Definitely, Maybe Agile

Blind Spots and Better Leaders with Jill Macauley


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What happens when your greatest strength becomes your biggest blind spot? In this episode, Peter and Dave sit down with Jill Macauley, COO of Behavioral Essentials, to explore how self-awareness shapes better leadership. They dig into why even talented leaders struggle with identity shifts, how generational expectations are changing the workplace, and why the best coaches focus on small tweaks rather than complete overhauls. From the reluctant engineer-turned-manager to the chef who can't slow down, this conversation gets real about the grief of letting go of old identities and the messy work of looking in the mirror.

This week´s takeaway: 

  1. Your gifts become your blind spots when overused. That strength that got you promoted? It might be working against you now. The key is recognizing when speed becomes recklessness, when confidence becomes rigidity, or when expertise becomes tunnel vision.
  2. Identity shifts are a grieving process. Moving from individual contributor to leader to leader of leaders isn't just a promotion. It requires letting go of the identity you've built your career on, and that loss is real. Give yourself (and others) permission to struggle with it.
  3. Skip the woo-woo, ask "why" instead. Self-reflection doesn't have to feel soft or abstract. Simple questions like "Why did I react that way?" or "What role am I playing in this?" are pragmatic tools that work in any meeting, with any team.
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Definitely, Maybe AgileBy Peter Maddison and Dave Sharrock


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