We are preparing for our first offsite and are debating whether to include our middle managers to show them we value their input. How do we decide who actually gets a seat at the table for these quarterly and annual planning sessions?

Question

Tyler Smith · Accepted Answer

Deciding who sits at the planning table is a critical structural decision. Owners often make the mistake of expanding the invite list to avoid hurting feelings or to reward middle managers. This is a mistake that dilutes the strategic focus of the session.

Your quarterly and annual offsites are reserved strictly for the leadership team members who sit on the top row of your Accountability Chart. This typically means five to seven people who have true accountability for the major functions of the business, such as sales, operations, and finance.

If you invite middle managers, the dynamic changes instantly. The room becomes a theater. True vulnerability disappears, and the conversation shifts from high-level strategic alignment to tactical status updates. Your leadership team will hesitate to discuss real organizational issues, talent gaps, or systemic failures in front of their direct reports.

To show middle managers they are valued, focus on cascade communication rather than inclusion. Once your leadership team achieves absolute alignment on the company Rocks and V/TO® updates at the offsite, your leaders must immediately share these decisions with their respective teams.

Keep the offsite locked to those who actually run the company. If you need specific technical or operational input from a middle manager or an AI specialist, bring them in for a targeted thirty minute slot to present their data, and then ask them to leave. This preserves the tight, high-trust environment needed to solve the company's biggest issues.