How to Deal With A Difficult Conversation

Difficult Conversations

… have to happen in life.

It’s not nice and most people feel very uncomfortable to be in that kind of difficult situation BUT leaving them to bubble or sweeping them under the carpet can lead to passive aggressive behaviour – which we all know is not good for our health.

Many people often shy away from these conversations which can often reinforce the behaviour of the negative party – rather than nipping it in the bud on the first occurrence.

Here are my top tips for dealing with difficult conversations:

1) It’s hard as you need to have your say but you do not know how to say it

Often sitting with a friend and going over what you want to say can often help you articulate what you want to get across.

One of the things I often do is write bullet points of what I want to discuss and cover in the conversation. If it does escalate or go off tangent I am then able to look back and check that what I needed to express has been covered.

it reinforces my confidence and strength especially if the other person is dominant and/or aggressive.

difficult conversations

2) Do not belittle the point by making it smaller than it is

This is a very British thing to do.

If it has got to the point that you need to raise to another person it is not something that is small.

Many people instantly go to making a joke or belittling their point at the first sign of confrontation which leaves the other person questioning what point you had to raise in the first place.

Be firm and be calm and work out the issues till both parties have a mutual understanding.

3) Keep it objective: Unless it is a personal attack do not make it personal

This is very important. Do not take things personally. If it is Work – keep it professional.

If someone is not pulling their weight, taking credit for your work or doing something within the professional realm that is not ok – address as you would any other business meeting.

Address the point – articulate how it impacts your work – express how you would like to move forward and then leave it at that.

difficult conversations

4) Find the outcome you want and work backwards

When going into difficult conversations most people forget what they want the outcome to be. I find if you work out what you want the outcome to be you can then start to look at the journey to get there.

If you do not know the outcome then the conversations will not have a definitive end.

5) Be open to the other person’s point of view

This is a conversation, not a dictation – therefore remember there are always two sides to every outcome and be prepared to meet in the middle to move forward.

To mutually agree a way of dealing with any difficulty situation will always be the best solution.


As I said, no one likes to have a tough conversation, but you will be far more respected by being open in your communication and setting boundaries.


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  • Reply
    February 13, 2018 at 1:53 pm

    This helps more than you know! Thank you!

    • Reply
      Cyntra Charlesworth
      February 23, 2018 at 5:47 am

      So glad it helped chica x

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