Essential Skills for Courageous Conversations

What’s the courageous conversation you need to have?  If just thinking about initiating a difficult conversation makes you feel anxious, and you find yourself avoiding the conversation, read on.

In the workplace, there are some big subjects that leaders should be talking about – but which they sometimes avoid.

😔 Mental health
😨 Stress
😡 Bullying
🥺 Discrimination
😲 Poor performance
👺 Unethical behaviour
🤑 Money
🤐 Something else?

How would you actually tackle these challenging conversations? It takes some courage and confidence, but there are also communication skills you can learn, that will support you in the process.

Before you begin, the prerequisite for both people to participate in a courageous conversation is feeling psychologically safe. 

Psychological safety is the feeling that it is safe to speak up with your concerns, questions and ideas, or to acknowledge your mistakes, without fear that you will be embarrassed, shamed, rejected or punished.

Ten factors that build psychological safety

How to create psychological safety is a big subject. The short version is summed up in this list of ten factors that build psychological safety. If you’re consistently doing these ten things as a leader, people will feel safe to speak up and to acknowledge mistakes, without any fear.

  1. Always behave ethically – honesty is key
  2. Create a positive team climate
  3. Take an interest in people and show them you genuinely care
  4. Ask questions rather than assuming or judging
  5. Express your appreciation
  6. Provide support
  7. Be clear about expectations
  8. Follow through on your commitments
  9. Consult people on changes that affect them
  10. Acknowledge your own mistakes

Let the conversation begin!

Assuming you’ve taken steps to create psychological safety, the courageous conversation can begin!

To initiate a courageous conversation, you will need to draw on a key emotional intelligence skill -expressing emotions. Often, the emotions you get in contact with, when you’re initiating a difficult conversation, are negative. So, what would be involved in expressing negative emotions? It certainly doesn’t mean dumping your negative feelings on the person who is the target of your negativity.  When we express negative emotions – whether in the workplace or in another area of life – the purpose is always to build empathy, and to get back in connection with another person when there has been a rupture in the relationship.

Acknowledging a negative feeling might be as simple as acknowledging it to yourself – or to a trusted confidante. It’s not always appropriate or necessary to express a strong negative emotion to the other person or people involved. It really depends on the situation – and the emotion concerned.

Communicating a negative emotion will only be ever helpful if it’s done without anger or blame, in the moment when you communicate it. In other words, wait until the “heat” of your negative emotion has subsided. It also helps not to have any particular expectations about the outcome. The purpose of communicating what you’re feeling is simply to get back into positive connection with the other person, not to blame them, or to make them feel bad, or even to make them change.

One approach I teach draws on Marshall Rosenberg’s work on nonviolent communication (Rosenberg, 2003). Rosenberg offers practical strategies and skills to tackle even the most challenging conversations. Here’s Rosenberg’s four-step nonviolent communication process, followed by a real-life example.

1.  Observation
Share your observation about what’s going on. Do this without judging or even evaluating the situation. This is just an objective observation of the facts.

2. Feelings
Explain how this made you feel. Do this calmly and without blame. Remember to wait until the heat of the emotion has subsided.

3.  Needs
Explain what you need, connected with what you’ve observed.

4. Request
Make a request. This should be something specific that would help improve the situation.

When you put the process together, you get a simple but very effective way to talk about difficult subjects, in a way that builds empathy and connection:

“Mary, you were shouting at me when I was speaking in the meeting today. I felt really upset and anxious because I need a calm atmosphere to be able to get through the meeting agenda. Would you be willing to pause and collect yourself before you speak at the next meeting?”

This conversation will go very differently from a conversation that is based on judgment, defensiveness, anger or blame. I know which conversation I would find more helpful.

It’s the empathy that’s facilitated by this process that changes every-thing. It’s hard to be defensive or angry when another person simply observes what happened, expresses their own feelings and needs in the situation, and makes a request. Of course, you are free to refuse the request, but when both parties in the courageous conversation learn and practice these skills, the answer to the request to behave differently next time is very often “yes”.

When you initiate a courageous conversation using Rosenberg’s formula, you will build empathy, connection and authenticity by avoiding judgment, defensiveness and blame. This will give you the courage and confidence you need to have even the most difficult conversations that you tend to avoid. 

Maria Brett
The Growing Edge

Maria Brett is a former CEO who has been a practitioner of mindfulness for more than 25 years. Maria’s Courageous Leadership Program helps participants make deep and lasting to the way they lead, including how to have courageous conversations.  To find out more, contact Maria.


Rosenberg, M.B. (2003). Nonviolent communication: a language of life. 2nd ed. Encinitas, CA: PuddleDancer Press.

© Maria Brett, 2022