'The difficult conversation'

October 14, 2026

The very term ‘the difficult conversation’ is challenging – what is it that is actually difficult?

Difficult topics?

There are several elements of a conversation that can be difficult. Of course, it may be a difficult topic to raise – do you have to ask someone to change their behaviour? Is the conversation about a conflict? Are organisational changes in the form of downsizing and redundancies necessary? Has there been a whistleblowing report about censurable conditions, and do you have to start untangling what it is about?

What feels like a difficult topic is subjective, and is shaped by what you yourself find difficult, what experiences you have had before, and what thoughts and feelings are stirred up in you. The common denominator is that they can trigger reactions in the person you are going to talk to.

Difficult reactions?

Different topics can be difficult to raise because you yourself find them challenging, but also because they can be challenging for the person you are going to talk to. A matter you think might be difficult to raise may be received well – and then the topic is no longer so difficult!

Emotional reactions are not easy to predict, which makes them challenging to prepare for.

Which reactions are painful to handle is linked to who you are: what you find difficult, and what such a reaction might trigger in you.

Facing other people's expressions of emotion can be demanding. Some find it difficult to deal with other people's tears. Others find it harder to face anger. For others again, the worst thing may be to encounter arrogance or to be ridiculed.

Who wants to be the one who makes an employee or colleague angry, frustrated or sad? Most of us would much rather the people around us were happy! And very few of us want to put ourselves in a position where we are likely to be told off, criticised or lose trust and standing/respect.

Your role

Another element that affects how difficult ‘the difficult conversation’ is, is linked to the role you have in the conversation and your relationship with the person you are going to talk to. In a work context, the difficult conversation is often linked to your role. As a manager, you must raise the matter if an employee is not delivering; as an HR manager, you may have to deal with dismissal cases, etc. It is the role that determines who takes part in the conversation and how the matter is handled.

There can be a big difference between going into such a conversation with someone you feel closely attached to, or someone you know is doing their very best without managing the tasks well enough. Not to mention how difficult it can be to give a negative message to someone you know is in a challenging life situation. If you also have to keep dealing with this person for a long time after the conversation, it can be extra demanding to get into the substance.

Relationships

The most difficult thing about ‘the difficult conversation’ is ultimately that the conversation can challenge, affect and shape the relationship between you and the person you are talking to.

How should I approach ‘the difficult conversation’?

Whether the conversation becomes difficult is therefore very much about what you yourself find difficult to put into words, and how you feel you can handle the various reactions that may come.

Dreading something can sharpen your senses and help you mobilise. Going into a ‘difficult conversation’ with a little nervousness and unease can push you to prepare well and help you keep your attention and focus throughout the dialogue.

Avoiding ‘the difficult conversation’ can make matters worse. It rarely pays to put something off just because it feels demanding. If you tackle uncomfortable topics as they arise, you can turn the difficult conversation into ‘the necessary conversation’.

My challenge to you is this: think of ‘the necessary conversation’ as necessary to hold because it is important.

Such a starting point can help you to:

  • tackle difficult topics at an earlier stage, ideally before they become so difficult
  • handle any reactions better – they are part of it
  • communicate more clearly – it is easier to know what you stand for and mean

This helps build trust and strengthen relationships! And remember: Expectations tend to be fulfilled – including expectations that things can go well!

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Skrevet av
Nina Hetland
Head of customer success & senior organisational advisor

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