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Episode 344

The Exact Moment a Difficult Conversation Goes Wrong (and How to Spot It)

If you’ve ever plucked up the courage to have ‘that’ conversation, and planned it carefully so that you can be kind and clear –  but two minutes in, it goes south – you’ll know what it feels like when their face changes, your chest gets tight, and suddenly you’re both defensive and you’re both feeling got at.

This replay from January 2025 is part of our season on conflict and difficult conversations, re-released while I’m in the middle of writing my book How to Say No When Someone Might Die. I keep coming back to it because it names the exact moment the conversations tip and we go ‘over the net’ – a concept Carol Rubin and David Bradford talk about in their book ‘Connect’. It’s nuanced, but once you see it, you can’t unsee it. There is a certain thing we do that triggers defensiveness in them, and a certain thing they do that triggers it in us.

You will hear why assuming you know what the other person intends can be devastating, and how our ingrained programming tells us we have to please everyone all the time to feel good enough. Learn how one tiny change in language – staying with what you saw and the story in your head, instead of what you decided they meant – may help you carry a patient or client complaint, an official grievance or being criticised by your team differently. Because if you don’t spot it, it will affect your next decision, and the one after that.

We cover:

  • Why we can suddenly click into defensiveness two minutes into a careful conversation
  • What going ‘over the net’ means – and the three things to watch out for in every conversation
  • Why being misunderstood feels like such a threat to high achievers
  • The exact language swap: from “I felt dismissed” to “the story in my head was…”
  • How to find your highest intention – what’s in it for them AND for you
  • Why assuming good intent creates safety to hear hard things
  • Ditch the final third: say it kindly, then stop and listen
  • Curious questions that keep you on your side of the net

This episode is for you if… you are a high achiever in a high-stakes role like medicine who has to have the conversation nobody else will, who has to make the call someone disagrees with, and lies awake replaying a decision you had to make. If you leave difficult conversations thinking I’m not cut out to be the senior one who has to do the hard things, maybe I’m not good enough – this one may help you see what’s actually happening.

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