22 Leadership Retreat Activities to Try in 2025

When you’re picking leadership retreat activities, each one should be strategically selected to meet a specific goal. In this article, you’ll learn about 22 leadership retreat activity ideas you can try and the outcomes each one will provide.

Updated: March 31, 2025

Leadership retreats are vital to the success of your organization, and the right leadership retreat activities can make the difference between a good event and a great one.

With thoughtful planning, your leadership retreat will help to:

• Grow the leaders of your company to future-proof your business
• Equip your leaders with the skills they need to lead strong teams and support a successful organization 
• Facilitate connection, collaboration, and communication between team leads and departments 
• Create alignment on your company’s purpose, mission, vision, and values

The key to success?

Setting specific goals for your event and then strategically selecting leadership retreat activities that will bring them to fruition.

Feeling unsure where to start? Fear not.

Below, you’ll find an extensive list of leadership retreat activity ideas alongside the skills and goals they’ll focus on so that you can ensure your event creates a valuable and long-lasting impact.

Table of Contents

• Picking Leadership Retreat Activities: 12 Key Skills and Outcomes to Focus On
• 22 Leadership Retreat Activities to Try in 2025
  • 1. Play Some Icebreakers
  • 2. AI-Powered Leadership Simulations
  • 3. Hire a Guest Speaker
  • 4. Hollywood Murder Mystery
  • 5. Group Discussions
  • 6. Cross-Functional Innovation Labs
  • 7. Goal Setting
  • 8. CI: The Crime Investigators 
  • 9. Shadow Boards & Reverse Mentoring Roundtables
  • 10. Ethical Foresight & Scenario Planning
  • 11. Creative Thinking Sessions
  • 12. Wheelchairs for Charity
  • 13. Live Podcast or Leadership Storytelling Panel
  • 14. Confident Decision Making
  • 15. Leader-Led Breakout Discussions
  • 16. Clear Communication
  • 17. Tech Detox + Analog Strategy Session
  • 18. Positive Team Dynamics
  • 19. Scavenger Hunts
  • 20. Purpose-Driven Offsite Challenge
  • 21. Celebrate Success
  • 22. Recharge with Wellness

Picking Leadership Retreat Activities: 12 Key Skills and Outcomes to Focus On

When you’re deciding on leadership retreat activities, nothing should be selected at random. Your leadership team’s time is incredibly valuable. So, it’s important to make sure you’re filling your retreat schedule with activities that will benefit them.

That’s why every leadership retreat activity you choose should be picked with a specific outcome in mind.

This can include:

• Problem-solving
• Personal and professional wellness
• Team building
• Leadership skill-building
• Conflict resolution
• Organizational transformation
• Company culture and growth
• Employee engagement
• Trust-building
• New technology
• Strategic planning
• Brainstorming

Each organization will have its own unique set of goals to achieve or skills that its leadership team could benefit from practicing.

So, before picking your leadership retreat activities, spend some time getting introspective about what you’d like to get out of your retreat. Set goals for what you’d like your team to take away from their time together. From there, you can reverse-engineer those goals to choose the right leadership retreat activities.

22 Leadership Retreat Activities to Try in 2025

Now that you’ve determined what you want to achieve, it’s time to start picking leadership retreat activities for your event.

Here are 22 options to consider—as well as the types of skills they’ll help develop and the goals they’ll help achieve.

1. Play Some Icebreakers

Skills practiced: Trust building, company culture and growth

For most leadership teams, their connections are strictly professional. That’s no surprise considering they’re primarily interacting in a professional capacity.

But reinforcing your professional bonds with interpersonal relationships is essential to working effectively together. Knowing your colleagues on a human level makes for a more tightly-knit team.

That’s why it’s wise to chat through some icebreaker questions that will help your leadership team get to know each other better.

