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How to Plan a Leadership Team Offsite with the Highest ROI (and lowest Cheese and Kumbaya)

In the world of leadership, the offsite meeting can be a powerful catalyst for team growth, strategic alignment, and breakthrough thinking.

The difference between a waste-everyone’s-time gathering and a transformative offsite lies in the design of it. With a strategic approach, you can ensure your next leadership offsite delivers the highest return on investment (ROI) possible.

I designed a two-pager Offsite Strategy Tool that helps you nail down the why, what, who, and how of your offsite (in that mandatory order)—or decide if you need one at all.  It’s my no-strings-attached gift to you, aimed at never hearing about “bad offsite” ever again, and instead hearing the stories of reset and team transformations that I know are possible after an intentional time together.

Here’s how to leverage the tool to plan an event that truly moves the needle for your team and organization (you can watch a video instead here)

#1 Define Your Purpose Clearly

Start with the ‘why.’ Understanding the core reasons behind organizing the offsite is crucial. Is it to foster better teamwork, outline strategic directions, or address specific challenges? Knowing this sets the stage for everything that follows and ensures every single activity contributes towards these overarching goals (so no forced fun, right?!)

#2 Set Concrete Outcomes

What exactly do you want to achieve? Go beyond vague aspirations by specifying what you want team members to hear, think, feel, learn, and do as a result of the offsite. If there is specific output you want to see, prototype it and work backwards from it. This clarity will guide the design of your agenda, inform the required pre work and help measure the offsite’s success.

#3 Choose Your Participants Wisely

Deciding who attends is as important as the agenda itself. Include individuals who are crucial to achieving your outlined goals and consider the dynamics their presence will create. Remember, the right mix of people can make or break the collaborative spirit of your offsite. At times, you can have different people attend different parts of the offsite. For example, it starts with the executive team, and then cascades to the expanded leadership team or maybe functional teams.

#4 Time It Strategically 

Look back at your last offsite for lessons learned and consider how the timing aligns with your strategic calendar. Ensuring all key players can attend without pulling them away from critical tasks is a balancing act that pays dividends in engagement and productivity.

#5 Pick Appropriate Location

The setting of your offsite can significantly impact its effectiveness. Balance logistics and budget with the need for a space that inspires creativity, openness, and focus. Whether it’s a serene retreat or a dynamic urban space, ensure that the choice is informed by your objectives and facilitates the desired outcomes ( not the other way around!) Given hybrid or remote set up, offices or co-working spaces can offer what you need without a dent in the budget.

#6 Decide on Facilitation

To DIY or not to DIY? That is the question. Evaluate whether an external facilitator could add value by bringing in expertise, ensuring neutrality, or simply allowing everyone to participate fully without worrying about running the meeting. Use the checklist in the tool to see whether you need an external facilitator or speaker. And if you are using an internal facilitator, make sure they possess these competencies to be effective.

#7 Start Designing Agenda & Activities

Activities should never be fillers; they should reinforce your goals, foster learning, and build trust within the team. Think strategically about how each segment of your off site contributes to the bigger picture, and builds on each other. Consider energy and productivity levels, and always allow for some unstructured  thinking and buffer time. It’s shocking to many how smart adults can self-organize without structure as well, and the group wisdom that emerges. Don’t be scared by white space!

#8 Ensure Success from Start to Finish

Draw on past experiences with the group to shape your approach, addressing potential obstacles and setting the stage for success. Think about who else should inform the design (so it’s relevant to all parties!) and whether there are things to be addressed before the time together (What is the elephant in the room?!)

From the pre-offsite preparations to the follow-up, every phase should be thoughtfully orchestrated to maximize impact. Remember that your offsite does not start when people walk into the room. It starts now. And it also does not end as you all are driving off, make sure to think through how to reinforce,  integrate and cascade as needed down the organization. In my philosophy, an offsite is just a beginning of the journey.

By following these guidelines and utilizing the Offsite Strategy Tool, you’re not just planning another team meeting; you’re crafting an experience that can elevate your team’s performance, cohesion, and strategic direction.

The highest ROI from an offsite comes not from the lavishness of the setting or the cost of the activities but from the clarity of purpose, the relevance of the content, and the engagement of every participant.

Design with intention, facilitate with mastery and watch your leadership team thrive!

(Remember to watch the video to avoid 7 deadly mistakes of planning a leadership team offsite and more details how to use the Offsite Strategy Tool)

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