“We need to get on the same page.” It’s a common refrain when organizing corporate retreats, and on the surface, it seems straightforward enough. But is “getting on the same page” really what your team needs? The difference between a stated objective and what can actually make this happen can mean the difference between a transformative retreat and a missed opportunity.

When planning retreats, there’s often a gap between the initial ask and the deeper organizational needs – a gap that can only be bridged through careful investigation and honest dialogue.

So here are five key factors that can bridge the gap (credit to the Braintrust Professional Institute):

1) Pre-retreat Intelligence: Beyond industry and trends research, Interview each participant before the retreat. Very often there will be patterns and perspectives that weren’t visible in the initial planning conversations. When multiple people highlight the same challenge from different angles, it signals an important area that might need addressing.

2) External Perspective Advantage: Outside facilitators often uncover insights that internal stakeholders miss. Without any political “baggage”, they are able to gather candid feedback and identify common threads far more easily.

3) Balancing Competing Needs: Sometimes what’s needed and what’s asked for aren’t the same thing. For example, a request for “leadership training” might actually mask a need for better decision-making processes, or a bonus plan that encourages greater collaboration. The skill lies in addressing both the stated objectives and the underlying needs.

4) Setting Expectations: Once the insights are collected and analyzed, they can be used to set clear expectations with both the senior leadership, and participants. This ensures everyone arrives prepped for the retreat, and which may be a very different experience than previous retreats.

5) The Flexibility Factor: Build flexibility into both the retreat design and its execution. The idea isn’t to be a slave to the schedule, and when necessary, adapt in real-time as the retreat unfolds. If a particular discussion strikes a chord or when an unexpected challenge surfaces, these are opportunities. Being willing to deviate from the planned agenda – whether that means extending a productive discussion, reorganizing breakout sessions, or pivoting to address an emerging issue – can lead to breakthrough moments. The key is maintaining enough structure to achieve core objectives while remaining responsive to the group’s actual needs and energy in the room.

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