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How to Have That Conversation You’ve Been Avoiding

October 23, 20253 min read

We all have that conversation we’d rather not have. Maybe it’s a direct report who’s underperforming. A peer who keeps stepping over boundaries. Or a manager who consistently overlooks your contributions.

The problem? Avoiding it doesn’t make it go away. In fact, silence often makes the issue worse. Left unaddressed, frustrations build, trust erodes, and what could have been a manageable conversation grows into a much bigger challenge.

The truth is: courageous conversations are a cornerstone of effective leadership. And when handled with intention and empathy, they don’t damage relationships—they strengthen them.

🔍 Why We Avoid Tough Talks

If you’ve ever postponed a difficult conversation, you’re not alone. Leaders at every level fall into this trap. Why?

  • Fear of conflict. We’d rather keep the peace than risk confrontation.

  • Fear of damaging relationships. We worry that being direct will create tension we can’t repair.

  • Fear of being misunderstood. We don’t want our intentions to come across the wrong way.

But here’s the reframe: avoiding tough talks isn’t kindness—it’s avoidance. And over time, avoidance costs more than discomfort. High-performing leaders learn that addressing issues directly, respectfully, and early is an act of integrity.

🎯 The “CARE” Framework

When you feel the weight of a conversation you’d rather not have, use the CARE Framework to guide you:

1. Clarify the Issue

Don’t go in vague. Be specific about the behavior or situation that needs to change. Instead of saying, “You need to do better,” say, “I’ve noticed deadlines slipping over the past three projects, and I’d like to understand what’s going on.”

2. Ask for Perspective

Conversations are two-way streets. Before you lead, listen. Give the other person space to share their side—there may be factors you’re unaware of. This step shifts the dynamic from confrontation to collaboration.

3. Respond with Empathy

Acknowledging someone’s feelings doesn’t mean you excuse poor behavior. It means you respect their humanity. A statement like, “I hear that you’re feeling stretched thin, and I want to work with you on this,” balances compassion with accountability.

4. Establish Next Steps

Don’t leave the conversation hanging. End with clarity. Agree on a plan forward—whether it’s resetting expectations, offering support, or outlining consequences. Accountability is what makes conversations stick.

💡 Client Story

Monica, a senior operations director I coached, had been avoiding a conversation with a toxic high performer who disrupted team morale. She feared addressing the issue might drive him out—or worse, spark backlash.

Together, we worked through the CARE framework. Monica clarified her concerns, gave the employee room to share his perspective, responded with empathy, and set clear expectations for change.

The result? To her surprise, the employee didn’t quit—he adjusted his behavior. Within weeks, tensions eased, collaboration improved, and the team’s productivity rose by 20%.

What Monica once saw as a risk became a turning point in her leadership confidence. She not only solved the problem—she proved to herself that she could lead with both courage and compassion.

💬 Final Word

The conversations you’re avoiding might be the very ones that change your career. Hard conversations are never comfortable, but they are powerful catalysts for growth—for you and for those you lead.

Each time you step into discomfort with clarity and empathy, you not only resolve problems—you strengthen trust, credibility, and influence.

The leaders who thrive aren’t the ones who avoid conflict. They’re the ones who face it head-on and transform it into opportunity.


difficult conversationsconflict resolutionworkplace communicationleadership courageconstructive feedbackiPropel You
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Coach Tamara

Coach Tamara Williams, CEO of iPropel You, is an author, renowned career strategist, and executive coach dedicated to empowering ladder climbers to cultivate their professional brand, navigate their journey, and elevate their leadership in career, business, and life to new heights. 7K+ propelled in 25+ countries since 2015.

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