The Art and Science of Difficult Conversations

Hosted by Chris Wong & Lucie Tesarova

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132

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Jun 2026

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About the show

Ever had to have that difficult conversation with someone that you dreaded? You are not alone. Join us to explore how to improve how you handle difficult conversations with your team or loved ones. When we communicate better, we lead better, we perform better, we have better relationships, results and ultimately, a better life. Ready to learn? Make sure you subscribe so you don't miss any future episode. Want to be a guest on our podcast? Let us know! https://bit.ly/3z4Sn5w

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60 recent

June 16, 202621 min

How to Communicate as a Leader when Times are Tough

In this episode, Will Hobart shares insights on leadership, transparency, managing anxiety, and building trust within organizations. Discover practical strategies for effective communication and authentic leadership in challenging times. About our guest:   Will Hobart is an education leader, strategist, and nonprofit executive with more than 15 years of experience helping organizations navigate complex challenges, build strong partnerships, and create opportunities for student success. His career has included roles as a middle school teacher, school district administrator, and nonprofit leader, providing a unique perspective on how communication, trust, and collaboration drive meaningful change.  Throughout his career, Will has led efforts to expand college access, strengthen career pathways, and improve outcomes for young people. He is passionate about bringing people together across diverse perspectives to solve complex problems and create lasting impact.  Will believes that many of the most important breakthroughs in organizations and communities begin with honest, courageous conversations. He has led teams through periods of growth, uncertainty, and transformation, and has seen how empathy, curiosity, and clarity can strengthen relationships and move people toward shared goals. Contact Will:  Will Hobart - LinkedIn Golden Apple Foundation for Excellence in Teaching Connect with us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

June 9, 202638 min

Balancing empathy and performance in leadership

How do you align a team that doesn't seem to be reading the same page, or even the same book? In Part 1 of our conversation with nonprofit leader Will Hobart, we dig into one of the hardest tensions in leadership: caring deeply about your people while still driving toward clear goals and results. Will shares the lessons that shaped him, from a fifth-grade conflict-resolution program to the rigid, resource-constrained world of public education, to scaling a 90-year-old nonprofit. Along the way, he gets honest about the moment hard feedback forced him to confront the gap between his intent and his impact, and how he learned that his team's different needs and ambitions weren't a lack of drive but just a different seat at the table. If you've ever felt pulled between the strategy you're accountable for and the empathy your team needs from you, this one's for you.   About our guest:   Will Hobart is an education leader, strategist, and nonprofit executive with more than 15 years of experience helping organizations navigate complex challenges, build strong partnerships, and create opportunities for student success. His career has included roles as a middle school teacher, school district administrator, and nonprofit leader, providing a unique perspective on how communication, trust, and collaboration drive meaningful change.  Throughout his career, Will has led efforts to expand college access, strengthen career pathways, and improve outcomes for young people. He is passionate about bringing people together across diverse perspectives to solve complex problems and create lasting impact.  Will believes that many of the most important breakthroughs in organizations and communities begin with honest, courageous conversations. He has led teams through periods of growth, uncertainty, and transformation, and has seen how empathy, curiosity, and clarity can strengthen relationships and move people toward shared goals. Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

June 2, 202624 min

Unlock Your Potential with CIDER Strategies: A Step-by-Step Guide

In this interview with leadership coach Lucie Tesarova, Tina Paulus-Krause shares her transformative methodology, CIDER strategies, designed to help individuals achieve clarity, set intentions, maintain discipline, and manage energy for personal and professional growth. Discover practical tools for self-awareness, overcoming burnout, and creating a meaningful leadership legacy. 00:04 The CIDER Methodology for Transformation 12:16 Self-Awareness and Grace in Leadership 16:11 Key Takeaways and Legacy in Leadership Resources & Links Tina Paulus Krause - Official Website Your Leadership Legacy Podcast Connect with Tina: LinkedIn Website Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

May 26, 202633 min

From Burnout to Bliss: Transformational Leadership and Self-Awareness with Tina Paulus Krause (part 1)

In this inspiring interview, Tina Pullous Kraus shares her transformative journey from burnout and personal struggles to becoming a transformation trainer. Discover practical insights on emotional intelligence, authentic leadership, and how to create lasting change in your life and relationships. Chapters 00:00 From Burnout to Bliss: A Personal Journey 04:54 Generational Healing and Transformation 10:18 Awareness and Emotional Intelligence 13:47 Difficult Conversations: Starting with Ourselves 18:18 Overcoming Limiting Beliefs and Shame 23:11 Redefining Leadership: Collaboration Over Control 25:05 Defining Core Values Resources & Links Tina Paulus Krause - Official Website Your Leadership Legacy Podcast Connect with Tina: LinkedIn Website Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