These can be funny, unique, debatable, and beyond. Here are a few options to consider:

• Do you love working from home or in the office? Is there a balance of both that you like best?
• Where do you work most frequently from at home? Your office? Your kitchen table? The backyard? Your bed?
• Can you give a tour of your office space? 
• Be honest, how often do you work from bed?
• What does your morning routine look like when working from home?
• How many cups of coffee, tea, or beverage-of-choice do you have each morning?
• What is one thing on the very top of your bucket list?
• If you’re not from this city, why did you end up here?
• What is your guilty pleasure?
• If you could change anything about the way you were raised, what would it be?
• What’s the craziest thing you have ever done?
• If you had a million dollars, what would be the first thing you bought?
• What’s your favorite thing about your job?
• What’s something you are really proud of accomplishing?
• What’s something interesting about your family history?
• Have you ever been in a movie, TV show, or play? What was your role?
• If you could hang out with any cartoon character, who would you choose and why?
• If you could be in any movie, what would it be and what character would you play?
• Which actor would you want to play you in the movie about your life?
• What book did you read that changed your life the most?
• If you could see one movie again for the first time, what would it be and why?
• You have your own late-night talk show. Who do you invite as your first guest?
• What would the title of your autobiography be?
• What is your favorite thing to do locally?
• If you could either live where it only snows or the temperature never falls below 100 degrees, which would it be?
• If you could live in any country, where would you live?
• If you could be any supernatural creature, what would you be and why?
• If you were a vegetable, what vegetable would you be and why?
• If you had to lose all your memories, which one would want to lose last?
• What are your biggest phobias?
• If you were left on a deserted island with either your worst enemy or no one, which would you choose? Why?
• What would be the most surprising scientific discovery imaginable? 
• If you could add anyone to Mount Rushmore, who would it be and why?
• If someone offered you a million dollars to give up your smartphone forever, would you do it?
• What’s your cellphone or computer wallpaper? 
• If you were a superhero what would your superpower be and why?
• What’s the best piece of advice you have ever been given?
• What’s the best advice you’ve ever given?
• If you could be guaranteed one thing in life (besides money), what would it be?
• Would you rather go for a run or go for a hike?
• Would you rather watch a TV show or watch YouTube?
• Would you rather be on a survival reality show or dating show?
• Would you rather be a detective or a scientist?
• Would you rather go to the movie theater or watch a movie from home?
• Would you rather live in a remote destination or the heart of a metropolitan city?
• Would you rather have telekinesis (the ability to move things with your mind) or telepathy (the ability to read minds)?
• Would you rather be forced to sing along or dance to every single song you hear?
• Would you rather be in jail for five years or be in a coma for a decade?

Looking for even more icebreaker questions you can tap into for a leadership retreat activity? Check out our list of 400+ team building icebreaker questions.

2. AI-Powered Leadership Simulations

Skills practiced: Strategic thinking, communication, emotional intelligence

Here’s a simple, tech-savvy way to help your team practice tough leadership conversations—without needing a facilitator or expensive simulation software.

In this activity, pairs of leaders will roleplay real-world scenarios using ChatGPT to simulate how the “other person” might respond. One person plays the role of the leader. The other plays the employee, client, or stakeholder—by entering the leader’s words into ChatGPT and reading back the AI’s response.

For example:

• The leader says, “I need to talk to you about your recent performance.”
• The partner types that into ChatGPT: “Imagine you’re an employee receiving this message from your manager. How would you respond?”
• ChatGPT generates a realistic reply—something like: “I’m surprised to hear that. I thought I was meeting expectations. Can you be more specific?”
• The roleplay continues, with ChatGPT guiding the back-and-forth conversation.

You can run multiple scenarios across the group: coaching a struggling employee, addressing pushback on a tough decision, or handling a sensitive issue with empathy.

Each pair wraps with a short discussion:

• What was challenging about that exchange?
• Did anything in the AI’s response surprise you?
• How would you handle this in a real-life situation?

It’s an easy, modern twist on roleplay that encourages leaders to practice empathy, navigate uncertainty, and adapt in real time—all with just a phone or laptop and a little creativity.

3. Hire a Guest Speaker

Skills practiced: Specialized skills, new technology

Consider hiring an external speaker as a leadership retreat activity—someone who can offer specialized knowledge and experience on the topics you want to cover. You can also think about having an external person moderate discussions or activities to reduce unintended bias—a realistic possibility when an internal staff member leads.

You can also use external speakers to provide presentations that motivate or otherwise encourage your leadership team. The speaker you choose can vary based on the retreat’s theme or the types of skills you want to promote within your team. They may represent experts in your industry or an expert in an area of professional development, such as leadership, creativity, or diversity and inclusion.

