HOW TO INITIATE A DIFFICULT CONVERSATION: A Guide for Senior Leaders

There are few moments in leadership more defining than the conversations we would rather not have.

Whether it is addressing underperformance, navigating a shift in role, or delivering news of redundancy, having difficult conversations with your people is part of the job. But they are also an opportunity. Handled well, they can build trust, clarify expectations, and even strengthen relationships.

Handled poorly, or avoided altogether, they can erode culture, damage morale, and leave people feeling disrespected or blindsided.

So how do you lean into these moments with clarity, confidence and compassion?

Let’s explore a practical approach, drawing on the insights of Simon Sinek, Jefferson Fisher and Mel Robbins [1][2][3].

1. Start with the Why (and the Who)

Simon Sinek’s now-famous mantra, Start With Why, is not just for TED Talks and brand strategy. It is a powerful lens for leadership communication.

Before you step into a difficult conversation, ask yourself:

Why does this conversation need to happen?
Who is this really about?
What outcome am I hoping for?

If your intent is to punish, prove a point or offload frustration, pause. That is not leadership. That is reaction.

But if your intent is to support growth, uphold standards or lead through change with integrity, then you are on the right track.

As Sinek puts it, “Being uncomfortable is part of being human.” Avoiding discomfort does not make it go away—it just delays the inevitable and often makes it worse [4].

2. Lead with Empathy, Not Authority

It is tempting to default to position power, especially when the stakes are high. Jefferson Fisher reminds us that “your tone carries more weight than your words” [5].

People don’t remember every detail of what you said. They will remember how you made them feel.

Mel Robbins adds that empathy is not weakness—it is leadership. She encourages leaders to “acknowledge responsibility upfront” to level the playing field and reduce defensiveness [2].

You might say:

“This is not an easy conversation to have, and I appreciate you being here.”
“I want to talk about something that matters, and I want to do it respectfully.”
“Please be patient with me as I try to get this right.”

These small openings can lower defences and create space for real dialogue.

3. Use the FBI Framework

Sinek recommends a simple structure for difficult conversations: Feelings, Behaviour, Impact.

Let’s say you need to address a conduct issue. You might say:

“I was a bit concerned when I saw how the team meeting unfolded yesterday. The way you responded to the feedback came across as quite dismissive, and I feel like it impacted the team’s willingness to speak up.”

This approach reduces the blame and focuses on observable behaviour and its consequences. It also invites reflection rather than resistance.

4. Ask, Don’t Assume

One of the most powerful tools in your leadership toolkit is a well-timed question.

Jefferson Fisher encourages leaders to “ask questions that invite reflection, not defensiveness” [5]. Mel Robbins reinforces this by advocating for open-ended questions that deepen understanding and connection [3].

Try:

“How are you experiencing this situation?”
“What do you need from me right now?”
“What would help you move forward?”

These questions signal that you are not here to lecture, you are here to lead. And leadership is a two-way street.

5. Name the Tension, and Then Lean Into It

Sinek advises leaders to acknowledge discomfort upfront. It might sound like:

“This is going to be a tough conversation, and I want to be honest with you.”

Naming the tension does not make it worse. It makes it manageable. It gives the other person a moment to breathe, to prepare, and to meet you in the space with a little more openness.

Avoiding the tension only amplifies it.

6. Be Clear, Not Cruel

Clarity is kindness. Vagueness is not.

Mel Robbins emphasises the importance of being clear and concise. The clearer your message, the less room there is for misinterpretation [3].

If someone’s role is changing, tell them what is changing, why, and what support is available. If a redundancy is on the table, do not sugar-coat it. Be direct, be human, and be prepared to sit with the emotional weight of the moment.

You don’t need to have all the answers. But you do need to be honest.

7. Hold the Space, Then Close the Loop

A difficult conversation is not a one-and-done event. It is a moment in a longer journey.

Make space for the other person to respond. Listen without interrupting. Resist the urge to fix or defend. Just be present.

Mel Robbins reminds us that active listening is not passive—it is powerful. Maintain eye contact, avoid interrupting, and validate their experience [3].

Then, follow up. Send a note. Schedule a check-in. Keep the door open.

As Fisher says, “The goal isn’t to win arguments—it’s to understand and be understood” [5].

Final Thoughts

Difficult conversations are not a sign of failure. They are a sign that you care enough to engage.

They are not about being right. They are about being real.

And they are not just a test of your leadership—they are a chance for you to model the kind of culture you want to build: one where honesty, respect and accountability are not just values on a wall but lived experiences in every conversation.

Mel Robbins often says, “Communication is your hidden superpower.” [1] Use it wisely. Use it bravely. And use it to lead with both courage and compassion.

Are you ready to take the next step in your leadership journey?

Let’s chat. Reach out to The Workplace Coach today and explore how coaching can elevate your leadership and help you start having real conversations with your people.

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