Difficult conversations are still difficult 

The year was 2023. And it was last week. And I was doing leadership training, as I do. And the leaders in the group brought up the topic of difficult conversations. And so they should. Because difficult conversations are still difficult. 

I once had a CEO tell me that the conversation was going to be that difficult, they feared it would be a relationship ending discussion. That’s full on. In her book Radical Candor, I think Kim Scott provides the best process, whereby you need to care personally before you challenge directly. For Kim, you should never give feedback until you have asked for feedback. Leadership conversations should not end relationships, and here is how you make them both easier and more successful. 

1. Prepare, prepare, prepare 

Effective preparation is key to conducting successful, difficult conversations. Take the time to define your objectives and desired outcomes before engaging in the discussion. Gather all relevant information and facts, ensuring you have a clear understanding of the issue at hand, and its potential impact on individuals or the team as a whole.  

By preparing thoughtfully, you’ll approach the conversation with confidence, ensuring your message is delivered effectively. For me, I use the three-bullet-point approach. I have three bullet points that I want to talk though, and I follow those as a script. That works a treat! 

2. Listen, listen, listen 

Listening is a skill that can significantly influence the outcome of difficult conversations. Strive to create an environment where the other person feels heard and understood. Actively listen to their perspective, concerns, and emotions without interrupting or judging. Paraphrase and summarize their points to demonstrate that you genuinely understand their viewpoint. Active listening fosters trust, encourages open dialogue, and paves the way for finding mutually beneficial solutions. 

3. Language, language, language 

The language you use during difficult conversations can either escalate or de-escalate the situation. Language goes straight to the emotional part of the brain, and it can trigger emotional hijacks. 

Be mindful of your tone and choice of words, ensuring that they remain respectful and empathetic. Clearly communicate your expectations while considering the impact your words may have on the other person. Aim for clarity, avoiding ambiguous or vague statements that may cause confusion or misunderstanding. Strive for a balanced approach that maintains professionalism while acknowledging the emotions involved. 

Remember, difficult conversations provide an opportunity for growth, understanding, and improvement. As leaders, our role extends beyond delivering difficult messages; it involves actively contributing to a supportive and inclusive workplace culture.  

I would love to know what has worked for you in the past! 

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About Anton

Anton has dedicated his working life to helping leaders to upgrade their mindset, upskill their leadership, and uplift their teams! With a focus on helps leaders to better lead under pressure. Anton is an entrepreneur, speaker, consultant, bestselling author and founder of The Guinea Group. Over the past 19 years, Anton has worked with over 175+ global organisations, he has inspired workplace leadership, safety, and cultural change. He’s achieved this by combining his corporate expertise, education (Bachelor of HR and Psychology), and infectious energy levels.

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