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

February 10, 2026
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Opinions expressed by Entrepreneur contributors are their very own.

Key Takeaways

Clearly outline the targets of your management retreat to make sure it addresses key enterprise challenges and doesn’t waste invaluable assets.
Exchange typical icebreakers with purpose-driven team-building workouts and keep away from compelled participation for extra real engagement.
Rent an exterior facilitator early within the planning course of to design significant experiences and preserve post-retreat momentum for lasting change.

Management retreats may be actually hit and miss. Some are partaking and transformative, whereas others are extremely boring. What precisely units aside those the place contributors say, “Wow, we have to have these extra usually!” from these the place contributors are scrolling by way of their electronic mail, feeling pulled away from “actual work?”

Whereas well-intended, there are delicate but vital variations between mediocre retreats and people who really ship. Over the past decade-plus, I’ve designed and facilitated lots of of retreats and coaching applications. I additionally accomplished a doctorate in grownup schooling, which, in easy phrases, is the examine of how adults be taught and retain data. The next steps will assist you reduce yawns and guarantee your leaders go away feeling as in the event that they spent their time properly.

Join How Success Occurs and be taught from well-known enterprise leaders and celebrities, uncovering the shifts, methods and classes that powered their rise. Get it in your inbox.

Make clear your off-site objectives early

Begin by figuring out the objectives in your retreat early on. In truth, it is advisable to make clear the aim earlier than you even resolve to have an occasion. You shouldn’t plan a retreat after which decide the aim except your group has money and time to waste, which is unlikely on this economic system. Your retreat needs to be geared toward fixing a key enterprise drawback.

Listed here are just some examples of high-level retreat objectives from earlier applications I’ve facilitated:

Strengthen communication and collaboration abilities between cross-functional groups in a hybrid work surroundings.Drive elevated gross sales by serving to groups higher perceive purchasers with various personalities.Enhance psychological well-being and stop burnout amongst tech leaders who’re managing heavy workloads.Retain key senior leaders within the division by inspiring them to convey their “entire” selves to work.

Your retreat size, agenda, location, venue and facilitator ought to all instantly align along with your objectives. For those who don’t know your retreat objectives, don’t transfer ahead with planning.

Swap icebreakers for significant team-building actions

As a significant introvert (sure, I’m knowledgeable public speaker and workshop facilitator who’s an introvert), I nonetheless cringe once I hear the phrase “icebreaker.” Most leaders I discuss to really feel the identical manner. That’s as a result of they’ve endured actions that have been uncomfortable, irrelevant or only a waste of time.

Each exercise throughout your management retreat ought to help your objectives, together with any introductory actions. But even probably the most expert facilitators usually default to boilerplate actions like “Two Truths and a Lie.” As an alternative, select opening workouts that align with the retreat’s objective, construct psychological security or — in case you can’t discover any that match — skip them altogether.

Keep away from compelled participation in any respect prices

There may be nothing leaders dislike greater than being compelled to take part in a office exercise that makes them uncomfortable. To at the present time, I nonetheless recall attending a retreat the place, earlier than the occasion, I shared a easy request: Please don’t name on me or make me do actions that require bodily contact. Properly, you guessed it — the primary exercise was a human knot, adopted by random callouts to share reflections. To say I used to be displeased is an understatement.

For those who’re struggling to get individuals to interact within the content material, compelled participation isn’t the reply. Focus as a substitute on creating psychological security and an surroundings the place individuals can share once they’re prepared and in ways in which go well with them finest. Provide a number of participation codecs, similar to particular person reflection, journaling, paired discussions or small-group dialogues. There are numerous methods to interact attendees with out forcing them into discomfort.

Usher in an exterior facilitator — early

Many organizations attempt to save cash by skipping an exterior facilitator. Even in case you’re reducing prices on journey or venue, take into account the wage prices of everybody attending. If it’s necessary sufficient to convey individuals collectively, it’s necessary sufficient to usher in knowledgeable facilitator.

That mentioned, don’t wait till the final minute. I’m usually contacted by first-time retreat organizers only a week or two earlier than their occasion. The sooner you herald a facilitator, the extra impactful the expertise can be. You need them concerned in goal-setting, attendee listing administration and expertise design to allow them to really perceive your corporation and targets — not simply present up chilly.

Efficient retreat planning takes time. For instance, would you like contributors to finish an evaluation or stock earlier than the occasion? Will they have interaction in pre-retreat teaching periods? Are you asking them to evaluation articles or video clips? These particulars elevate the expertise but additionally require individuals’s consideration and time.

Hold momentum going

Keep away from standalone retreats with out follow-up. People not often soak up new materials or maintain conduct change primarily based on a single day. You may consider it like going to the health club. Attending as soon as received’t rework you. Solely constant effort results in actual, lasting outcomes.

Work along with your facilitator to resolve how finest to combine retreat learnings afterward. This may embody ongoing teaching for executives, follow-up periods or revisiting key takeaways throughout month-to-month or quarterly conferences. Make clear your plans earlier than leaving the retreat, as a result of pleasure fades rapidly as soon as everybody’s again to their inboxes.

Closing ideas on management retreats

In immediately’s economic system, many executives are questioning whether or not to maintain investing in management retreats and different growth applications. Figuring out your coaching objectives from the get-go, making certain your team-building actions are intentional, avoiding compelled participation and bringing knowledgeable facilitator in early will guarantee your massive day is a memorable one.

Don’t cease there. Construct in follow-through, preserve accountability and hold the momentum going after the occasion so your management retreat isn’t simply memorable however transformative. You’ve bought this!

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Key Takeaways

Clearly outline the targets of your management retreat to make sure it addresses key enterprise challenges and doesn’t waste invaluable assets.
Exchange typical icebreakers with purpose-driven team-building workouts and keep away from compelled participation for extra real engagement.
Rent an exterior facilitator early within the planning course of to design significant experiences and preserve post-retreat momentum for lasting change.

Management retreats may be actually hit and miss. Some are partaking and transformative, whereas others are extremely boring. What precisely units aside those the place contributors say, “Wow, we have to have these extra usually!” from these the place contributors are scrolling by way of their electronic mail, feeling pulled away from “actual work?”

Whereas well-intended, there are delicate but vital variations between mediocre retreats and people who really ship. Over the past decade-plus, I’ve designed and facilitated lots of of retreats and coaching applications. I additionally accomplished a doctorate in grownup schooling, which, in easy phrases, is the examine of how adults be taught and retain data. The next steps will assist you reduce yawns and guarantee your leaders go away feeling as in the event that they spent their time properly.



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