The Gray Area: Leadership Lessons from Imperfection and Presence with Kelly Woolf
Description
In this episode, we dive into the messy, meaningful space where true leadership lives—the gray area. Join us for a candid conversation with Kelly as she reflects on what it really means to lead with compassion without enabling, the importance of boundaries and early intervention, and why being an expert isn’t a prerequisite for great leadership.
We explore the misconceptions of perfection in leadership, the value of trusting your gut (spoiler: it’s not just a feeling—it’s a collection of lived experiences), and the often-overlooked truth that leadership requires training, not just tenure. Kelly shares how her background in social work shaped her approach to hard decisions, presence, and professional growth—and reminds us that real leadership means growing through the discomfort.
Whether you're new to leadership or knee-deep in managing people and purpose, this episode is a heart-forward, wisdom-packed reflection you won’t want to miss.
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