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Difficult Conversations & How to Have Them

Posted on Thursday, 29th March 2018

Sometimes situations arise and we have to have a difficult conversation with someone. They might have done something to annoy or upset us and we need to address it. Or, we may be approached by someone who needs to speak to us about something.

Confrontation can so be difficult and something we often go out of our way to avoid. However, communication is nearly always the best option and the result is usually worth the uncomfortable feeling during the process.

Usually with difficult conversations there will be two roles. The initiator- the person initiating the conversation and the one with an issue they wish to discuss. And the recipient- the person who is on the receiving end of this conversation.

So I’ve compiled a list of some things I think are important and helpful to keep in mind for both roles. While writing this I suppose I had in mind friends, partners or family. I would take a bit of a different approach in a work setting.

This is a little longer today- so grab a cup of tea and settle in- it is the bank holiday weekend after all!


Think about the setting

This is worth just giving a little thought to. Do either of you have to leave soon, leaving the conversation halfway through or making it feel rushed? Should it happen in a neutral location? Sometimes it can help if you’re not sat opposite each other in an intense environment. So going for a walk together can be conducive to an open conversation.

Focus on the other person’s actions…

Usually the thing you want to discuss is an action/s someone has done, rather than who they are. I.e. they’ve done something that has upset you, but you still like them as a person overall. It’s the action you don’t like. I think this message is important to get across to prevent the other person feeling too attacked.

…and your feelings

We always need to try and remember that how we interpret someone’s actions is just that- our interpretation. And how we interpret something is allll about us and our history, assumptions and preconceptions.

So instead of- ‘You were late to meet me, you obviously don’t value our time together’, try ‘You were late to meet me, which makes me feel like you don’t value our time together.’

Take some time beforehand

This will be different for different people. I personally always need to take some time to gather my thoughts, process how I’m feeling and why and then realise what I need the other person to understand from me. This will not be the same for everyone and for some people the processing time does not need to be long at all. However, I would always advise to at least take a bit of time, so you feel clear about how you feel and what you wish to say. Which leads on to the next point..

What do you want to get out of it?

When entering in to a difficult conversation it is important to know what we want out of it. Do we just want to let the person know how we feel? Do we want them to do something as a result? If we know what our expectations are and perhaps manage them, then we are more likely to leave the conversation with a clearer idea of how it went.

The recipient

Focus on the issue at hand

If someone comes to us with an issue, it can put us on the defence. We may be tempted to reply with something we feel they’ve done wrong. This can be unhelpful. The initial issue isn’t being addressed, an additional issue has been introduced and both people are left feeling defensive.

Try your best to stay with one topic and focus on resolving that. If then you feel you wish to bring something else up, then do it afterwards.

Be curious

Sometimes what the other person is saying we really might not understand or agree with. Try and always have a curious mind. Ask questions. Be willing to understand. Chances are the person does have their reasons for feeling how they do. Try and work together to understand each other.

Remember they care

Having these conversations is difficult. If someone approaches us to talk about something they’re not happy with, it is easy for us to feel attacked or upset. But take a moment to remember that they have taken the time to come and talk to you. They are having the conversation with you and therefore want to resolve it. You’re someone who matters to them.


Throughout the conversation I think the following points are helpful for both parties to think about.


Try to understand the other person’s point of view or what they might be feeling.

If a friend tells you about a difficult situation they are experiencing (e.g. a work problem or an argument they’ve had with someone) chances are you usually see their point and empathise. This is because you are hearing it from their point of view and their experience. Yes you may also be able to see the other side, but you really understand why your friend is finding it difficult.

It can be helpful to transfer this thinking to when you are in a difficult conversation with someone.

It can be so easy to just see something from our point of view and feel that the other person is in the wrong. But what if we put ourselves in their shoes. Why are they acting this way? Is it coming from a place of insecurity? Do they have something going on in their life which is making them act this way?

Get to the heart of it

What is this really about? Often an event can trigger an argument, but the heart of the argument is actually about something deeper. The event can just be a catalyst. Whether you are the recipient or initiator, try your best to locate and focus on the heart of the matter. Is this really because that person was late to meet you, or does that action speak to a bigger issue?


De-escalation is such a useful skill to have. It is something that came up in so much of my training when working in mental health hospitals and residential homes.

The basic premise is — go quieter and smaller. If someone raises their voice, make yours so quiet that they have to quieten theirs in order to hear you. If someone is standing up and looking agitated, sit down.

If we respond like with like then the voices get louder and louder and shoutier and shoutier and the situation can escalate very quickly.

I’ve been amazed at how quickly these simple actions can work.

How to go forward

So you’ve had the conversation, things have been said, everyone feels heard and the situation is hopefully resolved. The next step is to think about how to go forward. What can be done to avoid this happening again? What actions if any need to be put in place?

If you think you would benefit from talking to someone about this, or any issues around communicating with loved ones, why not get in touch.

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