Top Three Tips for Making Difficult Conversations Easier

September 24, 2021
Keely Wilkinson
Evidence Specialist Evidence Based Practice Team, HMPPS Insights Group

Keely Wilkinson from the Evidence Based Practice Team talks us through what we can do to make difficult conversations easier, and work towards their resolution.

From time to time we will all need to have difficult conversations. It might be with someone in prison or on probation, or it might be with a colleague. We might have to turn down a request, resolve a conflict, speak to someone about problematic behaviour or tackle a sensitive subject.

These conversations can feel challenging for lots of reasons. You might feel there is a power imbalance between yourself and the other person. Perhaps it’s something you’ve tried to resolve before without success, or you might not know where to begin to solve the problem. We might feel that the other person is purposively behaving in a way that causes the issue, or there may be cultural barriers that stop the problem being understood.

If we avoid having difficult conversations the problem is very unlikely to go away and may well become worse. Often, conversations we believe will be challenging turn out to be much easier in practice. Usually, being able to resolve the issue can make the discomfort of having the conversation worthwhile.

Here are our top three evidence informed tips to make these conversations feel less challenging and more likely to succeed:

1. Prepare and Rehearse.

  • Try to find a private neutral location without distractions and give yourself enough time for the conversation.
  • Think ahead about the outcomes you want and what support you can offer towards them. Where can you compromise or be flexible?
  • Try to understand the situation from all perspectives.
  • Establish all the facts and try to keep your emotions separate. If you’re feeling emotional, think about postponing the conversation.
  • Prepare for responses which might “push your buttons”.

2. Connect and Resolve.

  • Thank and acknowledge the other person for having the conversation.
  • Be clear from the beginning about the reason for meeting.
  • Use statements beginning with “I” when sharing your thoughts and feelings.  
  • Try to use “What” / “How” questions, rather than “Why”.
  • Keep your tone neutral and calm and avoid judgemental or blaming statements.
  • Use listening skills, open questions, mirror what you observe and paraphrase.
  • Be self-aware of your own non-verbal cues, spot times to pause, rephrase and ask questions.
  • Avoid inappropriate humour and subtle hints.
  • Be alert to differences in age, gender, culture, or literacy which might lead to misunderstandings
  • Be mindful of your own and the other person’s stress levels. Watch out for and acknowledge signs of confusion and fatigue.

3. Allow time to regroup and reflect.

  • Look at the problem together, find common ground and agree mutually beneficial solutions.
  • Make an action plan you both want to succeed. Keep communication open between you.
  • Thank the other person for the time and input  

This short (9 minute) video that explains these steps in more detail. Please feel free to share this with others who may find it useful:

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