The kindest thing you can do is the conversation you’re avoiding

You know the one.

It’s been sitting in the back of your mind for weeks (maybe months). It comes back on the drive home, when you see their name in your inbox, when they walk into the meeting late again. You’ve rehearsed it in the shower. You’ve decided, more than once, that this week is the week.

And then something comes up. The timing isn’t right. They’ve got a lot on. It might sort itself out.

It rarely does.

The myth

Most managers carry a belief they’ve never quite said out loud: difficult conversations damage relationships. Raise the problem, and you’ll lose the goodwill. They’ll be hurt, or defensive, or they’ll stop trusting you. Better to keep things pleasant and hope.

It’s an easy belief to hold, because it lives in the body, not the head. The dread is real. The tight chest before you knock on the door is real. So the brain draws a reasonable-sounding conclusion: something that feels this bad must be bad for the relationship.

But your mind and body are reacting like it’s being chased by a woolly mammoth thousands of years ago, not like you’re about to have a reasonable and needed conversation!

What avoidance actually does

While you’re waiting for the right moment, the other person isn’t standing still.

They can usually tell something is off because you’re a bit shorter in your replies, you check their work twice, you stop giving them the interesting projects. Nobody has said anything, so they fill the silence with their own story, and it is almost always worse than the truth.

Meanwhile, your frustration builds. By the time the conversation finally happens, often in an appraisal months later, it isn’t one conversation. It’s six months of them, delivered at once.

That’s the moment the relationship takes real damage. Not because you raised the problem, but because you raised it late. The person on the other side of the desk hears one thing: you knew, and you didn’t tell me.

Avoidance feels like kindness. More often, it’s self-protection wearing kindness as a costume.

What a good difficult conversation looks like

The good news is that this is a skill, not a personality trait. Managers who handle these conversations well aren’t braver than everyone else. They’ve usually just learned a few things that make the conversation smaller and safer for both people.

They go early. A small observation on a Tuesday (“I noticed the report went out without the figures checked, what happened?”) is a two-minute conversation. The same issue saved up for three months becomes a performance problem.

They are specific. “Your attitude needs to improve” gives someone nothing to work with and plenty to be hurt by. “In the last two team meetings you’ve talked over Sam when she’s raised a point” is something a person can actually change.

They talk about the work, not the person. The aim is to describe what happened and its effect, not to deliver a verdict on who someone is.

And they treat it as a conversation, not a speech. The most useful question in any difficult conversation is some version of “what’s going on from your side?” Half the time there’s a reason you didn’t know about. The other half, asking still changes the tone from accusation to problem-solving.

None of this makes the dread disappear. It makes it smaller, and it makes the conversation far more likely to end with the relationship intact, or stronger.

What changes on the other side

In one of our recent cohorts, we had a guy called Brandan (not his real name) who hadn’t given feedback at all to anyone since becoming a manager. He had all these examples of things people in his team were doing wrong, but he hadn’t told them because he didn’t want to be a ‘mean manager’. During our feedback workshop he realised he was already being a ‘mean manager’ by NOT giving the feedback. He was letting the people he cared about actually make more mistakes because he wasn’t telling them what they were doing wrong.

After the workshop, he decided to give one piece of feedback that he has been sitting on for more then 3 months. We planned it, wrote out what he was going to say, looked at it from different angles, and he went away to have the conversation.

The next month he came back and told us how it had gone. It has gone better than well! The person had been receptive; they hadn’t realised they were getting something consistently wrong and thanked Brendan for giving the feedback.

Brendan said ‘I feel awful that I waited so long’. He could see now that bringing it up was actually the ‘kind manager’ thing to do! And, now that team member is in line for promotion because they have fixed the one thing holding them back.

The one to have this week

Here’s the thing about reading a piece like this. Somewhere around the second paragraph, a name came into your head.

That’s the conversation you need to have.

It won’t feel easier next month, it will feel harder, and it will cost more. So don’t wait for the perfect script, just find ten quiet minutes this week, start with what you’ve noticed, and ask what’s going on from their side.

The relationship you’re trying to protect is the reason to have it.