The Conversations Every Manager Needs to Have (But Often Avoids)

A few weeks ago, I joined Cuddy Cudworth for the recording of one of his podcast episodes: Mind Management Mentors. You can watch it here.

Here are some of the takeaways:

We talked about the elephant in the room and the conversations business owners should be having with their staff.

Not the fluffy, theoretical HR stuff, I mean the real conversations. The ones managers put off. The ones that feel uncomfortable. The ones that, if we’re honest, we sometimes hope will just go away.

They don’t.

And the longer you leave them, the bigger they get.

In my discussion with Cuddy,  I shared how to handle these situations properly, because this is what I’ve been doing for over 30 years in HR. And trust me, there isn’t a lot I haven’t seen.

Why Managers Avoid Difficult Conversations

Most managers aren’t lacking capability, but they are lacking confidence.

It’s the fear of:

• Saying the wrong thing
• Getting an emotional reaction
• Making the situation worse

And sometimes it’s simply because no one has ever taught them how to do it properly.

So, what happens?

They avoid it. They delay it. They hope it fixes itself.

But it doesn’t!

Stop Calling Them “Difficult” Conversations

Here’s the first shift I always encourage:

Stop calling them difficult conversations.

Because the moment you do, you’ve already made it bigger than it needs to be.

These are simply conversations that need to be had.

Yes, you’re dealing with people. Yes, you don’t know how someone will react. But avoiding it creates far more risk, both for your business and your team.

Start With Care and Curiosity

When something happens, don’t jump straight in with blame.

Start with two very simple questions:

• “Are you okay?”
• “Talk me through what just happened.”

That’s it.

You’re showing care, and you’re gathering facts.

Because more often than not, there’s something going on underneath the behaviour; stress, health issues, lack of support, or something else entirely.

Your job isn’t to jump to conclusions.

Your job is to understand.

Separate the Person From the Behaviour

This is one of the biggest mistakes managers make.

They attack the person instead of addressing the behaviour.

A simple shift in language makes a huge difference:

“Would it surprise you to know that I’m disappointed in what I’ve just seen?”

Not you.

What I’ve just seen.

It’s subtle, but it completely changes how the conversation lands. It reduces defensiveness and keeps things constructive.

Ask Questions. Don’t Lecture

You don’t need to have all the answers.

In fact, the best conversations come from asking the right questions:

• “What do you think needs to change?”
• “If you were in my position, what would you do?”
• “What support do you need?”

When people are part of the solution, they take ownership of it.

And that’s when you start to see real change.

Handling Sensitive Workplace Conversations

Some conversations are more uncomfortable than others.

Body odour. Bad breath. Emotional outbursts. Health issues.

But avoiding them doesn’t help anyone.

A respectful, honest opener works far better than dancing around the issue:

“This is going to feel uncomfortable for both of us, but I need to share some feedback with you.”

You’re acknowledging the awkwardness, but you’re still addressing it.

And more often than not, people are grateful that you’ve been honest with them.

Be Prepared — But Stay Human

You don’t need a script, but you do need to think ahead.

Ask yourself:

• What actually happened?
• What outcome do I want?
• How will I respond if they push back?

Because whilst most conversations aren’t as bad as we imagine, you should still be prepared for emotion.

And whatever happens … stay calm.

If you lose control, you risk making the situation far worse.

Why This Matters for Your Business

People don’t leave businesses.

They leave poor management.

And poor management often comes down to one thing … avoiding conversations.

If you want to retain good people, build strong teams, and create a positive workplace culture, you have to be willing to have these conversations.

Openly. Honestly. Respectfully.

Be Frank (In Every Sense of the Word)

In my world, we talk about having “frank” conversations.

Not aggressive. Not confrontational. Just clear and honest.

Because the reality is this:

Most people would rather know where they stand than be left guessing.

So don’t avoid it.

Have the conversation.

That’s what good management looks like.

Watch the Full Podcast

If this resonates, you can watch the full podcast where we go deeper into real-life scenarios, practical examples, and exactly how to handle these conversations step by step. You can watch it from here.