How to Win-Win Any Difficult Conversation

Learn to navigate hard conversations with confidence. 

Say what you want and feel heard.

Imagine going into a difficult conversation
with your parent, partner, adult children, client, colleague or service provider.

Your difficult conversation might be with a doctor about a new diagnosis, a spouse about your marriage, a parent about whether she is still safe driving, or a manager to ask for a raise.

Now imagine going in feeling confident of a good outcome for all parties.
That’d be a game changer, right?


Imagine participating in a trio of conversations via Zoom
with a facilitator and a handful of other women that would:

  • Give you the confidence to have that difficult conversation
  • Validate that your wants and needs matter
  • Teach you a framework for your difficult conversation
  • Help you listen from a position of curiosity and objectivity, and
  • Give you strategies to make your communication more effective

"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 and ability to create community, combined with content, role-playing and strategy for participants, 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."  

Sound interesting?  Then join us to:

  • Learn to promote mutual understanding in your conversations
  • Practice using your 5 communication superpowers
  • Role play to make those superpowers second nature, and
  • Reach a win-win outcome for all

Regularly $199

Now only $169!

Email now to express interest in joining our next cohort

- OR - 

"I took Debra’s How to Win-Win Any Difficult Conversation Zoom 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.”

Debra A. Woog, Crisis Navigation Partner®, has 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 also 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 an MBA from the 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. 

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