What Makes Difficult Conversations Work? A Leadership Perspective

One of the recurring themes I encounter in my coaching work with leaders is the challenge of having difficult conversations. These may be performance-related discussions, interpersonal tensions, or high-stakes decisions like restructuring or terminations. The situations vary—but in every case, the leaders are tasked with communicating effectively when the stakes are high and the discomfort is real.

There’s no shortage of excellent books or frameworks offering tools for these moments. Difficult Conversations (Stone, Patton, and Heen) and Crucial Conversations (Grenny et al.) are two I return to again and again. But my most meaningful learning has come from watching leaders in action. Here are five consistent things I’ve seen the most effective leaders do when approaching these tough moments:

They Set Clear, Controllable Goals

We all go into difficult conversations with hopes—maybe that the other person will understand, agree, or change. But those outcomes are outside your control. What is within your control is how you show up—calm, composed, and thoughtful—and what you say—concise, direct, and clear. Leaders who focus on their own role in the conversation tend to stay grounded and effective.

They’re Comfortable Saying Less—and Sitting in Silence

Difficult conversations often trigger a rush to explain, justify, or soften the message. But the most effective leaders know when to pause. They make their point, then stop talking. It’s uncomfortable—but it gives the other person space to process and respond. People can only take in so much, especially when they’re under stress. Keeping things simple and giving the other person time to absorb the message is a form of respect.

They Have a Way to Slow Things Down

When a conversation takes a turn—when someone reacts emotionally, challenges an assumption, or says something unexpected—you need a move to regain your footing. One helpful approach: acknowledge what was said and ask for time. A phrase like, “You’ve said a lot. I’d like to think it through before responding,” creates space for both people to gather their thoughts. Difficult conversations can feel intense, but they’re rarely actual emergencies.

They’re Clear About What’s Open for Discussion

Effective leaders are honest about what’s open to discussion—and what isn’t. If a decision has been made, don’t imply otherwise. Pretending there’s room for debate when there isn’t only erodes trust. At the same time, being clear about where input is welcome shows respect and fosters transparency.

They Take Time to Debrief

Even well-handled conversations can leave leaders feeling drained or unsettled. That emotional residue matters. Taking time to reflect—either on your own or with a trusted colleague—helps you restore balance and integrate what happened. This isn’t about second-guessing; it’s about resetting and offering yourself a bit of grace.

In Closing

Difficult conversations are part of leadership. Most of us will never love them—but we can grow to see their value. These conversations are where clarity, conviction, and credibility come through. Done well, they reinforce all three.

The good news? Like every part of leadership, success here depends far more on who you are—your presence and values—than on mastering a specific script or skill set.

What else have you seen that helps navigate tough conversations? What have you learned? I’d love to hear.

Coaching can be a valuable tool for leaders looking to grow their capacity to lead with intention—especially when it comes to how they show up in moments that matter. If this feels like the right time to do that kind of work, let’s talk.

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