How to have a difficult conversation that goes well

There’s a saying, isn’t there, that people are more afraid of public speaking than jumping out of an airplane? Or something like that. I’m pretty sure, after working with hundreds of managers over the years, that having a difficult conversation with a member of staff, colleague or boss is also somewhere on that list of dreaded things.

As Benjamin Franklin said, “If you fail to plan, you are planning to fail”. This goes to the very heart of what can make a difficult conversation go well… or make a bad situation worse.

The following list of things to do are a culmination of my own experience of having many difficult conversations, along with the experiences of the managers I’ve coached and supported.


  1. Be clear about the outcome you want to achieve.

2. Think about how you need to behave in order to achieve your desired outcome.

3. Write down the key points you want to make. Emphasis is on key – not a long list of things.

4. No surprises. Show respect for the other person(s) by letting them know the purpose of the meeting so they can prepare too.

5. Make sure you have some time before the meeting to get your head in the right space, even if it’s just five minutes. Avoid going straight into a meeting from the one before.


6. Agree some ground rules. Contract with each other how you will each ensure the meeting goes well.

7. Make it a two-way conversation. Ask questions in a spirit of genuine inquiry (as opposed to inquisition).

8. Focus the conversation on the problem rather than making it personal about the individual.

9. Challenge rudeness or aggression in the moment by going back to the ground rules. Do this from a compassionate place.

10. If things get heated don’t be afraid to take a time out. Give a five minute break. Get both of you a cup of tea, or some water. If the other person cries, give them some space by getting some tissues.


11. Take some time to decompress. Even if it’s just five minutes. Go for a walk. Listen to some music. Get a drink. Try to avoid going straight into another meeting or back to your desk.

12. Take 10 minutes, the following day, to write down your lessons learned from the difficult conversation. What did you do well? What would you do differently?

What do you do to help you have a difficult conversation?

Did you find this post helpful? I’d love to know, so Tweet me, or drop me a note on LinkedIn. If you have any colleagues that you feel should read this, too, please share it with them. I’d really appreciate it.

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