Advice for planning and facilitating successful corporate, executive, and leadership retreats.
Excellent leaders are flexible and quick on their feet to handle the many day-to-day responsibilities of their organization or company. However, the day to day grind can sometimes make it hard to take a step back and focus on the big ideas or vision of the future.
That’s where leadership retreats come in! Depending on budget, your organization may take a trip over a few days or host a one-day event locally or virtually. This time can be spent training the leadership team’s natural abilities to support the organization and its goals. It can also help them reflect on issues like innovation, strategy, vision, etc.
In this article, we’ll share some general advice for organizations and companies designing, developing, and implementing leadership retreats.
What is a leadership or executive retreat?
Executive retreats provide an excellent opportunity for leaders within an organization to “get away” from the day-to-day operation of their business and instead focus on the broader picture. Retreats traditionally happen in person, although the COVID-19 pandemic has further normalized the idea of a virtual retreat in which participants can join remotely from anywhere. Retreats can happen over several days or just be a one-day session to address a specific issue. Some organizations analyze and work on multiple areas of interest during their retreat, while others choose one clear goal to try to accomplish.
Simply put, an executive retreat can help the leadership team at your organization or company tackle your own unique challenges, brainstorm future goals, and build a global vision moving forward.
Why organize a leadership retreat?
There are several reasons you may be interested in organizing a leadership retreat. The first is if your leaders are struggling to see past the day-to-day grind of business. Without a clear vision for the future, organizations “drift” and fail to accomplish key objectives or goals set for themselves.
A second great reason to consider holding a retreat is to improve team building and bonding. For organizations with multiple locations or fully remote or distributed teams, this retreat can be a crucial event to bring everyone together in the same place (in person or virtually). Leaders can work together to align on company goals, improve their skills, and share valuable insights.
On-site vs virtual leadership retreats
When it comes to where to hold the event, the answer is it depends! Some organizations who already deploy virtual or hybrid work models may find it easier and more comfortable to hold their leadership retreat virtually as well. On the flip side, remote teams may wish to devote time to an in-person retreat once a year to reinforce company vision.
Whatever structure your organization currently uses to work, an in-person or virtual leadership retreat can work for you. The decision simply comes down to personal preference, budget, employee location and distance from each other, and other intangibles.
Ideas for corporate retreats
No matter what style or format you end up going with, here are some ideas that hold true for both virtual and in-person retreats.
- Start with icebreaker activities. Icebreakers are useful beginning exercises even for teams who know each other quite well. These games or other activities let participants “relax” and feel more comfortable in the retreat environment before the real work begins. Icebreakers can also be used throughout the retreat to facilitate different groupings with creative thinking and problem solving purposes.
- Focus on reflection. Be intentional about reflecting on the future and current state of your organization. Ask your leaders questions such as: what success are they celebrating most from the last year? what’s an area that didn’t go as planned? what’s an area they think needs to be focused on more this coming year?
- Reflect on the “why.” Every organization and company should have their own “why” that describes why they do what they do. Aside from that, every leader should also have their own personal why. Why are they personally engaged and invested in the organization and its goals moving forward?
- Include skill building sessions. Your retreat can also be great time for leaders to focus on developing hard or soft skills that will be invaluable to their job. Depending on your budget and schedule, you may also consider hosting multiple optional sessions so participants can make their own choices based on skill areas they feel they could use further development help on.
- Celebrate successes and show appreciation. Don’t forget to take a little time during or near the end of retreat to celebrate all of the wonderful work your leaders have done and show appreciation for their continued dedication to your success!
Leadership Retreat Facilitators
The role of leadership retreat facilitator is a critical one. You want an experienced and skilled facilitator who also has the ability to improvise and change the gameplan during the day if needed. A great executive or corporate retreat facilitator is also a designer. They design the key activities for the participants and storyboard for the day. We have facilitated over 100 onsite and virtual leadership retreat style events and workshops. Contact us online today to learn how we many design and facilitate your leadership retreat.
