7 Common Mistakes to Avoid When Planning a Retreat

And how to ensure your retreat is impactful, stress-free, and smooth…

At Wesley Woods we’ve been working with retreat groups for a long time. Retreats are one of the most powerful events you can do with your group. Whether it’s a youth group, college group, church group or even corporate reset, retreats can be a powerful way to recharge.

However, even well-intentioned retreats can fall flat if key details are overlooked in planning.

If you’re not careful in planning, your retreat can be derailed. Luckily, if you can avoid these key seven mistakes- you’re well on your way to planning a fantastic retreat.


Mistake #1: Waiting Too Long to Get Started

When you’re a guest at a well-run retreat, everything feels smooth. It may feel effortless, but that’s a result of the leaders putting a ton of effort and thought into the retreat planning process- that doesn’t happen overnight.

The best retreats are those that begin planning around 6 months in advance. While retreats can be thrown together in a quicker time frame, there’s plenty of logistics that need to be thought through to make your retreat is a reality.

At Wesley Woods, we recommend groups try to reserve their spot within 4 to 6 months in advance- though we’ve seen groups run successful retreats in a shorter time frame. We also recommend leaders meet to plan and strategize twice with their team prior to the retreat.


Mistake #2: Not Clarifying the “Why?” of Your Retreat

It might seem simple, but knowing the reason and goals behind your retreat is a crucial ingredient for success. Planning an overnight retreat for your youth group looks very different from a vision retreat with your church’s leadership team. Whether it’s a church group, corporate group, or family reunion- knowing your objectives is key.

If your group is looking to plan a wellness retreat- the appropriate time needs to be allocated to spending time outside and doing relaxing activities.

If your main goal is to create more cohesiveness on your team- you need to not only plan team-building activities, but make sure they line up with your group’s capabilities and objectives- something we can help with at Wesley Woods.


Mistake #3: Overloading the Schedule

It may be tempting to fill every single minute of your schedule and want to cram as much in as possible. You get excited about all of the activities in planning and want everyone to experience everything.

The only problem is this often leaves retreat groups exhausted and defeats the purpose of getting away to recharge!

One way you can combat this is by allocating part of your schedule to free time. This looks like adding in a set number of parameters around what specific activities your group can do during this free time. Additionally, some folks may not like the name “Free Time”. You can call it something that still implies a level of structure like, “Your Choice” or “You Choose”.

Some great free time activities include:

  • Hiking

  • Rest Time

  • Board/Card Games

  • Arts & Crafts

  • Open Rec Time

  • And more!

We always recommend groups have at least one free time session per full day to give folks a sense of relaxation and autonomy over their schedule.


Mistake #4: Ignoring Your Group’s Needs

One of the biggest mistakes you can make when planning your retreat is over-relying on past experiences with other groups. 

While experience in planning retreats is important, any group leader is wise to consider not only their specific group type, but also demographics.

If you’ve successfully led retreats with a college group on the west coast, a successful retreat looks very different compared to a high school retreat in Western PA. 

While it’s important to build in time for your group to grow, you don’t want to push them too much. Very few retreats would benefit from 8 hours of team-building in one day, but almost every group can benefit from a 2 or 3 hour block of team-building activities.

If you notice your group is starting to drag, or just look plain exhausted, one of the best things you can do is switch up to schedule to allow everyone time for a less demanding activity. We’ve also seen groups thrive by balancing physically and mentally taxing activities, as to not overtax your group’s bandwidth. An afternoon of high ropes course activities could be followed by some variation of a trivia game in the evening.


Mistake #5: Under-Communicating Logistics

Communication is key. Communication is not just between you and your leaders, but also with your participants and your host site. Think about the last time you had a new experience at a new place as a group. Did your group leader properly explain all the expectations of the retreat? Did you get the phone number of your point of contact at the host site for your weekend? Were there any surprises- pleasant or unpleasant?

One of the ways we handle this at Wesley Woods is by having a pre-retreat meeting with each group the week leading up to their retreat. This final point of contact prior the retreat allows us to see what’s changed since the original conversations and what adjustments our team may need to make the retreat as smooth as possible.

When talking with your host-site, make sure to share an itinerary of your schedule as soon as you have one- even if it’s just a draft. This gives your site plenty of time to communicate with you if there are any conflicts in the schedule.

Lastly, when communicating with your group itself, give them one of the best favors you can- a packing list! Over my career in camping and retreats, I’ve seen many leaders skip the packing list and inevitably, someone misses something important for the retreat. Whether it’s the right clothes and shoes, materials you may have given before hand, or even basic toiletries and the right size sheets- having the right info is crucial.


Mistake #6: Trying to Do It All Yourself

It’s easy from the outside to think that retreats just come together. We can think of a super hero on the planning team throwing the whole thing together, but that’s never the case.

Behind every successful retreat is a successful team. 

If one of your team members is leading the talks- try to free that person up to focus solely on their sessions. 

If you’re providing food for your group, don’t overload the kitchen team by asking them to do the kitchen and 3 other things.

When groups are short on staff, some leadership groups may be too small for the roles needed. Your host site may be able to help with different things such as cooking or facilitating activities. Another way group navigate this is by giving some of the team members leadership roles. While they’re still there for the retreat, this not only gives attendees a sense of ownership, but it can help prepare them for future leadership roles.

Bottom line: Lean on your team.


Mistake #7: Forgetting to Follow Up

Not just an appreciatory text to your leaders, but to make your retreat a repeatable success with lasting impact you want to follow up with your participants and your host site.

Throw together a quick survey to both your participants and your leadership team. Ask them questions like:

  • What went well?

  • What could go better?

  • Favorite part of the retreat?

  • Least favorite part of the retreat?

  • On a scale of 1-5, 1 being not good and 5 being very good, how was the food?

  • And more

It may help to debrief with your leadership team after the retreat and get their feedback in an open conversation. Take your team out for a meal and get their honest thoughts. Between that and a survey, you’re well on your way to committing to an improving retreat each year.

Don’t forget to follow up with your host site too. You can let the site know about any issues you had as well as what you really appreciated. You can get valuable feedback from them too about ways to improve your retreat, and any hiccups in communication from your end.


Conclusion

Retreats are powerful tools in your arsenal as a leader. When they’re done with care and intention, they can help your team build, grow and become more cohesive. 

Avoiding those seven mistakes helps you plan a retreat that isn’t just smooth, but one that’s transformative. 

Thinking about a retreat? Contact our team today to see if we’d be a good fit for your group!

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