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How to Host an Effective Offsite Leadership Meeting

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Leadership offsites are multi-day meetings held away from the office. The purpose could be anything from strategic planning, to team building, to airing of professional grievances. However, such meetings all have the same basic aim: to create cohesion among the participants.

Leadership offsites have higher stakes than other meetings because of time and cost. Organizers ask the participants to sacrifice time away from their daily responsibilities to focus on other issues. By the time you factor in the expenses associated with travel and meeting space, as well as participants’ time itself, a two-day offsite can quickly add up to a significant annual budget line item. For the time and cost invested, it’s important to have a productive meeting. But how, exactly, can you ensure it’s a worthwhile investment?

Meeting hosts and organizers feel this pressure, and they focus on adding the right ingredients for a productive session. They create a list of objectives, draft an agenda, send out material to read in advance, and maybe even do a mini-survey of participants to determine what exactly they want to accomplish. These are necessary steps. But there is an underlying question that—when answered—helps to knit all of the group’s activities and events together: When the meeting is over, how do you want the group to feel?

I’m serious. This may sound way too soft and difficult to measure for some. But here’s the thing: There is only so much actual work that can be accomplished during a meeting. Real change happens after the meeting, when people show up and work differently. “Differently” might be defined as employees rearranging their priorities, collaborating more often across group lines, seeking more input from outside experts, or dozens of other possibilities. And one’s feelings about their work, the team, and their future in the organization will outlast any tenuous agreements made during a meeting.

The good news is that there are only a handful of answers to the question of how you want people to feel. Most leadership meetings have one of three goals: to build awareness, set a vision, or increase trust.

Feeling aware:

•    Are there significant programs or new initiatives employees should know about?

•    Do attendees need to agree to action items?

•    Do participants need to set priorities based on a broader knowledge of what’s going on in the organization?

•    Do these coworkers need to get to know each other better?

Activities typically include presentations, breakouts to develop action items, and voting on priorities.

Feeling optimistic and excited:

•    Is there a shared understanding of the big challenges and opportunities currently facing the organization?

•    Are there divergent paths to be explored?

•    Are creative, fresh solutions to current problems needed?

•    Is there a shared vision for the future?

Activities include reaching agreement on the current problems, defining the ideal future, and brainstorming ways to reach those goals. This may include bringing in a speaker from outside the organization to inspire participants to think bigger or differently.

Feeling secure, heard, and valued:

•    Are there past “wrongs” that need to be addressed?

•    Is the group guarded around each other or reluctant to share?

•    Is there an understanding of different perspectives and concerns?

•    Are participants prepared to handle externally-driven change?

•    Have their views been considered by top leadership?

Activities typically include exercises to get attendees to open up and share their concerns, looking for differences in perspectives, gaining acceptance of multiple viewpoints, defining new team norms, and establishing more effective ways to work together.

Leadership offsites can be a combination of any of these models. However, if you mix and match methods, it’s important to be clear and intentional about what you want to achieve in order to strike the right balance. To get the desired outcome, you must ensure the activities and discussion topics will get you there.

When people feel connected to their colleagues, in sync with the mission, optimistic about the future, invested in the strategy, etc., they make decisions that align with those feelings. This outcome is important: Thousands of little decisions are made between the beginning and the end of a big project. The leadership team will meet and collectively review and decide on roughly a dozen of them. The rest will be handled by managers. After all, that’s why they exist—to lead and manage. The most effective groups have a common set of feelings about the work, and each other, on which to base those decisions. As a result, these groups are more consistent, and they get more done faster.

Reflecting honestly on this question will shape the objectives and activities of your offsite. As an organizer, you dramatically increase the chance of ending with that outcome when the opening remarks, presentations, discussion questions, breakout groups, and conclusion are all laced with that theme in mind.

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