Hiring a guest speaker can be a big and challenging job. So, if you’re not sure where to start, check out our resource: 10 Considerations for Picking Guest Speakers for Corporate Events.

4. Hollywood Murder Mystery

Skills practiced: Critical thinking, collaboration, communication

Being a leader is fraught with unique and unexpected challenges, and being able to overcome them as a team is critical to the success of your organization.

That’s what makes Hollywood Murder Mystery such a valuable team building activity for CEOs and senior executives.

In this activity, a famous actress is found murdered. So, you’ll need to put your problem-solving skills to the test as you share theories, collaborate, and think outside the box with your fellow investigators.

Together, you’ll review case files and evidence including police reports, coroners’ reports, photo evidence, tabloids, interrogations, and phone calls as you determine the motive, method, and murderer and bring justice for the victim.

5. Group Discussions

Skills practiced: Problem-solving, brainstorming, organizational transformation, strategic planning

Focus on taking some time to facilitate a structured conversation where leaders can discuss key issues facing the company, share ideas and experiences, and brainstorm solutions.

This is critically important to understanding each person’s perspective and coming up with innovative ideas for how to overcome challenges.

It’s also helpful in reducing silos between departments that may not communicate as openly as they could.

6. Cross-Functional Innovation Labs

Skills practiced: Collaboration, creative problem solving, systems thinking

Instead of a structured “innovation lab,” keep it simple with a timed group challenge that brings different departments or roles together to solve a real business problem. Break your team into mixed-function groups and assign each one a big-picture prompt like:

• “What’s one thing slowing down communication across our team—and how would you fix it?”
• “What new service or process could make our customer experience 10x better?”

Give each group an hour to brainstorm, sketch a rough solution, and prepare a short pitch. Then, have them present their ideas to the rest of the retreat team.

This low-pressure activity encourages collaboration across silos, sparks fresh ideas, and gives everyone a chance to practice leadership through creative problem solving. You’ll often walk away with ideas you can test or implement after the retreat—without needing a whiteboard wall full of sticky notes or a formal design sprint.

7. Goal Setting

Skills practiced: Organizational transformation, company culture and growth, brainstorming

Goal setting is a critical leadership retreat activity because it provides an opportunity to collectively set new internal and external objectives and milestones for your organization with its key players at the table.

You could focus on goals like:

• Building stronger relationships and trust among team members
• Identifying and addressing communication challenges within the organization
• Improving overall team performance and productivity
• Setting specific goals and action plans for each department or team within the organization

Each organization will have its own unique set of goals, but discussing them together in a collaborative format can get everyone on the same page and working towards the desired outcome.

8. CI: The Crime Investigators 

Skills practiced: Problem-solving, critical thinking, communication

Clear communication, critical thinking, and problem-solving skills are among the most critical points of focus for any leadership team.

With a team building activity like CI: The Crime Investigators, you’ll need to think analytically and work together to collect evidence, decipher clues, and solve a mysterious and deadly crime.

9. Shadow Boards & Reverse Mentoring Roundtables

Skills practiced: Active listening, empathy, inclusive leadership

One of the most powerful things a leadership team can do is stop talking and start listening—especially to the next generation of talent. Shadow boards and reverse mentoring roundtables flip the traditional dynamic by inviting rising stars and early-career employees to share their ideas, perspectives, and challenges directly with senior leaders in a structured setting.

During the retreat, set aside dedicated time for these rotating conversations. Junior employees (or pre-selected emerging leaders) join small-group discussions where they offer feedback on company culture, strategic direction, or what it’s like to grow a career at your organization. Leaders take on the role of listener and learner—not defender or explainer.

The outcome? A clearer view of blind spots, a better connection to what matters to your workforce, and often, a goldmine of ideas you wouldn’t have gotten otherwise. These sessions also build trust and transparency across levels, making future collaboration that much stronger.

10. Ethical Foresight & Scenario Planning

Skills practiced: Strategic foresight, values-based decision making, critical thinking

The best leaders don’t just react to what’s happening now—they anticipate what’s coming next. Ethical foresight and scenario planning is a powerful way to help leadership teams stretch their thinking beyond the day-to-day and explore how they would navigate complex, future-facing challenges.

