The Two Meetings That Turn Long-Term Strategy Into Motion

The Two Meetings That Turn Long-Term Strategy Into Motion

From Chronicles from a Caribbean Cubicle Podcast by Francis Wade

May 5, 2026 · 18 min

About this episode

This episode discusses the challenges executives face in maintaining momentum towards long-term strategic goals and the importance of effective planning processes.

Most top executives can generate urgency around a quarterly target. The mechanisms are familiar: dashboards, deadlines, compensation levers. People move. But ask those same executives to build genuine momentum toward a grand aspiration which needs a fifteen-year horizon, and something strange happens. They show up. They nod. They wait for the pressure to pass. This isn’t insubordination. It’s a rational response to a broken process. And if you’ve ever led a strategic planning cycle that produced a polished document nobody touched again, you already know the symptom. The question is whether you’ve correctly diagnosed the cause. The Real Problem Is Sequence, Not Ambition CEOs who struggle to activate major aspirations or breakthrough results typically frame it as a people problem — their teams aren’t bold enough, disciplined enough, or strategically literate enough. Frequently, they apply pressure to fix the problem and become too directive. They hope their personal energy fills the void. Perhaps just as often, they do the opposite and become too passive. In this mode they back off, hoping organic energy fills the void. It rarely does. Neither framing is quite right. In the end…

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Host: Francis Wade

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