12 Leadership Retreat Ideas

Let’s implement team building activities specifically tailored to team leaders. Check out these 12 leadership retreat ideas to learn more.
12 Leadership Retreat Ideas
Growing professionally, learning new skills, and always adapting to ever-changing situations are just some of the notable characteristics that describe team leaders.

Leaders are supposed to be strong, intelligent, and ready to overcome the challenges ahead, but oftentimes, companies forget that leaders are human beings as well.

Leadership team building activities are important - they help companies identify rising leaders among all team members.

However, if your company already has an established leadership team, then it’s time to consider these 12 leadership retreat ideas. 

Conference training with colleagues

Are Leadership Retreats Effective?

Leadership retreats offer plenty of benefits in the day-to-day operations of every business.

A short report by Harvard Business Review (HBR) shows us that executive retreats are some of the only times of the year when leaders get to connect with each other, talk transparently, and build bonds together.

The report shows that, in the past year, engaging in a single leadership retreat brought many benefits to team leaders, including employee engagement and a reduction in work-related stress.

Leadership teams are an integral part of the office, as they have a big impact on other team members. 

For example, 50% of employees cite bad leadership and poor management as one of the main reasons for leaving a job. Moreover, 3 out of every 4 companies believe that leadership could be improved (ThriveMyWay).

Leadership retreats are great for leadership development, team bonding, stress management, and the development of emotional intelligence.

34% of team members say that having executive retreats positively affects their mental health, as all of them had their best ideas after retreats (critical thinking skills), according to TravelPerk.

Consequently, integrating leadership retreats into your company’s formal agenda is a great way to continue growing and keep leaders engaged.

How to Choose Effective Retreats for a Leadership Team

Choosing effective leadership retreats is not always easy.

One of the main reasons why leadership retreats fail is that leaders don’t feel engaged enough with other team members (MRSC).

Retreat planning is the cornerstone behind efficient lead-focused activities, which is why it’s necessary to consider these three steps:

  1. Set team building objectives: What is the goal of the retreat activity? Do you want leaders to improve their problem-solving skills, or would you rather make them feel more relaxed and engaged in their work activities?
  2. Define the Retreat Schedule: Leaders are usually under a lot of pressure and never-ending work-related tasks. Before choosing a leadership retreat idea, make sure to communicate it to the team so everyone is on the same page.
  3. Choose the Right Leadership Retreat Activities: Once you have defined the schedule and set the objectives, it’s time to look into the different leadership retreat activities and choose one that suits your team.

12 Leadership Retreat Ideas

Before choosing leadership retreat ideas, it is important to consider that the time of team leads is extremely valuable.

This creates the need to keep things as organized as possible in order to ensure the expected results from these activities. Let’s check out 12 leadership retreat ideas that can bring great benefits to your leadership team.

1. Fun Outdoor Team Building Retreats

The first type of leadership retreat we are going to talk about is quite simple: outdoor activities.

Outdoor activities can be varied, fun, and have more benefits than many believe. For example, some of the most engaging outdoor activities offered by Teamland include Carnival Games, Mini-Golf Sessions, Amazing Races, and more.

The objective is to have fun. Instead of improving creative thinking or thinking about work, let team leaders just have some fun and fresh air.

Play team sports, visit a local painting gallery together, explore a local park, and let leaders enjoy their time. Clearing our thoughts and focusing on out-of-office stuff sounds like a simple thing to do, but it’s actually one of the best wellness activities to engage in.

  • Activity Duration: From 1 to 2 hours.
  • Group Size: All in-office group sizes. 
  • Materials Needed: Vary depending on the activity (sports, gathering, picnics, visiting museums, and more). 

2. Icebreaker Questions

If you are looking for a way to facilitate relationships among team leaders, then icebreaker activities can help lighten the mood.

Not all team leads know each other, and certainly, not all members of leadership teams have enough time to show their human side.

A simple icebreaker game, such as asking funny questions, things in common, and past life experiences, can build stronger relationships among leadership team members.

  • Activity Duration: From 45 minutes to 1 hour.
  • Group Size: All group sizes (remote and in-person). 
  • Materials Needed: Imagination to ask icebreaking questions and a place to gather together. 

