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  • Writer's picturePeter McKenzie

How to Have a Difficult Conversation at Work

“Nobody likes to have tough conversations, but if you´re a leader, you can´t avoid them”

John C. Maxwell

We have all been there. There is a tough situation that needs clearing up. However, we know it will be painful. There will likely be a fallout. We are afraid of the consequences. Maybe it is just better to wait and see if the whole thing just sorts itself out.


That is not the way to lead. As a leader, all eyes are on you and people are picking up more signals than you think. The longer you avoid a tricky situation, the worse it will get. On top of that, you will lose your authority. Worst of all, your confidence will begin to erode.

As a coach, it has always surprised me that one of the first things that many senior executives, often with years of experience, ask me for is help with handling conflict (with their boss, a peer, or an employee), addressing poor performance or breaking bad news to someone…essentially how to have a difficult conversation.

Perhaps it shouldn´t come as a surprise to me at all, because I still remember when I first became a team leader, the one thing I found hardest was precisely this. My new team was previously my teammates (or even read “mates”!). How exactly was I going to have difficult conversations with them when they didn´t pull their weight or perform as I expected? Additionally, it was years before I finally got some training in the subject, so I struggled with this subject for a long, long time.

One of the first things that I found out was that having a difficult conversation is a skill that can be learned. You can prepare steps before tackling this unpleasant and often unavoidable situation. There are quite a few frameworks and tools available (I will share my favorite resource at the end of this post).

Finally, the best way to get good at tackling difficult conversations is to simply practice and not avoid them in the first place.

So, here is a summary of what you need to know about becoming a master at handling difficult conversations at work:

1. Have them, don´t avoid them

If I hadn´t already made that clear, here it is again. Rather than seeing the conversation as a problem, think of it as a learning situation where you can put yourself to the test and try out your skills as a leader. This mind shift in itself will make the process easier.

2. Begin with the end in mind

OK, here I am quoting the second of Stephen Covey´s principles from “The Seven Habits of Highly Effective People”. It is my favorite and one that I use on my coaching clients and my team perhaps more than any other. Ask the question “What do I want as an outcome from this conversation?”. Focus on that as your goal. Then you are ready.

3. Get to the point and start with facts

Be really clear from the start what the conversation is about and what you are looking to address. This shows confidence and also respect for the other person. No skirting about the bush or small talk. Take a deep breath and dive straight in. If you have prepared your opening statement, much better as this will allow you time and space to remove any emotion from the beginning of the conversation.

The other key element here is to stick to what you see as the facts at the beginning of the conversation. The aim is to look for points of common ground that you both agree on. Leave emotions for later.

4. Give space and Listen

It is crucial to show respect and to remain as calm as possible from the start. Your objective is to make it safe for the other person to express their point of view and also express their feelings.

When they do this, listen. I mean really listen! Don´t fall into the trap of thinking about your next response whilst they are talking. One way to try and stay focused on the other person is to mirror back to them what they have just said. This maintains your focus, confirms your understanding, and shows respect, as it proves you were paying attention.

5. Be bold. Express how the situation made you feel

A crucial moment (in a “crucial conversation”) is to state your view of how the situation has made you feel. If the situation made you displeased, angry, disappointed or whatever, it is really important to tell the other person this. It shows honesty and is the key to unlocking a favorable outcome. This does not mean that you have to do this with emotion! It is enough to tell the other person how their behavior made you feel, without demonstrating it to them.

6. Stay calm and don´t take it personally

Remember that the other person is a human being, not an enemy. All that you can control are your actions and your response to the situation. You cannot force the other person to agree with you, nor to like you. The best approach is to stay calm and to see the conversation for what it is. A conversation.

You should hope for the best outcome, but it may not happen. It is guaranteed that it is much better to have had the conversation than to have avoided it.

At a minimum, you have shown courage by tackling the situation head-on. You will have resolved a problem and grown as a leader at best.

If you want to investigate the topic further, my recommended resource is:

“Crucial Conversations – Tools for Talking When Stakes Are High” by Patterson, Grenny, McMillan, and Switzler.

Also, you may contact me for one-to-one coaching on this subject (that I love!)

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1 Comment

Gordon Tredgold
Gordon Tredgold
Mar 05, 2022

great advice; thanks

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