Preparing for Difficult Conversations

Confronting performance problems, giving tough feedback, being candid about smoldering conflicts, delivering bad news: these are the impending conversations that keep you up at night, or that you wake to in the morning. They occupy your mind while you’re trying to do other work. You wonder, “How am I going to bring it up?” Your mind makes movies about what will happen, with you in the leading role: confident, wise, compassionate, firm. But at the end of each film, you still feel uncertain about how you’ll break the news in reality, and how you’ll deal with the other person’s reactions. When you finally do bring it up, you still feel unprepared. Things rarely go as you expect; it’s a wild ride with an uncertain ending.

If you are reading this in hopes of finding the silver bullet for difficult conversations, you won’t find one, because there isn’t one. No magic words will make the conversation easy or end happily ever after. But not saying anything simply makes things worse—and blurting things out can leave a bloody trail to clean up later. What makes the biggest difference is how you get your mind and your words ready for the conversation. With thoughtful preparation and three simple but powerful actions, you can raise difficult issues directly and create a playing field where they can be resolved in a professional way.

  • Manage your self-talk.
  • Speak objectively about behavior and consequences.
  • Listen more than you talk.

Manage Your Self-Talk
Heading into this conversation, unbeknownst to you, your self-talk has been hard at work. It has been planting ideas about how difficult this will be to bring up, showing you special previews of how badly the other person will react, even telling you how right you are to be indignant about what’s happening. It’s also been keeping you up at night and waking you up in the morning. Left to its own devices, self-talk feeds the fire of anxiety about difficult issues, and trains your mind to expect the worst—to the point of creating a self-fulfilling prophecy.

It’s time to manage your self-talk instead of having it manage you.

The first step of managing self-talk is to be aware of it. It’s talking to you all the time—even right now. Maybe you can hear the little voice in your head saying, “What do you mean talking to me all the time? What do you mean, right now?” It’s the voice that says to you as you look in the mirror, “Whoa! Look at that white hair!” or “You really shouldn’t have had that ice cream sundae last night.” And regarding difficult conversations it’s feeding all your fears, mumbling, “If you say that, no one’s going to think you’re a nice guy” or “Don’t rock the boat; who knows what will happen?” or “I can’t say that. I’ll just blow it.”

To manage your self-talk in difficult conversations, start by looking at all the potential impacts of the conversation—not just the negative ones. Sure, the worst could happen, but so could many other things. What positive things could come out of this conversation? What’s a likely outcome? What will happen if you don’t speak up? The conversation could ruin the relationship, but having the conversation may ease your stress about this issue. It might improve the relationship. Perhaps things will change for the better as a result. Nothing will happen unless you do say something and handle yourself well.

Also ask yourself, “What is my goal for the conversation?” Training your mind to focus on the positive or achievable results, in a clear-sighted, realistic way, will help you find that target in the conversation.

Then, weed out the negative self-talk whenever you hear it and replace it with constructive self-talk. If your self-talk is telling you, “If I say this, everyone is going to think I’m the bad guy,” you can say to yourself, “I can’t control how other people react but I can control my part of the conversation so that I’m professional.” Or if it’s telling you, “I can’t say that. I’ll just blow it,” you can say to yourself, “I can manage this conversation; I have some tools for handling the situation constructively.”

Put yourself in the right frame of mind before you have the conversation. Then think through what you’ll say, and how you’ll respond to the other person by listening.

Speak Objectively About Behavior and Consequences
People in difficult conversations get off track for two reasons. First, they don’t speak objectively about the situation: “You’re not being a team player…” “You don’t have a sense of urgency…” Vague statements will take you off into the weeds. If you say, “You’re not being a team player,” the other person could respond: “What do you mean I’m not a team player? I stayed late for a week to do my part of the work—no one else did that!” Now the other person has taken the focus of the conversation and you’re no longer talking about your concerns. You haven’t explained what the problem is, or what needs to be different.

