![Climbing What's in Front of You-- Interview with Tony Ross [S2 Ep9] Artwork](https://www.buzzsprout.com/rails/active_storage/representations/redirect/eyJfcmFpbHMiOnsiZGF0YSI6MTY0NTMyMDQ2LCJwdXIiOiJibG9iX2lkIn19--8f475e6b0c6108419faa8cb623d2092b6df27eff/eyJfcmFpbHMiOnsiZGF0YSI6eyJmb3JtYXQiOiJqcGciLCJyZXNpemVfdG9fZmlsbCI6WzYwMCw2MDAseyJjcm9wIjoiY2VudHJlIn1dLCJzYXZlciI6eyJxdWFsaXR5Ijo2MH0sImNvbG91cnNwYWNlIjoic3JnYiJ9LCJwdXIiOiJ2YXJpYXRpb24ifX0=--0b154cb6b88107719b1a277923d35676ba5519cc/TWOY%20Cover%20Art%20S2E9.png)
The Work of You
This is a podcast about the leadership that matters most — the kind that starts from within.
Hosted by certified behavioral coach and Enneagram expert Jen Ostrich, The Work of You is for high-achieving humans ready to stop repeating patterns and start leading themselves differently.
Through insights from coaching, the Enneagram, and her own personal inner overhaul, Jen brings honesty, humor, and sharp emotional clarity to the table. With real talk, self-awareness tools, and a healthy dose of tough love, she helps you uncover what’s driving you, shift what’s no longer serving you, and ultimately do the work of you — one honest episode at a time.
This isn’t about fixing yourself. It’s about finally understanding yourself — so your choices, relationships, and leadership can actually align with who you truly are.
The Work of You
Climbing What's in Front of You-- Interview with Tony Ross [S2 Ep9]
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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 (see below for his The Work of You advice) -- this is a must watch episode.
In this episode, we explore:
- Why moving from individual contributor to manager requires a complete mindset overhaul, not just a promotion
- How Tony reshaped team norms and built connections at scale to humanize executive leadership
- Using tools like the Enneagram and intentional development plans to fuel both personal growth and stronger team dynamics
- What summiting Denali taught Tony about mindset, resilience, and taking bold steps before “someday” slips away
The Work of You Resources -- via Tony Ross
- Stay Curious -- question things, take on new challenges, push yourself out of your comfort zone and set concrete goals each year
- Keep Growing!
About the Guest:
With over 20 years of operational leadership at Apple, Tony brings deep expertise in global supply chain, planning, and product operations. He currently advises mission-driven startups like Crowdstake and serves on nonprofit boards focused on health and economic growth. His career began as a Navy engineering officer and continued through senior roles in the tech sector, supported by degrees from Cornell and Stanford GSB. Today Tony is dedicated to mentorship, community engagement, and amplifying organizations that create positive impact.
Resources | Links:
Simon Sinek Video [where one of Tony's favoriate quotes lives]
