Having Difficult Conversations: A Leadership Coach’s Perspective

Having Difficult Conversations: A Leadership Coach’s Perspective 

By Mark Wager

As a Leadership coach, I often encounter leaders who struggle with difficult conversations. Whether it’s addressing a team member’s repeated tardiness or navigating a challenging moment in a personal relationship, these conversations are often avoided because of fear. Fear of confrontation, fear of worsening the situation, or simply fear of the unknown. Yet, every time we hesitate, the problem grows—not just externally, but within us. We build it up in our minds until it feels insurmountable. But here’s the truth: avoiding these conversations is the only sure way to guarantee a negative outcome. Sound familiar? Then read on.

Difficult conversations are not just about addressing problems; they are opportunities for growth, for understanding, and for building trust. As a Leadership coach, I’ve guided many through the art of tackling these moments with confidence. Here’s how you can do the same by following five transformative steps.

Step One – Be Honest with Yourself

True leadership begins with honesty—not just with others, but with yourself.

When you’re avoiding a difficult conversation, ask yourself why. Be brutally honest. Often, the reasons we give—“I don’t want to hurt their feelings” or “It’s not a good time”—are just rationalisations. At the core, we’re usually afraid of the conversation itself. We imagine the worst possible scenario, and that fear paralyses us. But avoiding the issue only creates a breeding ground for frustration and resentment.

As a coach, I’ve seen this time and again. When my clients finally confront the truth—both with themselves and others—they realise the conversation wasn’t nearly as difficult as they feared. By facing the issue head-on, they unlock their potential as a leader, becoming the person they were always meant to be.

Step Two – Take Ownership of the Issue

Empowerment comes from taking control of your life, your actions, and your conversations.

One of the most empowering moments in leadership is when you realise that you are responsible for addressing the challenges in your life. It’s easy to point fingers, to blame circumstances or other people for our difficulties. I once had a client who was frustrated with his team’s performance. He blamed them for lacking initiative, but after we explored the situation together, he realised that the problem wasn’t just with his team—it was with how he communicated his expectations.

When we take ownership of an issue, we reclaim our power. We stop being victims of our circumstances and start becoming leaders of our destiny. As a coach, I often ask, “What are you allowing in your life that’s contributing to the problem?” Once you take ownership, the solutions will start to present themselves.

Step Three – Don’t Assume the Other Person’s Intentions

The most effective leaders know that assumptions create barriers to understanding.

In leadership, one of the greatest mistakes we make is assuming the intentions of others. We think we know why someone is behaving in a certain way, and we jump to conclusions before even having the conversation. In my coaching sessions, I see new managers fall into this trap frequently. A manager might assume that a staff member’s chronic lateness is due to a lack of respect or a bad attitude, but without asking the right questions, they never uncover the real reason.

Instead of assuming, approach the conversation with curiosity. Explain your observations, express your concerns, and allow the other person to explain their perspective. More often than not, you’ll be surprised by what you learn. As a leader, your goal should always be to create understanding, not to impose assumptions.

Step Four – Explain the Problem Clearly

Transformation begins when people understand the impact of their actions.

Once the conversation starts, clarity is key. Don’t dance around the issue or soften the blow too much—state the problem plainly, but respectfully. It’s important to articulate how the other person’s actions are affecting you, the team, or the organisation. Often, they haven’t even considered your perspective.

In leadership, this moment is crucial. I’ve worked with many clients who have been hesitant to express the full impact of an issue, but once they do, the other party gains new insight. If necessary, ask them to put themselves in your shoes. But remember, this is a process—change doesn’t happen overnight. As a coach, I remind leaders to be patient. If it were easy to see from someone else’s perspective, the issue wouldn’t have arisen in the first place.

Step Five – Work Together to Find a Solution

True leadership is about fostering collaboration, not imposing solutions.

Finally, once the issue is on the table, shift the focus from the problem to the solution. Leadership isn’t about dictating outcomes; it’s about collaboration. Share the responsibility for finding a resolution, and you’ll empower both yourself and the other person.

I always encourage my clients to adopt a three-part strategy. First, be open to all ideas, no matter how unconventional they may seem. Some of the greatest innovations come from ideas that were initially dismissed. Second, ensure that expectations are clear—everyone should understand what will happen if the issue isn’t resolved. Lastly, confirm roles and responsibilities. Both parties should leave the conversation knowing exactly who will do what moving forward.

The Courage to Lead Through Conversations

Leadership is not about avoiding the hard conversations—it’s about having the courage to confront them.

In my work as a Leadership coach, I’ve seen the remarkable transformation that occurs when leaders face difficult conversations head-on. These moments, as challenging as they are, create pathways to deeper understanding, stronger relationships, and more cohesive teams. By summoning the courage to have these conversations, you are not only addressing problems—you are shaping the leader you are destined to become.

Remember, every difficult conversation is an opportunity for growth. The key is to approach it with honesty, ownership, and a willingness to understand the other person. By doing so, you will not only resolve the issue but inspire those around you to follow your example.

Best of luck—and keep talking.

Ready to take your leadership to the next level? Whether you’re looking to overcome self-doubt, empower your team, or refine your leadership strategy, I’m here to help. Contact me today to discuss how personalised coaching can unlock your potential and transform your leadership journey.