How to take the ‘difficult’ out of difficult conversations

We’ve all been there and felt that churning feeling in the pit of our stomach when a difficult conversation is approaching that we are dreading. Whether it’s giving an employee feedback, asking for something you want badly, facing up to your boss when you know you haven’t delivered or tackling a thorny issue with your partner.  Who hasn’t come out of one of these conversations thinking to themselves ‘why couldn’t I have said or thought of that’!

By taking appropriate steps before, during and after these difficult conversations you can set yourself up for success every time.

Before – Preparing for a successful outcome:

I don’t believe there are any silver bullets when it comes to dealing with something important.  These conversations are usually important to us otherwise they wouldn’t give us palpitations and sleepless nights.  With the right preparation, however, we are more likely to get to the outcome we want than without it. I also think it’s key to be in the right frame of mind and I prefer to use the term ‘important’ rather than ‘difficult’ – as it’s a much more positive description of the conversation you are about to have.

  • Adopt a positive mindset – what you think is what you get
  • Expect a positive outcome
  • Get clarity on what you want to achieve – what is important to leave the conversation with
  • Write down the main points you want to cover
  • Anticipate what the other person’s perspective is and how you want to respond
  • Be with your emotion: how are you feeling about this conversation and what factors are influencing that
  • What do you know to be true
  • Prepare for what the other person might say
  • Create a vision of what a successful conversation would look like and keep replaying that in your mind
  • Where and what are you prepared to compromise



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During – self-managing in the moment:

When it comes to preparing there are things we can do that will put us in good stead that we can work on in advance.  We should also give some thought to how we want to be ‘in the moment’when emotions are running high, and we may not be thinking clearly.  Part of the preparation should be around planning how we’re likely to be feeling during the conversation and how best to self-manage.

  • Ask Powerful Questions
  • Be aware of and control of your emotions
  • Listen with genuine curiosity
  • Be open to possibility – there may be factors you were not aware of
  • Dance in the moment – be prepared to be flexible
  • Find common ground – what works for both of you
  • Be empathetic and show you care about the other person
  • Discuss impact rather than blame
  • Ask for the other person’s point of view – how do they see things and how does this influence your perspective

After – reflect and learn

It’s important after any meaningful conversation that you consider what went well and what didn’t. Be gentle with yourself if things didn’t go exactly to plan and take away the things you would do differently next time. If you’ve prepared, chances are that it did go well so make sure to celebrate that too.

  • Ask yourself what worked
  • What didn’t work
  • What would you do differently next time
  • Be kind to yourself
  • Surface and get clarity on what you learned
  • Celebrate your success
  • Apply your learning to your next conversation

What else would you add?

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Photo credit: Giorgio Montersino via Visualhunt / CC BY-SA


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