Having difficult conversations at work

Last updated on 29 February 2024

You may find yourself, as a manager, having to discuss a multitude of difficult conversations with your employees. [Source: Adobe Stock]

No one enjoys initiating difficult work conversations, but sometimes they are unavoidable. Despite often being a confronting task for all involved, this is an important step towards overcoming worker disagreements and conflict.

How can you end up in this position?

You may find yourself, as a manager, having to discuss a multitude of difficult conversations with your employees.

It could be as little as asking someone to stop leaving their dirty dishes in the sink to bigger conversations around their performance or their behaviour towards other coworkers.

Some reasons you may need to have a difficult conversation with an employee include:

  • Not meeting work expectations
  • They are not performing or they are lacking necessary skills
  • Company policies have not been followed
  • Behaviour has been exhibited that is considered “unprofessional”
  • Ongoing disagreements or issues with another employee
  • Redundancies or termination

No matter the seriousness of the conversation with an employee, these difficult discussions should be approached in a professional, compassionate and respectful manner.

So how can you facilitate those conversations in the best way possible? You have five basic steps to follow: Notify the employee of a meeting, choose an appropriate setting for the meeting, deliver the information sensitively, listen with compassion, and set actionables for the person.

Give a heads up

The last thing you want to do is let your staff member walk into a meeting they weren’t expecting. By not telling them what the meeting is going to be about, it leaves it up to the imagination of the worker.

You should be open with your employer about the fact that you:

  • Need to talk to them about the situation
  • A brief description of what the discussion will be about
  • If they should prepare anything
  • When and where
  • If they need to bring, or can bring, a support person

Did you know that “Can we catch up for a quick chat?” can be an anxiety trigger to your workers? Even if a conversation is only meant to be five minutes long, you should be giving context when talking to workers – don’t let them interpret what the catchup is going to be about.

You should be upfront about the meeting’s agenda, as it will reduce their anxiety because they have the facts beforehand.

It also gives them appropriate time to mentally prepare and not feel like they’re being put on the spot.

Choose an appropriate setting

If you are talking with a person about an awkward or difficult topic, the last place you should be having that meeting is in the office with their coworkers or around the water cooler in the kitchen.

Make a time and a place to catch up with the individual – this could be in your office, a board room, or during a walk around the block.

You should make this decision based on the conversation you need to have and what would make the individual most comfortable. Also, consider if there is a possibility that the person may get emotional due to the nature of the conversation. You don’t want to take someone into an office with windows if there is a possibility they could become upset.

Additionally, think of the timing of the meeting. Is this conversation going to leave them upset for the rest of the day or do they have somewhere to be right afterwards? Timing can be really important when scheduling an important conversation.

And if it is necessary for a particular situation, let the employee know that they can have a support person with them for the meeting.

Deliver the news sensitively

When having the conversation it is important that you touch on all the necessary areas – so that the person understands why they have been brought in for a meeting – and that the messaging is put across in a respectful way.

You should not have a difficult conversation with negative emotions behind it, as it could result in the person closing themself off. Instead, you should be transparent, open and honest.

So at the start of your meeting, make sure to frame the conversation with the individual. Touch on the issue that was raised, explain the problem, as well as what you are hoping to understand from the person.

Framing the conversation is an important way of ‘setting the stage’ and ensuring you are able to control the flow of the conversation with the individual. Having that control in a conversation will be really beneficial for difficult situations with an employee.

Make sure you give the person the right of reply and try to understand their point of view and where they are coming from.

When they are responding to a difficult conversation you have raised, it is important that you are calm, compassionate, understanding and professional.

Avoid expressing emotions that may impact the employee, as they may become nervous to raise any issues they are having or could result in hostility.

Be a good listener

When you are having an honest or difficult conversation with someone, it is important that you give your undivided attention. This means you are actually listening to what is being said.

The person should feel like you understand what is being said and that they have had a fair opportunity to explain themself. When listening to an employee’s response to a difficult conversation, you should be engaging in active listening.

Active listening means you are:

  • Giving the person your full attention and maintaining eye contact
  • Listening to understand what is being said, not to put forward your own opinion
  • Avoiding interrupting them while they are speaking
  • Asking questions to further your understanding of a situation
  • Showing empathy and acknowledging their feelings
  • Watching for any non-verbal cues that may further explain how they are feeling

If an employee walks away not feeling heard, it could potentially lead to further issues down the track.

If you need more information following your conversation, you may need to organise another time to discuss the situation so it can be resolved quickly.

Walk away with clear actionables

Once you have ripped the bandaid off and had that difficult conversation, you can begin working on a solution with the individual.

Having a difficult situation is only the first part of the task, you need to ensure that the individual is walking away with clear steps, as well as take ownership for any mistakes or actions they have made.

If a situation involves another worker, it may be good to mediate a catchup so that each party can come to an agreeable outcome. You can learn more about handling this in our article, ‘Managing workplace disputes‘.

Be mindful that for honest conversations to be had, your employees need to have a level of trust in you – that means they should be assured everything they said remains confidential.

If, for some reason, the conversation doesn’t go in the direction you hope, you may need to give the employee some time to think about the meeting and come back to you. But set a clear deadline to bring up the discussion again, so it doesn’t get forgotten.

Depending on the severity or importance of the conversation, you should document what was said and provide a record to both your employer and the employee.

Once you have had the discussion with your employee and they have had time to let the conversation sink in, check in with them at a later stage. This is where you can review the points or actions they were supposed to complete and see how they are going.

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difficult conversations
workplace management
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