May 19, 202620 min

How to address underperformance when the employee is a friend (Part 2 with Ashley Cox)

In our follow up to last week’s episode, Ashley and Chris continue talking about navigating difficult conversations, especially when dealing with friends or family in a professional setting.  Especially when they start bringing things back up or get more defensive, it can feel like you’re on the edge of losing an employee AND a friend.  Hear how Ashley walks us through: -          How to address underperformance in friends or family. -          How to maintain your humanity to be an effective leader. -          How to set clear boundaries and expectations prevent future conflicts. -          How to use empathy and understanding to resolve issues with friends or family. -          How to take ownership to turn problems into opportunities for growth.   About Ashley Ashley Cox, PHR, SHRM-CP is a leadership mentor for ambitious women business owners who have a team but no time. She empowers them to become courageous and confident leaders, and build high-performance teams they can trust and rely on (without constantly chasing them to get things done). Ashley is also a sought-after speaker, author of the book Transform Your Stories, and host of The Impact Ripple Podcast   Connect with Ashley Website: www.ashleycox.co Book: www.ashleycox.co/transform Podcast: www.ashleycox.co/podcast  LinkedIn: www.linkedin.com/in/ashleyncox Instagram: www.instagram.com/ashleycox.co Facebook: www.facebook.com/ashleycox.co   Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

May 12, 202621 min

How can women in leadership thrive? (Part 1 with Ashley Cox)

In this week’s interview, Ashley Cox, a leadership mentor and expert in women in business, joins Chris to share her insights on leadership, gender dynamics, and building successful, people-centered businesses.  Lucie, unfortunately couldn’t make it, but Ashley and Chris still had a great time talking about the specific barriers that women face.  Together, Ashley talks about:  How to balance profitability with compassion  The unique barriers that women face  How to reframe some of the mindsets women are raised with  About Ashley Ashley Cox, PHR, SHRM-CP is a leadership mentor for ambitious women business owners who have a team but no time. She empowers them to become courageous and confident leaders, and build high-performance teams they can trust and rely on (without constantly chasing them to get things done). Ashley is also a sought-after speaker, author of the book Transform Your Stories, and host of The Impact Ripple Podcast Connect with Ashley Website: www.ashleycox.co Book: www.ashleycox.co/transform Podcast: www.ashleycox.co/podcast  LinkedIn: www.linkedin.com/in/ashleyncox Instagram: www.instagram.com/ashleycox.co Facebook: www.facebook.com/ashleycox.co   Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

May 5, 202618 min

How to deal with difficult emotions in Difficult Conversations (Part 2 with Laura Morgan)

If last week was helpful (or if you didn’t watch it, go back now and listen!), this week kicks it up to the next level.  In part 2 of their conversation with Laura Morgan, she helps us navigate some tricky situations: -          What if someone is yelling at you? -          What if they start crying? -          What if they’re using crying intentionally to manipulate and get out of consequences? -          What if they keep harping on “how things used to be”? Laura is the real deal, and she gives us some great strategies to navigate the hardest situations. About Laura  Laura Morgan began her career as a psychotherapist, where she developed a deep understanding of human behavior, transformation, and the conditions that allow people to grow and thrive. That clinical foundation continues to shape her work today, informing a leadership approach grounded in empathy, insight, and intentional design. Laura is currently the Director of Human Resources at Meketa Investment Group, where she partners with senior leaders to shape talent strategy, compensation philosophy, and organizational culture. She is passionate about building systems and environments where clarity, trust, and purpose enable both people and organizations to reach their full potential.  Contact Laura:  LinkedIn: https://www.linkedin.com/in/laura-m-morgan/  Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

April 28, 202619 min

How to get comfortable with emotions in difficult conversations (Part 1 with Laura Morgan)

