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Published by Chris Wong & Lucie Tesarova
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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Sorry for the click-bait title, but as season 3 comes to an end, Lucie and Chris have some big news to share. They also spend a few minutes talking about the rise of AI, especially how it impacts difficult conversations. Then they share some BIG news for listeners. How will you spend the summer? 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
In part 2 of their conversation, Frank joins Chris and Lucie to talk through the steps of facilitating restorative circles, the preparation that makes group conversations successful, and the secrets of facilitating well. Together, they go through practical tips for facilitators and leaders to create safe, impactful spaces for dialogue and healing. Key Takeaways: Setting the right container is crucial for meaningful conversations. Preparation involves both logistical planning and internal readiness. Facilitators should be flexible and follow organic conversation cues. Incorporating joy and positive memories helps balance heavy topics. Facilitators need to recognize emotional fatigue and practice self-care. About Frank (He/Him/His) Storyteller Extraordinaire, Social Justice Warrior, and Relationship Cultivator! In relentless pursuit of racial and gender equity, Frank’s warmth brings folks together to talk through the tough stuff. To Frank, every person’s story matters like each ingredient in a yummy bowl of gumbo. Each standing on its own, but together making something unforgettable. From major conferences like the Nonprofit Storytelling Conference, AFP ICON, and AFP Lead to training rooms everywhere from Walt Disney World to the MGM Grand Las Vegas, Frank has reached thousands of folks with narratives that just hit different, leaving each group invigorated with his unique blend of storytelling magic, quick wit, and social justice fire! As the Founder of 4 Da Hood and the visionary behind the Ascending Leaders in Color leadership program, Frank forges pathways for Peeps of Color to step into their power - authentically, courageously, and with unapologetic joy. Because for Frank, advancing equity isn’t just a job - it's about thriving in a world our ancestors dreamed for us, a world where communities of color have the same access and opportunity to build their generational wealth. And he's doing it one connection, one story, one courageous conversation at a time. Connect with Frank: LinkedIn - https://www.linkedin.com/in/fvelasquezjr/ Contact Frank directly: frank@4dahood.com 4DaHood - https://4dahood.com 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
In this week’s episode, Frank Velásquez Jr. joins Chris and Lucie to share his journey into restorative justice, leadership as a person of color, and how restorative circles can transform organizational culture. Discover practical insights on authentic leadership, facilitation, and creating safe spaces for difficult conversations. Leaders of color often struggle with authenticity due to organizational and societal pressures. The importance of being authentic to yourself What are Restorative Justice Circles and how are they different from other types of group facilitation? How can you use agreements to change the tone of your group sessions About Frank (He/Him/His) Storyteller Extraordinaire, Social Justice Warrior, and Relationship Cultivator! In relentless pursuit of racial and gender equity, Frank’s warmth brings folks together to talk through the tough stuff. To Frank, every person’s story matters like each ingredient in a yummy bowl of gumbo. Each standing on its own, but together making something unforgettable. From major conferences like the Nonprofit Storytelling Conference, AFP ICON, and AFP Lead to training rooms everywhere from Walt Disney World to the MGM Grand Las Vegas, Frank has reached thousands of folks with narratives that just hit different, leaving each group invigorated with his unique blend of storytelling magic, quick wit, and social justice fire! As the Founder of 4 Da Hood and the visionary behind the Ascending Leaders in Color leadership program, Frank forges pathways for Peeps of Color to step into their power - authentically, courageously, and with unapologetic joy. Because for Frank, advancing equity isn’t just a job - it's about thriving in a world our ancestors dreamed for us, a world where communities of color have the same access and opportunity to build their generational wealth. And he's doing it one connection, one story, one courageous conversation at a time. Connect with Frank: LinkedIn - https://www.linkedin.com/in/frankvelasquezjr/ Twitter - https://twitter.com/frankvelasquezjr Restorative Justice Practices - International Institute for Restorative Practices - https://www.iirp.edu/ 4DaHood - Organization founded by Frank Velásquez Jr. - https://4dahood.org/ Ascending Leaders of Color Program - https://ascendingleaders.org/ 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
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
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
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
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
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
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
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
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
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-Up 00:06 Delivering Bad News Effectively 05:45 Self-Regulation in Difficult Conversations 08:32 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
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
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
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.
