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How to handle a difficult conversation-at-work

How to handle a difficult conversation-at-work
Marie Ryan

Marie Ryan


Why does it matter how you handle difficult conversations?

How you handle difficult conversations impacts your relationships with team members. A difficult conversation, handled well, is a chance for you to show good leadership and help the employee and company grow. 

Who are you when you’re under pressure? Are you mild-mannered Bruce Banner, or do you turn into the Incredible Hulk?

We’ll outline the steps so you’ll be able to handle difficult conversations like a pro, without the slightest tinge of green.

State your intention throughout

You want to help the employee, so say it. “I’m here to help you meet your goals” or “I want to work with you to find a solution”. 

Avoid distractions

If you leave distractions in the room, you’re more likely to use them when the conversation becomes challenging. Leave your phone and computer out of the room. Take a glass of water if you need it.

Ask questions

You need to understand the other person’s point of view. Ask lots of questions to clarify the issue, their part in it and what needs to happen in the future. When you have the full picture, you’ll be in a better position to decide and take next steps. 

Questions to ask:

  1. I’d like to hear it from your point of view
  2. What do you think is causing the problem?
  3. Have you thought about solutions?
  4. Is there anything I can do to help?


It’s important to really listen to your conversation partner. We hear what we want to hear. It’s frustrating for the other person if they don’t feel heard. Take notes, pause. Ask for clarification. When the person finished speaking, paraphrase what they said and repeat it back to them.

Keep an open mind

Whatever the issue is, there might be a perfectly reasonable explanation. Prepare for it and be ready to listen. 

For example, the employee who is always late. They might say that they drop their children at school before work and they cleared it with their line-manager. 

If they are out sick a lot, they might have medical certifications. They’re more likely to open up and be transparent if you’re open with them. 

Don’t interrupt

As tempting as it is to cut the person off mid-sentence, don’t. This will make the situation worse. Let them speak until they are finished, then say your piece. Don’t let them interrupt. 

Collaboration instead of confrontation

You could tell the employee exactly what you want them to do. You could warn them of the Draconian consequences if they don’t meet expectations. 

But it’s better if they come up with the solution themselves. Encourage a conversation instead of conflict. 

Aim for understanding, not consensus

You want them to understand your position and the path forward. They don’t have to agree with you, just understand. 

For example, if you’ve ever potty trained a toddler, they need to know that you want them to go in their potty. The child is content with their current situation, toddling around in their own filth. They will never agree with you that the potty is better. They just need to understand what's happening. When they are older, they will understand why you did that, but for now they just need direction. Adults are a lot like children. It takes people time to gain perspective and change their mind. 

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Make a sandwich

With the sandwich method of giving feedback, you say something positive, negative, then end on something positive. 

“You’re a valued member of the team, we’re happy to have you here. We need you to work on punctuality, so you’re here at the same hours as everyone else. Your performance is always great, especially last quarter.”

The reason it works is by giving praise, the employee knows you understand them. That you aren’t out to criticise them for the sake of it. That you’re there to help them. It makes the negative points easier to listen to, and harder to dismiss. 

Stick to the facts

Facts speak for themselves, so let them. If the issue warrants discussion, it must be severe. If you need to embellish, add value to judgements or make snide remarks, the conversation doesn’t need to happen at all. Stick to the facts or else the conversation could turn into an emotional mess. Keep your cool. You’re criticising the behaviour, not the person. 

Deal with the issue, only the issue

When emotions are charged, it’s tempting to bring up other transgressions to prove that you are right and they are completely wrong. If you do that, you’ll win the fight. And make an enemy. 

Stick to the issue. Employees appreciate professionalism and leadership. If there’s an issue in the future, they will know that there is only one issue, and you won’t blindside them. 

Offer reassurance if necessary

If you rarely have one-to-one meetings with employees, they might be worried about having one. If the conversation is relatively minor, say it. 

“Don’t worry. Your performance is outstanding, we’re all thrilled with you. I wanted to speak to you about your hours of work.”

Look for signs of agreement

If the employee agrees with any of your points, it’s a good sign. It shows self-awareness and openness. Encourage it and the conversation will go more smoothly. Any sign of agreement is a turning point, e.g. “Well I suppose I could come in earlier”. 

Validate what’s true

When the employee explains their point of view, there will be some elements that are true. Validate the parts that are correct, to let the employee know you’re listening and are on their side. When you discuss the areas that need to change, they will be more willing to listen. 

  • Don’t validate everything they are saying. Just the parts that are true. For example, if work hours are from 9:00am to 5:30pm. And the employee arrives at 9:30am and stays to 6:00pm. You can say, “yes, you work the correct number of hours. You stay late to make up for the time. But we need you to arrive at 9:00am, in line with the rest of the team. “

Don’t backtrack

By the end of the conversation, you’ve agreed that they will arrive on time. Don’t backtrack by saying, “Well, maybe you can come in late, sometimes”. 

You might think you’re being nice, but it’s confusing for the employee. They will leave the meeting not knowing what they are supposed to do. 

Don’t make it about you

It’s tough to have difficult conversations with people. But the focus of the conversation is the employee, not your feelings. Don’t act like the victim by saying “It’s difficult to reprimand someone”. It’s not the time to look for pity, and the person you’re speaking to is not the person to give it. 

If you need to speak to someone, tell a friend beforehand and leave the office to call them after the meeting. 

Leave the room

If you reach a stalemate or emotions are running high, take a break. Come back after a few minutes, or reschedule the meeting for a later date. When emotions are high, you won’t be able to have a genuine conversation. You’ll go around in circles and say something you regret. 

Stay calm

Keep your cool no matter what. If you keep your cool while the other person is angry, when they reflect, they will be embarrassed. If you lose your cool, the conversation will spiral. We have a separate article on how to handle your emotions during the conversation. 


At the end of the conversation, recap the key points, actions and next steps. It reduces the chances of them saying that you didn’t say something. 

Discuss next steps

When you’ve agreed or explained what you need the employee to do, decide what the next steps are. Arrange a follow up meeting if needed, or outline the plan. The employee needs to be clear on their expectations during the meeting, so they can take the right actions.


Difficult conversations are a necessary part of business. Handling it the right way ensures a better outcome. You can increase your reputation and standing in the company, while increasing productivity and performance. It’s a key skill to master. 

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