A Masterclass on Hard Conversations: Part 1 – Preparation

A Masterclass on Hard Conversations: Part 1 - Preparation

A Masterclass on Hard Conversations: Part 1 – Preparation

Welcome to episode 273 of DREAM THINK DO. We’re doing an experiment over these next few weeks. 3 episodes on the important topic of having HARD conversations.   Actually, I want to reframe that as how to have RICH conversations.  Because… they really can be both right?

Hard conversations usually involve a difficult subject but with the right prep… they can be incredibly RICH conversations too.  Right?  Oh… and each episode will be about 15 minutes long.  YOW… you know me so this is a stretch!  But it’s going to be gooooood.  So let’s get to it!


Listen To The Podcast:

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All right… I’m excited about this.

Experiments are always fun.  And I’m feeling stretched to keep this shorter.  A little uncomfortable… and that’s good… right?

This is going to be PART 1 in a series called a “Masterclass in Hard Conversations.”

NOTE: This series is not geared towards ONLINE conversations.  Nope.  

This is for REAL conversations.   

Do you remember REAL conversations?  

Face to face.  Eye-ballers.  Real deal conversations.  

In our current situation of COVID-19, etc… this may look a little different but what we’re going to be talking about is one-on-one conversations.  We might be talking about using something like Zoom or the phone… but it’s all about talking to someone that’s important to you.

They’re important to you… because they’re:

  • Family member
  • Friend
  • Co-worker
  • Boss
  • Someone you’re wanting to get to know better

Now… something about them may ping the shiznitz out of you… but you still need or want to have a conversation.  And yes, some of those might be “hard” conversations.  So, let’s get you ready!



“You have power over your mind – not outside events.  Realize this and you will find strength.”

Marcus Aurelius


Queen Elsa 

“We are not all in the same boat, but we are in the same storm.”

Origin of the quote



  • 0:02 What to expect the next three episodes
  • 2:11 Now is the time to have a rich conversation
  • 5:03 The three-bucket questions
  • 6:57 Create an environment for ‘us’
  • 8:32 How fight or flight plays into conversations
  • 10:53  Give yourself a minute
  • 14:00 Mitch asks in a difficult conversation
  • 14:41 Remain respectful



So… one of the things I needed to be reminded of this week has been the importance of “Just giving yourself a minute.”  It’s a concept I’m REALLY familiar with when it comes to my “typical” workday.  And/or when I’m preparing to take the stage in front of an audience.  But amid all of the wildness that is 2020, I’ve realized that it’s so important to just stop once and a while and take a breath.  To rest.  To be present.  That’s critical.  So I appreciated that prompt to just stop, to pause, and to breathe.  

How about you?  What’s something that stood out to you?  

What’s something YOU are going to try this week?

Also, I want to hear from YOU on your favorite strategies for navigating hard conversations.  Comment and let me know.  And hey, if I use your concept I’ll give you a shout out in the episode too!  Cool?  Cool.

Leave a comment and let me know!  I can’t wait to hear from YOU!

  • Doug Branscombe
    Posted at 21:18h, 20 June Reply

    I’m not sure if it’s been mentioned because I can’t see other comments. Crucial Conversations is an excellent book that covers this subject in depth.

    • Mitch Matthews
      Posted at 08:45h, 24 June Reply

      Love it Doug! That IS such a powerful book. Thanks for adding it to the list of tools for this series!

  • Lesley Stubock
    Posted at 20:51h, 09 July Reply

    It is critical to manage your emotions before the discussion if you know it will be difficult. Acknowledge your feelings and accept that you are feeling some sort of way.

    • Mitch Matthews
      Posted at 05:55h, 10 July Reply

      Lesley… thanks so much for the wisdom! Totally agree.

  • Mark Dunny
    Posted at 10:49h, 10 July Reply

    This is so well done. Our church, long before the pandemic, has been searching for opportunities to bring people together for open discussions on issues our community is facing. The formula of: A) setting (preparation) the environment of respect focused on the issue/issues B) recognizing perspective (we are “in the same storm but not the same boat) C) Create an objective of Learning, not Winning, has set a nice baseline for respectful open discussions. However the zoom meetings don’t seem to carry the energy or openness of in person discussions. so we have stalled in our efforts. Recognizing and respecting the passion of people on topics important to them is so critical. Giving them the chance to share perspective is often a great bridge.

    • Mitch Matthews
      Posted at 12:53h, 10 July Reply

      Mark – Thanks so much for the strategy and the vision. Love it. I hear you on the zoom meetings not being quite the same as face to face… but it sounds like you are doing some great work my friend. So stay the course… even if the online experience isn’t quite as good… it sounds like the importance of what you’re doing could totally outweigh the shortcomings of the online convo! Thanks for listening!

  • Teddy Jones
    Posted at 13:02h, 11 July Reply

    Man Mitch!!! This could not have come at a better time. I have a very very hard convo that I must have very soon. This helped a whoooooollllleeee lot. Thanks

    • Mitch Matthews
      Posted at 18:14h, 13 July Reply

      Glad to hear it resonated Teddy! Hang in there and know we’re pulling for you!!!

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