The Art and Science of Difficult Conversations

By Chris Wong & Lucie TesarovaSociety & Culture Business Education Relationships Management

The Art and Science of Difficult Conversations episodes

March 24How to make difficult conversations simpler (Part 2 with Travis Dalrymple)
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 – [email protected]
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
23 min
March 17 How to make difficult conversations simpler (Part 1 with Travis Dalrymple)
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 – [email protected]
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
28 min
March 10 How to deal with overbearing parents (Part 2 with Roberta Dombrowski)
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 – [email protected]
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
33 min
March 03How to set boundaries with your family (Part 1 with Roberta Dombrowski)
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 – [email protected]
Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders
Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment
20 min
February 24 Roleplay: Dealing with Inappropriate Jokes in the Workplace (Part 2)
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:
[email protected]
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 – [email protected]
Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders
Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment
20 min
February 17How to Navigate Disrespectful Behavior in the Workplace with Rachel Platt (Part 1)
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:
[email protected]
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 – [email protected]
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
32 min
February 10Roleplay: Performance conversations with Peter Vinge (Part 2)
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 – [email protected]
Chris – https://www.myleadershippotential.com | www.linkedin.com/in/chriswonglmhc | download the Difficult Conversation Playbook for Leaders
Lucie – www.mindfittery.com | www.linkedin.com/in/lucietesarova and take the Saboteur Assessment
29 min
February 03How to Address Performance Issues with Peter Vinge (Part 1)
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 Conversations
01:53 The Journey into HR
05:02 Understanding Performance Feedback
08:01 Identifying Performance Issues
11:00 The Importance of Documentation
13:56 Preparing for Performance Feedback
16:47 Managing Emotions in Feedback
19:48 Navigating Sensitive Conversations
23:09 The Role of Performance Improvement Plans (PIPs)
30:41 Navigating Performance Improvement Plans (PIPs)
34:51 Role-Playing Difficult Conversations
34:52 Introduction to Performance Conversations

Connect with us:
Email – [email protected]
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
35 min
January 27 How to Create Teams that Innovate (Part 2 with Kristina Joy Carlson)
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 – [email protected]
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
32 min
January 20 How to Create Teams that Innovate (Part 1 with Kristina Joy Carlson)
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 – [email protected]
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
26 min

About The Art and Science of Difficult Conversations

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The Art and Science of Difficult Conversations

The Art and Science of Difficult Conversations episodes

About The Art and Science of Difficult Conversations