Exceptional Leadership

#43 Stuck in the Middle? Why Middle Managers Face the Toughest Job in Leadership

Mathew Hamilton Episode 43

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Middle management is often the most demanding layer of leadership—caught between frontline realities and executive expectations. In this episode, we explore why middle managers have one of the toughest jobs in any organisation.

I unpack the unique pressures middle managers face: staying connected to daily operations, acting as the escalation point for junior leaders, and serving as the crucial link between the executive team and the broader workforce.

We also dive into the challenge of translating high-level strategy into meaningful, practical actions—often for teams who aren’t emotionally invested in the process. And we explore the hidden risk: middle management is frequently the first target in cost-cutting initiatives.

Whether you’re currently in middle management or aspiring to move through the ranks, this episode offers practical insights on how to lead effectively from the centre and stay resilient under pressure.


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Mathew Hamilton leads a high performing team of professionals and has worked across numerous industries in both the public and private sector.

He holds an MBA from the Australian Institute of Business.