How to have Courageous Conversations

The key to having courageous conversations is to utilise your emotional intelligence, strategic thinking, communication presence and influence, writes Sarah Cupitt.

1. What is a Difficult Conversation?

For many, a conversation becomes difficult when there is a severe concern about the reaction and high emotional attachment to the outcome, and this can be in regards to professional or personal issues weighing someone down. Learning to articulate thoughts and opinions to avoid awkward moments, clear up misunderstandings and create positive relationships is what having courageous conversations is all about so that you can ask questions like:

My work has changed substantially, can I get a pay rise? Are you aware that your work isn’t meeting standards? Do you realise this comment is offensive? When will you be able to pay me back?

2. Reflection and Ownership

“The real art of conversation is not only to say the right thing at the right place but to leave unsaid the wrong thing at the tempting moment.” ― Dorothy Nevill.

Every conversation (and situation) has at least two players. In your reflection, it’s essential to think about what you bring to the table ‐ what parts of the problem/situation/conflict do you own?

When reflecting on your reaction and attachment to an issue, cognitive biases and other people’s perspectives, you can find recurring themes or ‘triggers’. It’s crucial you know what types of conversations will trigger you so that when your peers, leaders or teams approach you for a courageous conversation, you can check your responses. You should take some time to unpack and reflect on an issue beforehand by asking yourself questions such as:

Reaction: How concerned are you about the response the other person will have? How do you think they’ll react to your message? What’s the best that could happen? What’s the worst that could happen?

Attachment: How personally invested are you in the outcome? What’s the worst that could happen if the people or things relevant to your issue don’t change? What’s the best that could happen if they do change? What are the consequences if you do nothing?

Actively think about your answers and rank them on a scale of 1–10 of importance. Overcome your fears, deal with your ego and start thinking about why you want to have a courageous conversation, what the issue is you want to discuss, and how this issue is affecting you.

3. Useful Frameworks to Follow

Some diverse frameworks you can use to frame and approach conversations you find difficult:

4. Preparing for a Courageous Conversation

Once you know what your goal is, it can be valuable to see how close you already are to achieving it, which can change the way you approach the situation. Prepare yourself to experience the discomfort, be realistic about your expectations, and look forward to solutions.

5. Avoid Common Mistakes

Sometimes we can mess things up, and that’s ok, keep going and remember that practice makes progress. To ensure you have the best chance of success, avoid talking too much or talking too fast, using informal language, sounding like a robot reading off a memorised script, not considering other people’s feelings, not conveying a clear message, oversimplifying a problematic conversation and losing sight of the shared goal.

6. The Conversation

NOTE: You may not always get the outcomes you want when resolving relational conflict. If you keep having courageous conversations, your relationships in your professional and personal life will flourish and grow, with time, and practice.




Feminist journalist and writer advocating for social change. Poetry is my creative form of expression.

Love podcasts or audiobooks? Learn on the go with our new app.

Recommended from Medium

How To Deal With Dating Rejection

How To React When Someone Comes Out

I lost a friend who didn’t know me

The stars don’t say anything

Women Aren’t Illogical. Here is how to Understand Them Easily. Part 1 Respect

After breaking up with ex boyfriend, he introduced his buddy to me

3 Tips to Become The Best Listener You know

6 Things You’ll Never Change In a Partner

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store
Sarah Cupitt

Sarah Cupitt

Feminist journalist and writer advocating for social change. Poetry is my creative form of expression.

More from Medium

Not all fathers deserve a day

Juggling Too Many Commitments And Passion Projects Nearly Finished Me… Now Here’s How I Study…

Exercising Self Control like a NBA athlete

5 Things I Started Doing in 2022 to Be Closer to My Perfect Self