The Art and Science of Difficult Conversations

Chris Wong & Lucie Tesarova
  • 5.0 (3)
  • MANAGEMENT
  • UPDATED WEEKLY

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

  1. 16H AGO

    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

    21 min

  2. MAY 12

    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

    21 min

  3. MAY 5

    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

    18 min

  4. APR 28

    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

    19 min

  5. APR 21

    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

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

    APR 14

    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

    29 min
  7. How to Advocate for Self and Others - Roleplay (Part 2)

    APR 7

    How to Advocate for Self and Others - Roleplay (Part 2)

    In this insightful interview, Gift Tshuma shares practical strategies for inclusive leadership, effective advocacy, and navigating difficult conversations in the workplace. Discover how to approach accessibility issues, support marginalized employees, and foster a more inclusive environment. Key topics: Inclusive leadership strategies Advocacy and storytelling, Handling difficult workplace conversations Role of HR in diversity and inclusion Mediation and escalation processes Guest Gift Tshuma (He/Him) Advocacy Specialist, March of Dimes Canada Co-Executive Director, Blurring the Boundaries — an organization creating accessible digital instruments for people with disabilities (UK & Canada) Co-Founder, Tshuma Consulting — accessibility assessments, training, and strategic consulting EDI Officer, The Centre for Sustainable Practice in the Arts Musician & Artist — R&B/Gospel singer, co-founder of United Tribulation Choir, trained in classical and jazz vocals, mentored by Oliver Jones Originally from Zimbabwe, based in Canada 35+ years of lived experience and 17+ years of leadership in accessibility & inclusion LinkedIn: linkedin.com/in/gift-tshuma 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

    22 min
  8. How to Speak Up When the System Wasn't Built for You (Part 1)

    MAR 31

    How to Speak Up When the System Wasn't Built for You (Part 1)

    Episode Overview In this powerful Part 1 conversation, hosts Chris Wong and Lucie Tesarova sit down with Gift Tshuma — disability rights advocate, accessibility specialist, musician, and co-founder of Tshuma Consulting — to explore what advocacy really means, why storytelling is its foundation, and how to navigate the difficult conversations that come with pushing for inclusion in organizations and systems that weren't designed for everyone. Guest Gift Tshuma (He/Him) Advocacy Specialist, March of Dimes Canada Co-Executive Director, Blurring the Boundaries — an organization creating accessible digital instruments for people with disabilities (UK & Canada) Co-Founder, Tshuma Consulting — accessibility assessments, training, and strategic consulting EDI Officer, The Centre for Sustainable Practice in the Arts Musician & Artist — R&B/Gospel singer, co-founder of United Tribulation Choir, trained in classical and jazz vocals, mentored by Oliver Jones Originally from Zimbabwe, based in Canada 35+ years of lived experience and 17+ years of leadership in accessibility & inclusion LinkedIn: linkedin.com/in/gift-tshuma Key Topics Discussed Advocacy as storytelling and influence Overcoming fear and internal barriers Strategic influence and systemic change Notable Quotes "Access isn't something that you just give. It's not served on a silver platter. You have to fight for it. And you have to sometimes build it yourself." "Advocacy isn't charity work. It's not about being a hero. It's about shifting the power and building disability literacy." "When you are not telling your story, you are robbing someone for their life to be changed." "I'm not arguing about ramps or software. I'm arguing about whose time matters, whose comfort level matters, whose productivity is treated as a default." "We are community-based beings that need support from everyone. Don't be ashamed to ask for help." This Week's Challenge Pick one thing you've been wanting to advocate for. Be it at work, in your community, or in your personal life, and practice telling that story to someone you trust. Start in a low-stakes environment, just like Gift did. Get comfortable with your story before you bring it to the room that needs to hear it. 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 Next Episode Preview Coming Next Week: Part 2 of our conversation with Gift Tshuma — including role play scenarios that bring these advocacy conversations to life. Remember: When you communicate better, you live better.

    30 min
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out of 5
3 Ratings

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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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