Start by presenting a few provocations grounded in emerging trends—like an AI tool that accidentally creates biased hiring outcomes, a climate regulation that disrupts operations, or a public backlash to a brand partnership. Then break into small groups to map out possible responses: What would we do? What values would guide us? Who would be impacted? What’s at risk?

These discussions don’t need a “right” answer. The goal is to build muscle around ethical leadership, long-term thinking, and the ability to lead through uncertainty. Bonus: the conversations often surface meaningful insights about your team’s shared values and strategic blind spots.

11. Creative Thinking Sessions

Skills practiced: Innovative thinking, critical thinking, problem-solving, company culture and growth, strategic planning

Creative thinking sessions can be incredibly beneficial as leadership retreat activities. These sessions are designed to:

• Foster innovation
• Generate new ideas
• Help leaders think outside the box

This can include:

• Brainstorming: This is a classic creative thinking exercise that can be used to generate new ideas and solutions. Leaders can break into small groups and brainstorm on a specific topic or challenge facing the company. They can share their ideas and build on each other’s contributions.
• Design Thinking: Design thinking is a structured process for solving problems and developing new ideas. It involves understanding the needs of the end-user, generating ideas, prototyping, and testing. This process can be used to develop new products or services or to improve existing ones.
• Innovation Games: You can try out interactive exercises that can be used to generate new ideas and insights. They can include activities such as “what-if” scenarios, “reverse thinking,” or “mind mapping.” These games can be a fun and engaging way to get leaders thinking creatively.
• Role-Playing: This can be used to help leaders think about a problem or challenge from a different perspective. They can take on different roles and try to see the situation from different viewpoints. This can help to uncover new insights and generate new ideas.
• Creative Problem Solving: This is a structured approach to problem-solving that involves defining the problem, generating ideas, evaluating alternatives, and implementing solutions. It’s a valuable process that can be used to solve complex problems facing the company.

When used as a leadership retreat activity, creative thinking sessions can help leaders to generate new ideas, solve complex problems, think more creatively about the challenges facing the company, and foster a culture of innovation and creativity among their leadership team.

12. Wheelchairs for Charity

Skills practiced: Collaboration, communication, strategic thinking

Doing good deeds has been scientifically proven to reduce stress and make people feel better. That’s why philanthropic team building activities are a big hit among senior executives.

Our Wheelchairs for Charity activity fuses philanthropy with real-world learning outcomes to help participants give back while sharpening their business skills. Together, teams will build and test fully functional wheelchairs before donating them to those in need.

This exercise is great for helping leadership team members increase their empathy while enhancing their communication and collaboration skills.

13. Live Podcast or Leadership Storytelling Panel

Skills practiced: Communication, vulnerability, storytelling

Behind every successful leader is a story—usually one filled with missteps, hard lessons, and unexpected wins. A live podcast-style panel is a great way to bring those stories to the surface in a format that’s relaxed, engaging, and deeply human. Invite a few team members to share short, personal reflections on pivotal leadership moments: a risk that paid off, a failure they learned from, or a moment that shaped their leadership philosophy.

Keep the vibe conversational—more coffee chat than keynote. You can even record the session as a podcast episode or internal resource for onboarding and development. The audience gains insight into the real people behind the titles, and the storytellers often come away with renewed clarity about what they stand for as leaders.

This kind of format builds psychological safety across the team, reinforces shared values, and sparks meaningful conversations that extend well beyond the retreat.

14. Confident Decision Making

Skills practiced: Decision-making

Each day, leaders are faced with dozens of decisions, ranging from minor to major. That means the ability to make effective decisions quickly and confidently is of paramount importance.

With the Confident Decision Making training and development program, your leadership team will learn best practices for tackling complex choices, avoiding common decision-making traps, and becoming more accountable.

15. Leader-Led Breakout Discussions

Skills practiced: Facilitation, peer learning, adaptability

Skills practiced: Peer learning, facilitation, adaptability

Instead of setting every session in stone, carve out time in your retreat agenda for open-format breakout discussions—led by the leaders themselves. Start by having each participant jot down one question, challenge, or topic they’d love to explore with their peers. It could be something like:

• “How do you build trust across remote teams?”
• “What’s your go-to strategy for managing burnout—your own or your team’s?”
• “How do you lead through ambiguity when the answers aren’t clear?”

