

Miscellaneous tips

Keep your employees involved and updated

The best way to make sure that everyone enjoys the offsite is by keeping everyone updated and involved. Ask employees for their opinions and votes. When we wanted to decide on certain food options or name tags, we asked our employees to vote for their favorite options among the given. This kept them updated about all that we were working on and allowed them to pick what they loved.

planning retreat

Predict what can go wrong

If you’re in Step 1, think about how Step 3 can go wrong. It is important to be prepared and aware of what challenges you might face. There are plenty of common issues when it comes to planning a retreat, room availability being disturbed, food requirements, etc. These can be well-prepared for while planning itself. You need to give your best to avoid these challenges and start working on preventing them.

Take this team offsite as a learning experience

This might sound simple but it is very difficult yet important to remember. If your first offsite doesn’t go completely as planned, it is absolutely okay. With so many people coming from different cities, confusions are bound to arise. These will act as learning experiences for your next company offsite.

Just have fun

Alongside all the planning, the main goal is to HAVE FUN, don’t forget that in the rush. The entire purpose behind these company offsite ideas lies in those two words. So you might be overwhelmed, but remember that the fun you will have with your teammates next to you. Just make sure all your employee engagement agenda is secured seamlessly and you’re good to go.

Dhristi Shah

I am an Associate Content Marketer at Springworks. I love writing new content that relates to and helps you all (aka my readers).

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