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Managing Difficult Conversations

Updated: Nov 12, 2023

Difficult conversations are something that no one looks forward to. They can be just as uncomfortable for the person initiating the conversation as they can be for the person on the receiving end.

Emotions can run high if the conversation is not approached with care and thought, making sure that considerations have been made for timing, location and the other person’s thoughts and feelings.

When managed effectively, however, these conversations can prevent problems from developing into conflict and sustain positive working relationships.

Knowing how to tackle these conversations is an essential leadership skill, as avoiding them can have a negative effect on our relationships with colleagues and even impact our health and wellbeing.

By approaching these conversations properly we can build trust, create progress, clear up misunderstandings, and build essential skills. So even if it may feel uncomfortable to initiate challenging conversations in the short-term, there are a lot of long-term benefits.

How to Have Difficult Conversations

There is never a perfect time to approach a difficult conversation, but it is important to be mindful of the other person’s schedule and commitments. You wouldn’t want to approach them just before they went in to an important pitch and you wouldn’t want to try and squeeze a difficult conversation into a 5 minute slot. Try to have the conversation in person where possible and choose a location that is private and won’t be overheard by others.

Try to refrain judgement and reflect on the purpose of the conversation beforehand.

One of the key things you should ask yourself is:

What am I aiming to accomplish by having this conversation?

Ensuring that there is a clear aim helps to confirm that the conversation is necessary and that there is a positive outcome for both yourself and the other person.

Don’t enter the conversation with the assumption that your prior knowledge or understanding of the subject is correct. Empathy is more important than ever in these situations so you should seek to understand their perspective and make sure that you acknowledge it appropriately. Techniques like paraphrasing what they have said and saying this to them, are great to let them know that you have properly understood what they were trying to communicate.

You should always aim to work together to reach a resolution and maintain the dialogue by asking questions and allowing them a fair chance to speak. After the conversation, take some time to reflect on what was said and check in with the other person to see how they are feeling.

How to Resolve Conflict in the Workplace

Sometimes people may be left with strong feelings of embarrassment, anger or resentment after a difficult conversation or you may have a situation that has escalated before you have had chance to address it.

Misunderstandings and differing opinions can be found in any workplace. When an issue arises, approaching it early as possible and in an open way is a great way to prevent the problem from developing into a serious conflict.

When there is conflict, it is even more important to actively avoid judgement and fully understand the other person’s perspective. Always stick to the facts and aim to focus more on listening to the other person than you do on explaining your point of view.

Our feelings can be a barrier in effective communication if we are not aware of them and how they are being conveyed. However, when we acknowledge them, they can aid positive communication. One useful tip is to replace ‘you’ with ‘I’ at the beginning of sentences. This helps the other person to understand how you feel and also prevents the other person from feeling attacked.

Difficult Conversations At Work: A Summary

In summary, difficult conversations can be uncomfortable and challenging but they are an essential leadership skill that helps to build trust and maintain positive working relationships. Avoiding these conversations doesn’t help anyone but by seeking to understand the other person's perspective, working together to reach a resolution and acknowledging our own feelings, we can iron out misunderstandings and prevent conflict.

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