Let’s be honest—most of us would rather avoid tough conversations. They’re uncomfortable, unpredictable, and can stir up emotions we’d rather not deal with. But in business, dodging these discussions doesn’t just keep things "easy"—it holds companies, teams, and individuals back.
I’ve been on both sides of these conversations. I’ve had to lay people off, deliver difficult feedback, and even check in with someone on their last day when it felt like there was nothing left to say. Every time, I’ve learned that avoiding the conversation is always worse than having it.
Why Do We Avoid Tough Conversations?
Before diving into how to handle these conversations, it’s important to check in with ourselves first. What makes this conversation feel tough?
Are we afraid of damaging a relationship?
Do we feel unprepared or out of our depth?
Is there an emotional or high-stakes element that’s making it personal?
This self-awareness is critical. If we don’t understand why we’re hesitant, we won’t be able to show up fully when the moment arrives.
The book Crucial Conversations describes high-stakes discussions as moments when emotions run strong and opinions differ. And yet, these are the exact moments when clarity, honesty, and courage are most needed.
The Cost of Avoidance
When leaders and teams avoid tough conversations, the damage is real:
A struggling employee doesn’t get the feedback they need—until it’s too late.
Unspoken tensions create a toxic work culture that festers.
Damaged relationships that take time to rebuild—and in some cases, may never fully recover
Every conversation we avoid becomes a barrier to progress.
Real-World Tough Conversations (and How to Handle Them)
1. Letting Someone Go with Respect
Laying someone off or terminating their employment is one of the hardest things a leader has to do. It’s tempting to distance ourselves emotionally, but people remember how they were let go just as much as the fact that they were.
How to approach it:
Be prepared for their emotional response and give them space to have it—as long as it is safe for you.
Be direct and clear—this is not the time for ambiguity.
Offer next steps, even if it’s just a moment of human empathy.
2. The Last-Day Check-In
It’s easy to avoid a departing employee on their last day - especially if their exit wasn’t ideal - trust me, I know. But those final moments matter. I’ve seen situations where a leader ignored someone on their way out the door, and that bitterness spread to the rest of the team.
How to approach it:
Simply check in; start by asking how are you doing?
Ask if they have any outstanding questions or if there is anything they need from you on their way out.
If appropriate, ask for honest feedback—what worked, what didn’t?
Provide a space for them to share any thoughts or concerns.
Even if the departure was complicated, a respectful send-off keeps the door open for the future.
3. Giving Honest Performance Feedback
We tend to sugarcoat feedback, thinking we’re being kind. In reality, holding back keeps people from growing.
How to approach it:
Start with curiosity: What’s your perspective on how this is going?
Use the STAR method (Situation, Task, Action, Result) to provide clear, structured feedback.
Focus on observable behaviors: Instead of saying, "You are lazy," say, "You have been unprepared for several meetings, and I need you to have your updates ready."
Frame it as an opportunity for improvement, not a personal failure.
And always ask how you can help them be successful.
Leading with Courage
The best leaders aren’t the ones who avoid conflict; they’re the ones who step into it with clarity, respect, and a willingness to listen. If you find yourself avoiding a tough conversation, ask yourself:
What’s at risk if I don’t have this conversation?
How can I approach this with honesty and empathy?
What would I want if I were on the other side?
Business success isn’t just about strategy and execution—it’s about having the courage to have the conversations that matter.
Are you avoiding a conversation right now? If so, take a moment to reflect—what specifically is making you hesitate? Is it fear of conflict, uncertainty about the outcome, or concern about the other person’s reaction? Acknowledge these feelings, but don’t let them be the reason you stay silent. Progress, trust, and growth come from stepping into discomfort and choosing to engage.
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