3. Skill Development Workshop

Having skill-building sessions helps prevent the loss of vital personnel and increases motivation levels among teams (Indeed UK).

Consider engaging in a skill development workshop to develop the soft skills and interests of your team, which can be very varied.

Instead of focusing on leadership skills, consider more fun and engaging activities, such as nutrition workshops, social media practices for senior team leads, terrarium workshops, and more.

There’s a multitude of workshops and session types that can work as a leadership retreat for your team, whether your goal is to focus on professional development or personal growth.

  • Activity Duration: From 1 to 2 hours.
  • Group Size: Small and medium-sized remote and in-office teams. 
  • Materials Needed: Select a skill workshop that the whole team likes, and hire professionals (Teamland) to participate in the workshop. 
Casual young people sitting at the seminar

4. Future-Proof Exercise

Most industries live in an always-changing space where new industry trends, technologies, and processes appear year after year.

Team leaders have the duty to adapt to these changes in order to overcome the challenges ahead.

Gather your leadership together, and talk about the potential implications of new technologies in your company.

Think about how the latest trends, technologies, and tools can help team leaders fulfill the organization’s vision, which ultimately leads to the company’s success.

Having brainstorming sessions together and fostering innovative thinking can help the group to have a deeper understanding of the company’s needs.

Furthermore, doing a future-proof exercise helps develop strategic planning and strategic thinking, which are two valuable skills that all leaders should have.

  • Activity Duration: From 1 to 2 hours.
  • Group Size: Small and medium-sized teams. 
  • Materials Needed: Gather information about the latest industry trends to discuss them together in a leadership retreat. 

5. Public Speaking Training

Learning how to speak in public is one of the best team building activities for all team sizes, as it helps team members to develop valuable and useful skills.

In Teamland’s Public Speaking Training, external speakers and industry leaders will offer specialized knowledge to leadership team members.

This helps with professional development and improves the overall communication skills of the entire leadership team. 

  • Activity Duration: From 1 to 2 hours.
  • Group Size: Small and medium-sized teams (hybrid event). 
  • Materials Needed: Teamland’s Public Speaking Training from a 2-time TEDx speaker. 

6. Lunch for Wellness

One of the best ways to approach a leadership retreat is to consider wellness activities. Leaders are responsible for several tasks, ongoing processes, and team management.

This can heavily affect their mental health, which creates the need to protect your team’s well-being through simple yet highly efficient activities.

Teamland’s Amazing Team Lunches are simple in concept but highly beneficial.

Organized team lunches in a leadership retreat help teams boost morale, feel more engaged in work, and connect more with their coworkers.

Pick what to eat, include fun activities in the lunch, and have a great time together to form a more united leadership team.

  • Activity Duration: From 1 to 2 hours.
  • Group Size: Small and medium-sized in-person teams. 
  • Materials Needed: Let Teamland’s Amazing Team Lunch activity organize everything for you, which includes the meal menu, activities to play, topics to discuss, and venue to eat. 

7. Survivors

It’s time to get the creative juices flowing - people in leadership roles tend to have strong personalities, but how will they collaborate with each other toward a common goal?

Teamland’s Survivors is a fun experience that takes your team into a fierce competition that only a few can win. 

In Survivors, some leadership members will need to act as leaders, whereas others need to follow the leader’s instructions in order to win the game.

This fosters creative problem-solving skills, as team cooperation is the only way to win the games.

Moreover, identifying how each team member approaches a solution with innovative ideas works to segment leaders by leadership styles.

8. Emotional Intelligence Training

Regulating our own emotions is a challenge that many team members face every day.

Team leaders need to learn how to have complete control over their emotions so they don’t end up affecting work-related processes.

Teamland’s Emotional Intelligence Training teaches team members how to efficiently manage their emotions so they don’t interfere with their professional tasks.

This interesting workshop helps to improve both personal and business performance of leadership roles, which brings great results to everyone in a company.

Group of young people listening at a business training.

9. Virtual Discussion Break Room

Remote team leaders tend to feel more isolated than in-person team members.