Stick all the ideas up on a wall or whiteboard, then let the group vote on which topics to tackle. Break into smaller groups based on interest, and give each group 30–45 minutes to dive into the discussion, share stories, and offer advice.

This creates space for honest, relevant conversations that meet your team exactly where they are. No slides. No outside facilitator. Just a chance for leaders to learn directly from each other.

16. Clear Communication

Skills practiced: Communication

Strong communication skills are vital to the success of any leadership team, but they aren’t always intuitive.

With a training and development program like Clear Communication, your senior executives can learn to hone their verbal and written communication skills, interpret and understand non-verbal communication signals, and enhance how they communicate during conflicts and decision-making.

These skills can be seamlessly exercised in a team building activity such as Code Break or Clue Murder Mystery.

17. Tech Detox + Analog Strategy Session

Skills practiced: Focus, presence, creative thinking

In a world of nonstop notifications, giving your team time to unplug can be one of the most productive things you do. A tech detox strategy session invites leaders to step away from screens—no laptops, no phones, no slides—and engage in analog problem-solving using just pens, paper, sticky notes, and conversation.

Choose a meaningful strategic prompt, like “What’s holding our team back from moving faster?” or “Where do we want to be a year from now?” and let the group explore it free of digital distractions. Without the temptation to check email or default to a PowerPoint, conversations tend to run deeper, ideas flow more freely, and leaders are often surprised by how energizing it is to go low-tech.

The session creates a shared sense of focus and creativity that’s hard to replicate in a typical meeting environment—and it reminds your team how powerful it is to slow down and think deeply, together.

18. Positive Team Dynamics

Skills practiced: Company culture and growth, communication, trust-building, employee engagement

The most successful teams have one thing in common: a positive team dynamic. In order to create this, it’s important for leaders to be able to build a framework for what a successful team looks like, enhance the way their employees work together, and, most importantly, the way they contribute to the team.

With the Positive Team Dynamics training and development program, your leadership team will learn to get aligned, create increased productivity, build trust, collaborate effectively, and take on greater ownership and accountability.

19. Scavenger Hunts

Skills practiced: Teamwork, communication, collaboration

Business leaders spend a lot of time outside of their comfort zones. It’s the nature of the roles.

So, company retreat activities don’t always have to be about work. Sometimes the best goal is to focus on getting you and your colleagues together and having some fun in an energetic and engaging way.

Scavenger hunts are a great option for this. Here are a few you might like.

Wild Goose Chase

In this scavenger hunt activity, your team can get out of the office and explore your city in a whole new way. Together, your team will need to think outside the box, bond as a group, and venture outside into the community in order to complete a series of fun and unique photo and video challenges.

You’ll need to tackle a list of challenges, including:

• Snap a photo of your team standing next to a large public clock that reads EXACTLY 22 minutes past the hour
• Search for a business that is open 24 hours 7 days a week and snap a photo of a team member with the sign showing the business’ hours
• Snap a photo of a teammate next to a vehicle that has an “antique” or “collectible” license plate
• Head to a nearby playground and take a photo of your entire team balanced on a seesaw. Here’s the catch: everyone’s feet must be off the ground while balanced!
• Find a hopscotch course or use a piece of chalk to create your own on a sidewalk. Record a 5-second video of a teammate hopping and completing it
• Stage a martial arts battle with another team in a nearby park. Record a 5-second video of both teams facing each other (with plenty of space between you) and doing the famous crane kick

The team with the most points when time runs out will be named the winners!

Neighborhood Scavenger Hunts

Looking for a scavenger hunt idea that helps build a sense of community and create bonds? Send your team out into their neighborhood (or the one surrounding your office) to chat with people and ask for help finding items on the list.

They can look for things like:

• A unique building in the neighborhood
• Landmarks in the neighborhood
• The number of houses in the neighborhood
• Visit a veteran who lives in the neighborhood
• Specific types of businesses in the neighborhood

With this scavenger hunt idea, make sure your employees inform everyone they talk to that they’re on a scavenger hunt and ask if they’d be willing to help. Some people may not want to be involved, and that’s their prerogative.

