Difficult conversations at work can feel uncomfortable, but they’re essential for growth, trust, and collaboration. Whether it’s giving feedback, addressing conflict, or speaking up, mastering courageous conversations helps build stronger relationships, more cohesive teams and a healthier workplace.

Something that often comes up in coaching conversations is the need to have a brave or difficult conversation. This need for a courageous conversation, can feel like grit building up in our shoes. Something happens, you ignore it, but you can feel that bit of grit. Then another thing happens, and another, and suddenly, the grit builds up so much that it’s hard to keep walking. These difficult and courageous conversations are how you clear out the grit.
These moments and conversations can be tough, but they’re crucial for building an open, honest workplace where everyone feels heard and respected. Whether it’s raising a concern about a project, giving feedback, or addressing a conflict, learning how to approach these conversations can lead to better outcomes and stronger relationships.
This blog was written in collaboration with one of our Collaborative Partners, Jacqui Sjenitzer, an experienced coach who specialises in creating meaningful connections through presence, powerfulness, and care.
These practical steps to approach tough talks with confidence, clarity, and empathy, can help turn discomfort into productive dialogue.
1. Identify the conversation you need to have
Begin by clearly identifying the conversation you want to have. What is the main focus? Do you need to explore the issue openly or is it more about sharing your thoughts and feelings? Understanding what kind of conversation you're entering will help you prepare effectively and approach it with the right mindset.
2. Be clear and concise
When you're planning the conversation, try to distil your main message down to a simple statement. Can you summarise what you want to say in just 10 words or fit it on a postcard? This exercise helps you get to the heart of the matter and ensures that your message is clear and easy to understand, reducing the risk of confusion or misinterpretation.
3. Outline your key points
Think about the three main points you want to make. Having a few key points helps you stay focused and ensures that you communicate the most important parts of your message without getting sidetracked.
4. Reflect on what’s important to you
Take some time to reflect on what really matters to you in this conversation. What are the key values or outcomes you hope to achieve? Knowing what’s important to you will help you stay grounded during the discussion and ensure that you communicate authentically. Try considering what a great outcome would look like and use this to guide the conversation toward a positive result.
5. Be open to ongoing dialogue
Remember that not every issue can be resolved in a single conversation. It’s okay if the first discussion doesn’t solve everything. Sometimes, it’s more effective to have multiple conversations, allowing time for reflection and understanding. This approach takes the pressure off trying to make everything perfect in one go and can lead to more thoughtful and productive outcomes.
6. Focus on what you can control
You can’t control how the other person will react or how they will interpret what you say. However, you can control your approach, your intentions, and how clearly you communicate your message. Focus on being open and honest about your feelings and what’s important to you. By doing this, you help create a space for a more meaningful and constructive conversation.
7. Approach with the right intention and clarity
Ultimately, the main thing you can control is the mindset you bring into the conversation. Aim to come from a place of understanding and genuine curiosity. Be clear about what you want to communicate, but also be open to hearing the other person’s perspective. This approach helps build trust and shows that you value the relationship, which can make even the toughest conversations more productive and less intimidating.
Having difficult conversations is never easy, but it’s a vital skill for both personal and professional growth. By approaching these discussions with empathy, clarity, and a willingness to understand, you can transform them into opportunities for deeper connection and positive change.
If you’re ready to clear out the grit and take those brave first steps, our dedicated course on Courageous Conversations in our Online Learning Library is here to help. Packed with practical techniques and strategies, it’s designed to build your confidence, sharpen your skills, and help you create stronger, more open relationships.