Planning a successful weekend retreat

So it happened. You started an organization, got elected, recruited, etc. Either way, you’re now at the top of the totem pole and you’ve realized that your organization doesn’t have a plan. Each semester is haphazardly thrown together at the last second. Ready to make a change? Make a disruption to the status quo that could last for years to come in your organization? Well, you’ve found a good place to start. Let’s look at what it takes to plan a successful weekend retreat!

Have a pre-meeting

The first thing you’ll want to do in preparation for planning a retreat is to make an agenda. My friend Brian’s favorite quote is, “If you don’t have a plan, you’re planning to fail.” Too often organizations “plan” meetings where they have a loose idea of what to discuss. The meetings can quickly derail off-topic, or the group can get hyper-focused on one tiny detail that, in the grand scheme of things, doesn’t really matter.

One thing that can help with this is to have a meeting with your team where you plan out the weekend retreat. Try to have this at least a few weeks or months prior to your retreat. There’s a lot of things to consider at this meeting. Where should we have the meeting? What goals do you want to reach by the end of the weekend? Are you planning out the events for the upcoming semester? Creating a membership enrichment program? You can literally do anything, so you should have an idea of what you want to do prior to actually planning it out. 

Some things you’ll definitely want to consider at this meeting:

• A venue (Most aren’t free, but your school typically is!)
• Consider inviting past alumni and officers. (Props if you give them a gift at the end of the retreat)
• Dates (You’ll need this for the venue and any other people you invite)
• Topics and Goals (What are we planning? How do we know we planned well?)

Create an agenda

After or during the pre-meeting, create a rough outline of the agenda for the weekend. It doesn’t have to be perfect, but having an idea of around what time each activity will take place is a good start. This is the time where you think about the big items, such as:

• When should everyone arrive?
• Should people eat before arriving?
• Will this be an out of town meeting? If so, what will the living situation be?
• What should we do about food?

Once you have a general outline and notes for the agenda, send it out to your team to get feedback. Maybe Gary has free hotel nights you can use for the weekend, Rachel might know cheap places to eat in town, etc. 

After getting some feedback, start trying to finalize the agenda and get into the nit and gritty. Start breaking planning tasks into sessions with breaks in between. It’s hard to expect people to go over an hour at a time without a break, so plan on mini-breaks during sessions and longer half-hour breaks between sessions. It’s always better to plan on events taking a bit longer to give your team some wiggle room if a particular discussion runs long.

Another thing you’ll want to consider is having activities that break from the tedious planning and work. Small icebreakers and team-building exercises can be a fun temporary distraction. Don’t plan on going from dawn to dusk either. Around eight to ten hour days (including breaks for rests, lunch, etc.) should be sufficient. You want to give everyone time to process the events of the weekend instead of overloading them.

If this sounds ridiculous and overwhelming, for your organization, it might be! The above steps are deep-diving for larger, more structured organizations. If your organization is small and doesn’t require a lot of coordination, just do what works for your organization.

Reach your inner teacher: Assign homework

Now that you’ve got a finalized agenda, you’ll want to warn everyone ahead of time with their expected homework, such as what to bring, what to prepare ahead of time, and what to expect. Include the finalized agenda with this email.  For example, it’d be handy if the Treasurer knew the current account balance, the upcoming cash flows, etc. It would also be helpful if the Secretary gathered a list of major holidays, events, and the school schedule calendars in preparation for the retreat.

By assigning homework to your team ahead of time, will help them to show up prepared with the data they need. The last thing you want is to spend the first half of your meeting finding out what you should’ve known before the meeting even started. Hopefully, by this point, the event is still a couple of weeks out. That will give your team and yourself time to prepare for the event.

Extra tips

• Try to have this retreat a week or two before the beginning of the school year. Or maybe right after the end of the prior one. Work it out how you want, but at least a week or two before school starts gives you time to plan and execute, instead of rushing against the clock.

• For long-term goals planning, I recommend having a bi-annual planning meeting. At each one, you discuss the upcoming semesters to-do’s, planning etc, and make general long term plans for the semester after. The latter can be helpful when you want to involve outside companies or plan a large event in coordination with the school. Then you can use the long term plans from the last meeting as the basis for the current one!
• Have fun! No really. If your retreat is extremely serious and boring, no one’s going to enjoy themselves, which will stifle creativity, and probably make everyone agree you suck at coordinating meetings.
• If your organization has the dough to spare, look for a local team building business. I’ve been to some that have ropes courses and awesome outdoor team building activities. After hyping up the group, you jump in a room and start collaborating!

Have any other suggestions for weekend retreats? What does your organization do to prepare for the upcoming semester and year? Let us know!