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Facing up to difficult conversations

‘I need to be better at handling difficult conversations’ is a statement that I hear far too often. 

So, for any of you suffering from this misconception that you haven’t got the skills to make all conversations easy,  let me help. 

You and I both know that if you reach out to anyone for help with a difficult conversation you need have, you will probably provoke one of the following unhelpful responses:

              ‘Oh! Rather you than me’, or 

               ‘Good luck with that one’, or

                A sharp intake of breath followed by, ‘that’s going to be a toughie’. 

All these responses are linked to how they think the other person is going to react. And, when we strip everything away, that’s what you are most fearful of isn’t? How the other person may react. That’s the bit that you see as being the most difficult thing you will have to cope with. 

Making assumptions about someone's reaction to what you are about to say fills  your mind with all the what ifs?....What if they get upset? Cry? Shout? Walk out? Or heaven forbid what if they tell you that you are wrong?

Those are the concerns that will swim around and play tricks with your confidence. 

So, firstly, let's remove the word difficult. It has negative connotations and implies that it is going to be a stressful experience before you have even uttered one word. 

It’s rare to find someone that will genuinely help you with these situations, so using my 6 ‘P’s model ;  Position, Plan, Prepare, Practice, Patience and Post Conversation Reflection I am going to give you some useful questions so that you are able to help yourself: 


  1. Positioning: Think about how you will describe this conversation. Change the word difficult to important. Suddenly, this action alone will help you and other people recognise that there is an element of responsibility that lies within the outcome and so it needs to be taken seriously with an eye on what really matters here.  

Q: Why is it important to have this conversation? 

Q: What do I want to achieve? 

Q: What positive outcome will it have on me/them/my team/the business? 

  1. Plan: Use the word plan instead of worry. Plenty of wasted time and energy is usually spent worrying about how to handle the event, some people will let it affect themselves so much that they even lose sleep. Channel that time and energy into  how you want it to work best, rather than preparing for what may go wrong.  Approach it like any other project you may be dealing with:

Q: When will be the best time for it to take place?

Q: Where would be the best location?

Q: What would be the best way for me to start the discussion? 

Q: What structure would work best? 

Q: What facts do I need to present? 

Q: What questions do I need to ask?

Q: What will be important to them? 

Q: What would be good for us both to agree on?

Q: How do I want them to feel at the end of the conversation?

Q: How do you want to feel afterwards? 

  1. Prepare: Now you know how you are going to approach the conversation, reflect on what response and questions you may get in return.

Q: What is the reaction I am likely to get?

Q: What will I do if they get upset?

Q: What else might be on their mind at the moment? 

Q: What would be important for them to hear? 

Q: What if they respond really positively?

Q: What would be the next steps that I would like them to take? 

  1. Practice: If you lack experience, or are worrying too much, why not practice? Practice helps you refine your skills and gives you insights to draw on in the heat of the moment.  

Q: How do I need to come across?

Q: What tone of voice should I use? 

Q: What do I need to do to manage my emotions? 

Q: How can I put them at ease? 

Q: What do I need to do if we go off topic? 

Q: How do I want them to feel at the end of the conversation?

Q: What would be a good way to end so that they leave understanding the importance of what we have discussed? 

  1. Patience: This matter may have been on your mind for some time, and you know what’s coming. They won’t. In their eyes, this already gives you an unfair advantage. Understanding that what you are saying to them may be a shock, or if you have given them warning they may be tired through loss of sleep, either way, their response won’t be as considered as yours. 

So, now’s the time to demonstrate how important it was to put all this preparation into place and give them a chance to speak, air their views and ask you questions.  

Q: What do I need to do for them to trust that I will listen and reflect on what they say? 

Q: How do I help them to see that I am open to them asking questions? 

Q: How can I use this as quality time together to build our working relationship? 

Q: How can I use this experience to find out what additional support, training or advice they need? 

  1. Post conversation reflection: In order for you to use this as a learning experience to help you improve, after it is all over, reflect on what you have learnt. 

Q: What have I learnt from this conversation?

Q: What worked /went well?

Q: What would I do differently? 

Q: How much more confident will I be the next time a similar important conversation arises? 

Q: How this situation helped me? 

The more important conversations you have with important outcomes, the better you should get at handling them. See each one as a milestone to never being worried about saying what needs to be said ever again.  

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