Leadership Retreats Are Hit or Miss — How to Make Yours a Hit

Leadership retreats can be really hit or miss. Some are engaging and transformative, while others are incredibly boring. What exactly sets apart the ones where participants say, “Wow, we need to have these more often!” from those where participants are scrolling through their email, feeling pulled away from “real work?”

While well-intended, there are subtle yet significant differences between mediocre retreats and those that truly deliver. Over the last decade-plus, I’ve designed and facilitated hundreds of retreats and training programs. I also completed a doctorate in adult education, which, in simple terms, is the study of how adults learn and retain information. The following steps will help you minimize yawns and ensure your leaders leave feeling as if they spent their time well.

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Clarify your off-site goals early

Start by identifying the goals for your retreat early on. Truthfully, you need to clarify the purpose before you even decide to have an event. You shouldn’t plan a retreat and then determine the purpose unless your organization has time and money to waste, which is unlikely in this economy. Your retreat should be aimed at solving a key business problem.

Here are just a few examples of high-level retreat goals from previous programs I’ve facilitated:

• Strengthen communication and collaboration skills between cross-functional teams in a hybrid work environment.
• Drive increased sales by helping teams better understand clients with diverse personalities.
• Improve mental well-being and prevent burnout among tech leaders who are managing heavy workloads.
• Retain key senior leaders in the department by inspiring them to bring their “whole” selves to work.

Your retreat length, agenda, location, venue and facilitator should all directly align with your goals. If you don’t know your retreat goals, don’t move forward with planning.

Swap icebreakers for meaningful team-building activities

As a major introvert (yes, I’m a professional public speaker and workshop facilitator who’s an introvert), I still cringe when I hear the phrase “icebreaker.” Most leaders I talk to feel the same way. That’s because they’ve endured activities that were uncomfortable, irrelevant or just a waste of time.

Every activity during your leadership retreat should support your goals, including any introductory activities. Yet even the most skilled facilitators often default to boilerplate activities like “Two Truths and a Lie.” Instead, choose opening exercises that align with the retreat’s purpose, build psychological safety or — if you can’t find any that fit — skip them altogether.

Avoid forced participation at all costs

There is nothing leaders dislike more than being forced to participate in a workplace activity that makes them uncomfortable. To this day, I still recall attending a retreat where, before the event, I shared a simple request: Please don’t call on me or make me do activities that require physical touch. Well, you guessed it — the first activity was a human knot, followed by random callouts to share reflections. To say I was displeased is an understatement.

If you’re struggling to get people to engage in the content, forced participation isn’t the answer. Focus instead on creating psychological safety and an environment where people can share when they’re ready and in ways that suit them best. Offer multiple participation formats, such as individual reflection, journaling, paired discussions or small-group dialogues. There are countless ways to engage attendees without forcing them into discomfort.

Bring in an external facilitator — early

Many organizations try to save money by skipping an external facilitator. Even if you’re cutting costs on travel or venue, consider the salary costs of everyone attending. If it’s important enough to bring people together, it’s important enough to bring in a professional facilitator.

That said, don’t wait until the last minute. I’m often contacted by first-time retreat organizers just a week or two before their event. The earlier you bring in a facilitator, the more impactful the experience will be. You want them involved in goal-setting, attendee list management and experience design so they can truly understand your business and objectives — not just show up cold.

Effective retreat planning takes time. For example, do you want participants to complete an assessment or inventory before the event? Will they engage in pre-retreat coaching sessions? Are you asking them to review articles or video clips? These details elevate the experience but also require people’s attention and time.

Keep momentum going

Avoid standalone retreats without follow-up. Humans rarely absorb new material or sustain behavior change based on a single day. You can think of it like going to the gym. Attending once won’t transform you. Only consistent effort leads to real, lasting results.

Work with your facilitator to decide how best to integrate retreat learnings afterward. This might include ongoing coaching for executives, follow-up sessions or revisiting key takeaways during monthly or quarterly meetings. Clarify your plans before leaving the retreat, because excitement fades quickly once everyone’s back to their inboxes.

Final thoughts on leadership retreats

In today’s economy, many executives are questioning whether to keep investing in leadership retreats and other development programs. Knowing your training goals from the get-go, ensuring your team-building activities are intentional, avoiding forced participation and bringing a professional facilitator in early will ensure your big day is a memorable one.

Don’t stop there. Build in follow-through, maintain accountability and keep the momentum going after the event so your leadership retreat isn’t just memorable but transformative. You’ve got this!

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Leadership retreats can be really hit or miss. Some are engaging and transformative, while others are incredibly boring. What exactly sets apart the ones where participants say, “Wow, we need to have these more often!” from those where participants are scrolling through their email, feeling pulled away from “real work?”

While well-intended, there are subtle yet significant differences between mediocre retreats and those that truly deliver. Over the last decade-plus, I’ve designed and facilitated hundreds of retreats and training programs. I also completed a doctorate in adult education, which, in simple terms, is the study of how adults learn and retain information. The following steps will help you minimize yawns and ensure your leaders leave feeling as if they spent their time well.