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  • Writer's pictureJim M. Morgan

Leadership Retreats: Five Fundamentals

Having led corporate and nonprofit communications for more than two decades, I have planned and participated in my fair share of leadership retreats. Some of these have proved beneficial and productive; others, well…not so much. What makes the difference? As I see it, there are five fundamentals to making a leadership retreat successful, and I encourage anyone planning a retreat to consider them closely.


1) Plan by committee


By their very nature, leadership retreats are intended to bring people together. In some cases, a retreat is about bonding and team building; in others, it’s about tackling thorny issues that need a collaborative approach. Regardless of intent, it’s helpful to have multiple perspectives when planning the retreat. A retreat planned by the CEO alone, for example, may miss key opportunities that other leaders can help identify. Ideally, a diverse committee of three to five leaders from across the organization would work together to determine the agenda for the retreat.


2) Perfect the agenda


When assembling the retreat agenda, consider what needs to be accomplished. If the goal is team building, the agenda will likely include exercises or collaborative projects specifically designed to get people interacting in new ways. For example, attendees may be broken into two or more teams and asked to develop competing approaches to new market penetration in a “war games” scenario. Or maybe each attendee is asked to write a newspaper headline that will capture where the organization should be in 10 years. Developing (and sharing!) an agenda in advance gives attendees a chance to consider their perspectives before they walk in the door. And the very best agendas rely on questions rather than statements. “Where do we want to be in five years?” is a more provocative agenda item than “develop a strategic vision.”


3) Select the venue


With your agenda in hand, select a venue that will allow you to accomplish your goals. If you’ve decided to base your retreat on a series of small-group table discussions, for example, your venue must be able to accommodate this. Ideally, the space you choose would be comfortable and spacious, well adorned but without unnecessary distractions. An off-site room outside the normal confines of the office works best. Being in a new space often allows attendees to think in fresh ways, which can be extremely valuable for problem-solving. Oh, and don’t forget snacks. Asking attendees what snacks they prefer – and then providing them – shows that, because you listen to their small requests, you will also listen to their big ideas.


4) Identify a facilitator


When planning a retreat, consider bringing in a facilitator from outside your organization. Serving as an objective third party, a facilitator can help make sure discussions stay on track and that you follow your agenda. They can serve as an impartial referee if differences of opinion boil over. They can also make sure that everyone feels heard, and they can help summarize and capture key decisions made during the retreat. Of course, not all facilitators operate in the same way, so you must be clear on what you really need. Are you looking for someone to keep you on time and take notes, or to ask hard questions and push back (when needed) on leadership? Interview a few potential facilitators, and check references. Selecting the right facilitator will go a long way toward ensuring your retreat is a success.


5) Ensure follow-up


Okay, so you’ve had a great retreat, but it does not end there. A retreat is most valuable if the ideas that were voiced and the decisions that were made are both captured and shared after the event. Your facilitator can help with this, but ultimately it is up to leadership to ensure that progress continues. Best practices dictate that the same committee that planned the retreat should meet again after the fact to debrief on how things went and plan for next steps.



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