The Art and Science of Difficult Conversations

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 – [email protected] – 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/ [email protected] https://www.linkedin.com/in/jevon-gondwe/ Connect with us:Email – [email protected] – 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

This week, Chris and Lucie interview Laurel Engbretson, a VP of strategy and operations, discussing the complexities of difficult conversations in leadership. Together, they explore Laurel's journey and her journey to building the courage to give feedback to her own manager. Laurel is a big advocate in the role of trust and the gradual process of building confidence in difficult conversations. Together, they talk about: - Building trust is crucial for giving and receiving feedback. - Finding your voice takes time and practice. - Trust is built over time and through shared experiences. - Assuming positive intent can improve difficult conversations. - Personal growth can enhance professional effectiveness. 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. 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: [email protected] Website: https://www.acebusinessdev.com Connect with us: Chris - LinkedIn / Newsletter Lucie - LinkedIn / Saboteur Assessment