There’s No Such Thing as a Difficult Conversation

I'm going to say something that might upset a few leadership trainers.

I hate the term 'difficult conversations'.

Absolutely hate it.

I've lost count of the number of leadership programmes I've seen with a module called 'Having Difficult Conversations'.

It's become one of those phrases we just accept in the world of management and leadership.

But I've got a problem with it.

Because I genuinely believe that most of the conversations we label as difficult shouldn't be difficult in the first place.

And quite often, the reason they become difficult has very little to do with the person sitting opposite us.

It has everything to do with what we, as leaders, have or haven't done beforehand.

Let me explain.

We create the difficulty long before the conversation happens

Imagine you've got someone in your team who isn't performing as you'd expect.

Maybe they're missing deadlines. Maybe their attitude isn't quite right. Maybe the quality of their work isn't where it needs to be.

You notice it.

Then you notice it again.

You think about saying something, but they're having a busy week.

Then they're on holiday.

Then you're busy.

And before you know it, three months have passed and you're sitting there thinking:

"Right, I need to have a difficult conversation with them."

Do you?

Or do you need to have a conversation that you should have had three months ago?

Because they're two very different things.

Avoiding a conversation doesn't make the issue disappear. It just gives it time to become a bigger one.

And the longer you leave it, the more emotion, frustration and assumptions you bring into it.

Suddenly, something that could have been a straightforward five-minute conversation has become a formal meeting, with notes, nerves and probably someone from HR involved.

We've created the difficulty ourselves.

"Remember when we agreed...?"

I was speaking at an event recently about accountability, and one of the points I made was that clarity is the foundation of accountability.

And I genuinely believe that.

Clarity is the foundation of accountability.

Because how can you hold someone accountable for something if you've never been clear about what you expected of them in the first place?

Think about it.

We talk a lot about wanting people to take ownership, deliver results and be accountable for their performance.

But how often do we stop and ask ourselves whether we've actually given them the clarity to do those things?

When someone joins your team, takes on a new responsibility or agrees to deliver something, how clear are you about what good looks like?

And I mean genuinely clear.

Not a vague job description.

Not a quick conversation where you both nod along.

Not assuming they know because they've been doing the job for years.

I mean sitting down and agreeing what success looks like, what's expected, by when, and how you'll both know whether it's happening.

Because when you've done that properly, you've got something incredibly powerful to come back to.

"Remember when we agreed that...?"

That's your anchor.

You're not suddenly introducing a new expectation.

You're not making it personal.

You're not pulling a standard out of thin air.

You're simply returning to something you both understood and agreed.

"Remember when we agreed that customer enquiries would be responded to within 24 hours? I've noticed that's not happening consistently. Talk me through what's getting in the way."

That's not a difficult conversation.

That's a conversation about an expectation that isn't being met.

And, importantly, it creates an opportunity to understand why.

Because accountability isn't about catching people out.

It's about helping people take ownership of what happens next.

If the first time someone finds out they're not performing is during a formal 'difficult conversation', the problem probably started long before that meeting.

If it's a surprise, something has gone wrong

Here's something I feel strongly about.

If the first time someone finds out they're not performing well enough is during a formal performance conversation, I'd be asking some serious questions of their manager.

How has it got to this point?

Where was the feedback?

Where were the check-ins?

Where were the conversations about what good looks like?

Now, of course, people have a responsibility for their own performance. I'm not suggesting otherwise.

But leadership comes with responsibility too.

You can't spend months allowing something to happen, saying nothing, and then suddenly expect someone to understand why it's become such a big issue.

That's not fair.

And it's not particularly good leadership either.

Feedback shouldn't be an event.

It should be part of how you work together.

A quick conversation today can prevent a much bigger conversation three months down the line.

And it doesn't always need to be formal.

Sometimes it's as simple as:

"Can I just give you a bit of feedback on something I've noticed?"

Or:

"That's not quite what we agreed. What's happened?"

Or even:

"Have you got five minutes? I want to pick something up before it becomes an issue."

No drama.

No big build-up.

Just two people having a conversation.

Uncomfortable doesn't mean difficult

Now, before someone tells me that some conversations genuinely are difficult, I agree.

Of course they are.

Conversations about redundancy, serious misconduct, bereavement or someone's personal circumstances can be incredibly difficult.

I'm not pretending that every conversation can be made easy by agreeing a few objectives.

But that's not what I'm challenging.

I'm challenging the everyday performance conversations that managers put off because they don't want to upset someone, create tension or deal with an awkward reaction.

There's a difference between a conversation being difficult and a conversation making you feel uncomfortable.

And I think we confuse the two far too often.

You might feel nervous giving feedback.

You might worry about how someone will react.

You might not enjoy challenging someone.

That's human.

But your discomfort doesn't automatically make the conversation difficult.

And it certainly doesn't make avoiding it the right thing to do.

Sometimes good leadership means being prepared to feel uncomfortable because the other person deserves clarity.

Clarity is a form of kindness

I know that might sound a bit soft coming from someone who bangs on about accountability and high performance.

But hear me out.

If I work for you, I want to know where I stand.

I want to know what you expect of me.

I want to know when I'm doing well.

And I want to know when I'm not.

Not six months later.

Not in my annual review.

Not when something has become such a problem that you've decided we need a formal meeting.

I want to know while I've still got the opportunity to do something about it.

Because that's what good feedback gives people.

An opportunity.

An opportunity to improve, to ask for help, to understand something differently or to take responsibility.

And when you avoid giving that feedback because you don't want to make someone uncomfortable, you're potentially denying them that opportunity.

Think about that.

The thing you're doing because you think you're being kind might actually be doing them a disservice.

So what should managers do differently?

I'd start with three things.

First, get ridiculously clear on expectations.

Don't assume people know what good looks like. Talk about it. Agree it. Check understanding. Make sure you're both working from the same picture.

Second, stop saving feedback for special occasions.

If something needs saying, say it. Respectfully, fairly and with the intention of helping someone improve. The longer you leave it, the harder it usually becomes.

Third, get curious before you get critical.

When something isn't happening as expected, don't immediately jump to conclusions about attitude, effort or capability.

Ask questions.

What's getting in the way? What's changed? What support might be needed?

Accountability and empathy aren't opposites. The best leaders understand that you need both.

And remember, having a clear expectation doesn't mean being completely inflexible. Circumstances change. Priorities shift. Sometimes expectations need to be revisited and agreed again.

That's leadership too.

Stop teaching managers to fear conversations

Here's where I land on all of this.

I think we need to stop presenting everyday performance conversations as these big, scary events that managers need special techniques to survive.

Of course, communication skills matter.

Of course, knowing how to listen, challenge and give feedback matters.

But I'd much rather spend time helping leaders create clarity, build trust and establish good habits than teaching them how to rescue a conversation that's gone wrong because they avoided the previous ten.

Because when expectations are clear, feedback is regular and people understand what they're accountable for, most performance conversations become exactly what they should be.

Normal conversations between two people who want things to go well.

And if you're a manager who's currently putting off one of those so-called difficult conversations, I've got a question for you.

Have you made your expectations clear enough that you can genuinely say, "Remember when we agreed...?"

If you haven't, maybe that's where the conversation needs to start.

And maybe that's the bit of leadership development we should be focusing on.

Confident leaders. Stronger teams. Real results.