What do you hold onto when almost everything is changing? David Kenny — co-founder of Digitas, former CEO of Nielsen, and one of the most sought-after board members in tech and media — has a simple answer: find your true north and don't deviate from it.

In this episode of Unbossing, hosts Rishad Tobaccowala and Drew Ianni go deep with David on the leadership questions that are defining this moment: how to manage fear within teams, why AI makes curiosity more valuable than expertise, and the difference between managing and governance as a member of a board. He also makes a data-backed case for diversity as a winning business strategy — and shares what the 38 CEOs he's developed have taught him about resilience, failure, and what it actually takes to lead.

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Jim Lesser started his career as a receptionist at a New York ad agency. His last role in that same industry was CEO of BBDO San Francisco — one of the few creative directors in advertising to ever make that leap. Now, as Chief Brand Officer at ServiceNow, he's doing something nobody expected: turning a B2B enterprise software company into a brand people actually know and feel something about.

This week on Unbossing Jim Lesser talks with Rishad and Drew about what he had to unlearn to go from receptionist to CCO, from CEO to CMO.

Jim opens up about the unlearning that comes with every major career transition and how he went from the fun uncle to the responsible parent, from focusing on his team to focusing on every team. He makes the case that craft and taste is more important in the world of AI than ever before and that micro managing and attention to detail is a very different thing.

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What if the fear of failure is the biggest thing standing between your team and greatness? Tariq Hassan — former CMO and Chief Customer Experience Officer of McDonald's and former CMO of Petco — has spent his career contemplating this question.

In this episode of “Unbossing,” hosts Rishad Tobaccowala and Drew Ianni sit down with Tariq for a candid conversation about the leadership lessons hiding inside failure, the importance of psychological safety, and how the Grimace shake TikTok craze became a masterclass in knowing when to get out of the way of the consumer.

Tariq opens up about his late discovery of dyslexia — and how unlearning to hide it became one of his most powerful leadership tools. And he shares his framework for rooting out the "ghosts of culture past" that haunt organizations long after the people who created them are gone. Plus, hear Tariq’s career advice for everyone—no matter which career stage you’re at.

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