How We Design and Facilitate Your Leadership Retreat
We have designed and facilitated over 100 onsite and virtual leadership retreat style events and workshops. The advice above holds for most retreats. What follows is how we approach designing one for a specific group.
Most leadership retreats fail in the design rather than in the room. A team is pulled out of the office for two days, given an agenda built from last year’s agenda, and sent home with a list of action items nobody owns. The location changes and the meeting does not.
We use design thinking to design the retreat itself. That means treating your participants as the people we are designing for, and treating the venue, the history of the group, and the reason you are gathering as raw material rather than logistics.
Purpose: what has to be different afterward
Every retreat we design starts with a question sponsors are rarely asked directly: what should be true on the Monday after that is not true today? Alignment on a strategy, a decision that keeps getting deferred, trust between two functions that have been avoiding each other, a plan people actually believe in. The answer shapes everything else, and it is often different from the stated topic.
People: who is in the room and what they arrive carrying
A leadership team that has just been through a reorganization needs a different opening than a team celebrating a strong year. A group where three people do all the talking needs activities that quietly redistribute airtime. We ask about the group’s history, the tensions nobody names in the planning call, and who needs to leave feeling heard.
Place: using the location instead of booking it
This is the part most retreat planning skips. We have designed retreat activities around Frank Lloyd Wright’s work at Taliesin, used an outdoor space at the University of Wisconsin for activities that would not have worked indoors, and turned a consulting firm’s own office into something that felt like a retreat because travel was not in the budget. A hotel conference room with round tables is a real constraint, and it is also a structure for putting a hundred people into teams of five.
You can watch short videos of retreats and offsites we have designed and led to see what these sessions actually look like.
Leadership Retreat Formats We Facilitate
Executive and Leadership Team Retreat
For strategy, alignment, and the conversations that need more room than a standing meeting gives them.
Multi-Day Leadership Summit
For larger organizations bringing several teams, functions or regions together around one agenda. See our work on designing innovative leadership retreats, conferences and summits.
One-Day Local Retreat
A focused session on a single issue when budget or calendars will not stretch to travel.
Design Thinking Retreat
A design thinking workshop given real time in a retreat setting, so the method gets practiced rather than described.
Team Building With Substance
Often built on LEGO SERIOUS PLAY or a gratitude storytelling experience, where connection is the point rather than a side effect.
Virtual and Hybrid Leadership Retreat
For distributed teams, designed so remote participants are taking part rather than watching. See our tips for virtual offsites and remote retreats.
What a Leadership Retreat Agenda Looks Like
We do not work from a standard agenda, because the value is in the fit. What most of our retreats share is a shape: an opening participants do something in within the first fifteen minutes rather than a welcome slide, divergent work before convergent work so the group is not simply ratifying whatever the most senior person said first, something made rather than only discussed, reflection built into the schedule where the insight usually lands, and a close that names decisions and who carries them instead of listing action items.
What We Ask Before Designing Your Retreat
What is the real reason you are gathering, including the reason that is not on the agenda? Who is coming, and is there anyone whose buy-in determines whether this works? What did the last retreat feel like, and what do you want to avoid repeating? What is the venue, and what does it make possible that a conference room would not? How much time do we actually have, once travel and meals are honest? And who owns what happens next, and what do they need from the retreat to do that?
Some of these answers change the design completely. That is why the planning conversation matters more than the agenda template, and why we treat retreat design as a design problem rather than an events problem.
We also receive more inquiries than we take. When your retreat would be better served by a facilitator based in your country, or by someone who specializes in a particular method, we will say so and point you toward a person or firm we recommend. Most people reaching out are not looking for us specifically. They have a retreat to run and they want it to go well.
Leadership Retreats Conclusion
InnovationTraining.org is your source for innovation and design thinking focused resources and training that can be used during a corporate leadership retreat. Visit some of our other articles to see what you can learn to turn your leadership event into a reality. For even more content and resources beyond the topic of leadership retreats, browse the related articles below and our innovation and design thinking blog.