Difficult conversations at work: prepare your part, not theirs

Difficult conversations at work feel hard because there's uncertainty on both sides.

You might not know exactly what to say. You might wonder whether it's your place to say it at all. And even when you do know what you want to say, you can't control how the other person is going to respond.

Our brains tend to fill in those gaps, and usually not with the best-case scenario.

We imagine them getting defensive. We worry we'll upset them. We think we'll say the wrong thing, or somehow turn something relatively small into something much bigger.

So we prepare.

But sometimes we prepare for the wrong thing.

I spoke with someone recently who had gone into a conversation expecting to say A, B, C and receive D, E, F in response.

Instead, they got X, Y, Z.

The conversation went somewhere they hadn't expected, very quickly.

That's one of the problems with mentally scripting difficult conversations.

You can prepare your part.

You can't prepare theirs.

So rather than giving you another script, what follows are some questions to reflect on before, during and after a difficult workplace conversation. They can help you work out what you know, what you're trying to achieve, and what your next step should be.

Why are difficult conversations at work so hard?

A lot of it comes back to uncertainty.

Your brain doesn't particularly like uncertainty. When it sees the possibility of conflict or rejection, avoiding the conversation can feel like the safer option.

The problem is that avoiding something doesn't necessarily make the problem disappear.

Sometimes it just delays when you have to deal with it.

How do I know if I actually need to have the conversation?

Not everything needs to become a difficult conversation.

Before you say anything, one of the most useful questions you can ask yourself is:

What do I know, rather than what do I think I know?

Then ask:

What outcome am I actually hoping to achieve?

Sometimes something happens once and it doesn't need to become anything bigger.

There's also a difference between addressing something because it genuinely needs addressing and approaching someone because you're frustrated and they happen to be in the firing line.

If there's unlikely to be any useful outcome, it's worth considering whether the conversation needs to happen at all.

But there are times when it does.

If you've noticed a repeated behaviour, there's a genuine risk of harm, patient or customer safety is involved, a project or piece of work is being affected, equipment or reputation is at risk, or other people are being negatively impacted, then the balance changes.

Your discomfort becomes less important than the potential consequence of saying nothing.

And you don't necessarily need a management title to respectfully raise a concern.

When is a difficult conversation not enough?

Sometimes an issue has moved beyond an everyday workplace conversation.

If you're dealing with an allegation of bullying or harassment, serious misconduct, or a situation involving significant psychosocial risk, sitting two people down for a chat may not be the right next step. Your workplace may have a formal process that needs to be followed, and that is where the right HR, safety or investigation support matters.

Clear Boundaries has a useful guide on what to do when you receive a bullying or harassment complaint if you need a clearer picture of what formal escalation can look like.

The point isn't to escalate everything. It's knowing the difference between something that can be worked through in a conversation and something that needs a more formal response.

How do I prepare for a difficult conversation at work?

Prepare your part, not theirs.

Come back to:

Then think about the context.

In the A, B, C example earlier, the person giving the feedback didn't think the topic was particularly significant.

But the other person may have been tired. They may have had a difficult shift. They may have missed lunch. There may have been ten other things happening that the person giving the feedback knew nothing about.

The issue itself might have been small.

The timing wasn't necessarily small.

That doesn't mean you should try to predict every possible response.

It means leaving enough room in your preparation for the possibility that you don't know the whole story.

When is the right time to have a difficult conversation?

If someone is visibly busy, overwhelmed or deeply focused on another task, it probably isn't the ideal time to walk up and say:

“Hey, can I give you some feedback?”

Ask instead.

“Have you got ten minutes later so we can talk about what happened yesterday?”

Give them some idea of the topic where appropriate.

That allows the other person to decide whether they have the capacity to talk now or whether you should find another time.

And be realistic about how much time you need.

When has “Can I have a minute?” ever actually meant a minute?

If you think you need ten minutes, ask for ten minutes.

You're trying to create the conditions for a useful conversation, not ambush somebody between two other tasks.