Scavenger Hike

Nothing helps your team to relax and recharge like getting out into nature. So, consider heading out for a day hike or nature walk with your group and doing a scavenger hunt while you’re at it.

Before you go, create a list of things your team will have to take photos of. This could include:

• Birds
• Animal tracks
• A tree growing out of a tree trunk
• A stream of river
• A waterfall
• Berries
• Wildflowers
• A cave
• Trail markers
• A beautiful view
• Fruit on trees
• Rock formations
• Spiderwebs
• Trash or litter you can clean up
• Fallen branches or trees

This will vary depending on where you live, but you can tailor your hiking scavenger hunt list to align with your geographical location.

Want even more scavenger hunt ideas? Check out our list of free and paid scavenger hunt team building activities for workgroups.

20. Purpose-Driven Offsite Challenge

Skills practiced: Service leadership, empathy, values alignment

Sometimes, the most impactful leadership development happens far from the boardroom. A purpose-driven offsite challenge gives your team a chance to step into a shared mission that reflects your company’s values—whether that means rebuilding a local trail, helping a nonprofit brainstorm growth strategies, or supporting a social enterprise with hands-on work.

This isn’t just about volunteering—it’s about experiencing leadership through service. Participants have to quickly organize, communicate, and collaborate in a new context, often outside their comfort zone. And because the work has real-world impact, it brings a level of emotional investment and meaning that sticks.

The challenge also creates space for deeper conversations around purpose, impact, and how your organization shows up in the world. It’s a powerful way to strengthen culture, foster humility, and give your team something to feel truly proud of long after the retreat ends.

21. Celebrate Success

Skills practiced: Team building, company culture and growth, employee engagement

As much as it’s important to plan ahead, set goals, and practice essential leadership skills, it’s equally important to reflect upon and celebrate team successes thus far.

This can be as simple as calling out the hard work and achievements of individual leaders or teams. It can also be as significant as reviewing the company’s success throughout the past year and recognizing how individual achievements made it possible.

Celebrating success allows you to reconnect your leadership team with its mission and reinforce its sense of purpose within the organization.

22. Recharge with Wellness

Skills practiced: Personal and professional wellness

Your company’s leaders work hard and they deserve a bit of downtime away from the daily stresses and pressures they contend with.

That’s why wellness-focused leadership retreat activities can be incredibly valuable for your leadership team and their mental and physical well-being.

You can incorporate things like:

• Mindfulness Meditation: This is a simple and effective way to reduce stress and improve mental clarity. A guided meditation session can be led by a trained professional or can be done using an app or audio recording.
• Yoga or Stretching: A gentle yoga or stretching session can be a great way to start the day and help participants to loosen up their muscles and improve their flexibility.
• Nature Walks or Hikes: Spending time in nature has been shown to have a positive impact on mental health and well-being. A guided nature walk or hike can be a great way to get some fresh air, exercise, and connect with nature.
• Massage or Spa Treatments: Professional massage or spa treatments can be a luxurious way to help participants unwind and reduce stress.
• Fitness Activities: Group fitness activities, such as a fitness class, boot camp, or team building activities like outdoor challenges or scavenger hunts, can be a fun way to promote physical wellness.
• Nutrition Workshops: Learning about healthy eating and nutrition can be an important part of overall wellness. A workshop led by a nutritionist or chef can provide useful tips and advice on healthy eating habits.
• Mindfulness and Stress Management Workshops: Workshops on mindfulness, stress management, and other wellness-related topics can provide participants with tools and strategies for improving their overall well-being.

When it comes to wellness-focused leadership team activities, there’s one thing that’s important to remember: everyone has varying physical abilities and comfort levels, so make sure you’re picking something that works for everyone.

Hosting leadership retreats is essential to ensure your team remains engaged and performing at a high level—and, in turn, can confidently and comfortably lead your organization to success.

But when picking leadership retreat activities, be sure to align them with your overall goals for the event in order to ensure that every minute of your retreat is maximized.

Does your organization host leadership retreats for its executive team? If so, what type of leadership activities do you enlist and why? Share your thoughts in the comments section below!