After failing to become a professional basketball player in Australia, Chris March took a leap that would define the next 16 years of his life—and his entire leadership philosophy. What started as a rite of passage trip to London became a career spanning three continents, multiple industries, and a deep understanding of what middle managers really need to thrive in "the squeeze."

In this conversation, Chris shares his journey from Sydney to London to Vancouver to Toronto and finally back home, revealing how each bold move taught him that growth comes from putting yourself in slightly uncomfortable positions. Now an executive coach working with middle managers and seven- to nine-figure founders through The Entourage, Chris brings a unique perspective on navigating the challenging space between frontline work and senior leadership.

We explore the reality of being a middle manager—carrying the organization's vision and culture while managing up, down, and sideways with limited resources and often conflicting priorities. Chris introduces the concept of "the squeeze," where middle managers bear the weight of organizational expectations while trying to maintain their own sanity and career progression. His advice? Ask for feedback early and often, turning what most people fear into a powerful tool for growth and team building.

Chris shares his daily self-coaching routine using AI, including powerful reflection questions like "What will make today great?" and "What outcome today moved you closer to your overall goal?" He demonstrates how modern tools can democratize access to coaching insights, making professional development accessible even without a formal coach.

We also discuss why fear-based leadership is not just outdated but fundamentally counterproductive. Chris's message to middle managers is clear: You're doing important work, and with the right mindset and tools, you can navigate the squeeze while building toward your next career chapter.

Resources & Links Mentioned

Chris March on LinkedIn

chrismarchcoaching.com

The Entourage

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