In this candid conversation, Chief People Officer Jevan Lenox reveals how an impressive résumé can actually intensify imposter syndrome — especially when you’re expected to have all the answers on day one.Jevan shares how a rocky first year at Square shook his confidence, why starting over in sales ops (a field he knew nothing about) became a turning point, and how leading through curiosity instead of expertise reshaped his entire approach to leadership.He and Melanie dive into navigating new executive roles, interrogating your own experience, resisting over-engineered HR processes, and choosing the highest-ROI path even when it’s not the most familiar.A sharp, honest look at what happens when expectations collide with reality — and how not knowing can become your greatest strength.

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