Difficult Conversations Are the Work

One of the most persistent myths in leadership is that experience makes difficult conversations easier.

It doesn’t.

What experience does give you is clarity about what is at stake, and that awareness can make the weight of the conversation even heavier.

Over the course of my leadership career, I have had to engage in many difficult conversations. The kind that sit with you before you fall asleep. The kind that replay themselves in your head on the drive home. The kind where you know there is no version of the conversation that ends with everyone feeling satisfied or relieved.

Even now I am facing a difficult conversation, knowing it will be hard but also that not having it will create lasting discomfort.

These are not moments leaders seek out, but they are moments that shape schools, businesses, organizations, even families.

Difficult conversations are not interruptions to leadership.
They are the work of leadership.

Why These Conversations Feel So Hard

Most difficult conversations are not hard because we do not know what to say. They are hard because we care about people, about relationships, about the culture of the organization, and about the long-term impact of our decisions.

They are hard because:

• Power dynamics are real.
• Emotions are involved.
• The outcomes matter.
• Avoidance feels safer in the short term.

But avoidance always sends a message, and often it is not the message we intend.

When leaders delay or soften conversations that require clarity, the cost is rarely neutral. Confusion grows. Resentment festers. Others carry the weight of what goes unnamed. Over time, trust erodes, not just in the leader but in the system itself.

The Trap of Wanting It to Go Well

One of the most important lessons I have learned is that the goal of a difficult conversation cannot be for it to “go well.”

When that becomes the goal, leaders often:

• Over-explain
• Over-apologize
• Soften language until meaning is lost
• Take on responsibility that is not theirs to carry

A difficult conversation does not need to be comfortable to be ethical.
It needs to be clear, grounded, and fair.

That shift, from hoping a conversation goes well to committing to staying steady and speaking truthfully, changes everything.

What Steady Leadership Looks Like in Hard Conversations

When I reflect on the most difficult conversations I have had to lead, I notice that steadiness matters far more than eloquence.

Steady leadership in difficult conversations looks like:

• Regulating your own emotions before entering the room
• Being clear about the purpose of the conversation
• Naming observable behaviours rather than interpretations
• Holding boundaries without defensiveness
• Resisting the urge to convince, rescue, or repair in the moment

It also means accepting something that can be deeply uncomfortable. You cannot control how the other person receives what you say.

Your responsibility is not to manage their reaction.
Your responsibility is to speak with integrity.

Separating the Person from the Impact

In schools, the context in which I lead, we work with people who care deeply. Harmful actions are often not rooted in malice, but that does not make their impact any less real.

One of the most important distinctions leaders must learn to hold is the difference between intent and impact. When leaders avoid naming impact because they fear damaging relationships, the harm does not disappear. It simply shifts elsewhere, often onto colleagues, students, or the broader culture of the school.

You can translate that into any context in which you lead. Because as leaders, we care about the people we serve.

Naming impact is not an attack.
It is an act of responsibility.

It requires leaders to sit with discomfort long enough to let clarity emerge.

Why Structure Matters

In emotionally charged situations, relying on instinct alone is risky. When emotions run high, thinking narrows. Words get tangled. The conversation drifts.

That is why I no longer walk into difficult conversations without first slowing my own thinking down.

Before engaging, I ask myself:

• What exactly is happening, not what I feel is happening?
• What is within my role and responsibility to address?
• What outcome am I actually hoping for?
• What boundaries need to be named, even if they are hard to hear?

This kind of preparation is not about scripting the conversation. It is about grounding it. It helps leaders stay anchored when emotions surface, both theirs and the other person’s.

Perhaps most importantly, it allows leaders to leave the conversation knowing they acted with integrity, even if the outcome is painful or unresolved.

A Final Thought for Fellow Leaders

If you are avoiding a conversation right now, I do not judge you. I understand it.

But I would gently invite you to consider:

• What is the cost of not having this conversation?
• Who is carrying the weight of what remains unsaid?
• What kind of leader do you want to be in this moment?

Difficult conversations will never stop being difficult.
But when we approach them with steadiness, clarity, and care, they become moments of leadership that matter, even when they hurt.

Sometimes, the bravest thing a leader can do is stay present, speak honestly, and trust that steadiness will carry them and their community forward.

So, how do you prepare for a challenging or difficult conversation?