Our next quarterly planning offsite is coming up, and several of our directors want to bring their top middle managers into the room to get their input and secure early buy-in on our next set of Rocks. Is this a good idea, or should we keep the session strictly limited to the core leadership team?

Question

Tyler Smith · Accepted Answer

Keep your quarterly offsites strictly limited to your core leadership team. Inviting middle managers to these sessions is a common mistake made by owners who confuse transparency with alignment. Your leadership team must be a completely healthy, cohesive, and unified unit. To achieve that, you need a safe, confidential space where you can have unfiltered debates, address hard issues, and solve organizational problems. Bringing middle managers into the room completely changes the dynamic. It stifles honest discussion because directors will naturally hesitate to share raw problems or engage in heated debates in front of their direct reports. Cracks at the leadership level appear as canyons to the rest of the organization, and showing misalignment during a planning session will only cause anxiety among your staff. Keep the offsite to the leadership team. Once you have argued, aligned, and finalized your quarterly Rocks and updated your V/TO, use a structured cascade message to share the results. Meet with your middle managers within twenty-four hours of your offsite, share the direction, and give them the opportunity to ask questions. This maintains leadership team cohesion while still building trust and alignment throughout the entire company.