Optimist Performance

How do you handle difficult conversations? Do you try to avoid them? Or do you feel anxious and uncomfortable when thinking about it? 

The majority of people see conflict as a negative thing and don’t like having difficult conversations. However, the more we avoid them, the bigger the issue becomes. So, this month, we’ve asked some of our Eternal Optimists about their tips, tricks and advice to handle difficult conversations. 

3 Tips to handle difficult conversations in the Workplace

David Berkeley

  • difficult conversations - David BerkeleyKeep it outcome-focused. What positive outcome do you want to happen after the conversation?
  • Keep it objective and not personal. Avoid personal attacks or subjective opinions where possible. 
  • Give the other person time to process the conversation. They might not be prepared to reply at that moment so give them time and space to come back to you another time if they need to.


  • Seek to understand why people are choosing to say what they say.
  • Pre-mortem the conversation… what their reaction might be and what body language/tone/etc would be helpful to you?
  • Ask great questions (‘can you help me understand…?’)


  • Being honest and transparent throughout the process, don’t try to hide facts, or lie.
  • Have what you want to say planned and think about how you’d like to put your points across in advance. 
  • Try to empathise with the other person. Try as much as you can to understand their point of view.

How would you prepare for a difficult conversation?

David Berkeley

Run through how the other person could interpret what you’re saying. Put yourself in their shoes to help see it from their side. It might help you to empathise with them. 

difficult conversations - Russell EarnshawHave a positive outcome of what you want to achieve with the conversation. For example, ‘By the end of this conversation, I hope our personal communication will be improved.’ That way there’s a good intention to the conversation and that will help it be more positive.


Extensively… where will we meet and why? When? What will my opening line be? Does anyone else need to be there? What do I want them to say at the end? Etc.


I think the most important thing is to plan what you want to say, what message you’d like to get across and what outcome you want from the conversation. Then, reflect on how best to communicate that to the specific person: should you prime the person ahead of the conversation, and give them time to prepare? how can you explain it so they see value in the conversation too?

What advice would you give to someone who is avoiding a difficult conversation?

David Berkeley

Just do it. You’ll only build it up more to be a bigger thing the longer you postpone it. You can always have a less difficult conversation first and build confidence. 

difficult conversations - Ollie PhillipsRussell

Emotion will follow action… get going!


Reflect on why this conversation is important to you and what it is challenging you about the situation. 

I’d also think about how to put processes in place in order to avoid getting into a really difficult conversation in the future, “what can I do better next time so it doesn’t get to this point?”

The Optimist View…

Most of us don’t enjoy difficult conversations, it makes us feel uncomfortable, however, as we always say “we need to get comfortable with being uncomfortable”. And while it may not be something we enjoy, it will help us grow and evolve. 

You can also bring someone who would help you mediate those difficult conversations. Through our group and individual coaching, we help clients with difficult conversations and challenging situations. Get in touch to learn more about how we can help you and your team.