5 Easy Steps to Having Difficult Conversations in the Workplace

Updated on May 16, 2020
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Kate has over eight years of experience as an employment and personal injury legal executive. She runs LawCat, a legal explanations website.

If you work in any kind of position of leadership, from a team leader right up to a CEO, there will be times when you will find yourself having to have an uncomfortable conversation with other members of staff. It’s a part of any leadership role and should not be avoided. To be a stronger leader, you will need to deal with both good and bad aspects of your role.

However, there are ways to deal with these types of situation that can help your team, department, or company grow and become stronger, and ways that can damage your team, department, or company. All good leaders will want to minimise any damage and instead use this as an opportunity to strengthen their team and their position as leader.

When an issue comes to light, this could be regarding performance, sick leave, a workplace squabble, or any topic that may make either you or the other staff member uncomfortable, you will need to understand how best to manage staff expectations so as to minimise any conflict and resolve the issue promptly and fairly. .

This article will discuss the five key steps that you should follow to have successful talks about difficult topics in your workplace.

When You May Have to Have a Difficult Conversation

Now and then, if you work in a supervisory role, be it a team leader, supervisor, or management, you will have to deal with a difficult situation with those who work under you.

Difficult conversations can involve many topics, but the most commonly are related to poor performance or conduct, a worker’s personal problems that may be affecting their work, or investigating complaints and grievances.

Remember; no matter how much you might not want to have these types of conversation, it is always better to have them than not, and the sooner you can have them the better. The earlier the issue is addressed and dealt with the easier it will be to sort out.

Step One: Are You the Right Person for the Job?

Before you do anything else, make sure you are the right person to be having this conversation. If you are not sure, then check with your manager or your human resources department. If you are the right person for the job, it is always best to make sure HR and/or your manager knows exactly what you are planning on doing. This will also help you feel more supported.

Once you have established you are the right person for the job; then it’s time to get cracking!

Step Two: What to Do Before the Meeting/Conversation

Make sure you know the facts, what has happened, when and why. You need to know 100% what has been going on. How could you expect to have a helpful discussion with only half the facts at your disposal?

Think about what you know about the person you need to talk to, is the reason you need to speak to them something you would expect from them? Or is it completely out of character? Take this into account before speaking with them, there could have been a misunderstanding and you want to go into this discussion with as open a mind as possible.

Check your company’s policies; you may need to advise a course of action so you should know what company policy is, so as to be in a strong position to advise.

Step Three: Plan the Meeting

When planning the meeting keep the following in mind:

  • A face to face conversation is more effective than a phone call.
  • Sitting opposite someone is a very formal way to speak, sitting next to them is less threatening.
  • Allow for the time; you don’t want to rush the meeting, the employee may want to talk at length about the situation, so make sure you give the meeting enough time.
  • You should also give some consideration to a possible resolution, this may be difficult given that you have not discussed the issue with the employee yet, but you should already be aware of the issue and have several ideas regarding potential outcomes.

Step Four: Running the Meeting

When holding the meeting keep the following in mind:

  • Set out from the beginning how the meeting will run and the issues to discuss, be clear and concise.
  • Remain objective and non-judgemental at all times.
  • Adopt a calm and professional manner.
  • Be as specific as you can, use examples if possible.
  • Use supportive/encouraging language and gestures.
  • Take notes.

Ask questions but don’t interrupt every few minutes. If possible try to save your questions till the employee has finished speaking.

Always remember that you are in charge of the meeting. It is up to you to keep the meeting on track, you will need to stop the conversation going down unrelated paths.

So, in a nutshell, your meeting should look something like this:

  • Open the meeting; explain why the meeting is taking place and what will be discussed.
  • Go over the issues, be clear and concise.
  • Ask for an explanation.
  • Listen to what the employee has to say, listen, keep an open mind.
  • Explore the issues together.
  • Agree on a way forward

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Step Five: A Way Forward

Once you have had your meeting, you should be in a position to decide a way forward. Indeed if possible, this should have been done during the meeting.

You need to think clearly about what is the best way to resolve the situation to stop it occurring again. Remember this is not just the best resolution for you and the company, but the best decision for the employee as well.

If necessary, you can discuss matters with other, more experienced, managers or with HR.


In conclusion, you need to decide if you are the right person to be having this discussion, if so then you need to investigate the matter thoroughly. Once thoroughly investigated you need to take the time to carefully plan your meeting, do not just barrel headlong into it. Once planned your meeting needs actually to happen. By the end of the meeting, in an ideal situation, you will have been able to agree on a way forward with your employee. If not then you need to make a decision as promptly as possible.

This article is accurate and true to the best of the author’s knowledge. Content is for informational or entertainment purposes only and does not substitute for personal counsel or professional advice in business, financial, legal, or technical matters.

© 2019 Katie


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