How to


Any Difficult Conversation

Video Course

Learn to navigate hard conversations with confidence. 

Say what you want. Feel heard.

Think of a conversation you’re dreading.

Perhaps you need to discuss something important with a parent, partner, or child. Perhaps you need information from a service provider, or to negotiate with a client, boss, or colleague.

Your might need to speak with a doctor about a new diagnosis, a spouse about your marriage, an elderly parent about whether she is still safe driving, or a manager to ask for a raise.

How do you feel? 
How does your body respond?
What thoughts fill your mind?

For many people, emotional responses to an anticipated difficult conversation include fear, anger, hopelessness and loneliness.

Some experience a sense of panic, an accelerated heart rate, or an adrenaline rush triggered by the fight or flight response. Some freeze. Thoughts may come up like "I don't want to have to do this alone!" or "I shouldn't have to deal with this right now!"

While all of these thoughts and feelings are understandable, none of them help lay the groundwork for a successful outcome.

Wouldn't you rather walk into a difficult conversation feeling confident that all parties will benefit?  

You can learn the skills and develop the mindset to…

  • Clearly say or ask for what you want
  • Move through resistance and challenging responses
  • Stay calm and focused throughout

Having taught this content throughout my career as an organizational change consultant and leadership coach to hundreds of people, I know the How to Win-Win Any Difficult Conversation™ strategies make all the difference in feeling heard, getting results, and relieving stress and overwhelm.

Now, through my new online video course, you can learn all these concepts and tools in under an hour, on your own schedule. Even better, you can go back to each module to review the material whenever you want a refresher.

"I took Debra’s How to Win-Win Any Difficult Conversation course a couple of months ago and it changed the way I think about and handle conversations I used to want to avoid. Her simple, clear steps break things down so I can get to the heart of what I want out of a conversation, and understand where the other party is coming from too. With her approach I am not distracted by emotion or old patterns that leave things unspoken or unresolved. Instead, I can own my intentions, plan for the greatest good of all and speak in a way that allows me to be heard.”

  • Discover how to reach a win-win outcome for all
  • Learn to promote mutual understanding in your conversations
  • Understand the 5 Communication Superpowers
Sound interesting? 

Full Price:


Website Special:


"I enrolled in Debra Woog's How to Win-Win Any Difficult Conversation™ course as a gift to myself.  This course went beyond my expectations and provided me with information, tools and practice I am now using in my day-to-day life. Debra's expertise, caring, compassion... yielded the perfect mix of theory and practice.  One thing Debra said stays with me, "We don't have to handle difficult conversations alone".  Ahhhh! Reviewing the types of  difficult conversations in communities, learning about strategies to succeed, planning the tools to use, maintaining curiosity, and practicing were all so helpful.  Highly recommend this course!  Thank you, Debra, for your guidance."  

We respect privacy.  Information collected through this site will
never be shared with or sold to other organizations.

Debra A. Woog (pronounced like “Vogue” magazine), is a Crisis Navigation Partner™ with 30+ years of experience as a leadership researcher, executive and advisor. Debra provides highly competent women with expertise, structure and empathy so that they can process difficult situations, connect with necessary resources, communicate effectively, and lead with a clear mind and a solid strategy.

Having experienced her own crises and crossroads, Debra realizes the importance of an outside resource to provide perspective while navigating difficult circumstances, decisions, and conversations. 

Debra’s career has included conducting primary research at Harvard Business School for an award-winning book, directing admissions and career development for the MIT dual-degree MBA program Leaders for Global Operations, and advising nine technology start-ups as Director of People Strategy for Cambridge Incubator. The Boston Globe profiled Debra for her outstanding abilities to select talented candidates, motivate and develop employees, and resolve conflicts between people as well as between organizations. Her work has been featured in Forbes, Inc.US News & World Report and more.

Debra earned her B.A. in Psychology and American Studies from Wellesley College and M.B.A. from MIT Sloan School of Management. MIT Sloan recognized her leadership abilities and community contributions by awarding her the Miriam Sherburne Scholarship. After training as a mediator and an ombudsman, she also studied with Brené Brown to become a Dare to Lead professional.

She's a voracious reader, theater-lover, occasional intuitive painter, and sometimes knitter who delights in roasting vegetables. Debra relishes time with her son and daughter when they are home from college.

Copyright © 2022 Connect2 Corporation. All rights reserved.