The Best Ways to Navigate Difficult Conversations

Although most of us would rather avoid them, there are solid ways to navigate difficult conversations.

This isn’t to say you won’t experience any nervousness or stress when engaging in them. Yet avoiding them altogether will never bring any resolution.

So if you’re determined to have that difficult conversation but feel wary, that’s understandable. It’s a difficult situation. But when done with mindfulness and intention, you’ll help the other person better understand your feelings. You might even improve the situation or relationship with them.

How to Navigate Difficult Conversations

First and foremost, prepare yourself for the difficult conversation.

Before going into it, arm yourself with an awareness of your intention. What is the purpose of the conversation? Do you have a goal or ideal outcome in mind? This first question is important because while you may have good intentions (i.e. educating a teen or making a deeper connection with a friend), it’s all too easy to descend into critical or condescending language. Focus on being supportive rather than punishing.

On the flip side, notice your assumptions about the other person’s intentions. Understand that just because you may feel belittled, ignored, or even intimidated in a conversation, that doesn’t mean the other person intended to make you feel this way. It could be that some old wounds are being unearthed or that you’re being triggered in some way. Stay aware of your emotional state.

In addition, what is your stance going into the conversation? If you’re anticipating a difficult or unsuccessful conversation, there’s a good chance this self-fulfilled prophecy will come to be. As much as possible, adjust your attitude so you’re not loaded for bear before you even start speaking.

Finally, really ask yourself about the other speaker. Are they aware there’s a problem? And if so, how do you think they’re seeing it? What sorts of needs or fears may they possess? Could there be common concerns the two of you share or are you seeing the other person as an opponent? This last question is key. If you’re seeing the other person as an opponent, you’re setting up for an argument that needs to be won rather than a productive conversation. Instead, consider them a partner with whom you’re trying to find common ground.

Once you’ve created this non-defensive stance, enter into the conversation with the following intentions:

1. Communicating Clearly and Directly

If you tend to falter in conversations, you may want to plan beforehand what you want to say. Gather up any facts you might need to back up your point of view.

Then, start by explaining your thoughts, feelings, and the ‘why’ behind them. Try to avoid sentences starting with ‘you’ and go with ‘I’ instead. For example, rather than saying, “You don’t care what I think,” you’d say, “I feel I’m not being heard, and that makes me sad.”

It’s also helpful if you can clarify what you hope to get from the conversation. Do you want an apology? An acknowledgment of your point of view? For them to behave differently? Be clear on this so you both know the direction of the conversation.

2. Practicing Empathy

You already know how you’re feeling. And it can be easy to get caught up in this. Especially if you’re hurt or vulnerable. It’s in these states where we most often jump to conclusions.

So try to remember that a difficult conversation isn’t always about you – even though it feels that way. When practicing empathy, you honor that the other person has his or her own point of view too. Consider whether you may have unintentionally done or said anything that upset them. Are there other things going on in their life that could be factoring into their behavior? Putting yourself in their shoes will help create an even playing field.

3. Deeply Listening

Never underestimate the value of deep listening.

With deep listening, you’re committed to REALLY understanding their point of view rather than formulating your response while they’re talking. You ask questions like, “Can you tell me more?” or “How do you feel about that?”. And you don’t talk over them.

Deep listening can help you see the situation from a new perspective while possibly learning something new about the other person. Plus, when you engage in deep listening, you’re more likely to get the same respect from the other person.

4. Knowing When to Take a Break

There will be times when you’re fully prepared and practicing empathy and deep listening, but the other person isn’t willing to do the same. If it feels safe to do so, you can encourage them to express their emotions so they can clear their slate. Or you might bring in a neutral mediator to help you both try to reach a workable outcome.

If you’re still not getting anywhere, then the best course of action is to step away from the conversation. Either the timing isn’t right, or the situation simply cannot be resolved. You can agree to disagree and move on.

Sure, this can be disappointing. But it’s important to choose which battles are worth fighting and focus on those. And by all means, give yourself credit for having the courage to start the conversation in the first place. Each time you do, you’re gaining valuable skills and increased confidence.