We all recall three kinds of difficult conversations. The ones we regret not having, the ones we remember for the care that went into them, and the ones we still carry the scars from. They come with the role, with leading, and with being part of a team.

Dear Aunty Treacle, how do you approach difficult conversations in a way that’s firm but fair, and stops them feeling so personal or overwhelming?

Anna Keen and Stuart Hughes take this one on between the two of them. Stuart works through his own back catalogue, the ones he had, the ones he avoided and the ones that landed badly, and shares the line he now opens with: “This could be 1,000% unfair, but it’s my observation.” Anna unpacks why we make these conversations hard, why clear is kind, why nobody ever says “I’m so glad I waited”, and whether you need to turn up the care or the clarity.

Where they land: they deserve the information. What they do with it is their choice.

PS: Stuart’s continued confusion with numbers introduces this as episode five. It is episode three. Apologies for the consistent numberwang.

Share your story on this question:
https://auntytreacle.substack.com/p/the-can-opener-s2-q3-difficult-conversations

Full write-up and team practice guide: auntytreacle.substack.com
Got a question? ask@auntytreacle.com

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