6 Mistakes To Avoid When Planning A Leadership Retreat

Leadership retreats are supposed to be something to look forward to: spending time in a relaxed setting, developing plans without the constant distraction of the office and the strengthening of team relationships and dynamics.

If that’s the case, then why do so many people dread a leadership retreat like the plague? They don’t want to go and when they get there, they can’t wait for it to be over. Pretty much like many of us guys feel about our annual physical!

The answer lies in the structure of the retreat itself. Avoid the following, commonly made mistakes, and you’ll be well on your way to having a successful, productive leadership retreat.

  • Don’t get lost – The old saying, “if you don’t know where you’re going, how will know when you get there?” is definitely applicable to planning a leadership retreat. You need to have predetermined objectives. Otherwise  attendees will come with their own objectives/agenda, or none at all. In the months leading up to the retreat, maintain a list of what you want to accomplish. Then prioritize your objectives and announce them to your team prior to the retreat.
  • Don’t bite off more than you can chew – Too often we try to cram more into the agenda than we can possible accomplish. As a result, discussions get rushed, or cut short, and people get frustrated. Instead, only select the number of objectives that can be thuroughly discussed in the time set aside for the retreat. Be sure to give yourself enough time to determine next steps and create a timeline.
  • Don’t keep people in the dark – When people don’t know why they’re attending a retreat or meeting, they can tend to become close minded. Definitely not what you want! Be sure to share the topics, objectives and goals of the retreat far enough in advance so that people have ample time to get prepared.
  • Don’t self-facilitate – You, as the boss, should not facilitate your own leadership retreat. I’ve personally made this mistake… more than once. If you facilitate, the tendency is for your people to simply follow your lead and offer the answers they think you want to hear. Guess what? Those may not be the best answers! Instead, bring in an experienced facilitator. Someone objective who can ask the hard questions and hopefully lead the group to come up with fresh answers.
  • Don’t shy away from fireworks – Bringing together people who are passionate about their ideas can often times create ‘fireworks’. Don’t be afraid of this. I know this is something I struggle with. When the sparks start to fly among my staff, I tend to want to become the ‘peacemaker’ and try to keep everyone happy. The result can be a watered down meeting that frustrates everyone. Next retreat try going into it hoping for fireworks. They’re a great sign of passion and creative energy.
  • Don’t drop the ball – How many times have you attended a retreat that generated a lot of great ideas, but then nothing happened? Did that frustrate you? I know it does me. Don’t make the same mistake. The end of the retreat should be just the beginning. Before ending the retreat be sure to clearly communicate next steps, project assignments and a follow-up timetable.

What about you? Any mistakes you’ve seen made (or made yourself) that you could share?


  1. Oh boy, this brings up memories of events I’ve attended in the past, where things didn’t go so well. Focus is key – know where you’re going and what your end-result should be.

    I agree that it can definitely be valuable to have someone else there to facilitate, but I’ve also been at meetings where we ended up in a place we never wanted to be, and it was all because the facilitator took us there. Well, I should also say that it was also because the boss didn’t tell the facilitator we didn’t want to go there. So, the facilitator needs to stay in close contact with the boss re: the expected outcomes.

    Great point re: the fireworks. Organizations have to learn how to have good discussions and disagreements while also helping to keep people on the same page and working toward the same goals.

    In my experience, the biggest frustration from meetings and retreats is the fact that things rarely change and that the things that were discussed don’t seem to make any difference moving forward. People need to see that the things they share do count and will make a difference.

    • Byron Hill says

      Great comments Rich. I’m actually in the pre-planning stage for a strategic planning retreat with our summer camp leadership team. In talking with a potential facilitator, we discussed in detail the need for he and I to constantly be on the same page before, during and after the retreat itself. I also agree that it’s very frustrating to invest time in a planning meeting and then not see anything change. Thanks for stopping by!

Your Thoughts?