Like any other decisions you are taking for your business, going on a retreat should come with a well-thought plan, clear expectations, and rules* that need to be communicated early on.
Once you have your purpose clear, planning and sharing that plan ahead of the event will help manage expectations. Yours and theirs. Including your team in some of the planning decisions, and asking about their expectations as well can be a great way to start engaging and create trust.
BUILD THE STRUCTURE ON WHICH THE RETREAT WILL FLOW
If you are serious about the success of your retreat (and we sure hope you are!) your planning needs to be very structured and specific.
Checklists are planners' favourites! The checklist structure is reassuring, helps delegating, and measuring progress, and will allow for everything to then run smoothly. A basic one can look like that (and get more specific as needed).
Who is joining? (Beware of the more the merrier narrative - Stay on track with your purpose)
find the location (nature, workshop spaces, room options, catering, and great wifi!)
agree on date
decide on the program (including activities and facilitators)
communicate - Information meeting
get RSVPs and diet requirements
book transportation & confirm rooms and food
send out a logistical email to attendees
Off you go!
Feedback and follow up
However, it is also important to make sure logistic does not make you forget why you are doing this. A well-planned event will have space to allow for "flow", which is usually where the magic happens. But flow without structure easily turns into chaos.
The plan is absolutely essential especially because not everything will always go according to it!
ASK THE RIGHT QUESTIONS
It is easier to be flexible with the plan when we have thought of the event behind the timetable and workshop schedule. That is why we also like to keep in mind these questions, whose answers will help stay aligned with our purpose:
What type of host do I want to be?
How to get the best out of the venue we picked?
How do we create a unique world we can all step in together?
How to make the meals a very special community-building moment?
How to make this event memorable?
How many will we be and to adapt the event to the size of the team?
How to create excitement and alignment before we even start?
Have regular unformal check-ins with the team on location (how is everyone doing, why are we here today?) and adapt planning if needed
Live space for "unconference" - Moments when anyone is invited to share on a topic of their choice or to lead an activity.
Keeping time. Ask yourself, is it more important to keep with scheduled time or allow for conversations to run over?
This is a different setting that might trigger different behaviors than at the [home] office. What to do in case of conflicts on location?
Do not just end. Ride the wave and harness the momentum.
Get face-to-face feedback when possible.
Communicate learnings, results, and plans.
BEFORE YOU SET OFF, THINK ABOUT COMING BACK.
It is easy to get lost in the excitement of such an event and let "future you" take on more than they can chew.
If all goes well, the team will be in great spirits after the retreat. Start thinking now about what you will do to ride that wave and keep the energy high. Make sure to create digital memories and maybe even content for your marketing team, plan ahead to have good quality pictures and recordings done, think about souvenirs, and any other way the effect of the retreat can last weeks after you are all back at the [home] office.
LAST BUT NOT LEAST, SET THE TONE.
As soon as you step outside of the normality of the routine the dynamic changes. People interact differently outside of the constraints of office policy and Zoom etiquette. This is something quite special to nurture and explore, but as mentioned earlier, it needs to have some guidelines.
That being said, never forget you can't write retreat without a "treat". Planning a team retreat is essential but we all know "All work and no play makes Jack a dull boy".
Your team must feel the excitement about going on this journey together. While communicating your plan and purpose, do not forget to share some of the fun activities and beautiful things there are to do and see where you are going.
Going deeper: We cannot recommend enough The Art of Gathering by Pryia Parker.
*If the word "rules" sound harsh remember that rules are good, even when it comes to fun.