10 Questions to Ask Yourself When Planning a Company Retreat

Planning a company retreat is exciting for any company, but it’s also a bit like herding cats. Without a clear plan, things can go off the rails quite quickly. Before you dive headfirst into organizing a leadership retreat or a strategic planning getaway, sit for a few minutes. Talk to yourself, have a meeting with others, and ask yourself some key questions. A well-thought-out retreat can help your team refocus, strengthen leadership skills, and build long-lasting bonds. A poorly planned retreat will make them resent spending a weekend with you.  

Having said that, what should you ask yourself before planning a company retreat. 

1. Why Do You Even Want to Have a Retreat?

First things first—what’s the purpose? Are you looking to develop leadership skills in your team, focus on strategic planning, or both? If it’s leadership development, you’ll want to tailor your retreat around activities that encourage collaboration, problem-solving, and personal growth. If you’re focusing on strategic planning, your agenda will need more time for planning and brainstorming sessions, team alignment, goals, budgeting, etc. 

Knowing your “why” sets the tone for everything else, so make sure you’re crystal clear on the purpose of the retreat.

2. What’s the Agenda?

Picture this: you’ve booked a stunning lakeside lodge, but nobody knows what they’re supposed to be doing. Not great, right? A clear agenda is key. Be specific about what needs to happen and when. It’s not just about keeping things organized, but about maximizing productivity and ensuring that every minute counts. Whether it’s scheduling meetings, planning team-building activities, or squeezing in some downtime, your agenda is your roadmap. Use it. 

And hey, leave a little room for spontaneity! The best ideas often pop up when people least expect them.

3. What Kind of Spaces Do I Need?

This isn’t your run-of-the-mill office meeting, so you’ll need a mix of spaces to accommodate different parts of your retreat. Does your team need a traditional boardroom setting for brainstorming sessions, or are you envisioning team-building activities in the great outdoors? Lakeside retreats like ours offer both indoor and outdoor spaces, from cozy meeting rooms to sprawling fields for outdoor exercises. 

Think about the vibe you’re going for, and make sure the resort can provide the variety you need to keep things fresh and engaging.

4. What Technology Do I Need?

You might be escaping the office, but you’re not necessarily escaping the need for technology. Will you need projectors, Wi-Fi, or video conferencing equipment? Fear not! Our resort is outfitted with all the tech essentials you need to stay connected and deliver those killer presentations, even if you’re nestled in a peaceful cabin surrounded by nature. 

Make sure you don’t just wing it with the tech—double-check everything ahead of time to avoid any “Why isn’t the projector working?!” moments.

5. How Will I Handle Food and Lodging?

Let’s be honest: hungry people aren’t happy people. How will you handle meals and lodging for your team? Good news: our resort takes care of all that. You don’t have to worry about running out for food or getting everyone back into town at the end of the day. From delicious catering to comfortable accommodations, we take care of everything. 

Be sure to inquire about dietary restrictions, room preferences, and any special accommodations your team might need!

6. How Do I Ensure Participation?

How do you ensure everyone is all in when it comes to your retreat? Expert retreat facilitators can make a huge difference here. Our resort works with professional facilitators who specialize in leadership development, team-building, and strategic planning. They know how to keep things fun, engaging, and productive. 

Make participation mandatory by making it irresistible! Fun, focused, and thoughtful programming ensures that no one will want to skip out on the next activity.

7. What Are Our Goals for the Retreat?

If you don’t know what success looks like, how will you know if you’ve achieved it? Setting specific goals for your retreat ensures that everyone is on the same page. Are you trying to improve communication between departments, align on the next quarter’s goals, or brainstorm new business strategies? Whatever it is, make it clear so you can measure your retreat’s success. 

Remember: the more specific your goals, the better. That way, you leave the retreat knowing exactly what was accomplished.

8. What Activities and Exercises Will Be Best for Your Team?

Don’t just rely on PowerPoint presentations and flip charts. Consider incorporating fun, interactive activities that get your team thinking creatively. Whether it’s trust falls (kidding), scavenger hunts, or problem-solving challenges, choose exercises that will resonate with your team and meet your retreat goals. 

Our resort offers a variety of team-building activities like outdoor obstacle courses, boating, or even fireside brainstorming sessions. Who says work and play can’t go hand in hand?

9. When Should You Hold the Retreat?

Timing is everything. Should you hold your retreat in the summer, when everyone’s excited about outdoor activities, or in the fall, when the weather is cooler and the kids are back in school? Each season offers something unique. Summer retreats are great for outdoor activities, while fall offers the beauty of changing leaves and cooler temps. Winter retreats can be cozy, while spring offers rejuvenation after a long winter. 

Consider your team’s schedule, the weather, and the type of activities you want to incorporate when deciding the perfect time.

10. How Can I Make It Unique and Memorable?

The best company retreats leave a lasting impression, not just because of the work that gets done but because of the memories created. Think about ways to make your retreat unique. Can you include a surprise guest speaker? Plan a themed evening event? Host a lakeside cookout or a s’mores night by the fire? 

Small touches like these ensure that your team leaves not just feeling refreshed and aligned but also bonded by shared experiences they’ll remember long after the retreat is over. 

  

Plan Your Company Retreat at Sugar Lake Lodge Today!