Planning leadership retreats? Here are 5 tips to ensure they provide value (With 5 examples)!

An offsite leadership retreat is a powerful tool for developing, motivating, and engaging the senior members of your company outside of the work environment. 

You get more from your decision-makers by allowing the executive team space and time away from the hectic day-to-day. This opportunity to focus on thought leadership, new ideas, and problem-solving, as well as both self-development and product development generates forward momentum. 

Semi-annual or quarterly leadership retreats can be run over one day or multiple days.

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Benefits of leadership retreats

Leadership retreats can be used for a range of important corporate priorities, including: 

  • Strategic planning
  • Generating ideas
  • Troubleshooting problems 
  • Wellness, both professional and personal 
  • Building inter-departmental bonds and reducing silos 
  • Leadership skill development
  • Company culture and growth
  • Embracing new technology
  • Corporate transformations 

Having said all that, there’s a time cost to these retreats. Your leadership team drives the company forward and their day-to-day activities are a key component of your business’s success. 

Making sure your leadership retreat has value for its participants and also drives value for your business is vital. 

How to get value from your leadership retreat


The benefits in our list above don’t happen by accident. Careful planning can help you achieve your goals and extract the maximum value from your retreat. 

Here are some tips to make sure your event does just that: 

  1. Define your goals early  

Step one to organizing a leadership retreat is understanding your key objectives. A leadership group doesn’t need to achieve all its goals in one event, but you should know what the event strives to accomplish. 

It could be as simple as team bonding and cohesion. It might be a training retreat during a time of corporate change, or you might be on the hunt for new product ideas. Have a clear idea of what you want to get out of the retreat before you even begin. 

  1. Engage the team

It’s important to note that the past few years have made immersive, in-person work less common, and less natural for your team. The leadership team is no different. 

Tips for keeping the team engaged include: 

  • Dedicated executive time: Of course, your company leadership needs to connect back with the office regularly. You can schedule time slots during the day to give them time to check in on the office and release the anxiety of being cut off from emails.  
  • Plan short days: Short and sharp exercises with well-defined stopping points make it easier for the team to focus and maintain attention. It also means there’s time on either side of the day’s retreat activities to tend to important work back at HQ. 
  • Make it fun: Mini competitions, fun and unusual activities, and games all help fire up creativity and maintain your team’s focus. 
  1. Communicate a clear agenda

It’s equally important to communicate clearly with your attendees. They should know what they’ll be doing, and when, with well-defined guidelines and start-stop points. This clarity helps keep everyone’s mind focused. 

Things you can provide guests to keep them informed include: 

  • Pre-event instructions 
  • A welcome package and retreat guide 
  • A detailed agenda sent by email or on an event app
  • A posted agenda in the venue lobby 
  • Signage and directions for each activity 

These tools will help everyone find the information they need easily. You might even print the retreat agenda or schedule on the back of your attendees’ name tags or badges. 

  1. Prepare for follow-up 

How will you make sure your leadership retreat has a tangible impact on your business going forward? Methods to achieve this include: 

  • Post-event reports on learnings 
  • Gather group input in surveys or reports  
  • Plan a calendar of status reports for the ideas and goals that were developed during your retreat 

By setting a direct course for employee engagement post-event you can continue the progress and make sure that your results have ongoing value. 

  1. Provide materials 

Another function of post-pandemic life is that people haven’t been out on events like this for a while. Make sure you have enough paper, pens, whiteboards, and other materials to work with. 

Leadership retreat ideas

A leadership retreat still has to be entertaining and enjoyable for your executive team. The goal here is to give them a break enough from the day-to-day that their minds are open to new ideas. It’s also a reward for their efforts. Here’s how to get the best out of your event: 

  1. Break down department silos 

Icebreaker activities and group challenges are a great way to break down interdepartmental silos and cliques. Try to arrange your seating arrangements and cabin allocations in a way that deliberately mixes up your team dynamics. Seat the VP of sales with the VP of accounting, for example. 

At Oak Hollow in California, nearby hot-air balloon rides are an innovative way to bring people together. You can assign balloon parties to help mix and jumble the normal groupings. Experiencing something unique and exciting together helps forge those personal bonds that lead to better in-office collaboration. 

  1. Remember the work 

Workspaces are an integral part of a leadership retreat. You’ll want to find venues and locations that are built for work as well as play. The Estate at Oak Hollow includes conference rooms with whiteboards, projector screens, and a variety of layouts to help your team work on new ideas and problem-solving. 

