The Planning Gap

Why Scaling Leaders Drift and How To Stop It

Most strategic plans don’t fail because leaders lack ambition.

They fail because there isn’t a system the team can actually follow. That gap between planning and execution is what Courtney calls the Planning Gap, and it’s why the plan that felt solid in January stops showing up in how your team actually works by summer.

In this conversation, hear Courtney and Kevin talk through where the Planning Gap comes from, why talented, capable teams still end up doing “sideways activity,” and what it actually takes to close it.

What You’ll Hear

  • Why planning stalls even when the people in the room are talented and motivated

  • The difference between a planning problem and a people problem

  • The three parts of planning most leaders never connect: long-term, annual, and implementation