Starter Guide to Corporate Retreat Planning: Create an Unforgettable Team Experience

By Mike Tan and Matt Oakes

Imagine your team, energized, unified, and aligned with your company’s vision, all thanks to a carefully-planned corporate retreat.

Whether you’re a CEO, Co-Founder, Head of People, Head of Events, or an EA tasked with planning your company retreat or offsite, this guide will help you create an extraordinary experience that your team members will remember and rave about for years to come.

Ready to transform your team’s dynamic and set the stage for breakthrough performance? Let’s dive in.

Table of Contents

Why Corporate Retreats Matter

Corporate retreats aren’t just a luxurious getaway; they’re a strategic investment with substantial return on investment (ROI).

Retreats offer benefits that extend beyond the immediate experience and provide lasting value to both your organization and its team members.

Here’s how retreats add more value than an on-site management meeting:

  1. Enhanced Communication: Retreats break down hierarchical barriers, fostering open communication and transparency. Employees feel more comfortable sharing ideas and feedback, leading to better decision-making and problem-solving.
  2. Team Bonding: Shared bonding experiences outside the office strengthen relationships and trust among team members. This camaraderie translates to a more collaborative and supportive work environment.
  3. Boosted Morale and Motivation: Taking time to recognize and reward employees for their hard work boosts morale. When employees feel valued, their motivation and commitment to the company increase. The result is higher productivity and job satisfaction.
  4. Strategic Alignment: Retreats provide an opportunity for leadership to align the team with the company’s vision, mission, and strategic goals. Through workshops and discussions, everyone gains a clear understanding of their role in achieving these objectives.
  5. Innovation and Creativity: A change of scenery and a break from routine can spark creativity. Engaging in activities that encourage brainstorming and thinking outside the box can lead to innovative ideas and solutions that might not surface in a typical office setting.
  6. Skill Development: Workshops and training sessions during retreats can focus on both hard and soft skills. Whether it’s leadership retreat focusing on training, conflict resolution, or technical skills, these in-person sessions equip employees with new tools and knowledge that enhance their performance.
  7. Stress Reduction: Retreats offer a much-needed break from the daily grind and help employees recharge and reduce stress. This leads to improved mental health, reduced burnout, and better overall well-being.
  8. Cultural Reinforcement: Corporate retreats can reinforce and even reshape company culture. Activities and discussions that reflect the company’s values help to ingrain these principles more deeply within the team, fostering a stronger, more cohesive culture.
  9. Retention and Recruitment: A strong, positive culture and a team that feels valued are powerful tools for retention. A company that invests in its employees through corporate events like retreats can also attract top talent.

Investing in corporate retreats is a strategic move that yields significant returns, enhancing every aspect of organizational health from employee satisfaction to overall productivity and innovation. Planning the next retreat is crucial to continue reaping these benefits.

“I think retreats provide so much value to our company in how we come together, work together, learn together, and grow together. It’s certainly a tradition everyone in the company finds important, and has some fun with, too!” Dusty Davidson, CEO of Flywheel

“Our retreats have always been one of these things where new people come meet people who’ve been there for a while and you walk away from that meet having such a keen understanding of who everybody is.” – Natalie Nagele, CEO & Co-founder of Wildbit

Investing in retreats is investing in your people, and the returns—enhanced team synergy, increased productivity, and improved employee satisfaction—are invaluable.

Step 1: Crafting Your Ideal Corporate Retreat Vision

Close at their retreat in France

Think of your corporate retreat ideas as a blank canvases. The colors you choose, the strokes you make, all contribute to the final masterpiece — your company retreat. Just as a painting starts with a vision, so does your event planning process.

The vision for the next retreat can build on the successes of previous retreats with continuous improvement that leads to greater impact.

Imagine a world outside the regular work environment, a world where team members engage in icebreakers and other bonding activities that enhance personal connections and trust.

Picture a setting where comfort zones are a thing of the past, where innovation and discovery are the new norm.

This world is not a figment of your imagination; it’s your next company retreat.

