Courageous Conversations: Five Detailed Tips

As a manager, the need to have difficult or courageous conversations with employees will often crop up. The key to addressing and overcoming these obstacles is communication– a fundamental pillar to effective people leadership. The good news is that this is a learned skill, and with practice and guidance you can learn to master the art of courageous conversations. 

1.Take Time to Reflect 

Being clear with yourself on the situation is important in preparing yourself for the conversation ahead. Be clear that the need for the conversation is not based on assumptions and ask yourself how the situation makes you feel. Are you anxious, angry, fearful, tense, or something else? 

Being aware of and addressing any emotional responses within yourself that may impede you from having a calm, honest and open conversation is key. Keeping an open mind to others’ point of view is critical to establishing a favourable resolution that does not alienate the employee. 

Ask yourself what a good outcome might look like? What are your parameters and how much are you willing to compromise? 

Once you’re clear on what you want to achieve by having the conversation and have your own emotions and self-limiting beliefs in check, you’re ready to talk.

2. Have the Conversation in Person

When having a conversation around sensitive subjects, it’s best to have the conversation in person. It’s easy for things to be taken out of context via email and phone conversations.  

Arranging a time and place to have the conversation demonstrates that you take both the matter at hand, and the other person’s position on the matter, very seriously.  The personal approach engenders a feeling of trust and approachability, and if handled correctly, will yield a far better result than the alternatives. 

3. Take Time to Listen 

Communication breakdown can happen when there is misunderstanding between what was said and what was heard and takes place when one or more of the parties are not actually listening to what is being said. If you’re concentrating on what you’re going to say next and waiting for a gap in the conversation to do so, it’s unlikely that you’re giving your full attention to what is being said to you.  

Similarly, you may feel so sure of what the other person is going to say that the content of the conversation becomes distorted to fit those expectations.  

To actively listen is to focus with full attention, understand and respond thoughtfully, and is a powerful communication technique that is essential when having courageous conversations.   

4. Communicate Clearly and Honestly

When having a touchy or difficult conversation, there is always the risk that emotions will escalate, and communication will break down.  

To communicate and interact with others effectively in the face of such situations, strong interpersonal skills are important. Understanding the various interpersonal skills that exist enables you to adapt your own style to suit specific situations and people in a way that increases both personal and professional success. 

Your ability to be mindful of time and to pace your comments will demonstrate your ability to truly listen and take an interest in what the other person is saying. 


  • Confirmation sounds such as ‘ahh’ and ‘ohhh’, and nods that reflect your understanding with appropriate eye and facial expressions will enhance the communication and level of trust between you and the speaker. 
  • Examine your own feelings around the situation that has brought about the need for a courageous conversation. Make sure you’re not making any dangerous assumptions or are being affected by your own emotional reaction to the circumstances. 
  • Be clear on what a good outcome looks like, and what compromises can be made to achieve that. 
  • Be direct and provide detail and evidence. Avoid making generalisations and avoid dangerous assumptions. 

5. Leverage the Power of Non-Verbal Communication  

Non-verbal communication is the process of communication through sending and receiving wordless messages. 

When you are speaking, the listener subconsciously ‘reads’ your voice as well as listening to your words. Non-verbal voice cues such as tone, pitch, volume, inflection, rhythm, and rate of speech are all important aspects of effective communication. These nonverbal aspects of speech are powerful clues to the speaker as to the level of genuine interest you have. 

As well as reading your voice, listeners also read body language to assess the conversation. The gestures, use of space, position of our arms and legs, physical distance between the communicators, nodding and other head movements and body language also convey information. Your non-verbal signs will either engender trust and a desire to continue the connection or they will generate disinterest, frustration, and confusion. 


  • Be aware of the space between you and the other person if you are both seated at a round table. If you sit too close you may be invading the person’s ‘space’, while sitting too far away may suggest that you are less interested in the conversation. 

It can be unwise to assume you know what someone is saying based on their body language alone. If you feel that there is discrepancy between what they are saying and their non-verbal cues, dig deeper in discussion to gain clarity and understand the real message. If this topic pushes a button for you, or your business, get in touch with us for a friendly chat and find out how we can help!