Tools for Difficult Conversations

Tools for Difficult Conversations

This week I’m getting to speak in Wimberley. The Chamber of Commerce is having it’s first ever small business week with a day of seminars and a day of exhibitions. The topic is difficult conversation tools so let’s chat about that that today.

As I prepared for the 1-hour workshop, I started by listing what does make conversations and conflict difficult at times:

  • Old pain and old stories that get triggered
  • Making the current conflict about way bigger themes instead of what is current
  • Getting defensive
  • Underlying shame getting triggered
  • Self protection patterns coming out as anger or avoidance or humor, etc.
  • Fear of rejection - leading to compromise or manipulation or sabotage
  • Emotions being so high that logic is difficult
  • Faulty thinking about oneself, the relationship, the world getting in the way

The list could continue but it is already overwhelming. It is almost more amazing that we ever actually can get through difficult conversations!

So, where to start if you want to make difficult conversations easier?

Prepare: Take time to prepare for potentially difficult conversations by reflecting and getting very specific with what you want to bring up. What are the 1 or 2 things that are core that you’d like to be heard on?

Discharge: Discharge some of the emotion by validating it for yourself - journaling is a great way to do this. Going in to a conversation expecting to be validated by the other person adds extra potential for the conversation to go sideways fast.

Listen: Be prepared to listen. One of the quickest ways to bring down someone’s defensiveness and anger is to actually hear them. Ask questions like “Can you tell me more?” or simply reflecting back what you are hearing, including the emotions, can really discharge their desire to escalate.

Take Turns: When we are trying to be heard at the same time as the other person, usually no one gets really heard. Delaying your response until they feel heard often simplifies or changes what you feel you need to say. When a conversation is really intense these turns can even be separated more severely. Listen to one person with no response and then take time to process.

Separate the Issue: Separate out the issue from the relationship. Whenever possible look at the upsetting issue or situation together as if it stands alone as something you can both brainstorm and strategize about. Two heads are better than one! Remembering that the issue is not the other person but a specific behavior or situation helps to keep it in perspective.

The absolute best relationships, highest functioning teams, companies, etc. have figured out how to embrace conflict and use it as an opportunity for growth and insight.

Are there difficult conversations you have been avoiding? What step are you willing to take next?

Until next week,


Marilyn Orr is a Professional Certified Coach, who, through her coaching business “Capacity Building Coaching”, thrives on building both personal and organization capacity through leadership coaching and development.

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