The Art and Science of Difficult Conversations

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

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 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 

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 

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 

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 

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 

In part 2 of their conversation, Chris and Lucie dive even deeper into the intricacies of networking with Jack Pittas, discussing essential strategies for building connections, the importance of tracking contacts, and the effectiveness of elevator pitches. They even persuade Jack to role play how to approach two different people at networking events. Takeaways  Networking is about building relationships, not closing sales.  Old-fashioned business cards are still relevant.  Elevator pitches should be conversational, not scripted.  Rejection is part of the networking process; learn from it.  Online networking can be as effective as in-person events.  Always be curious and ask questions to engage others. About Jack: Jack is a partner at Ace Business Development, which offers fractional sales, networking, and business development services to help small businesses build their pipeline and GovCons break into the government market. Jack and the Ace team use a "boots-on-the-ground" approach and their vast connections to build relationships on behalf of their clients to ultimately drive revenue opportunities.    Jack is also owner of PK Cyber Solutions which offers specialized content-writing on technical subjects including B2B tech, cybersecurity, and GovCon. Since 2020, Jack has generated a majority of his business via networking and building quality relationships.    Connect with Jack: Email: jack@acebusinessdev.com Website: https://www.acebusinessdev.com   Connect with us:  Chris - LinkedIn / Newsletter  Lucie - LinkedIn  / Saboteur Assessment