How to Make Difficult Conversations Easy – with Amanda Gilbert

In this episode of "A Job Done Well," James Lawther and Jimmy Barber are joined by learning and development expert Amanda Gilbert to tackle a topic we all face but often dread: difficult conversations at work (and beyond).

After a quick catch-up (including university choices and Jimmy’s book recommendation for every man who has a mother), the team discuss why tough conversations feel so challenging—and how we can handle them better. Amanda introduces the "Ladder of Inference" model, helping us see how our assumptions and stories can unnecessarily escalate situations (including James’ run-in with a taxi driver!). Amanda shows how quickly we can jump to conclusions and why stepping back to focus on the facts can de-escalate conflict.
The episode covers:

• The two main types of difficult conversations: relationship-based and message-based
• How to prepare for a tough conversation (know your triggers, clarify your purpose, plan your approach)
• Tips for delivering difficult messages with empathy and clarity
• The importance of listening deeply and allowing space for emotion—without trying to "fix" it
• Why adopting a collaborative, learning mindset (instead of a combative one) can transform even the hardest discussions

Amanda also shares practical tools, such as the "left-hand column" exercise for analysing your reactions. She offers a step-by-step process for preparing for, having, and reflecting on difficult conversations.

Whether you’re a manager, team member, or just someone who wants to get better at those tricky talks, this episode is packed with actionable advice and real-world wisdom.

Listen now and discover how to make your next difficult conversation a little bit easier.

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