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How to prepare for a difficult conversation at work

How to prepare for a difficult conversation at work
Marie Ryan

Marie Ryan


If you’re going to have a difficult conversation with an employee, preparation is key. Don’t leave it to chance or wing it. Preparation gives you and the employee the best chance of a successful outcome. Here’s how to do it:

Define the issue

Be clear about the issue that needs to be addressed. Be precise. 

Get the facts

Is the issue independently verifiable? For example, if the line manager says that an employee is always late, can they prove it? It’s embarrassing if they’re wrong and the employee has proof. 

Reframe the narrative

Your attitude going into the meeting affects the outcome. If you’re gearing up for a negative conversation, it will be negative. If you think there will be tears, there will be. Put a positive slant on it.

Your goal is the betterment of the company and to create a good culture for all employees. The conversation you’re planning to have supports the goals. It’s positive, not negative. 

If the employee has performance issues, the purpose of the conversation is to help them meet their targets. You’re going to work with them and give them the support, skills and training they need to be successful in the role and their career. 

They’ll be happier when they’re meeting expectations. They’re more likely to succeed and stay a long time. If the conversation goes well, they will look back in years to come and be grateful for the time and support you gave them.

Put yourself in their shoes

Picture it from the other person’s point of view. If it’s a performance issue, are they trying? Is the employee putting in the hours? How would they justify the behaviour to themselves? 

Let’s take a silly example to make it easier to understand. 

If the issue is that the employee eats fish for lunch and heats it in the microwave. Why wouldn’t they think it’s a big deal?

They might have a poor sense of smell. Or they might not think it matters because they’re on their lunch break. 

Whatever the issue is, they may not think of it as an issue at all. Are they late every morning, but stay late in the evening, so they think it’s ok? Spending time here will help you when you speak to them. 

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Ideal outcome

What would you like to happen after the conversation? Do you want the employee to be more punctual, be more productive, or stop eating fish? Be clear about the outcome and it’s more likely to happen. 

Possible scenarios

Imagine the different ways that the employee will react. Then have a list of actions you’ll take for each one. 

We’ll continue with eating fish. 

You tell them that a few of their colleagues commented on the smell. The colleagues like and respect them so didn’t want to say it. So they asked you, their HR manager, to have a friendly word. 

What are the possible reactions? People are complex, their reactions are unpredictable. But any response fits neatly into three categories: positive, negative or neutral. 

Positive: If the outcome is positive, the employee will say they didn’t realise that it was causing a problem, and switch to chicken. 

How will you respond?

Say thank you and go about the rest of your day. 

Negative: The employee informs you that what they eat is none of your business. They will eat what they want during their lunch break. Eating fish is good for them, so they want to include it as part of a balanced diet. 

How will you respond?

  1. Tell the team that you tried, then buy air freshener for the kitchen. 
  2. Put a sign up in the kitchen urging people not to use the microwave to heat fish. 
  3. Organise “Fish Friday” a day in which you encourage everyone to eat fish. The terrible smell will turn everyone nose-blind. 

Neutral: The employee is nonplussed and says they will take the feedback on board and think about it. 

How will you respond?

Make notes and see if a follow up is needed. 

By having a list of responses, you’ll know exactly what to do. 

Go deep

This is a CBT technique to help with anxiety. It’s useful here too. 

If you’re feeling nervous about a conversation, ask yourself, what’s the worst that could happen? 

Then make it ten times worse. 

We’ll keep with the fish analogy. The worst-case scenario is that they say no. How can we make it worse?

Imagine they scream and shout, then pull a fish out of their pocket and slap you in the face with it. 

  • Is that likely to happen? No. 
  • Would it be that bad if it did? No. 
  • Did it make you smile? I hope so. 

When you’re dreading a scenario, it’s easy to think it’s worse than it actually is. If you make it ten times worse and it’s still not that bad, then the conversation is going to be ok. It’s not worth dreading. 

Let’s do the opposite, make it ten times better. If Disney were writing the conversation, how would it go? 

In the above scenario, the best outcome is the employee apologises and stops eating fish. 

How can we make it ten times better?

Suppose the employee thanked you. He/she noticed people were avoiding them at lunchtime and they didn’t know why. 

The person leaves the office feeling triumphant. The other employees notice and start cheering. They pick him or her up and parade them around the office (This is Disney after all). 

Is this likely to happen? No. Their real response will be somewhere in the middle. 

The reason this works is that both scenarios made you smile, so when you start the conversation and remember both outcomes you’ll relax. It sets you up for a positive conversation.

Drop the expectations

Now that you’ve planned for different scenarios, be open-minded. If you’re wedded to a specific outcome, you’ll lose control of the conversation. Either you’ll stop listening or they will. You can’t control their actual response, you can only control yourself. 

Plan but don’t script

Don’t write a script. The conversation will be difficult enough for the employee, without it sounding rehearsed and robotic. 

Besides, the conversation will veer into unknown directions, making the script useless. 

Instead, create a checklist of discussion points and what you want to get across.

Take extra breaks

The more calm and centered you are, the better the conversation will go. Plan extra breaks on the day of the meeting. Go for a walk, and schedule time after to wind down. 

Questions to ask yourself:

Increase your self-awareness by asking yourself these questions:

  • Am I being fair and consistent? 
  • Am I focused on being right? 
  • Do I need a witness to document the conversation or consider legal issues? 
  • Where are we now?
  • Where are we going?
  • How would we like to get there?
  • What’s your role in the issue? Did you say or do anything that contributed to it?
  • What “buttons” of yours will be pushed? 

Think about logistics: location, location, location

Where you have the meeting is important. You don’t want to have a tough conversation in the canteen, or a meeting room with glass walls. 

If it’s onsite, pick a place where you and the employee won’t be seen. Online meetings from home guarantee privacy. 

Ask the employee what they want. “I’d like to have a chat with you on Tuesday afternoon. Will you be in the office or would you prefer an online meeting?”. 

Schedule plenty of time for the meeting so you aren’t rushed.

We need to talk…

Aim for neutral emails when requesting the meeting. Instead of sending a formal email, say “I’m curious to get your thoughts on….” Don’t email too far in advance. No-one wants to spend a week dreading a meeting. 


This is our complete guide to preparing for a difficult meeting. Use it whenever you need to, to create better outcomes at work.

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