In this episode, we revisit a powerful conversation with Chris Voss, former FBI lead hostage negotiator and bestselling author of Never Split the Difference.

In this insightful discussion with Jake and Damian, Chris shares his unique approach to communication, showing how the skills he used in life-or-death negotiations can transform the way we handle everyday conversations. From business meetings to family dynamics, Chris explains why listening more and speaking less can lead to better outcomes in every area of life.

Listen in as Chris delivers practical, transformative strategies to help you navigate pressure, connect with others, and negotiate like your life depends on it.

This new Essential Habits series breaks down the key habits behind high performance, one episode at a time. This week’s habit is deceptively simple: asking better questions.

Philosopher Alain de Botton joins us to explore how a single, uncomfortable question, “How have I annoyed you?” can deepen trust, defuse tension, and create stronger connections in every part of life.

Whether it’s at home, at work, or with close friends, we often avoid the conversations that would help us grow. Alain shows us a different way, one built on emotional generosity, honest listening, and the courage to be vulnerable.

In this episode, we explore:

• Why awkward questions build trust
• How to listen without getting defensive
• The science behind emotional connection
• What high-performing teams can learn from philosophy
• The hidden power of backstories and being 'truly heard'

Here is a list of studies referenced in the episode:

1. The Experimental Generation of Interpersonal Closeness. Arthur Aron, Elaine Aron (1997)
2. Understanding the conversation gap: Why employees aren’t talking, and what we can do about it (Braverly), referenced in How to Navigate Difficult Conversations with Employees. Harvard Negotiation Project
3. Rejection Really Hurts, published in Science (Oct 2003). University Of California - Los Angeles
4. Daring Greatly by Brené Brown

Listen to the full episode with Alain De Botton here: https://pod.fo/e/1f5db0

John Legend is a singer, songwriter, and producer known for his soulful voice, emotional depth, and ability to cross genres with ease. With multiple Grammy Awards, an EGOT to his name, and a career that’s spanned decades, John has also become a voice for compassion, activism, and vulnerability in the public eye.

In this episode, John opens up about some of the most intimate moments of his life, his complicated relationship with his mother, who faced deep struggles after family tragedies, and how that shaped him growing up. He also talks about the heartbreaking experience he and his wife, Chrissy Teigen, went through with the loss of their baby, and how sharing that pain publicly became a way to heal and help others facing similar grief.

John also reflects on his once close bond with Kanye West, a friendship that deeply influenced his early music career but has since grown distant.

This episode offers a raw and honest exploration of vulnerability, healing, and the strength it takes to navigate life’s toughest moments while staying true to yourself.

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