S2 Ep9: Climbing What's in Front of You-- Interview with Tony Ross

In this Season Two conversation of The Work of You, Jen sits down with (now retired) executive leader Tony Ross to explore the inner growth behind a 20+ year career at Apple. Tony reflects on the pivotal transitions from individual contributor to manager to leader of leaders, sharing candid lessons on delegation, strategy, culture-building, and leading across global teams. From navigating cultural differences in China to hosting “gelato with Tony” sessions to become more approachable, he offers practical insight into the mindset shifts that elevate good leaders into impactful ones. The conversation also highlights the role of self-awareness and continuous development—both personally and organizationally—including how tools like the Enneagram can strengthen team dynamics. Now in retirement, Tony shares how witnessing his parents’ health journeys inspired him to prioritize adventure and meaning, leading him to climb Denali—twice. His closing message is simple and powerful: stay curious, keep growing, and take the next step in your own leadership journey, one day at a time.