Alain de Botton, a modern-day philosopher and co-founder of The School of Life, delves into the power of uncomfortable questions in building trust. He argues that asking, 'How have I annoyed you?' can deepen relationships at home and work. The discussion emphasizes the importance of emotional generosity, honest listening, and vulnerability. Listeners learn how awkward inquiries foster deeper connections, the science behind emotional closeness, and the transformative potential of being truly heard in both personal and professional spaces.
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Ask the Hard Question Kindly
Ask the question "How have I annoyed you?" to deepen trust and open honest dialogue.
Listen without defensiveness and reflect back what you hear to make others feel understood.
insights INSIGHT
Power of Sharing Backstories
Sharing personal backstories about difficulties humanizes people and reduces conflict.
Calm explanations of why behaviors happen make everyone appear more lovable and worthy of understanding.
insights INSIGHT
Power of Mutual Self-Disclosure
Sharing personal stories in a gradual reciprocal way builds emotional intimacy.
Mutual self-disclosure creates trust as people reveal meaningful information bit by bit.
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In this book, Mark Manson argues against the typical self-help advice of constant positivity, instead suggesting that life's struggles give it meaning. He emphasizes the need to focus on what truly matters and to accept and confront painful truths. The book is divided into nine chapters and uses blunt honesty and profanity to illustrate its ideas, encouraging readers to find meaning through values they can control and to replace uncontrollable values with more meaningful ones.
Daring Greatly
How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead
Brené Brown
In 'Daring Greatly,' Brené Brown delves into the topics of vulnerability, shame, and courage. The book, inspired by a quote from Theodore Roosevelt's 'Citizenship in a Republic' speech, argues that vulnerability is essential for living a wholehearted life. Brown discusses how vulnerability is often misunderstood as weakness, but it is actually a sign of courage. She provides insights from her research on how vulnerability affects men and women differently and offers practical advice on overcoming shame and embracing vulnerability in personal and professional life. The book emphasizes the importance of connection, shame resilience, and the distinction between guilt and shame[3][4][5].
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:
The High Performance Podcast 
