EP 227: Why Multi-Location CEOs Are One Departure Away From a Serious Execution Problem

If you're running a multi-location, operations-heavy business in the eight-figure range and you still can't name three people who could step into a critical leadership role tomorrow, this episode is for you.

Alex D. Tremble sits down with Jamila Cowan, NA Public Sector Programs & Partnerships Strategy Lead at Dell Technologies, where she has spent nearly two decades in senior leadership roles spanning global service delivery, sustainability, ESG partnerships, and cross-sector strategy. Jamila has represented Dell at the United Nations, the World Bank, and the White House Leadership Development Program, leading high-stakes, multi-stakeholder initiatives across government, education, and industry.

In this conversation, Jamila and Alex dig into one of the most overlooked proactivity problems in growing companies: the failure to intentionally develop the next tier of leadership before the seat is empty.

You'll learn:

- Why reactive talent development leaves CEOs as the permanent decision bottleneck across locations

- How exposure, not just training, builds leaders who can represent you in the rooms you can't be in

- What happens to execution speed and trust when leaders are never brought into critical decisions before they need to make them

- Why the loudest person in the room is rarely the best choice for your next key role and what to look for instead

- How failing to communicate through change causes your team to fill in the gaps with their own conclusions, and why that kills execution

This episode is for you if: you've delayed succession planning because it never feels urgent until someone walks out the door, and you realize nobody is ready to step up.

Listen now, and take the free Scorecard Diagnostic to find your specific leadership bottleneck:

👉 https://gpsleadership.org/scorecard/