How to Say the Hard Thing (Without Damaging the Relationship)
Five strategies to navigate difficult workplace conversations with clarity, compassion, and confidence.
Difficult conversations are inevitable in any workplace. People misunderstand one another, expectations get crossed, and conflicts naturally arise. Yet most of us were never taught how to have hard conversations—so we avoid them, delay them, or stumble through them in ways that create unnecessary tension.
For more than a decade, I’ve helped couples navigate some of the most emotionally charged conversations imaginable. If people can communicate clearly and compassionately in their marriages—where the stakes are high and emotions run deep—they can certainly do it at work.
Here are practical strategies you can use to say the hard thing without damaging the professional relationship.
1. Get Clear About Your Intention
You wouldn’t start a road trip without entering the destination into your GPS. In the same way, you shouldn’t step into a difficult conversation without clarity on your goal.
Ask yourself:
- Do I want us to walk away with a shared understanding of each other’s perspectives?
- Am I simply trying to provide missing information?
- Is my goal alignment? Awareness? Problem-solving? Closure?
When you enter the conversation with a clear intention, you stay grounded and avoid being pulled into emotional detours.
2. Let the Other Person Feel Heard First
Everyone—regardless of title, personality, or background—wants to feel heard.
The problem?
Most people enter these conversations overly focused on what they want to say and not at all focused on hearing the other person.
That creates defensiveness before the conversation even begins.
A better approach is to let the other person speak first. Try:
“Help me understand how you’re seeing this.”
Listen fully. No interruptions. No preparing your rebuttal in your mind.
When they’re done, you can say:
“Thank you for sharing that. I’d like to share my perspective as well—are you open to hearing it?”
Because you’ve modeled respect and listening, they’re far more likely to extend the same courtesy to you.
3. Be Direct (And Remember: Clear Is Kind)
When something feels hard to say, our instinct is often to soften it with extra words or circle around it indirectly. This is especially common for women who, generally speaking, tend to use more words to express the same idea.
But in difficult conversations:
More words usually equal more confusion.
You can be both direct and kind.
You can tell the truth without being harsh.
As Brené Brown famously says:
“Clear is kind.”
Say what needs to be said—simply, respectfully, and without unnecessary qualifiers.
4. Decide How You Want to Feel Walking Away
Before you enter the conversation, ask yourself:
“How do I want to feel when this is over?”
Maybe you want to feel calm, confident, supportive, grounded, or proud of how you handled yourself.
You may not be able to control the outcome, but you can choose the energy and intention you bring.
Holding this emotional goal in mind helps you regulate yourself and show up as the leader you want to be.
5. Know When to Stop
In difficult conversations, less is often more.
Once you’ve said what needs to be said:
- Don’t repeat yourself to “drive it home.”
- Don’t let your ego take over.
- Don’t fill the silence by over-explaining.
Say the thing, say it clearly, and then stop talking.
Silence can be a powerful part of communication—especially when the message is important.
Difficult conversations don’t have to damage trust or create tension. When you approach them with clarity, curiosity, and intention, they can actually strengthen relationships and elevate your leadership presence.
Saying the hard thing is part of the job.
Saying it well is what sets great leaders apart.
