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.