Identifying Retreat Objectives

Goal setting is crucial for every successful venture, and planning a company retreat is no exception. What do you want to achieve at your retreat? Is it a focus on work, play, or a mix of both? Perhaps you’re looking for specific work sessions or increased communication among team members?

These are essential questions to consider when defining your company retreat agenda.

Here are some example objectives and goals for a company retreat or offsite:

1. Team Building and Cohesion

  • Objective: Strengthen relationships and foster trust among team members.
  • Retreat Activities: Plan activities that encourage collaboration, like team-building exercises, trust falls, and group problem-solving challenges.

2. Strategic Planning

  • Objective: Align the team with the company’s long-term vision and strategic goals.
  • Retreat Activities: Hold sessions to discuss and develop strategic initiatives, setting clear action plans and milestones.

3. Innovation and Creativity

  • Objective: Encourage creative thinking and innovation.
  • Retreat Activities: Organize brainstorming workshops and creative problem-solving breakout sessions to generate new ideas and solutions.

4. Skill Development

  • Objective: Enhance specific skills relevant to the team’s roles.
  • Retreat Activities: Provide training sessions, workshops, and guest speakers that focus on leadership, communication, or technical skills.

5. Employee Recognition and Appreciation

  • Objective: Recognize and reward employees for their contributions.
  • Retreat Activities: Host an awards night to celebrate individual and team achievements.

6. Communication Enhancement

  • Objective: Improve internal communication and collaboration.
  • Retreat Activities: Conduct activities that break down communication barriers and encourage open dialogue, including feedback sessions and group discussions.

7. Cultural Alignment

  • Objective: Reinforce and align with the company’s core values and culture.
  • Retreat Activities: Integrate activities and discussions that emphasize the company’s mission, values, and culture.

8. Problem Solving and Decision Making

  • Objective: Improve the team’s problem-solving and decision-making abilities.
  • Retreat Activities: Facilitate workshops and simulations that practice strategic decision-making and problem-solving techniques.

9. Health and Wellness

  • Objective: Promote physical and mental well-being.
  • Retreat Activities: Offer activities like yoga, mindfulness sessions, and outdoor adventures to encourage a healthy lifestyle.

10. Networking and Relationship Building

  • Objective: Enhance internal and external networking opportunities.
  • Retreat Activities: Organize events like wine tasting or cooking classes that encourage team members to build relationships with colleagues from different departments and with external partners.

11. Conflict Resolution

  • Objective: Address and resolve existing conflicts within the team.
  • Retreat Activities: Conduct conflict resolution workshops and mediation sessions to improve team dynamics.

12. Change Management

  • Objective: Prepare the team for upcoming changes within the organization.
  • Retreat Activities: Provide sessions on change management strategies and facilitate discussions on how to navigate and embrace change.

13. Customer Focus

  • Objective: Enhance understanding of customer needs and improve customer service.
  • Retreat Activities: Organize sessions that include customer feedback analysis, role-playing scenarios, and service improvement strategies.

14. Fun and Recreation

  • Objective: Provide a fun and relaxing environment to recharge and rejuvenate the team.
  • Retreat Activities: Include fun activities like sports, games, and social events to boost morale and enjoyment.

15. Future Trends and Industry Insights

  • Objective: Stay informed about industry trends and future developments.
  • Retreat Activities: Invite industry experts for talks, or organize panels and discussions about future trends and innovations in the field.

Ideally, you should have 1 and at most two objectives for your company retreat or offsite. Any more than 2 objectives and the overall experience will feel diluted and scattered.

One of favorite clients we work with is Close, and here are their typical two main goals for their retreats (also here is their awesome Guide to Planning a Company Retreat):

●       “Create business alignment. That means talking about the current situation of the company and the areas of focus that are most important for the entire team over the next year. This requires prep work from the leadership team prior to hosting the retreat.”

●       “Strengthen the social connections of our team members. This means creating an intentional agenda and environment that encourages organic interactions between team members. Whether this is through working, activities, or sharing meals, think about each moment as an opportunity to develop and strengthen relationships. Ultimately your team culture will benefit.”