Pave your way through a difficult conversation with specific facts, observations, and behaviors. Before you raise the issue, be clear about what you’re seeing and experiencing. Someone can only guess what it means to be a “team player.” Explain what leads you to that conclusion: being absent from team meetings, submitting work later than targeted dates, communicating deadline delays to a few people rather than to the entire team, not responding to email requests from team members.

While these behaviors are blindingly obvious to you (and, you would hope, to the other person), they are still worth saying out loud. They’re difficult to argue with because they are factual. Most people prepare for difficult conversations by hoping that the other person won’t react defensively. Expect the other person to respond defensively, and you’ll be better prepared to handle it. Speaking objectively, rather than saying what you feel like saying, will minimize defensiveness in the other person. And, focusing on facts and behaviors helps you keep your cool.

Now you have a clear statement of the problem. There’s only one thing you’d want to add to that statement: what is the consequence of the problem? It might be: “I didn’t have the information I needed to discuss our progress in my meetings to senior management.” It’s hard for the other person to say, “So what?” to that while it communicates the seriousness of the issue.

As the Victorian author and salon host Dorothy Nevill once said, “The real art of conversation is not only to say the right thing at the right moment, but to leave unsaid the wrong thing at the tempting moment.” Now that you’ve determined the right thing to say, and what to leave unsaid, it’s time to listen.

Listen More than You Talk
People also go off road in difficult conversations when they talk more than they listen. Once you’ve made a clear statement of the problem and the consequence, stop talking and start listening.

You won’t want to listen when you have spent a lot of time thinking about this issue and have strong feelings about it. You’d rather lecture the other person about it. The trouble with lecturing is that the other person has just as much to say about the issue as you do. The minute you start talking, the other person will want to respond and they stop listening to you. Even if you’re right, you’ll get through the conversation more efficiently, and with less strife, when you stop talking and start listening. How then can we get our minds to listen when least want to?

One way to remind yourself to listen is to invite the other person to respond after you make your simple objective statement about the problem and the consequence. Asking, “Can you help me understand what’s going on?” or “What’s your perspective on this?” gives the floor to the other person and saves him or her the effort of trying to wrest it from you.

While the other person is talking, set aside your agenda so you can understand that person’s perspective. You may not agree with it or respect it, but you can’t even know what it is until you’ve listened to it. Too often in the heat of battle we think we know what other people are saying and thinking—in fact, we’re sure of it—but we aren’t listening. Don’t plan your response by trying to anticipate what other person is going to say.

Instead of planning how you’ll counter, try to summarize the other person’s response to you. Say, in a neutral tone of voice, “You think…” or “You feel…” or “From your point of view…” Keep listening until the other person is done speaking. You can tell when the other person feels heard because he or she stops talking. You may see the other person’s facial expression or body relax.

Listening during difficult conversations has an added benefit. When people feel heard, their minds open and they are ready to hear what you have to say. Before they reach that point of feeling heard, you make the situation worse by trying to persuade them of your point of view. They can’t listen when they need to talk. If you can have enough self-control to listen while they talk, they’ll eventually calm down enough to hear your perspective. You will get your chance to talk and be heard; you earn it first by listening.

Sometimes you may find yourself raising a difficult issue and forgetting to listen or speak objectively. If you find yourself in the middle of a messy conversation, remember the Turkish proverb, “No matter how far down the wrong road you’ve gone, turn around.” When you’re down that wrong road in a difficult conversation, the best way to turn around is to start listening. Then clean up your speaking by focusing on behaviors, observations, and facts. But don’t cling to them in a righteous way; you’ll never get out of the weeds unless you keep listening.

Eventually, if you can manage your self-talk, speak objectively, and listen, you’ll be on the road to problem solving. The fear of the conversation will no longer haunt you and you’ll have achieved some productive outcomes.

“First we make our habits, then our habits make us,” said poet and playwright John Dryden. Self-talk, speaking objectively, and listening are habits that will help you pave your way through these difficult conversations. You will not only be better able to manage the stress you feel in preparing for the conversation, you’ll keep the conversation on the right road.

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