How to handle difficult conversations
Many years ago working in a large corporate, I had a team member who could be described as challenging. What I really needed to do was to have a conversation about the gap between her behaviour and my expectations.
But I didn’t.
I did my best to get on with her. I made copious notes about situations where her behaviour wasn’t acceptable. I talked to her mentor and the HR manager.
To be fair, she had a long-standing reputation before I’d come on board and no one else had confronted her either – which made me feel on the back foot. However, I fully admit that I avoided having the conversation.
Why did I avoid it? I was afraid of not getting my messages across in the “right” way. I was afraid about how she’d respond – anger? recrimination? – and, more importantly, whether I could handle what came back. I was afraid of it getting nasty and that I’d only make things worse.
What makes difficult conversations difficult
Having difficult conversations is one of the most common topics in my coaching sessions with leaders.
As humans, we’re wired to maintain connection with others and to seek their approval and respect. Thinking back to our early human ancestors, being in relationship with others was safer for us than annoying everyone and being thrown out of the tribe.
Which means fears of conflict and rejection can get in the way of you initiating a conversation because it feels too risky – just like they did with me.
When you do share what’s on your mind, your nerves can hijack your intentions. Your heart races, you feel hot, you find yourself talking fast and you can’t seem to stop.
You can find yourself so worried about how your message will be received that you package it beyond recognition. A bit like diluting freshly squeezed orange juice until it’s more like orange squash.
I’m thinking of one Director I worked with who needed to give feedback to an underperforming team member. When they cried, she felt the urge to appease them, to make everything better. She found herself backtracking on the message she needed to give them and ended up where she started.
The 4 Cs for navigating difficult conversations
Part of your job description as a leader is doing things that feel uncomfortable. Which includes holding people accountable to deliver to expectations.
But gosh it can feel hard.
Here’s a framework I’ve created called the 4Cs to help you initiate and navigate difficult conversations :
- Clarity. When you’re tied up in knowing about how to say something and how it’s going to land, what you want to say can get lost. Start off by writing or recording what you want to say without censoring yourself. Then you can refine it.
- Conviction. When you doubt whether what you think and feel is important enough to express, it can get in the way of taking action. Ask yourself what your right is to have this conversation and what’s the cost of not saying anything – to you, to others, to the organisation.
- Courage. When you avoid situations that you’re afraid of, you may avoid feeling discomfort, but you’re compromising on what’s important to you. Brene Brown summed it up perfectly : “You can choose courage or you can choose comfort. You cannot have both.”
- Calm. When your fight flight response is activated and nerves take hold, it can be difficult to stay calm and think clearly. Pay as much attention to your state as your script – shoulders back, belly breathing and feeling your feet on the ground are common anchor points for my clients.
Finally, a quote from SAS soldier Adam O’Connell : “At times of heightened action, we don’t rise to the occasion, we fall to the level of preparedness.”
For more tips on how to handle difficult conversations, download your complimentary copy of my book “Unleash Your Leadership : How to Worry Less and Achieve More”.