PAUSE AND ACT: What are the 1-2 goals for your retreat or offsite?

Step 2: Budgeting for Success

Like a skilled architect, you’ve drawn the blueprint for your corporate retreat. Now, it’s time to gather the resources to turn your vision into reality.

Organizing a successful retreat requires careful financial planning to ensure all necessary aspects are covered without exceeding the company’s financial limits. Here are some best practices and examples to guide you through budgeting for a company retreat.

Estimating Company Retreat Cost

You want to provide an unforgettable experience without stretching your budget too thin. One way to achieve this balance is by determining a targeted price per person.

Based on data from the hundreds of clients and companies we’ve worked with at RetreatsAndVenues, the average spend for accommodations, food and activities (not including flights) is $688 USD per person per night. On the low end the average is about $400 USD per per person per night and on the high end (mainly for Executive Retreats) is around $2,500 USD per person per night.

Here’s an example retreat budget from Soapbox’s retreat:

● Facility: $8,175 (includes eco-challenge, two lunches, one dinner, sleeping, and a bunch of little things)

● Bus: $1348 (includes return trip, plus a hotel for the driver off-site)

● Beer: $259

● Snacks and Drinks: $118

● Shirts: $697

● Other expenses: $83

Total: $10,635 (about $425/person)

If you’re ready to start creating your retreat budget, here’s a handy company retreat budget calculator from our friends at Close.

Based on data from the hundreds of clients and companies we’ve worked with at RetreatsAndVenues, the average spend for accommodations, food and activities (not including flights) is $688 USD per person per night. On the low end the average is about $400 USD per per person per night and on the high end (mainly for Executive Retreats) is around $2,500 USD per person per night.

Here’s an example retreat budget from Soapbox’s retreat:

●       Facility: $8,175 (includes eco-challenge, two lunches, one dinner, sleeping, and a bunch of little things)

●       Bus: $1348 (includes return trip, plus a hotel for the driver off-site)

●       Beer: $259

●       Snacks and Drinks: $118

●       Shirts: $697

●       Other expenses: $83

Total: $10,635 (about $425/person)

If you’re ready to start creating your retreat budget, here’s a handy company retreat budget calculator from our friends at Close.

Allocating Funds Wisely

Allocating funds for a company retreat involves careful budget allocation, like a game of chess; each move must be calculated and purposeful. The ‘quarter rule’ can be your winning strategy, suggesting an even division of the retreat budget among:

  • Accommodation
  • Transportation
  • Food and beverage
  • Activities

But, there’s more! You can also unlock cost savings through smart choices. Selecting a retreat venue with built-in activities can provide team engagement without incurring additional costs.

Encouraging employees to carpool can also reduce individual travel costs: a win-win for both the company’s budget and the environment.

What about meals? Cooking meals as a team or organizing a potluck dinner can cut costs and foster team bonding.

To top it all, integrating team-building activities that yield tangible keepsakes can serve as cost-effective alternatives to traditional retreat swag.

Group discounts, off-season travel, and low-cost activities can all help you maintain a lean budget.

Make sure you keep a good record of your actual costs. That way you can optimize your future event spending based on past experiences.

Step 3: Choosing the Perfect Retreat Location and Venue

Illustration of a scenic retreat location suitable for corporate retreats

Venue selection is like choosing the ideal backdrop for a play. The right off-site setting can:

  • Enhance the theme
  • Support the broader goals and vision of the company
  • Provide a unique experience for your team members

You could choose the tranquil beauty of a countryside villa or the vibrant energy of a bustling city. The important thing is that your venue should provide diverse spaces to accommodate activities that foster bonding, creativity, and productivity as well as appropriate workspaces.

But how do you make sure the venue checks all the boxes?

Venue Considerations

When exploring potential retreat venues, don’t just look at the aesthetics. Conduct a thorough site inspection and ask yourself:

  • Does it offer package deals for accommodations and catering for large groups?
  • Can it provide meeting space, meals, and overnight accommodations all in one package?
  • How about special services, available activities, and their experience in hosting company retreats?

