6. Having Hard Conversations

Having Hard Conversations provides attendees an opportunity to practice one of those hard conversations that no one enjoys having but leaders understand they must learn to do to be effective and respected. We will look at the behaviors and guidelines for these conversations and practice working through one with someone from the class.


  • Read the Hard Conversations Preread packet.
  • Think about someone in your life (work or personal) where for you there’s a hard conversation out there that one of the two of you should probably initiate. There will be an opportunity to practice that conversation with another attendee during the session and “try it out.”


  • Who’s here and where are we going? (:10)
  • Working thru Conflict (:10)
  • Hard Conversations reasons, principles (:10)
  • Hard Conversation Demo (:10)
  • Hard Conversations practice (:15)
  • Leadership, HC and Conflict in action (:30)
  • Summary (:05)

Download HCv2 slides.

Going Deeper:


Lauren Mackler at Harvard – Difficult Conversations
Bestselling author and renowned coach, Lauren Mackler, is interviewed by Harvard Business School about how to handle difficult conversations. Lauren Mackler is one of the world’s foremost experts in human behavior and leadership.

How to Prepare for a Difficult Conversation – Dodging Landmines

Are your employees complaining about one of their team members—and now you have to handle it? Alliance Leadership executive coach Caty Everett says it’s critical to address the matter directly and develop a shared understanding of expectations going forward.

Difficult conversations – biggest mistakes
Author Jean Palmer Heck discusses the three biggest mistakes when it comes to having a difficult conversation.

How to Turn a Hard Conversation into a “Carefrontation” – Oprah Winfrey
Iyanla Vanzant says a hard conversation doesn’t have to be confrontation. Instead, think of it as a “carefrontation.” Watch as Iyanla explains the four main outcomes you want from a hard conversation and how to overcome your fear of having it.


  • In this helpful article, Iyanla Vanzant offers 7 tips on how to have hard conversations.
  • Here are a few more suggestions on how to have those less-than-desirable conversations with peers and/or loved ones.