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15 Tips for Difficult Conversations

  • Do you have 'Analysis Paralysis'?

  • Did someone cross a line, but you don't know how to tell them?

  • Are you avoiding giving feedback on poor performance or disruptive behaviour?

  • Are you worried how you'll break bad news to someone?

  • Does the thought of a particular conversation make your squirm?

  • Are you dreading an upcoming interaction?

  • Are you considering starting a discussion about ‘the elephant in the room’?

Most people are avoiding having at least three difficult conversations. Often, we logically know that the benefits outweigh the costs, however, we focus on the prospect of the conversation not going well along with the emotional turmoil. This causes us to freeze or potentially go to extreme lengths to avoid pivotal dialogue. In turn, this can result in unsafe and unhealthy working cultures, compromised professional standards and under performing teams.

“The culture of any team [organization] is shaped by the worst behaviour the leader is willing to tolerate.”Gruenter and Whitaker (2017)


Compassionate Leadership & Difficult Conversations

There is a preconception that compassionate leadership just means being nice to everyone and avoiding conflict. However, it’s quite the opposite. Compassionate leadership means investing our energy into helping people. It takes courage and wisdom to call out behaviour and support people to grow. Good leadership often means getting clear on boundaries and taking the hard road. The good news here is that the more ‘difficult conversations’ you have, the easier they get.

When we participate in difficult conversations we:

  • Demonstrate we care enough to bother (vs. sweep it under the carpet).

  • Build trust and respect in others and ourselves.

  • Stop being trapped and find our voice, giving confidence to lay down boundaries in other areas too.

  • Build confidence in ourselves and our relationships.

  • Broaden our perspectives and understanding.

  • Share a problem.

  • Role model great leadership and develop everyone involved.


Our 15 Top Tips

1. Design your message

There are a number of structures you can use (see main newsletter image), to open your conversation, state your case and outline your situation. Whether you use them in your discussions or not, applying them to your situation can be a useful preparation exercise. They will help you to get clear on what is upsetting you, why, the impact and what you want.

2. Double check your motives Get clear on why you are having the conversation? Are your motives healthy? Are you 'point scoring' or are there real benefits (not just for yourself)? Is your story based on facts, hearsay or your perception? Could bias or other influences have got tangled up in your points? 3. Forgive yourself for feeling emotional There are many reasons why certain subject make people emotional. Some potential ones: pent up stress, anxiety/fear, sleep deprivation, personal importance of the subject, values and morals have been crossed, unsaid feelings, revealing an emotional wound, shame, biological healing after a trauma. 4. Identify your Trigger points Which parts of the conversation are the ones which are most likely to trigger your emotions? What do those trigger points tell you about your values? Get clear on why it’s upsetting. 5. Create coping mechanisms Plan how you will manage yourself if you get upset. What usually stabilises you? The more you flex these self-management techniques, the better you’ll get at it. Distraction, grounding techniques, breathing, counting to 10, letting it all out, drinking water. What generally works for you? 6. Desensitise yourself from the message Practice saying it, role play it if you can. Take the sting out of it, get concise and clear about the 'nub' of the issue. When it comes to the moment of delivering your message, it might not come out as you planned, that’s ok. The important element is that you took the step. 7. Contingency plan What if they say...anticipate potential responses, plan for the best & worst case scenarios. How will you respond? 8. Build self-awareness of ‘The Story you are Telling yourself’ How we read and digest situations informs the story we tell ourselves and our ‘self-talk’. We play this story or belief (about the situation or the potential reaction) over and over in our minds, the stories gets louder and the people in the stories can take on bigger and bigger personas. At the same time, the other people involved are likely to also have their heads full of ‘their story’. Question yourself, is it really true? What is fact in this situation vs subjective viewpoints? 9. Consider using incisive questions The right questions elicit people to search in a new direction, consider a different perspective and be involved in problem solving. For example: How do you see the situation? How can we move this forward? How would you handle this if you were me? If we don’t address this, where do you think this could end up? What obstacles might stop change? What are the right next steps here? What support will be needed? Really listen to their response be prepared to learn something new, you may want to re-think your approach once you have considered their perspective. 10. Don’t talk in absolutes and always mention the positives too Our stories become richer if we use absolutes; ‘never’, ‘always’, ‘awful’ but this will often paint an inaccurate picture and can provide a trigger for dispute. Outline a balanced view. Deliver potential criticisms along with some positives of the relationship or situation. For example: ‘You are brilliant at a, b, and c and we generally work well together. However, recently I have been feeling concerned about a few things and I need to get it out in the open.' 11. Talk tentatively… Because of the previous point, outline your viewpoint as a ‘story’ rather than disguising it as a hard fact, using phrases such as these… I might be wrong but… I need to check this story I want to understand your perspective Help me to understand what happened here My experience is… What’s your perspective of this? Perhaps you were unaware 12. Feel the fear and do it anyway This meeting is likely to feel uncomfortable. The conversation is a step away from your usual communication style, habits and topics. You are breaking new ground. Outline a quick lists of potential conversation costs and benefits if you are having a wobble. 13. Give them time and space This first conversation is time for you to get your key messages across. Allow them to deliver their response after consideration, you might get a better outcome, rather than a knee-jerk reaction. Allow them time to think about a response. Don’t demand a response straight away. Set up a later meeting. Make it easy for the recipient to take a breath. 14. Get ready to listen Ask questions then hold the silence and really listen, not just with your ears. Notice the non-verbal communication, drink it all in, be really present. To get more information into the space, use follow on questions to prompt more explanation. • Tell me about… • Explain… • Describe… • Why was that…? • How did you feel then…? • What did you mean when you said…? • What else…? • Anything else…? 15. Reflect What went well? What did you learn about the other person’s perspective? How would you handle the situation differently next time? What did you learn about yourself under pressure? How do you feel now? What are the positives and negatives to take from the conversations? How will these outcomes inform the actions you take next? What message or learnings would you give to others about handling difficult conversations?

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