These considerations can make a significant difference in ensuring the venue can meet your event requirements. has experience with hundreds of high-quality retreat venues that fit a wide range of needs and budgets. We can help you choose the right location for your next retreat.

Accessibility and Convenience

Imagine planning the perfect retreat only to realize that the location is inaccessible for some team members? Accessibility matters when you choose a retreat location.

Locations in metropolitan areas often offer greater convenience for accessibility but can result in higher lodging costs. On the other hand, more remote, rural areas may have lower lodging but require extra transportation arrangements and expenses.

The proximity to airports and transportation hubs is one consideration: especially for retreats involving a distributed workforce.

“Accessibility is paramount, as a convenient location ensures the entire team can easily travel to the destination,” Nicole Dayan, Co-founder of The Pocketbook Agency

With an ideal location chosen our focus turns to accommodation and meeting space.

Accommodation & Meeting Space

Illustration of comfortable and functional meeting spaces and accommodations for a corporate retreat

Just like a symphony, a successful corporate retreat requires harmony between the various elements. Two of the most crucial elements are lodging arrangements and meeting space.

Whether you’re considering premium ensuite rooms or shared housing, accommodation should offer comfort and functionality.

Negotiating room blocks directly with the hotel or resort can ensure discounts for multiple rooms and give you the option to add additional rooms as your team size increases.

Meeting rooms, on the other hand, should be equipped with comfortable seating, WiFi, and adequate space for work sessions.

You want enough space for all attendees and a balance between comfort and functionality.

Comfort Meets Functionality

Your venue should be comfortable and functional. Like a perfect pair of shoes, it should also be sized appropriately for your guests.

The venue should have diverse spaces including technology-equipped breakout rooms and recreational areas.

Room for Everyone

A corporate retreat should be a shared experience, a collective journey that strengthens the bond among team members.

Effective capacity planning ensures there is enough space for all attendees, making the retreat more enjoyable and productive.

You might also want to involve the entire team in retreat planning, possibly through surveys, to understand their comfort levels and preferences.

Step 4: Designing a Balanced Retreat Agenda

Designing a retreat schedule is like choreographing a dance. It should have the right balance of structured activities and free time, incorporating both discussion-based and physically engaging team-building exercises.

Effective itinerary planning is essential to prevent burnout by managing work sessions and ensuring there are intervals of relaxation between sessions.

Work and Play

Activity scheduling is important to achieve a balance between engagement and focus. You might set aside whole days for business development tasks and training while reserving others for sightseeing or cultural exploration.

Incorporating local traditions and games into team building activities can reflect a company’s value of cultural engagement and appreciation.

Just as important as balance, is flexibility.

Flexibility Is Key

Just as a river adapts its course according to the landscape, a retreat schedule should offer schedule flexibility, catering to individual preferences and maintaining engagement.

Balancing scheduled activities with free time addresses the varying preferences for how individuals like to recharge. It also allows you to book in time for team members to check emails or take care of important tasks from the office.

Here are some tips for creating a flexible retreat schedule:

  • Allow team members to have some unstructured time to explore or unwind on their own.
  • Offer a variety of activities and options for team members to choose from.
  • Incorporate breaks and downtime throughout the day to prevent burnout.
  • Be open to feedback and suggestions from team members on the schedule.

By creating a flexible retreat schedule, you can ensure that everyone has a positive and enjoyable experience.

Here is a great example Retreat Agenda, Budget and other great tips from SoapBox’s company retreat to Algonquin Provincial Park.

This will help engage everyone even during more “fun” times like during team building activities.

Team Building Activities That Matter

Illustration of engaging indoor and outdoor team building activities at a company retreat

Activities that foster communication, promote collaboration, and increase employee engagement are the lifeblood of any corporate retreat.

How can you decide between indoor and outdoor engagement activities, and adapt them to represent your company’s culture?

