Business Guidance

Tips for Having Difficult Conversations

Is there a conversation you are anxious about having or maybe even delaying? Perhaps it’s because the issue is sensitive, requires giving or receiving negative constructive feedback, or includes asking someone for help. Maybe the conversation evokes emotion, like anger or frustration. It might involve how you feel about yourself or how others see you. By definition, these are difficult conversations and most of us struggle to know how we should approach them.

Navigating a difficult conversation begins with a shift in our mindset. We typically think we know what happened and want the other person to agree with us and our solution. This approach usually results in a battle of messages where both parties insist they are “right.”

Changing our mindset means approaching the conversation with an attitude of curiosity. Acknowledge that you can’t read the other person’s mind, so their perspectives aren’t fully known. Expect that a reasonable outcome will involve dialogue and understanding, not defending turf or getting your way.

Difficult conversations don’t mean giving up your point of view or dismissing your concerns. However, to encourage the best outcome you will need to explore the truth in new ways, examine your intentions, and share the blame. Here are ways I coach clients to develop a learning conversation mindset.

  • Acknowledge Multiple Stories – Ask, what’s my story of what happened and what is missing? Then ask, what do I think their story of what happened will be?
  • Reflect on Impact and Intention – Ask, in this situation, what were my intentions? How did their behavior impact me? Then ask, what do I think their intentions were (including maybe it was unintentional)? What might have been the impact of my behavior on them? How does this make me feel about what happened?
  • Consider Contributions – Ask, what did I contribute to this situation? Then ask, what did they contribute (from my perspective)?
  • Recognize Feelings – Ask, what feelings might underlie my judgments? Then ask, how might they be feeling?
  • Explore Identity – Ask, how does this situation threaten my identity (my self-image)?

How you implement the difficult conversation is also important. These tips will make a difference.

  • The setting must be private with both parties seated.
  • Allow enough time so you won’t feel rushed.
  • Your tone should be amicable.
  • Describe the topic of conversation as a third-party would so it feels impartial.
  • Explain how you are looking to problem-solve and will seek their input.
  • Offer your observations about the behavior or situation without placing blame.
  • Describe the impact of the behavior or situation on you and/or others. Include how this feels.
  • Explore their perspectives by asking open-ended questions and actively listening. Remember to check for understanding frequently.

In difficult conversations our “story” often evolves into victim, perpetrator, or rescuer. The process just outlined offers a way to re-frame your story and counter some of the perspectives and feelings that can turn any situation into the limiting script of “I’m right, you’re wrong, and here is how things will be.” Mastering these skills shifts the focus from what has happened, and why I don’t like it, to real problem-solving that creates a better future.


Ken Byler is a principal and managing partner with Higher Ground Consulting Group, LLC. Founded in December 2002, the firm provides high quality leadership development, facilitation, and executive coaching services.  Ken has delivered dozens of programs regionally and nationally.  He is a contributing author to a family business book published in 2007.  With more than 40 years of business experience, Ken is known for his ability to make learning fun and practical so that it gets results.  He is certified with Upstream Academy and The Fiscal Policy Studies Institute.  Ken has been an Authorized Partner for Everything DiSC (A Wiley Brand) since 2007 and a Five Behaviors of a Cohesive Team Authorized Partner since April 2014.

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