Have you ever rehearsed a conversation with your boss a dozen times, only to never actually have it?

Whether it's asking for a promotion, setting boundaries, navigating conflict, or simply speaking up in a meeting, difficult workplace conversations can feel intimidating—especially for younger professionals. But avoiding them often comes at the expense of confidence, career growth, and stronger relationships.

In this episode, Kellie interviews Debra Roberts, a Licensed Clinical Social Worker, author, trauma-trained clinician, and business consultant with more than 25 years of experience helping people communicate more effectively. Debra is the creator of the Relationship Protocol®, a practical and proven communication model that empowers people to express themselves with confidence, navigate conflict, and build stronger relationships both at home and in the workplace.

Debra has also been featured in The New York Times, Real Simple, Business Insider, and The Cut for her expertise in communication, relationships, and conflict resolution. Her approach is known for being practical, relatable, and actionable—making meaningful change possible, even in the most challenging conversations.

Together, Kellie and Debra discuss:

  • Why so many people, especially younger professionals, are afraid to have difficult conversations at work
  • How to confidently approach conversations with a boss or supervisor
  • The difference between being assertive and being confrontational
  • Practical communication strategies that build trust instead of conflict
  • How to set healthy boundaries without damaging professional relationships
  • How to advocate for yourself when asking for a raise, promotion, or more responsibility
  • What to do when a difficult conversation doesn't go as planned
  • Why effective communication is one of the most valuable leadership skills anyone can develop


If you've ever avoided sending the email, postponed the meeting, or talked yourself out of speaking up, this episode will give you practical tools to communicate with confidence, strengthen your relationships, and advocate for yourself, without sacrificing professionalism.

Show Notes~My Communication Tools MyCommunicationTools.com

Use Kellie's coupon code: DOBOTH to get 10% off the $79 program!

The Communication Protocol®  for the workplace.

Instagram: @debraroberts_lcsw

LinkedIn Debra Roberts 

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