How To Have a Difficult Conversation

“I want to talk to you about your timekeeping. You’re always coming in late at the moment.”

If someone said that to you, what would your first reaction be?

For most of us, it’s something like: “What do you mean, always? That’s not fair.” And just like that, the conversation has gone sideways.

In this episode of The Leaders Kitbag, I build on the previous episode about sharing feedback; if you’ve not seen it, you can watch or listen here.

One of the biggest worries I hear from leaders and managers when they need to have a difficult conversation is: what if they argue back? What if they get defensive or emotional?

Very often, we trigger that reaction ourselves. Not through what we say, but through how vague we are when we say it.

I explain how to have a difficult conversation without putting the other person on the defensive, what specific feedback looks like in practice, and why not having a specific example might tell you something important about the feedback itself.

Because vague feedback might feel easier to give. But specific feedback is far easier to receive.

In this episode, you will learn:

Why vague feedback triggers a defensive reactionHow words like “always”, “never” and “a bit” pull a difficult conversation away from the behaviourWhat specific, observable feedback sounds like, with a practical exampleWhy opening with a question rather than a verdict changes the whole conversationWhat to do when you don’t have a specific example to point toA simple way to prepare before you have your next difficult conversation

Ben’s Key Takeaways

When feedback is vague, people push back on the words that feel unfair or exaggerated. Before you know it, you’re no longer talking about the behaviour. You’re debating whether your description is accurate.