Help for difficult conversations
- Ben Westmancott
- Mar 11, 2020
- 3 min read
Updated: May 1, 2020

Sometimes achieving your goals is hampered by other people and their behaviours. You may find that you need to have a difficult conversation to help move things forward. And have you noticed that some people seem better than others at having difficult conversations? Some people just seem to be more able to confront things than others.
Just because people are more confident at starting a conversation, doesn’t necessarily mean they are better at reaching a good outcome. It is one thing to get something off your chest, quite another to move the relationship on to a better place for both parties.
Well here’s some light. Anyone can learn how to have difficult conversations, no matter what your starting position is.
Here’s a step-by-step guide to help you:
Step 1: Your physical response
When you think about the difficulty, how do you feel physically? Maybe there is some tension, tightness, maybe your breathing becomes shallower. Regain your composure by focusing on your breathing – keep it steady and controlled, breath in, hold for a few seconds, then breath out. Repeat until you feel your physical state change positively.
Step 2: What are you concerned about?
Think about what you are afraid of, what you want, and what you need. Write these things down and look at them. This will help you identify your priorities.
Step 3: Change your perspective
If you go into the conversation feeling self-justified and clear what you want to get across, you might deliver a great speech such as you’d see in a soap-opera but it is unlikely to achieve positive change for both parties. Spend some time thinking about what the other person’s fears, wants, and needs might be. How are they likely to feel going into the conversation and during the conversation? Generate a third perspective - what might a neutral observer think about the situation?
Step 4: Get your facts straight
There are things you know to be true, things you think you know, and things you don’t know. Write down relevant things under these three headings. For the things you think you know, and those you don’t, how will you find out answers to ensure you are as prepared as you need to be for the conversation?
Step 5: Risk management
What could go wrong? Have you set up a meeting? Have you made it clear what the meeting is for? How might they be feeling about it? Is the meeting venue appropriate for the conversation you want to have? Is the start time of the meeting OK? Have you set aside enough time to have a useful conversation? What will you both be doing immediately before the meeting and how might that impact on your mood and approach? The purpose of this step is not to become fearful but to increase awareness of the factors that might affect success and increase the control you have over them. You cannot control everything and do not aim to eliminate all risks before you act. Regain your composure by focussing on your breathing if you need to.
Step 6: Outcomes and options
Think through the potential outcomes. What is the best outcome you could hope for? What is the worst outcome? What is the most likely outcome?

Step 7: Top and bottom lines
What are your top and bottom lines and what are the points on which you are not prepared to compromise? What might they want from the relationship? What might they be prepared to compromise on?
Step 8: Prioritise your points
It is unlikely that you will be able to get across all the points you want to make. You need to make sure you leave space for the other person to think about your points, space to allow them to put forward their points, space for you to consider their points, and space for left-field things you might not be expecting. All this means that you are likely to overestimate what can be achieved. That said, you might be surprised! To avoid that feeling when you walk out of a meeting when you kick yourself and say, “Argh! I forgot to say the most important thing!” write down the points you want to get across and put them in order of importance.
Step 9: Remember…
…The only person you can really change is yourself. And that goes for the other person too. Pay attention to how you are in the meeting. Listen to understand, not to respond. Pay attention to how you are physically and don’t forget to breathe – controlled breathing that is, it will help you retain composure.
Step 10: Congratulations!
After the event, congratulate yourself on having had the difficult conversation. You’ve taken a great step towards achieving your goals. Well done!
Based on an original idea by Louisa Weinstein in The 7 Principles of Conflict Resolution.
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