6 Steps to Making a Hard Conversation Easier

We’ve all been there before. We know we need to have a sit-down conversation with the over-demanding boss, the flakey assistant, the meddlesome in-law, or the best friend who seems to have a knack for deflating our sense of joy. Or maybe the conversation we dread is with someone we have betrayed, someone whose trust we desperately wish to regain.



You can tackle those dreaded conversations with more ease in just six steps. As you read them, consider your default mode of communicating. Are you more passive (“I lose, you win”), more aggressive (“I win, you lose”), passive-aggressive (“We both lose because of lack of communication,”), or assertive (“We both win”)? Don’t judge yourself; our communication styles are complex and usually come from early conditioning and modeling from the adults in our lives. But knowing how you tend to communicate can be a great way to figure out what skills you already have, and which ones you want to develop from the list below.

1. Get clear about your intentions for the “hard conversation”.

Are you looking for clarity? Do you want the opportunity to share an important piece of information? Do you want a solution? Do you just want to be heard? Knowing what you want from the conversation will make it much more likely that you’ll ask for it, and possibly even get it!

2. Give up your “agenda” and be open to new solutions.

When we are curious and express our desire for solutions that benefit everyone involved, we don’t need to hold on so tightly to our particular way of doing things. This means that we can entertain possibilities we might not have previously even considered.

3. Listen more, talk less.

You think it’s hard for you to be having this conversation? Take a moment to empathize with the fact that it’s probably difficult for the other person, too. Show them that you want to know how they feel, what they think, and what they have to say. Give them plenty of space to respond, and listen without interruption, with curiosity and the desire to understand where they are coming from. Our judgments, fear, and self-righteousness can get in the way of really hearing another person’s truth. But when we listen, we prove to the other person that we can be trusted, and that a mutually beneficial solution is, indeed, possible.

4. Take responsibility for yourself and your actions.

Instead of bringing up a laundry list of everything the other person has done to hurt you, be accountable for your own thoughts, feelings, and behaviors. You are the only person in control of your experience, and blaming other people disempowers you. Instead, let yourself be vulnerable, and try to give the other person insight into what’s going on for you without pointing any fingers. This one can be hard, especially if we feel that the other person has harmed us in any way. Use language that shows you are fully owning your own part in the situation. This will invite more opportunities for cooperation, connection, and resolution.

5. Be grateful.

Remember, most people haven’t cultivated the skills to engage with difficult conversations, so it’s a big deal that you’re having one in the first place. So, congrats! Whether or not you feel it was constructive or if you want to have a follow-up with the other person, let them know how much you appreciate their time. You can even be transparent and say, “I realize this isn’t the easiest thing to talk about,” and honor the fact that they stuck with you during the conversation. Most of all, give yourself a pat on the back. You are stretching your comfort zone and learning to stay present and centered in some of the most challenging circumstances imaginable. That’s huge in and of itself!

6. Return to the scene.

At times, the experience of having a difficult conversation can be so cathartic that we forget it’s only the beginning of the process. You can’t just stop there! Whether or not you came to a conclusion about how you want to move forward, sit with the conversation for a while before you revisit it, first on your own and then in a follow-up talk with the other person (if they are open to it). How did your hard conversation go? Is there anything that still needs to be resolved? How do you feel about the issue, now that you have some distance from it? How can you apply these lessons to other areas of your life in ways that support your joy, confidence, and overall well-being?

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