Strategies and Tactics to Navigate Difficult Conversations with Confidence

Strategies and Tactics to Navigate Difficult Conversations with Confidence

This On-Demand event was originally presented on April 5, 2023 (60 min)


Difficult conversations are inevitable, but the anxiety and stress that comes with them don’t have to be. The skills for any conflict or difficult conversation are usually straightforward, but the real key to confidently using them is mastering the inner game. True confidence comes from understanding our own beliefs around conflict, our response to strong emotions, and the skills to manage someone else’s emotions. Whether you avoid difficult conversations to keep the peace, freeze up when trying to negotiate with others, or feel bad when you’re responsible for giving bad news, this webinar will give you the skills to confidently communicate and assert yourself.

Attendees will learn

  • What makes having difficult conversations so difficult?
  • The importance of preparing, and what truly matters in preparation and what doesn’t.
  • The components of the inner game that can limit your success, and how you can conquer yourself.
  • The 4 words that make any situation worse, and what to use instead.
  • A simple framework to guide the conversation and increase the probability of a collaborative outcome.
  • How to take your questions to the next level and use them strategically to get the information that can make a difference in the conversation.


Chris Wong started his career as a direct care staff member for adolescents in a psychiatric inpatient hospital. He enjoyed working with the youth so much that he went to Boston University School of Medicine where he received his Master’s in Mental Health Counseling and Behavioral Medicine. After graduating, he worked as a licensed therapist in a variety of settings, including an adolescent residential treatment center, outpatient clinics, and mobile crisis evaluations in the Boston and Cambridge area.

In 2016, he started work as a training manager at a non-profit child welfare agency, developing and facilitating trainings to support staff around clinical interventions, cultural humility, and any needed training support for programs. In 2019, he moved into a new role as Director of Employee Learning and Development, where he oversees leadership and career development for the organization. This includes training and coaching for leaders at all levels of the organization to both strengthen and build a leadership pipeline.

Chris is a certified executive coach and works with HR and L&D leaders on difficult conversations, conflict resolution, building powerful relationships, leadership development, productivity, leading change, diversity, equity, and inclusion.


Strategies and Tactics to Navigate Difficult Conversations with Confidence

Training Tools for Developing Great People Skills

This event is sponsored by HRDQ. For 45 years HRDQ has provided research-based, off-the-shelf soft-skills training resources for classroom, virtual, and online training. From assessments and workshops to experiential hands-on games, HRDQ helps organizations improve performance, increase job satisfaction, and more.

Learn more at

On-Demand Webinar Recording

Listen to the podcast

In this episode we’ll be delving into the webinar, Strategies and Tactics to Navigate Difficult Conversations with Confidence. We’ll discuss the changes happening in the L&D space, the exciting projects our guest, Chris Wong, is working on, and the key takeaways from the webinar. We’ll also dive into specific content-related questions, such as how to handle difficult conversations with limited preparation time, approaches for conversations with someone in a position of power, the value of bringing in a third-party, and strategies for setting ground rules when the other party is resistant. Get ready for a power-packed episode filled with practical wisdom and actionable advice to navigate those tough talks with confidence.
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