How do I start a difficult conversation at work?

Often, simply naming the topic is enough.

“Can we talk about what happened yesterday?”

If the person has enough awareness of the situation, there's a reasonable chance they already know the conversation is coming.

For other situations, I like starting with curiosity.

“Can you walk me through how you got to that outcome?”

Or:

“Help me understand what happened here.”

I use variations of this regularly at work when discussing things like documentation or decision-making.

I might already have a fact in front of me that I need to address.

But that doesn't mean I have all the context.

Someone might explain something I didn't know.

Starting with curiosity gives them an opportunity to tell me their side before I decide I fully understand what happened.

It also changes the tone.

Instead of:

“I know what happened and now I'm going to tell you what you did wrong.”

It becomes:

“This is what I can see. Help me understand the rest.”

What do I do if a difficult conversation goes badly?

Sometimes it will.

When that happens, come back to what the conversation is actually about.

If somebody starts bringing up unrelated complaints about you, you can acknowledge them without abandoning the conversation you're currently having.

Something as simple as:

“We can talk about that as well, but right now we're here to talk about this.”

That creates a boundary without pretending their concern doesn't exist.

You can also reset the conversation.

“What do we actually know here?”

And if you're being repeatedly interrupted, one of the best lines I've been taught is:

“I can't hear you when I'm speaking.”

It's simple, but it establishes that both people need an opportunity to speak.

If the conversation continues to escalate, it's okay to stop.

Having an exit plan doesn't mean storming out.

It can simply mean recognising that continuing the conversation in that moment isn't going to improve anything.

I've had conversations go badly myself.

During a particularly busy shift, a senior doctor and I disagreed about how things were being managed.

We went into an office to sort it out.

We did not sort it out.

We both became louder and more frustrated, and eventually someone else had to step in.

We took some time.

Later, we came back to the conversation, both owned our parts in what had happened, and repaired the relationship.

We can laugh about it now.

But there's an important lesson in it.

Being good at difficult conversations doesn't mean you'll never get one wrong.

Sometimes the skill is recognising that it has gone wrong, resetting, coming back and repairing it.

What should I do after a difficult conversation at work?

If you take on the responsibility of giving someone feedback, your job doesn't necessarily finish when you've said what you needed to say.

Particularly when the conversation is about improvement or development, there should be some thought about what happens next.

And importantly:

What can we do?

Feedback can be overwhelming.

Someone might walk away from the conversation and realise later that they didn't process everything you said.

Give them time to think.

Let them know they can come back with questions.

If you have more experience or insight into the issue, there's also an opportunity to take on a coaching or mentoring role rather than simply pointing out what went wrong.

There also needs to be clarity about escalation.

I don't think every workplace problem automatically needs to be sent straight to the next manager.

That doesn't necessarily build much trust within a team.

Where it is safe and appropriate, give people an opportunity to work through the issue.

But be transparent.

“We'll try this first. If we can't get to a resolution, we may need to involve the next person in line.”

That gives the conversation a fair chance while maintaining accountability.

What does a successful difficult conversation actually look like?

Success doesn't necessarily mean everybody agrees.

Sometimes success is simply having a clear next step.

Communication between two people might improve.

And if the conversation went badly, success might mean repairing the professional relationship afterwards.

The goal isn't to win the conversation.

It's to create enough clarity that people know what happens next.

The bigger picture

These conversations can look small when you view them individually.

But when they repeatedly don't happen, or they regularly go badly, the downstream effects start appearing elsewhere.

If you want to improve workplace culture, these are some of the things that have to happen first.

The skills people sometimes call “soft skills” aren't really soft at all.

They're Human Skills.

They're the glue that allows all the technical skills within a workplace to work together.

And this is also where everyday leadership happens.

Doing those things consistently is part of how trust and leadership are built long before somebody gives you a formal position.

Sometimes the shift is to stop treating every difficult conversation like it has to become a major event.

Sometimes it just needs to be a conversation.