Life is full of difficult conversations. Telling a direct report that their performance isn’t up to par. Letting a teammate know that their comments in a meeting hurt you. Asking your manager for something you think you deserve but haven’t been getting. These are stomach-flipping, palm-moistening, sleep-thrashing kinds of discussions. But if they’re unavoidable, how do you get through them with grace?

What Makes a Conversation Difficult?

First, it’s probably worth figuring out what qualifies as a difficult conversation. It might be difficult because it’s…

Difficult to Say

You know you’ll feel awkward or uncomfortable delivering the message. Perhaps you’ll be more candid or vulnerable than usual, and you’re worried you’ll ramble, obfuscate, get upset, or feel like puking the whole time.

Difficult to Describe

You don’t quite know how to parlay the message you want to send. The idea is a bit nebulous, or you don’t have the right words and are anxious about how to frame the issue. You imagine yourself fumbling your words, being ambiguous, and not landing your point.

Difficult to Hear

You expect the message you deliver to upset the person receiving it. It might cause self-doubt, hurt their feelings, or disrupt your relationship. You imagine the other person’s devastated face or deflated demeanor.

Difficult to Defend

You think the person might attack you in response. They might get angry, yell, or say vicious things about you (to your face or behind your back). You can think of a dozen ways that saying something could make things worse instead of better.

Difficult to Anticipate

You aren’t sure how the conversation is going to go. You don’t necessarily think it will be terrible, but the fact that it’s unpredictable is enough for the noisy narrator in your head to convince you that you should be nervous.

Difficult to Win

You aren’t confident that broaching the issue and making your case will work. You’re worried you will spend relationship capital and have nothing to show for it. Or worse, that you’ll burn bridges or erode trust. You won’t have another move after this one. Checkmate.

What else makes a conversation ‘difficult’ for you? Tell me in the comments.

How to Get Ready for a Difficult Conversation

You can take a few steps to prepare for a difficult conversation. Investing the effort will put you in the best position to maximize the positive outcomes of the discussion while minimizing the downsides. Spend a few minutes to work through each of these steps. If there are any that you can’t honestly say you’ve completed, consider holding off on the conversation until you do.

Clarify Your Message

Start by thinking about what it is you want to say. Are you sharing feedback? Asking for something? Raising a concern? Are you expecting the person to do something in response? If so, what?

Now, go one layer deeper. Why do you feel it’s important to share this message? Why now? Who will benefit? Does answering these questions lead you to a new understanding of the core message you want to deliver?

Articulate what you hope to achieve—for you, them, the team, and the business. Can you point to anything meaningful that will be better after the conversation, or are you just getting something off your chest?

If you’re not clear on your message and why it matters…WAIT.

Prepare Concrete Examples

Next, think of examples to help the person understand what you mean. Was there a specific piece of work they did that you’re reacting to? What about it left you feeling the way you feel? Your goal here is to find examples the person will remember and describe them in a way that will ring true to them.

If you can’t come up with any examples or describe them objectively, it might be better to wait before delivering your message. In that case, pay attention for the next little while and see if you can find an example of what you’re trying to describe.

Alternatively, ask someone you trust to help you. “I feel Sara doesn’t value my ideas, but I don’t want to say anything if I’m just imagining things. Have you seen examples that could explain what I’m feeling?”

If you don’t have a concrete example…WAIT

Interrogate Your Feelings

Now that you’ve been thinking about the issue, check in with how you’re feeling. Are you angry, sad, anxious, or offended as you reflect on the subject? Where are you feeling it? Are your thoughts spiraling, is your pulse racing, are your palms sweaty, or stomach lurching? Grab an emotion wheel and see if you can pinpoint an emotion more specifically than anger or sadness.

It’s okay to have a difficult conversation while feeling heightened emotions. It’s risky to have it if you aren’t aware of what those feelings are or how they affect your ability to have a rational discussion.

If your feelings are still overwhelming your thinking…WAIT

Test Your Story

You’ll notice now that what you’re feeling is directly related to what story you’re telling yourself about the situation and their behavior. What is that story? What are you assuming about their intent? How might their intentions have been different from their impact?

Consider alternative plot lines, especially ones where they aren’t the villain, and you aren’t the victim. My book, You First, has a chapter called Start with a Positive Assumption. Changing the door through which you enter the conversation can change everything. You want to have a difficult conversation, not a fight.

If you’re not ready to start with a positive assumption…WAIT

Write a Happy Ending

One of the more uncomfortable situations to find yourself in is being on the receiving end of a difficult conversation where the person just dumps their negative feelings or feedback on you with no guidance about how they want things to be different. Don’t be that person.

Before you share your difficult message, have a picture in your head of what you would like the person to do as a result. Are you asking for an apology, looking for different behavior, or asking them to accept your decision? What would be a good outcome? What would be fantastic? What’s the minimum that would be acceptable to you?

If you don’t know what you’re asking for…WAIT

Set the Scene

One last set of things to consider before having a difficult conversation—who, when, where, and how.

Who should be present for the conversation? Is it a one-on-one discussion with an individual, or are there others involved who need to be present? If multiple people are involved, do you need to speak with each separately before bringing everyone together?

When is a good time for the conversation? Are there days of the week or month when there is enough time to be measured and calm? What else is going on that’s creating stress that might intensify the conversation?

Where would be a good place to have the conversation? Can you find privacy somewhere in the office? Is there a spot where you can sit in parallel to reduce the intensity of too much eye contact? Where could you go so that if either of you get visibly emotional, you could exit without being seen?

How should you have to have the conversation? Are you remote from the person you need to talk with? Is this a situation for a video call, or could you revert to the relative intimacy and safety of a phone call?

You’ve gone to all the effort of preparing what you want to say; now make sure you’re equally deliberate about who, when, where, and how to foster a productive dialogue.

If you don’t have the right moment or the right spot…WAIT.

If you’re raising uncomfortable issues regularly, you’ll find that problems can be addressed before they rise to the level of a difficult conversation. But if you find yourself in a situation where the only option is to have a difficult conversation or get into further conflict debt, choose difficult conversation. Put the pieces in place to ensure you’re ready for a constructive discussion. In my next post, I’ll share some techniques to use while you’re in the middle of a difficult conversation.

Additional Resources

Pay Off One Conflict Debt in Your Life

How to Have an Uncomfortable Conversation Remotely

How to Tell if Your Work Conflict is Healthy