EPISODE · May 28, 2026 · 21 MIN
The Execution Gap: Why Great Strategies Fall Apart Before They Begin
from Extropy on AIR: Finance Transformation, AP Automation & AI in Finance · host Extropy Advisors
Most strategies don't fail because they're wrong. They fail because organizations can't execute them. In this episode, Mike Jasper sits down with Extropy Project Manager Cecile Brown-Smith to unpack the systematic forces behind that gap. They explore why entropy quietly erodes even the best-laid plans, how ambiguity stalls teams and kills momentum, and why the people closest to the work are often left out of the rooms where decisions get made. From tribal knowledge to missing legal sign-off, the execution gap is rarely dramatic. It's dozens of small breakdowns that pile up until the project is already off course. Tune in for a practical conversation on what it actually takes to convert strategic intent into daily behavior, and why structure, clarity, and the right people in the room make all the difference.
What this episode covers
Most strategies don't fail because they're wrong. They fail because organizations can't execute them. In this episode, Mike Jasper sits down with Extropy Project Manager Cecile Brown-Smith to unpack the systematic forces behind that gap. They explore why entropy quietly erodes even the best-laid plans, how ambiguity stalls teams and kills momentum, and why the people closest to the work are often left out of the rooms where decisions get made. From tribal knowledge to missing legal sign-off, the execution gap is rarely dramatic. It's dozens of small breakdowns that pile up until the project is already off course. Tune in for a practical conversation on what it actually takes to convert strategic intent into daily behavior, and why structure, clarity, and the right people in the room make all the difference.
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The Execution Gap: Why Great Strategies Fall Apart Before They Begin
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