Courageous conversations and how to have them

07 June 19

Courageous conversations, where difficult issues are addressed, can feel overwhelming.

It’s common for people to avoid taking action in the hope that the issue will be resolved without them having to say something. However, it is much more likely the problem will escalate and become even more difficult to resolve. It is far healthier to deal with issues early and avoid them getting any worse.

You need to be equipped to work with colleagues in challenging situations to maintain positive and productive relationships. If an individual makes sure they prepare for these conversations, develop the right skills and take the best approach, it is possible to achieve positive outcomes.

Tips for having a courageous conversation

  1. Establish the situation– be clear about your purpose (why do you need to have the conversation?). Try to understand what may be behind the issue (health, family, work, personal issues) and think about the outcome (what do you want to achieve?). Keep returning to your purpose if difficult moments arise.
  2. Be prepared– a successful outcome depends on how you are prepared and what you say.
  3. Plan the conversation – write out a plan to clarify your approach in advance. For example, how are you going to open the conversation? Practise the conversation in your head. Think about how the person might react and how you will respond to their reactions. Carefully choose a place and time and ensure the other person has enough time to prepare too.
  4. Think about your style – you may need to move out of your comfort zone and adopt a more assertive approach but make sure you have a mature, cooperative style. Think about your posture, body language and don’t interrupt them.
  5. Honest conversations – some people find it more helpful to think of honest rather than courageous or difficult conversations.  For some it is easier to think about being honest than it is to be courageous or raise difficult subjects.  Moreover, framing the conversation as difficult may end up being a self-fulfilling prophecy.
  6. Present and listen –ensure you listen to what they are saying, establish the difference between fact and opinion and demonstrate that you are genuinely interested. Practice the skill of Active Listening. Don’t assume they can see things from your point of view and don’t prejudge the meeting before it’s started. This will help to build trust.
  7. Radical Candour –aim to challenge directly while caring for the other person.  Radical Candour is a powerful tool for thinking about how and when to give feedback.
  8. Acknowledge emotions – both yours and theirs and direct these towards a useful purpose. Think self-awareness and self-control. If you are mindful of your emotions then you are supporting the other person to demonstrate a similar mindset. You won’t ever be able to guess exactly what will happen but there is likely to be defences, shock, sadness and maybe even tears, so give them space to respond but keep control of your own.
  9. Be positive– difficult conversations lead to changes in behaviour, so create an optimism that moves the conversation into action by finding a middle ground. Again, consider the language you are using, tone of voice and body language.
  10. Ensure there’s action– think about how you will close the conversation and commit to action.


Norman was commissioned to assist the Naval Families Federation as we embarked on a comprehensive review of our strategy. He is a skilled facilitator and helped us to ensure that the whole team’s input was heard and valued. His input gave us confidence in our approach and put us in a strong position to take forward work on our theory of change, and ultimately to deliver a coherent strategy to take the organisation forward.

Bridget Nicholson – Head of Strategy, Naval Families Federation