In this episode of the Connected Leadership Podcast, host Andy Lopata welcomes Nathan Farrugia, leader of the Vistage Group. Nathan is an experienced business coach with more than 20 years’ experience across technology, construction, healthcare, education, and hospitality, as well as a TEDx speaker, philanthropist and record-breaking adventurer. Nathan's impressive resume includes setting a world record for running 27 marathons in 27 countries in 27 days. Andy and Nathan examine the art of asking tough questions, a skill vital for leaders. Nathan believes many leaders, particularly those grappling with burnout and change, are not being asked the crucial question, "Is what you're doing aligned with your purpose in life?" This existential query, often avoided in everyday interactions, becomes a cornerstone of Nathan's coaching approach, prompting introspection and reflection. Exploring the delicate balance between assertiveness and vulnerability in coaching, Nathan emphasises the importance of earning trust before delving into deeper, potentially uncomfortable questions. He shares how his own experiences, coupled with strategic storytelling, help him build rapport and encourage clients to open up.  The episode highlights the importance of understanding emotional responses to tough, challenging questions, specifically drawing on the concept of the "chimp brain"—the instinctive, reactive part of our minds. Nathan explains how he recognises these reactions through body language and seeks to create a safe space for individuals to move beyond emotional defences and engage with their rational minds. Andy and Nathan explore the distinction between coaching and mentoring, with Nathan underscoring that while he may offer insights based on his experience, he never prescribes solutions. He prioritises empowering clients to discover their own answers through a process of exploration and self-discovery. What we discussed: 1.     Are you asking the right questions? 2.     Beyond the surface. Nathan's experiences highlight the importance of diving deep to understand the emotional drivers behind a client's challenges. How much are you truly listening to your team? 3.    The power of vulnerability. How can you create a space where open dialogue and authentic conversation flourish? 4.    Unlocking the "chimp brain." Learn how to recognise and navigate emotional reactions to challenging questions. 5.     The magic of group dynamics. Learn how to leverage the power of collective wisdom in your team? Connect with Andy Lopata: Website | Instagram | LinkedIn | X/Twitter | YouTube Connect with Nathan Farrugia: Website |LinkedIn |X/Twitter The Financial Times Guide to Mentoring