How to have challenging conversations at work

Wide road with elephant coming towards viewer. Used to get across how to overcome challenging conversations at work.

From time to time, managers find themselves facing challenging conversations at work, conversations that they may feel less than equipped to handle. Such difficult conversations are usually centered around performance, behaviour, feedback, sensitive personal issues or even job security.

Instigating a difficult conversation at work can be daunting and there can be a natural tendency for some managers to delay taking action, in the hope that the issue will resolve itself, without their intervention.

This isn’t always the best way forward, however, as this approach can often cause problems to escalate and become more difficult to solve.

If you would like some professional help with your challenging conversations technique: check out our virtual workshop: Challenging conversations.

Why do we avoid challenging conversations at work?

Many of us tend to put off difficult conversations because of the emotions that are involved, for both the manager initiating the challenging conversation and the other party.

This usually results in one of two approaches when having a difficult conversation. Under preparation vs over preparation.


Those who under-prepare tend to go into their difficult conversation with very little prior thought and just dive in. This approach can lead to a lack of structure, direction and consistency, allowing for both sides of the challenging conversation to become fragmented and wandering from the required topic.


Those who over prepare find themselves stressed about the situation, having spent hours, or even days, fretting and psyching themselves up for the difficult conversation. This can lead to increased tension and a less than positive experience for all involved.

What to avoid

That being said, the main thought process to avoid is “What do I want for me?”

This difficult conversation isn’t just about you as the manager. It is about your colleague too. So, a better question to ask is; “What do I want and what do they want from this conversation (in equal measure)?”

Our tips for having a challenging conversation

Getting acquainted with their needs in order to fix the potential problems, i.e. the causes for your difficult conversation, can help to make the process and outcome more collaborative and sustainable for the future.

Consider also the relationship that you have, and where you would like it to develop. If you want to build on your relationship, to keep it on an upward trend, it can give an even greater importance to the quality of your preparation.

Consider all of these areas before deciding on your approach and starting point.

For example; Lola has been consistently late to work recently, is coming to work with a negative attitude and is confrontational. But you know that this isn’t typical for Lola and suspect that there may be a personal circumstance that is causing this behavioural change.

Talking with Lola and demanding that she ‘sort out her attitude’ and start coming into work on time could damage the relationship between you both. It may also not get you the result you are looking for thus causing more conflict.

Employing some empathy and seeking to understand what is happening for Lola could lead to your being able to help her make positive improvements and thus achieve the change in behaviour you are looking for. Dialoguing rather than demanding might be the key that unlocks this situation.

This method of taking care of the relationship between manager and colleague can make challenging conversations at work easier and build your relationship. Especially during these challenging times, having open communication and a high level of empathy is increasingly important.

Final thoughts

What is your usual approach to a difficult conversation at work? Could you do more to consider the relationship between you both and still achieve your shared objectives?

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