Indoor vs. Outdoor Activities

Whether it’s the thrill of an outdoor scavenger hunt or the intellectual stimulation of an indoor trivia contest, offering a variety of activity options, including both indoor and outdoor team building activities, allows teams to cater to different physical abilities and interests.

Weather concerns come into play for some outdoor activities, so if you do have a heavily outdoor-based schedule, try to bake in extra flexibility. The great benefit of the outdoors is that fresh hair has demonstrable health benefits, and helps to promote more free thinking.

Customizing to Your Company Culture

Company culture is one thing your retreat can help reinforce more than at any other time. Your event should include tailored activities to reflect this.

Incorporating company-specific challenges into traditional activities can reinforce employee understanding and appreciation of company history and values.

Activities like Human Bingo can be customized with challenges related to the company, and Company Trivia can include questions on company-specific knowledge and history to boost engagement.

With a finalized agenda in place, it’s time to eat!

Step 5: Plan Meals That Energize and Connect Your Team

Illustration of diverse and inclusive food options at a company retreat

Food is not just a biological need; it’s an integral part of any gathering, including corporate retreats. Offering a diverse and inclusive menu caters to different cultural backgrounds and dietary restrictions and promotes inclusivity.

Exploring various catering options can help ensure that all team members are well-fed and satisfied.

Eating on-site will often save money versus eating every meal at a restaurant. It also saves travel time. There are many different ways to cater your retreat.

Hiring Caterers vs. Self-Catered Solutions

Every retreat planner faces this question.

Catering services can save time, relieve stress, and provide professional service. But they can also add to the retreat cost.

On the flip side, self-catered solutions offer potential cost savings and the opportunity for team bonding through collaborative meal preparation. Decisions, decisions! A mix of these options gives you the best of both worlds and more flexiblity.

Snack and Break Options

Snacks and refreshments during a retreat are like pit stops during a race; they allow participants to recharge and refuel for the next leg of the journey.

Offering a range of gluten-free nuts, granola bars, and fresh fruits can sustain energy levels during the retreat.

Include gluten-free and vegan options in snack selections to accommodate different dietary restrictions and ensure your entire team feels welcome.

Step 6: Announce Your Retreat And Send Out Invitations

The success of your company retreat begins with how you communicate and invite your team.

Start by announcing the retreat with save-the-date notices and formal invitations to mark the event on everyone’s calendar well in advance. Use multiple communication channels like email, the company intranet, and team meetings to ensure the message reaches everyone.

Next, provide comprehensive information about the retreat. Share a detailed agenda, logistical details, and a list of what to bring, so participants know what to expect and can prepare accordingly.

To make this easier, create a FAQ document that addresses common questions, helping to reduce uncertainty and build excitement.

Efficiently manage RSVPs by tracking responses and following up with those who haven’t replied yet.

Engaging your team early and clearly in the planning process sets the stage for a well-attended and successful retreat.

Next step after everyone has signed up for your retreat or offsite is to book the flights and ground transportation for all your team members.

Step 7: Book Flights and Ground Transportation For Your Team

Transport logistics and travel arrangements may not sound as exciting as team-building activities or gourmet meals, but they are a vital cog in the retreat planning machine.

Whether you’re considering charter or shuttle buses for local retreats or managing flight-related travel for more distant locations the type of transportation will depend on the venue, number of attendees, and the schedule of events.

Let’s examine the details of organizing group travel and offering individual travel support.

Coordinating Group Travel

Group transportation can be a challenging task, but with the right strategy, it can be a smooth ride. Here are some tips to make it easier:

  • Encourage carpooling among employees to reduce individual travel expenses.
  • Plan company retreats during off-season months like April, May, September, and October to lower travel and accommodation costs.
  • Hire a travel management company to streamline the planning process and manage group bookings for transport, potentially reducing costs and simplifying logistics.

Sometimes you’ll need to account for specific and individual travel needs.

Individual Travel Support

For remote teams, transportation is a significant part of the retreat expense. Here are some tips to ensure effective management of individual accommodation needs:

  • Provide clear guidelines for booking and expensing accommodation.
  • Consider using services like FlexiPerk, which provide flexible booking options and support individual travel adjustments.

