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Planning a leadership retreat? Here are some ideas to make it productive and inclusive

Leadership retreats are utilizing the precious, sought after time of leaders. Here are some ideas on how to spend it effectively and inclusively

After a few years of heavy virtual meetings, leaders are increasingly reconvening in person for deeper dive work. Yet, this shift has not been easy for most leaders. With leadership retreats and off sites on the rise, here are some things to consider in ensuring their effectiveness:

  • Prioritize discussion over presentations 
  • Have inclusive, immersive activities
  • End with next steps and accountability

Leadership retreats often cost six figures – accounting for compensation of executives, food, location and activities. That is a large budget item, one that should have a positive  return on the investment. Let’s unpack how to facilitate an inclusive meeting that maximizes the ROI.

Prioritize discussion over presentations 

Presenting information should be done by email or in a pre-read for the retreat. It is a terrible use of leadership’s time to listen to a presentation they could have been read in advance. Valuable in-person time needs to prioritize discussion of real issues leaders are facing. Have a strategic set of key questions that need to be resolved for future success. Consider some of these starting point questions:

  • What does success look like for our organization (3-5 years out)?
  • What are the challenges that we have to face to achieve that success?
  • What makes us unique from our competition?
  • What do our customers want that we do not currently offer?
  • What does support look like for our employees? 
  • What are the critical priorities to achieve future success (3-5 per leader)?

Leadership retreats should be about asking big questions. Questions that leaders don’t know the answers to and that require healthy debate. Outside facilitators can help garner different perspectives and ensure equitable participation from the leadership team. When someone dominates the meeting, it is harmful to the whole team. Ground rules to start help to set the tone for discussion over monologues. 

Have inclusive, immersive activities 

Gone are the days of trust falls and rope climbing courses to build psychological safety. Instead, activities that immerse people in a shared experience are key. Human beings are social creatures and once they connect in a shared experience together (especially in person), they form deeper connections and bonds. This allows leaders to bring up challenges they might not want to surface and be proactive in solving problems versus shying away from them or blaming others. 

One of my favorite in-person activities for leadership retreats is Visual Explorer. Leaders walk around the room with a prompt about how they’re feeling right now or the current state of the business and are asked to pick a visual image that most closely represents their feelings. This disrupts the norm. Often feelings are compartmentalized in the workplace even though humans are deeply emotional creatures. Setting the tone with a vulnerable exercise like this helps people shed their inauthentic work personas and show more of their human Side. It helps to set the tone for openness and psychological safety.

One of my clients uses a This is Me Wheel tool to facilitate discussion and help leaders get to know each other. The key is to get people talking and sharing, and not just about business. By focusing on the whole human, leaders can connect and talk through more difficult topics when back in the day-to-day work environment. I also have a plethora of activities and tools from our work on Allyship in Action.

End with next steps and accountability

Priya Parker, author of The Art of Gathering, recommends that leaders spend a considerable amount of time at the end of the gathering to decide what was decided. Often there’s a hurried conclusion to the meeting and people scurry off back to their day jobs and email boxes full of other priorities. I’ve seen so many well-intentioned leadership teams leave retreats with action items that people are not accountable for. I recommend at least 10% of the retreat’s time spent on making real life decisions and assigning people, resources and timelines to support the action plans.

A follow-up to the Retreat is also necessary. Usually, two to four weeks after the retreat, have a meeting to connect on action plans with leaders accountable for sharing updates. This forum should continue the theme of psychological safety – no one is in trouble, the idea is to talk through challenges and ideas to inform future success.

At Next Pivot Point we have lots of resources to help you facilitate successful diversity and inclusion training. Schedule some time with our team today to discuss where to start or how to do better. You can also check out: