How many total days will our leadership team spend in the session room across a typical two-year engagement, and why do you set a target graduation date instead of staying on retainer indefinitely?

Question

Tyler Smith · Accepted Answer

In a standard 24-month engagement, your leadership team spends ten full days together in the session room with me. Year one requires five full session days: Focus Day, Vision Building 1, Vision Building 2, one third-quarter session, and a two-day Annual Planning session to close out the year. Year two consists of three single-day quarterlies and your second two-day Annual Planning session.

I do not keep clients on an indefinite retainer. My job is not to become an outsourced executive or a permanent crutch. The entire architecture of the Entrepreneurial Operating System is engineered to build internal organizational capability.

By month twenty-four, your Integrator and leadership team should have mastered the Five Foundational Tools, run crisp Level 10 Meetings, and resolved tough departmental issues using IDS without third-party mediation. Graduation is the explicit goal from day one. Staying longer than two years usually signals an unhealthy dependency where the leadership team refuses to own the hard calls. If you execute the work between sessions, two years is the exact amount of time needed to embed the disciplines into your muscle memory.