With transport logistics figured out, we can now proceed to delivering and facilitating a 5-star retreat experience.

Step 8: Facilitate A 5-Star Retreat or Offsite Experience

When it’s time to conduct the retreat, execution is key.

Implement your meticulously crafted plan, but remain adaptable to accommodate any unexpected changes or opportunities that arise.

Designate a point person responsible for troubleshooting any issues, ensuring the retreat runs smoothly without unnecessary disruptions.

Actively engage participants throughout the retreat by facilitating activities and sessions that capture their interest and enthusiasm.

Encourage participation by creating an inclusive environment where everyone feels comfortable contributing.

This dynamic approach not only keeps the energy high but also fosters deeper connections and maximizes the retreat’s impact, ensuring it is both memorable and productive for all attendees.

And now with the retreat or offsite complete, it’s time to gather feedback to help make the next retreat even better.

Step 9: Post-Retreat Follow-Up

The retreat might have ended, but its impact continues. Conducting post-retreat surveys, analyzing feedback, and maintaining momentum through a well-planned follow-up strategy, including meetings and activities, are crucial for capitalizing on the retreat’s success.

This follow-up process can also provide valuable insights for planning the next retreat.

How can you carry out a post-retreat survey, and how can you sustain the retreat spirit? Let’s go over the specifics.

Conducting a Post Retreat Survey

Feedback collection through a post-retreat survey is like a compass; it guides you toward areas of improvement for future retreats.

Using a mix of closed and open-ended questions ensures comprehensive feedback, offering clear quantitative data and deeper qualitative insights.

Distributing surveys promptly after the retreat, while memories are fresh, can lead to higher response rates and more accurate reflections on the experience.

Feedback from these surveys can be invaluable in planning the next retreat, ensuring it meets the needs and expectations of all participants.

These check-ins can also help you maintain the retreat spirit long after it ends.

Keeping the Spirit Alive

A retreat is not a one-time event; its spirit should continue to echo in the office corridors long after it’s over through ongoing engagement.

Expressing gratitude to participants, sharing retreat highlights, and scheduling follow-up meetings are key to preserving the retreat’s impact.

Recommitting to the retreat’s action plan in a dedicated session where the facilitator and team review the plan can further embed the strategic goals within the company culture.

Developing visual and physical memorabilia of the retreat, such as videos or print materials, can also help to keep the retreat’s spirit alive.

Ready for Your Retreat?

From crafting a purposeful retreat vision to conducting a post-retreat survey, we’ve navigated through the exciting journey of planning a successful corporate retreat.

Remember, a retreat is a unique opportunity to foster team building, align with company goals, and enhance employee well-being.

It’s a chance to step outside the regular work environment, foster innovation, and discover hidden talents.

So, are you ready to plan your next unforgettable team experience? Reach out to today to get started!

Frequently Asked Questions

How do I identify the objectives for my company retreat?

Identify the objectives for your company retreat by aligning them with your company’s vision and values. Consider the focus on work, play, or a mix of both, the need for specific work sessions, and the goal of increased communication among team members.

What is the ‘quarter rule’ in budgeting for a company retreat?

When budgeting for a company retreat, use the ‘quarter rule’ to allocate 25% of the total budget to accommodation, transportation, food and beverage, and activities, respectively, for a balanced spending approach.

How can I ensure that my retreat location is accessible to all team members?

To ensure that your retreat location is accessible to all team members, consider proximity to international airports and transportation links, especially for distributed workforces. This will help accommodate those who may need to travel by air or use public transportation.

How can I balance work and play during a corporate retreat?

To balance work and play during a corporate retreat, designate specific days for business activities and learning, while reserving other days for sightseeing and cultural exploration. You can also incorporate local traditions and games into team-building activities to foster cultural engagement.

What should I include in a post-retreat survey?

Include a mix of closed and open-ended questions in the post-retreat survey to gather comprehensive, anonymous feedback while memories are fresh. This will ensure accurate reflections on the retreat experience.

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