These rooms are bright and engaging to help keep leaders engaged. Choosing the right equipment can help you achieve the goals you’ve defined. 

For example, a brainstorming whiteboard allows your execs to capture their ideas in creative product ideation sessions. 

  1. Make room for rest and relaxation 
Photo of steam boat realty, landscape shot with the sunset in the background

Corporate wellness begins with personal wellness. If you bookend your leadership event with activities that relax and recharge your team 

There are thousands of retreat venues on our website that offer relaxing environments. This mountain-side retreat location in Colorado, Bella Vista Estate, offers gorgeous accommodations nestled into the Colorado mountains far from light and noise pollution. 

It also features a yoga studio and spa with massage services to help recharge your group before the leadership work starts. Nearby golf courses are a great opportunity to spark some friendly competition and help group members from different silos bond. 

A canoe trip on the local river can help get your team all rowing in the right direction too. 

  1. Consider outside influences 

Guided group activities can really help accelerate new ideas and concepts. 

Team building activities might include: 

  • Escape rooms 
  • Guided hikes or tours 
  • Challenges and scavenger hunts 
  • Construction or art projects 

Some venues, like Mas Torroella retreat in Spain offer local volunteering opportunities that build a sense of accomplishment and achievement during your event. 

You can also bring in local facilitators to help manage your sessions or run team-building exercises. 

Guest speakers are a great way to infuse your retreat with new ideas or even encourage your leadership group to take on new challenges. 

  1. Drive action  

At the end of your retreat, your leaders should feel energized, fulfilled, and accomplished. It’s important to capture this momentum and solidify it. 

Set aside the morning of your final day for an event recap and consolidation session. If you’ve run different group workshops, now’s a good time to bring everyone together to consolidate that work in one place. 

You may also have group leaders give their summaries to the rest of the leadership team. Someone should be on hand to capture the key notes and takeaways from the event, and distill them into a task list of timetable that your leadership team can follow up on after the event. 

After that, the final day and evening can be a time of celebration. Find an event like golf, go-karting, or even a simple dinner that brings the squad together one final time. 

Plan your leadership retreat

Ready to put these ideas into action? makes it easy to find your perfect leadership retreat venue and execute a valuable and successful retreat for your corporate executive team. 

Start by defining your corporate goals and objectives for your retreat, and selecting who will attend. The type of leadership event you design depends on what you want to accomplish. Whether you’re looking for a small, local event to use for quarterly or monthly meetings or a larger, more exotic place to reward and energize your executive team we’ve got you covered. 

Book a meeting with our experts to create the perfect leadership retreat today. 

Leadership Retreat FAQs

What do you get out of a leadership retreat?

Your business will benefit from a leadership retreat because it gives the team a sense of purpose, helps foster meaningful collaborative relationships, and helps generate new ideas. These events serve a dual purpose in that they also help reward and reengage your busy executive personnel in a way that drives fresh ideas and action. 

What should be included in the agenda of a leadership retreat?

A detailed agenda for any of your corporate retreat ideas should include workshops for professional development or leadership training, activities to foster teamwork and morale building, as well as time to check in and reconnect with the office. Your agenda should align with the goals and objectives you’ve decided on prior to the event. 

What are some effective leadership retreat activities for team building?

Effective team-building exercises help break leaders out of their comfort zones and build stronger relationships. 

Guided hikes, collaborative competitions and skill-building tasks, as well as challenges that test participants’ decision-making prowess, will all build camaraderie. Escape rooms and scavenger hunts are other endeavors that can help your team be more cohesive. 

What are the best locations for a corporate leadership retreat?

Choosing the right location for a corporate retreat involves considering your goals, the time you have available, and the location of your executive team. Somewhere central might make travel easier to organize, or you might want somewhere exotic to reward your leaders. The best leadership retreat locations are accessible and yet also secluded so that your c-suite can both relax and focus during the events. 

What are the best practices for planning a successful corporate leadership retreat?

Best practices for a leadership or executive retreat include; creating a clearly defined goals, planning a detailed agenda, giving attendees time to reconnect with their office during the day, creating a follow-up plan to make sure the retreat takeaways are actioned, and ensuring there’s a good balance of rest and reward along with the work-related activities. 

How much does a corporate leadership retreat typically cost?

Retreats aimed at corporate leadership development can cost anywhere from $1,000 to $100,000. Factors include the number of team members who’ll be attending, the location, the level of resort, and the price of any outdoor activities. The key to a successful retreat is a focus on value over cost. 

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