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 reaction
• How words like “always”, “never” and “a bit” pull a difficult conversation away from the behaviour
• What specific, observable feedback sounds like, with a practical example
• Why opening with a question rather than a verdict changes the whole conversation
• What to do when you don’t have a specific example to point to
• A 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.

Being specific does two things.

It reduces the chance of a defensive reaction, because you’re describing what you’ve seen rather than passing judgement.

And it gives the person something they can actually work with. “Always late” is hard to do anything with. “Thursdays and Fridays” opens up a real conversation about what might have changed, and how you can help. That’s often what turns a difficult conversation into a useful one.

If you can’t point to a specific example, stop and ask yourself whether the feedback is valid. Is it based on what you’ve actually seen, or on an impression, a feeling, or something you’ve heard second-hand? If it’s the latter, hold off. Notice, observe, and come back when you can.

Before your next difficult conversation, write down one specific example. What happened, when, and how often. If you can’t, that tells you something too.

A final thought:

Vague feedback might feel easier to give. Specific feedback is far easier to receive.

Missed the last episode?

Listen to episode 19 here:

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• Break free from firefighting and become more proactive
• Learn how to inspire your team and deliver results…

Whether you’re looking to develop yourself, or you’re in HR or running a business and want to support someone in your team, now is a good time to act.

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Podcast Transcript

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?

Mine would be something like: “What do you mean, always? That’s not fair.”

And just like that, the conversation’s gone sideways.

In the last episode of The Leaders Kitbag, we talked about [link to previous episode].

And one of the biggest worries I hear from leaders about these conversations is this: what if they argue back? What if they get defensive, or emotional?

Here’s the thing. Very often, we trigger that reaction ourselves. Not through what we say, but through how vague we are when we say it.

When feedback is vague, the other person has nothing solid to engage with. So they push back on the words that feel unfair or exaggerated. “Always.” “Never.” “A bit.”

And now you’re not talking about the behaviour. You’re debating whether your description is accurate.

So what’s the alternative? Be specific.

Compare that opening line with this:

“I just wanted to check in with you. I’ve noticed that over the past three weeks, on Thursdays and Fridays, you’ve been getting in somewhere between 45 and 60 minutes late. I wanted to understand what’s going on.”

That’s a very different conversation. There’s nothing to argue with, because it’s simply what you’ve seen. And it ends with a question, not a verdict.

Being specific does two things.

It reduces the chance of a defensive reaction, because you’re describing facts rather than passing judgement.

And it gives the person something they can actually work with. It’s hard to do anything with “always late”. But Thursdays and Fridays? Maybe something’s changed on those days. Now you can find out, and help.

Vague feedback might feel easier to give. Specific feedback is far easier to receive.

Now, sometimes people say to me: “But what if I haven’t got a specific example?”

And my answer is a challenge. If you haven’t got a specific example… why are you giving the feedback at all?

It’s a genuine question. Is the feedback valid? Or is it an impression, a feeling, or something you’ve heard second-hand?

If you can’t point to what you’ve actually seen, hold off. Notice, observe, and come back when you can.

So before your next feedback conversation, write down one specific example. What happened, when, and how often.

If you can’t, that tells you something too.

That’s it for this episode.

As always, look after yourself, and look after those you have the privilege and responsibility to lead.

Until next time… lead on.