By implementing a virtual retreat, employees in a remote environment can feel like they belong to a group setting as they feel part of a company.

Start by “retreating” your remote team into a virtual space, such as a specific Zoom Room.

It is also possible to add training sessions with different workshops or activities. Leaders can opt to participate in these multiple optional sessions or not, which fosters human interactions between team leads as they also develop their leadership skills.

  • Activity Duration: From 1 to 3 hours.
  • Group Size: Remote teams (all team sizes). 
  • Materials Needed: Remote video conferencing software and remote workshops. 

10. The Sinking Ship

A ship is sinking, and team leaders need to handle the situation. To do so, they need to collaborate with each other.

Gather team leaders into a room (virtual or in-office), and ask them one by one how they would survive after their ship sinks.

This simple game helps teams develop event-planning skills and notice how certain leaders can improve their planning process by supporting others in emergency scenarios.

  • Activity Duration: 45 minutes to 1 hour.
  • Group Size: Small and medium-sized teams. 
  • Materials Needed: A place to gather together to start a brainstorming session and determine the best path to follow to overcome the sinking ship challenge. 

11. Charity Activity

Helping others in need will always bring a spark of joy into our hearts.

Find a charity activity that focuses on supporting the local community together as a united team with the willingness to collaborate.

For example, a Charity Bike Build by Teamland creates a relaxed environment in which leaders feel like they are making a difference in their community.

This improves interpersonal relationships and shows the importance of work-life balance, as there are many other important things outside work. 

  • Activity Duration: From 1 to 2 hours.
  • Group Size: In-person teams. 
  • Materials Needed: Identify a local charity activity to collaborate together. 

12. Remote Leadership Trivia

Trivia games are always fun as they foster creative thinking and let teams demonstrate their knowledge skills.

Virtual Trivia Time by Teamland is an activity that can be played with a “leadership” twist.

The questions can be modified to match leadership-related topics, such as the best way to solve work-related problems or general culture questions where team members collaborate with each other.

This virtual leadership retreat aims to connect remote employees with each other, as choosing a team leader for each Trivia team will encourage your team to find the answers by trusting their knowledge.

  • Activity Duration: From 30 minutes to 1 hour.
  • Group Size: Small and medium-sized remote teams. 
  • Materials Needed: Teamland’s Trivia Time

Summary: Best Team Building Retreat Ideas for Team Leaders

We are ready to choose the next leadership retreat for your team. Choose a retreat activity that suits your team leaders, gather feedback about the activity, and continue improving.

These are the best 12 leadership retreat ideas to implement in the workplace:

  1. Fun Outdoor Team Building Retreats: Engage in outdoor activities for fun and team bonding.
  2. Icebreaker Questions: Use funny or common-interest questions to break the ice among team leaders.
  3. Skill Development Workshop: Conduct varied skill-building sessions for personal and professional growth.
  4. Future-Proof Exercise: Discuss industry trends and plan for future challenges and technologies.
  5. Public Speaking Training: Improve communication skills through specialized training sessions.
  6. Lunch for Wellness: Organize team lunches to boost morale and team cohesion.
  7. Survivors: Foster creativity and teamwork through a competitive and creative game.
  8. Emotional Intelligence Training: Enhance emotional intelligence for better personal and professional performance.
  9. Virtual Discussion Break Room: Create a virtual retreat for remote teams to enhance leadership skills and team dynamics.
  10. The Sinking Ship: Promote event-planning skills and teamwork through a scenario-based game.
  11. Charity Activity: Participate in a charitable event to emphasize teamwork and community contribution.

Remote Leadership Trivia: Host a virtual trivia activity to connect remote employees and encourage engagement.

What you should do now

Whenever you're ready...here are a few ways we can help you:

1. Book a team social event. If you'd like to work with us to have more engaging team events, book an event.

Don't know what activity to pick? Use the Team Building Idea Generator for options.

2. If you'd like to learn remote work strategies for free, head to our blog where you'll find several guides and posts.

3. If you'd like to create a offering for companies for a skill that you have, then contact us and let us know.

4. If you know someone who’d enjoy reading this page, share it with them via email, Linkedin, Twitter, or Facebook.

More Articles