Summary: In part 2 of their conversation, Chris, Lucie, and Travis walk through practical strategies for having difficult conversations, asking effective questions, and improving communication in leadership. They also role play a performance conversation to show how asking questions and remaining curious can lead to powerful insights. In this episode, learn how to: Ask questions instead of making assumptions to understand others better. Use silence intentionally to give space for processing during conversations. Frame questions to avoid defensiveness, especially with sensitive topics. Prepare for difficult conversations by scheduling positive activities afterward. Practice curiosity and ask 'what' and 'how' questions to explore motivations. About Travis : Travis Dalrymple is a leadership advisor, author of How To Suck As A Leader , and the founder of The Leadership Lab—a program that helps small business owners and team leads stop managing people and start actually leading them. From placing 3rd on America’s Got Talent to leading high-performing teams in the business world, Travis blends entertainment, strategy, and real-life leadership lessons to help people become the kind of leader others actually want to follow—not just tolerate. He’s coached over 1000 entrepreneurs, fixed broken cultures, and taught teams how to lead themselves first, without the corporate jargon or BS. When he’s not coaching or speaking, you’ll find him golfing, hanging out with his family, or turning hard truths into Instagram reels. You can find him on IG @travdalrymple and you can grab your copy of How To Suck As A Leader at https://bit.ly/HowToSuckAsALeader . How to Suck as a Leader (Book) - https://a.co/d/09hOMoHQ Travis Dalrymple on LinkedIn - https://www.linkedin.com/in/travisdalrymple 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
Summary: This week, join Lucie and Chris as they interview Travis Dalrymple, a leadership coach and former entertainer, who shares his unconventional journey through various careers. He wrote a fun leadership book “How to Suck As a Leader” and shares his insights on leadership, communication, and culture, and practical strategies for difficult conversations and creating a positive organizational environment. He talks us through: - Why leaders tend to over-complicate things - Most organizational cultures are unintentional and reflect the personality of the leader. - How to get better at identifying your blind spots. - How to communicate more clearly - How to prepare for hard conversations About Travis : Travis Dalrymple is a leadership advisor, author of How To Suck As A Leader , and the founder of The Leadership Lab—a program that helps small business owners and team leads stop managing people and start actually leading them. From placing 3rd on America’s Got Talent to leading high-performing teams in the business world, Travis blends entertainment, strategy, and real-life leadership lessons to help people become the kind of leader others actually want to follow—not just tolerate. He’s coached over 1000 entrepreneurs, fixed broken cultures, and taught teams how to lead themselves first, without the corporate jargon or BS. When he’s not coaching or speaking, you’ll find him golfing, hanging out with his family, or turning hard truths into Instagram reels. You can find him on IG @travdalrymple and you can grab your copy of How To Suck As A Leader at https://bit.ly/HowToSuckAsALeader . How to Suck as a Leader (Book) - https://a.co/d/09hOMoHQ Travis Dalrymple on LinkedIn - https://www.linkedin.com/in/travisdalrymple 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
In part 2 of their interview with Roberta Dombrowski, Chris and Lucie pick her brain on how to deal with the guilt trips and the reality that sometimes these conversations happen over and over again – often pushing your boundaries. Roberta was so nice to role play with us and Chris and Lucie had SO MUCH FUN channeling their own moms to really see how to better handle these conversations. Listen as they talk about: - How to deliver difficult news to your parents - Techniques for boundary setting and maintaining peace - Handling family pushback and guilt tripping - Grounding and embodiment practices for presence - Expect and accept emotional reactions as part of the process. - Revisiting conversations over time helps in acceptance. About Roberta Roberta Dombrowski is a dynamic coach, consultant and mindfulness teacher dedicated to helping leaders thrive from the inside out. She has over a decade of experience spanning tech, non-profits, and academia. Her work has been featured by the Association of Talent Development, Learning Guild, and Product School. She holds PCC accreditation through the International Coaching Federation, CPCC through Co-Active Training Institute. Her unique approach blends the wisdom of the head, heart, and body - guiding clients to rediscover joy, resilience, and connection in their work and lives. By fostering deeper self-awareness and authentic leadership, Roberta helps individuals reshape how they relate to their careers, themselves, and their teams. Her personal experience as a transracial adoptee and over functioning tech executive heavily influences her approach to business. Resources Roberta’s In Her Words Podcast - https://www.learnmindfully.co/in-her-words Roberta’s Website - https://learnmindfully.co Adult Children of Emotionally Immature Parents (Book) - https://a.co/d/06JpDwi4 (we’re not affiliates and have no connection to this book or author) 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
Summary: In this week’s episode, Chris and Lucie get the privilege to interview Roberta Dombrowski, a coach who helps leaders function at their best. She’s also experienced in setting boundaries, both at work and in her personal life. she shares her journey from burnout to coaching, focusing on reclaiming confidence, setting boundaries, and improving communication in personal and professional relationships. In part 1 of their interview, learn why it’s so hard to set boundaries and what it takes to confidently step into them. Key Takeaways Boundaries are for yourself, not others. Family boundaries often meet resistance but are essential. Self-awareness and coaching help navigate complex family dynamics. Patterns from childhood influence adult boundary-setting. Revisiting difficult conversations multiple times leads to understanding. Follow Roberta LinkedIn - https://www.linkedin.com/in/robertadombrowski Website - https://www.robertadombrowski.com In Her Words podcast - https://www.learnmindfully.co/in-her-words 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 Assessme nt
Rachel Platt shares practical strategies for addressing disrespectful behavior, giving effective feedback, and fostering respectful workplace environments. This episode covers handling difficult conversations, timing feedback, and maintaining emotional regulation. Connect with Rachel: rplatt@PLATTinumconsulting.com https://calendly.com/plattinumconsulting/intro-networking https://www.linkedin.com/in/rachelplatt/ www.PLATTinumconsulting.com About Rachel: Rachel Platt brings 20+ years of experience helping organizations and individuals achieve enduring success through strategic human resources leadership. Through her roles as a Chief Human Resources Officer, Vice President, and Regional Director in diverse organizational structures and industries, she built her reputation on her track record of developing pragmatic solutions to meet complex organizational and people challenges. Rachel founded PLATTinum Consulting in 2018 to guide leaders in creating People Strategy initiatives in the areas of employee engagement, leadership development, culture assessment and improvement, performance management, staff training, communications, talent acquisition, HR process improvement, inclusion and coaching. As a certified Women's Business Enterprise (WBE), PLATTinum serves small and medium sized non-profits and commercial businesses across the US. PLATTinum partners with clients to maintain a transparent, ongoing, open dialogue. We provide a data-driven, responsive, organized approach. But most importantly, we are proactive, optimistic, approachable and occasionally funny. We place outcomes before egos and work with clients who share similar values. 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 Assessme nt
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