How to Have the Conversations You’ve Been Avoiding

Most of us don’t wake up eager for a difficult conversation. By their very nature, these conversations can feel uncomfortable, challenging, and awkward. You’ve likely faced one you dreaded, put off, or avoided entirely, whether with a partner, a child, a family member, a friend, or a colleague.

My own strategy for a long time was to avoid them altogether. I chose to ignore and override, letting things silently burn in the background. Or I’d show up so emotionally invested and determined to resolve everything in one go that I’d leave the conversation feeling drained, disappointed, and no closer to resolution. Neither approach worked.

The reality is that many of us were never taught how to have these conversations effectively. We may find ourselves negotiating internally: Is this worth bringing up? Should I let it go? Can I let it slide? We fear making things worse, damaging relationships, or rocking the boat, so we choose to stay silent instead.

But when we leave issues unaddressed, they rarely disappear. Instead, tension and conflict are likely to build. Avoiding difficult conversations entirely can lead to a breakdown in communication and trust and possibly even resentment.

Hard Conversations Are Often Worth the Effort

Difficult conversations matter because there’s usually something meaningful at stake that we deeply care about: a valued relationship, a workplace dynamic, team trust, or a chance to repair an unresolved issue. Yet we tend to focus more on the discomfort of the moment rather than the potential benefits of having the conversation.

I invite you to think about a difficult conversation you might need to have and ask yourself: What might happen if I have the conversation? And what might happen if I don’t?

When we create space for these hard conversations and take time to prepare, they can strengthen relationships, foster mutual understanding, and open the door to positive change.

Whether you’re approaching a colleague about a conflict at work, having a talk with a loved one about a sensitive topic, or delivering feedback, there are strategies that can make a difference in how you approach and navigate these hard conversations.

How to Prepare: Before the Conversation

Preparing your mindset and using the 3 C’s can help you navigate these conversations with more steadiness and clarity:

• Confidence: Give yourself time to prepare. Ask yourself: What do I want to talk about? Why does it matter? What is the end goal? Ensuring that you know why the conversation matters, what you hope to preserve, address, or resolve, and what an ideal outcome would be helps you show up steady and grounded in your intention.
• Clarity: Be specific. What is the one thing you want to talk about? This is not the time for bringing up the kitchen sink or laundry list of every past grievance. If you’re still sorting it through, talk it out with a trusted person before stepping into the conversation. As the one and only Phil M. Jones, author of Exactly What to Say, says, “the worst time to think about what to say is when you’re about to say it.”
• Control: Set the parameters around the conversation. Choose a mutually agreed-upon time and place for the conversation that respects both people. The idea is not to spring it on the other person or drop into these big topics in passing. Try: “There’s something I want to talk to you about. When would be a good time for us to give it about 10 minutes?”

What to Do During a Difficult Conversation

Preparation matters, and so does how you show up in the moment. Here are some ways to stay focused, respectful, and effective during a difficult conversation:

1. Set the tone: Skip the small talk and start directly. There’s no need for a long preamble. Begin with something simple like, “Thanks for being willing to have this conversation,” or “I appreciate you showing up for this.” This shows that you respect their time. You don’t need to be rude, just honest and clear.
2. Normalize the discomfort: Difficult conversations are uncomfortable. Acknowledging that can actually help ease tension and make space for both parties’ feelings, fears, and needs. Try saying, “This might be hard to hear,” or “This isn’t easy to talk about.”
3. Use collaborative, forward-focused language: Inspired by the work of Jefferson Fisher, a trial lawyer, leading voice on real-world communication, and author of The Next Conversation, use phrases like “I need your help understanding this...” or “I’d appreciate your insight on...” This puts you on the same team and makes the conversation collaborative, not adversarial. Invite their perspective, insight, or help, and then really listen to find a way forward.
4. Practice active listening: Instead of trying to figure out what you will say back, focus on being present when they are talking and allow yourself a moment before responding.
5. Aim for a solution or decision: Even when emotions are high, a forward-focused tone signals your intent to move forward. Try saying, “I feel optimistic that we can solve this,” or “I’m hopeful we can make this better.” Work together on possible next steps and why they matter for both of you.
6. Know when to walk away: If the conversation becomes unproductive or the other person seems unskilled or more interested in arguing than resolving, it’s okay to press pause. Not every issue can be resolved in one sitting. Sometimes, walking away (or possibly involving outside support) is the healthiest and wisest choice.

Dr. Marshall Rosenberg’s work on nonviolent communication is also helpful for navigating difficult conversations in a healthy and productive way. I talked about this approach to effective communication in a previous post.

Final Thoughts

Hard conversations come with the territory of meaningful relationships and meaningful impact. They are part of the work on a personal and professional level. When approached with care and preparation, they offer opportunities for growth, trust, understanding, and even repair. We can actually strengthen relationships when we move through (rather than around) difficult conversations.

And while we may never enjoy these conversations, we can get better at showing up for them.