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 parents, partner, 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 boss 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 to kick off 2020 as a gift to myself.  This course went beyond my expectations and provided me with information, tools and practice I am using in my day to day life.  Debra's expertise, caring, compassion and ability to create community mixes content, role-playing and strategy for participants was the perfect mix of theory and practice.  Setting the stage, something Debra said stays with me, "We don't have to handle difficult conversations alone".  Ahhhh! Reviewing the types of  difficult conversations in community, learning about strategies to succeed, planning the tools to use, maintaining curiosity, and practicing was 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

Join us next:

April 9 (11a-12p Eastern)

April 17 (11a-12p Eastern) and

April 23  (11a-1p Eastern)

Regularly $139.

Now only $79!

"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 just 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 (pronounced like “Vogue” magazine), president of connect2 Corporation, is passionate about guiding individuals to identify their unique capabilities, contributions and options. Her data-driven tools and proven processes ease leadership transitions: in the 15+ years since launching her private practice she has coached nearly one thousand thriving professionals.

Applying her expertise in career development, organizational dynamics, and conflict resolution, Debra helps leaders envision and effectively communicate their stories to achieve their desired success. She teaches and coaches professionals preparing for career change, finding and negotiating their next roles, optimizing their leadership, and launching and growing their own businesses.

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Debra’s own career story drives her effectiveness as a thought partner. Her experience includes leadership roles in for-profit and not-for-profit organizations, research at Harvard Business School for the award-winning book ​​​​​Breaking Through: The Making of Minority Executives in Corporate America (HBS Press), and author for national publications including Inc. and Forbes. While she led People Strategy for Cambridge Innovation Center,The Boston Globe profiled her outstanding ability to select and develop talented candidates. More recently Debra served on the MIT Sloan School of Management MBA Admissions Committee and directed admissions and career development for Leaders for Global Operations, the MIT dual-Master’s program in engineering and management.

Debra earned her BA in psychology and American Studies from Wellesley College and her MBA from the MIT Sloan School of Management, where she was awarded the Miriam Sherburne Scholarship for leadership and community service. She is also trained as a mediator and ombudsman. Residing in Arlington, MA, she relishes time with her high-school-aged son and daughter.

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