One of the most common questions we get is “how do we manage the emotions that inevitably come up in difficult conversations?”  And our guest this week, Laura Morgan, knows exactly how to deal with it.  With a background as a mental health therapist and now as an HR Director, she’s no stranger to heavy emotions in difficult situations of all kinds.  But, as she describes it – emotions aren’t a bad thing, and we need to learn how to lean into them.  Laura walks us through how: -        Emotions are data, not obstacles, in conversations. -        Preparing for the emotional aspects is as just as important as the content. -        Ownership of emotions involves acknowledgment and responsibility. -        Pausing and grounding techniques help regulate emotional responses -        People aren’t robots, and while we don’t have to dig into every aspect of their personal lives, we have to acknowledge what makes them human.  About Laura  Laura is Director of HR at Meketa Investment Group.  She’s passionate about reshaping organizational landscapes, bringing a holistic approach to shaping organizational dynamics. Her journey from a psychotherapist to HR leadership has equipped her with a profound understanding of human behavior, resilience, and growth.Laura holds dual US/UK citizenship, bringing a global perspective to leadership and is dedicated to creating workplaces where every voice is heard and valued.   Contact Laura:  LinkedIn: https://www.linkedin.com/in/laura-m-morgan/ Contact us:  Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

April 21, 202620 min

How to Deliver Bad News Effectively with Dr. Toby Campbell (Part 2)

Explore effective strategies for delivering bad news, managing difficult conversations, and fostering a supportive team culture with our guest today, Toby Campbell. Learn practical techniques, metaphors, and leadership insights to improve communication skills. About Dr. Toby Campbell Dr. Toby Campbell is Professor of Medicine, Thoracic Oncologist, Chief of Palliative Care and the Ellen and Peter O. Johnson Chair in Palliative Care at the University of Wisconsin-Madison.  An award-winning doctor,  writer, and podcaster, he conducts the most difficult, "once in a lifetime" type conversations with people and families every day and translates those skills into lessons for anyone who wants to make their hard conversations go better.  His communication tools have been featured on NPR, The Colbert Report, and Armchair Expert.  He is currently writing A Doctor's Guide to Hard Conversations (Post Hill Press) and created the Extraordinary Conversations podcast, exploring the rare and pivotal moments when lives intersect around organ donation and transplantation.  Dr. Campbell created and hosts the Palliatively Speaking podcast, where he interviews inspirational figures from the field of hospice and palliative care.     Chapters 00:00 Introduction and Warm-Up00:06 Delivering Bad News Effectively05:45 Self-Regulation in Difficult Conversations08:32 Creating a Supportive Team Culture Make sure you listen to part 1 of this interview here.  We cover: Strategies for delivering bad news Using metaphors to understand conversations Building team culture for hard conversations Managing emotions during difficult talks Leadership tips for effective communication   Resources:  Extraordinary Conversations Podcast - https://extraordinaryconversationspodcast.com We Talk Labs - https://wetalklabs.org Mindfitter Be Free Assessment - https://mindfitter.com/befree Difficult Conversation Playbook for Leaders   Connect with the Hosts Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

April 14, 202629 min

How to Deliver Bad News: Insights from end-of-life conversations (Part 1)

In this episode, Dr. Toby Campbell, an oncologist and expert in serious illness conversations, shares insights on how to navigate difficult medical discussions, especially around delivering bad news and organ donation. Discover practical frameworks, emotional engagement techniques, and the importance of communication skills in high-stakes situations. Chapters 00:00 Introduction and Warm-Up 00:00 Navigating Difficult Conversations in Healthcare 08:25 The Impact of Personal Experience on Professional Practice 09:20 Exploring the Transplant Experience 10:13 The Evolution of Organ Donation 13:17 The Emotional Journey of Donor Families 15:03 Training for Difficult Conversations 18:34 Empathy in Communication 22:27 Navigating Emotional Conversations 27:09 Delivering Bad News Effectively 29:14 Creating a Supportive Team Culture About Dr. Toby Campbell Dr. Toby Campbell is Professor of Medicine, Thoracic Oncologist, Chief of Palliative Care and the Ellen and Peter O. Johnson Chair in Palliative Care at the University of Wisconsin-Madison.  An award-winning doctor,  writer, and podcaster, he conducts the most difficult, "once in a lifetime" type conversations with people and families every day and translates those skills into lessons for anyone who wants to make their hard conversations go better.  His communication tools have been featured on NPR, The Colbert Report, and Armchair Expert.  He is currently writing A Doctor's Guide to Hard Conversations (Post Hill Press) and created the Extraordinary Conversations podcast, exploring the rare and pivotal moments when lives intersect around organ donation and transplantation.  Dr. Campbell created and hosts the Palliatively Speaking podcast, where he interviews inspirational figures from the field of hospice and palliative care.     Connect with the Hosts Email – tas.difficultconversations@gmail.com Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment