The Art and Science of Difficult Conversations

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.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – 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.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – 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.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – 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.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

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.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

In this conversation, Chris Wong and Lucie Tesarova engage with Rachel Platt, a people strategist, to explore the dynamics of difficult conversations in the workplace. They discuss the importance of addressing disrespectful behavior, the role of leaders in fostering a respectful culture, and the balance between achieving results and maintaining a positive work environment.   Rachel shares insights on navigating difficult conversations, identifying signs of disrespect, and modeling appropriate leadership behavior. The discussion emphasizes the need for curiosity, understanding, and proactive communication in creating a healthy workplace culture.   Takeaways: Rachel Platt helps organizations move past HR as paperwork. A people strategist focuses on aligning people strategy with business strategy. Curiosity is key in addressing difficult conversations. Disrespectful behavior often gets minimized in organizations. Leaders must recognize the impact of their silence on culture. High performers can create a different set of rules in the workplace. Addressing disrespect early can prevent larger issues. Intent matters, but the impact of words is more significant. Leaders should set clear expectations for respectful behavior. Creating a culture of respect enhances employee engagement and retention.\  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.  Chapters   00:00 Introduction to the Conversation 00:57 The Journey into HR and People Strategy 04:51 Navigating Difficult Conversations 12:42 Identifying Disrespectful Behavior in the Workplace 16:51 Balancing Results and Respect in Leadership 20:00 The Impact of Communication on Workplace Culture 23:58 Self-Reflection and Understanding Triggers 27:39 Understanding Intent vs. Impact 29:23 The Leader's Responsibility in Addressing Disrespect Connect with us: Email – tas.difficultconversations@gmail.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

How do you tell someone they are not performing at the level you expect or need them to, without crushing them or demotivating them, and instead making them feel supported and motivated to improve?  Hear how Peter Vinge does it in the different performance feedback roleplays with Chris Wong and Lucie Tesarova.  Missed part 1 of this conversation on performance discussions? Check out part 1 here.  takeaways Performance conversations can be approached without discomfort. Role-playing scenarios can help practice feedback delivery. Empathy is crucial in leadership and team dynamics. Leaders should focus on facts rather than emotions during feedback. Creating a safe environment encourages open communication. Empowering team members leads to better performance outcomes. Self-leadership is essential for effective management. Understanding individual challenges can improve team dynamics. Clear expectations help align team goals and performance. Building rapport is key to successful leadership. Chapters 00:00 Introduction to Performance Conversations 00:06 Role-Playing Difficult Conversations 07:15 Empathy in Leadership 15:25 Building Empathy and Understanding in Leadership 19:31 The Importance of Self-Leadership   About Peter Vinge Peter Vinge is the founder of TORBAY Consulting and a leadership advisor focused on helping leaders have clear, confident, and productive conversations. He works with executives and teams to strengthen accountability, alignment, and culture by addressing challenges head-on. www.TORBAYConsulting.com  https://www.linkedin.com/company/torbayconsulting  Connect with us: Email – tas.difficultconversations@gmail.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment

In this conversation, Chris Wong and Lucie Tesarova engage with HR consultant Peter Vinge to explore the complexities of performance conversations in leadership. They discuss the importance of clear communication, the distinction between kindness and niceness, and the necessity of addressing performance issues promptly. Vinge shares insights on how to prepare for feedback sessions, manage emotions, and navigate sensitive situations, including those involving protected classes. The discussion also covers the effective use of Performance Improvement Plans (PIPs) and the significance of building trust within teams. Takeaways Performance conversations can be approached without discomfort. Kindness creates clarity, while niceness avoids discomfort. Address performance issues immediately to maintain trust. Document patterns of behavior for effective feedback. Prepare data and facts before performance conversations. Emotions should be set aside during feedback discussions. Transparency builds trust in difficult conversations. PIPs should not be a surprise to employees. Clear expectations are essential for performance improvement. Empowering teams leads to better performance outcomes. About Peter Vinge Peter Vinge is the founder of TORBAY Consulting and a leadership advisor focused on helping leaders have clear, confident, and productive conversations. He works with executives and teams to strengthen accountability, alignment, and culture by addressing challenges head-on. www.TORBAYConsulting.com  https://www.linkedin.com/company/torbayconsulting  Chapters 00:00 Introduction to Performance Conversations01:53 The Journey into HR05:02 Understanding Performance Feedback08:01 Identifying Performance Issues11:00 The Importance of Documentation13:56 Preparing for Performance Feedback16:47 Managing Emotions in Feedback19:48 Navigating Sensitive Conversations23:09 The Role of Performance Improvement Plans (PIPs)30:41 Navigating Performance Improvement Plans (PIPs)34:51 Role-Playing Difficult Conversations34:52 Introduction to Performance Conversations   Connect with us: Email – tas.difficultconversations@gmail.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessme  

In the 2nd part of their interview with Kristina, Chris and Lucie explore the importance of fostering a culture of productive disagreement within teams. Kristina shares strategies for transforming meeting dynamics, encouraging open dialogue, and the value of contrarian perspectives.  She shares her advice on how to encourage people to speak up and she even goes through a role play in which she shows how a leader might handle someone pushing back on their idea.  Takeaways -        Creating a culture of productive disagreement is essential for team growth. -        Asking the right questions can foster open dialogue. -        Encouraging team members to find contrarian perspectives can lead to better decision-making. -        Learning from criticism can provide valuable insights for improvement.  About Kristina Joy Carlson Kristina Joy Carlson is a sought-after speaker and best-selling author of Essential Principles for Fundraising Success, and the soon-to-be released, Outrageous Kindness: A Mindset. A Method. A Movement, Kristina knows how to navigate change and turn challenges into opportunities. While leading businesses and driving global philanthropic growth, she managed nearly a decade of intense caregiving, profound grief, and her own cancer battle—an experience that reinforced the power of purpose, perspective, and action. Kristina has helped maximize the philanthropic engagement of former US Presidents and other heads of state, Fortune 500 CEOs, Forbes 400 individuals, faith leaders, celebrities, and everyday people. Today, as founder and CEO of Outrageous Kindness, she is applying that wisdom to create a movement that inspires leaders, philanthropists, and individuals to take bold, high-impact action, embrace accountability, and experience the magic of small acts that create big results. Learn more about her: Her website Get her book, Outrageous Kindness: Amazon Square Books   Connect with us: Email – tas.difficultconversations@gmail.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

This week, Chris Wong and Lucie Tesarova talk with Kristina Joy Carlson, founder and author of "Outrageous Kindness."  There’s lots of talk around the idea of psychological safety.  And one way that plays out in real life is a culture where open disagreement is not only accepted but encouraged. Kristina talks about how a culture of fear can stifle communication and innovation. She advocates for a mindset of generosity and constructive feedback, which is essential for personal and organizational growth.  She highlights the detrimental effects of a 'yes-man' culture, where assumptions replace data-driven decision-making. Takeaways -        If you want your teams to be good at communicating, you have to model that. -        A culture of assumptions can cost organizations tremendous potential, money, and more -        You have to commit to learning and hearing different perspectives. -        How to interpret team silence  About Kristina Joy Carlson Kristina Joy Carlson is a sought-after speaker and best-selling author of Essential Principles for Fundraising Success, and the soon-to-be released, Outrageous Kindness: A Mindset. A Method. A Movement, Kristina knows how to navigate change and turn challenges into opportunities. While leading businesses and driving global philanthropic growth, she managed nearly a decade of intense caregiving, profound grief, and her own cancer battle—an experience that reinforced the power of purpose, perspective, and action.   Through her executive leadership roles at Carter Global, Ketchum, and FundraisingINFO.com, Kristina guided transformational capital campaigns, raising billions of dollars around the globe while also creating bespoke training programs, and developing innovative technologies for some of the world’s largest nonprofit organizations including Habitat for Humanity International, World Vision International, Susan Komen and others. She has also helped maximize the philanthropic engagement of former US Presidents and other heads of state, Fortune 500 CEOs, Forbes 400 individuals, faith leaders, celebrities, and everyday people. Today, as founder and CEO of Outrageous Kindness, she is applying that wisdom to create a movement that inspires leaders, philanthropists, and individuals to take bold, high-impact action, embrace accountability, and experience the magic of small acts that create big results. Connect with us: Email – tas.difficultconversations@gmail.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

In part 2 of their conversation, Chris, Lucie, and Julian discuss the complexities of leadership and organizational design, emphasizing the importance of understanding resistance and fostering accountability. Like many things in life, organizational design is an ongoing process that requires regular assessment and adaptation. Julian encourages leaders to engage all levels of their organization in the design process to create a culture of collaboration and effectiveness, otherwise, it’s destined to fail.  Other big things we learn today:  -        Organizational design is a continuous process, not a one-time event. -        Resistance is better than apathy.  Resistance indicates engagement and concern -        Accountability is crucial for successful organizational change. -        Regular assessments of organizational structure are essential for effectiveness. -        The design of an organization should reflect its strategy and promise. -        Hierarchy is not inherently negative; it can provide necessary structure. -        Engagement from all levels of an organization is vital for successful design. About Julian Julian is the founder of 11A Collaborative, a social impact consulting firm dedicated to creating healthy society through healthy organizations. 11A supports purpose-driven businesses, nonprofits, foundations, public offices, and government agencies seeking to increase their impact by translating strategy into action through organization alignment. This means defining and refining strategy, designing the organization that will achieve the north star goals, and then stewarding the change to get there.   Connect with Julian 11A Collaborative – www.11acollaborative.com Connect with him on Linkedin: https://www.linkedin.com/in/julianchender/   Connect with us: Email – tas.difficultconversations@gmail.comChris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for LeadersLucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

This week, Chris and Lucie had the pleasure of chatting with Julian Chender, an expert in organizational design, to explore the difficulties of communication and structure within organizations.  Julian shared his journey in organizational design, emphasizing the need for strategic alignment and the human elements that influence organizational behavior.   Most importantly, he talked about how silos aren’t a 4-letter word, but leaders make common mistakes in managing change and fostering collaboration across silos. Big Takeaways -        Organizational design is about setting the container in which an organization operates. -        Silos are necessary structures that support organizational goals. -        integration across silos is crucial for effective strategy execution. -        Silos should be designed with 'doors' to facilitate collaboration. -        Understanding the strategic purpose of silos can enhance organizational effectiveness.  About Julian Julian is the founder of 11A Collaborative, a social impact consulting firm dedicated to creating healthy society through healthy organizations. 11A supports purpose-driven businesses, nonprofits, foundations, public offices, and government agencies seeking to increase their impact by translating strategy into action through organization alignment. This means defining and refining strategy, designing the organization that will achieve the north star goals, and then stewarding the change to get there. Over his career, Julian has consulted to purpose-driven organizations across sectors, from the Fortune 10 to nonprofits in education, arts, and public health, from intergovernmental European agencies to New York City public offices. He is a Certified Organization Design Practitioner and an ICF-Certified Coach who holds a master’s degree in Organization Development from American University and a B.A. in History from Swarthmore College. In 2020, he received the Emerging Practitioner Award from the Organization Development Network (ODN). He has served on the Board of Trustees of ODN and currently sits on the Board of Advisors for the Organization Design Forum.  Connect with us: Email – tas.difficultconversations@gmail.comChris – www.linkedin.com/in/chriswonglmhc and download the Difficult Conversation Playbook for LeadersLucie – www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

What does leading with emotional intelligence look like in practice? That’s what we’re exploring in today’s special compilation of The Art & Science of Difficult Conversations. You’ll hear highlights from four episodes: – Dr. Rick Fearnbaugh on growing as an emotionally intelligent leader, – Kelly Meerbott on creating psychological safety, – Chris Wong on helping your team take ownership and accountability, – and Dr. Summer Miller on handling layoffs in a compassionate and ethical way. Connect with us:Email – tas.difficultconversations@gmail.comChris – www.linkedin.com/in/chriswonglmhc and download the Difficult Conversation Playbook for LeadersLucie – www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

Episode Description: In this special compilation episode of The Art & Science of Difficult Conversations, we’re taking a break from work conversations and turning toward the relationships that matter most outside of work. You’ll hear three powerful clips on what it means to communicate honestly in love – with yourself, with a long-term partner, and in modern dating. Together, these conversations explore how to be more “you” in relationships, navigate conflict with care, and set boundaries that protect your energy and your heart. We revisit: Grace Gavin on open and honest communication, and six key practices that can transform the way you show up with the people you love. Heather Garbutt, psychotherapist and love & relationship coach, on navigating triggers, red flags, and tough conversations in committed partnerships – and how intentional dialogue can deepen connection instead of breaking it. Whitney Kobrin, dating and relationship expert, on modern dating, setting intentions, boundaries, and how emotional regulation and self-soothing can help you date with more confidence and self-respect. As you listen, notice this question: Where am I not bringing my honest self into the relationships that matter to me – and what might change if I did? In this episode, you’ll learn: Why open and honest communication is essential in close relationships Six practical practices to help you communicate more clearly and courageously How to recognize triggers and red flags in romantic relationships Ways to have intentional, deeper conversations in committed partnerships How dating has changed in recent years – and what that means for you How to set intentions and boundaries before and during dating Simple ideas for navigating first dates with less anxiety and more ease How self-soothing and emotional regulation support healthier choices in love Guests featured in this compilation Grace Gavin – Communication expert and co-founder of Know Honesty, helping leaders simplify their communication and close divides inside organizations. Heather Garbutt – Psychotherapist and love & relationship coach, supporting people in healing past hurts and creating healthier, more supportive partnerships. Whitney Kobrin – Dating and relationship expert, guiding people to date with intention, confidence, and clear boundaries. If you enjoyed this episode Share it with a friend who’s navigating a big relationship conversation Leave a rating or review to help others find the show Connect with Lucie and Chris for coaching, workshops, or speaking on difficult conversations and emotional fitness Connect with us:Email – tas.difficultconversations@gmail.comChris – www.linkedin.com/in/chriswonglmhc and download the Difficult Conversation Playbook for LeadersLucie – www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

Say the Hard Thing: Courageous Conversations Under Pressure Most difficult conversations don’t fail because we don’t know what to say. They fail because fear shows up, emotions escalate, or we lose clarity under pressure. In this compilation episode of The Art & Science of Difficult Conversations, we bring together three powerful conversations that walk you through the full arc of a hard conversation — from finding the courage to speak up, to staying grounded when emotions rise, to navigating real-world leadership pushback. You’ll hear: What courage really looks like in communication Why waiting to feel “ready” often keeps us silent — and how to speak even when fear is present. How to respond when someone becomes defensive or angry Practical tools for de-escalation, emotional regulation, and keeping the conversation productive instead of reactive. A real-life leadership roleplay: handling pushback from a team member How to balance empathy and accountability when you still need results — without escalating conflict or damaging trust. This episode is for you if: You avoid hard conversations longer than you want to admit You freeze or over-explain when emotions run high You’re a leader navigating resistance, pushback, or difficult dynamics You want to communicate clearly without losing yourself or the relationship Difficult conversations don’t require perfection — they require presence, courage, and practice. This episode gives you all three.   Connect with us:Email – tas.difficultconversations@gmail.comChris – www.linkedin.com/in/chriswonglmhc and download the Difficult Conversation Playbook for LeadersLucie – www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

How do you give feedback that actually builds a high-performing team? That’s the theme of our compilation episode today. In the first segment, you’ll hear a roleplay where one of our previous guests, Jevon Gondwe, gives performance feedback to Chris. In the next segment, Chris and I break down five practical steps you can use to give feedback that’s clear, honest, and supportive.   Connect with Jevon:https://www.influentialskills.com/ jevon@influentialskills.com https://www.linkedin.com/in/jevon-gondwe/  Connect with us:Email – tas.difficultconversations@gmail.comChris – www.linkedin.com/in/chriswonglmhc and download the Difficult Conversation Playbook for LeadersLucie – www.linkedin.com/in/lucietesarova and take the Saboteur Assessment 

In part 2 of their conversation with Laurel Engbretson, Chris and Lucie are joined by Sara Firestein.  This is especially fun because Sara reports directly to Laurel and together, the four of them discuss not only the process of giving feedback to your boss, but how to receive feedback too! They explore the importance of building trust and psychological safety, the role of feedback culture, and the impact of empathy in communication. The discussion highlights personal experiences and strategies for giving and receiving feedback, emphasizing the need for openness and collaboration in fostering effective team dynamics. Takeaways -        Feedback should be balanced with positive reinforcement. -        Specific examples help clarify feedback. -        Trust enhances team dynamics and collaboration. -        Leaders should invite feedback to disrupt power dynamics.   About Laurel: Laurel Engbretson is the national Vice President of Strategy & Operations at LISC. In this role she leads LISC’s Strategy & Operations team to facilitate strategy development and drive operational excellence toward LISC’s enterprise-level priorities. Laurel started at LISC as a Program Officer in the Bay Area, where she lived for 30 years before moving to the East Coast to join LISC’s national office. Before LISC, Laurel worked at the San Francisco Housing Accelerator Fund, JPMorgan Chase, the Oakland Mayor’s office, and in residential real estate. She has an MBA/MPP from Mills College and a BA in Sociology from the University of California, Santa Cruz.   About Sara: Sara Feierstein is a nonprofit strategy and operations specialist. Her work experience and education have focused on using data to drive impact in the nonprofit industry. She has spent the last several years working in the Community Development sector where she has been implementing strategies to help her organization align internal operations with programmatic goals. Sara has a Master in Business Administration from NYU’s Stern School of Business where she specialized in Business Analytics and Nonprofit Strategy. She holds a Bachelor of Arts in Economics from New York University. Follow Laurel: https://www.linkedin.com/in/laurelengbretson/ Follow Sara: https://www.linkedin.com/in/sara-feierstein-22878066/   Connect with us:  Chris - LinkedIn / Newsletter and download the Difficult Conversation Playbook for Leaders Lucie - LinkedIn  / Saboteur Assessment