Chapter 14

Conducting Difficult Conversations

Many of us find ourselves in professional situations when we believe someone has wronged us, just plain made us mad, or treated us badly. The advice often given by the experts in this book is to have the courage to have an honest conversation; air the grievance. No one can help you solve a problem if she doesn’t know you have it. But that’s easier said than done, right?

We’ve gathered advice from some of the world’s top thinkers on communication challenges in the workplace. If you have a strategy for difficult conversations before you need one, you’re far more likely to get through them successfully. Here’s how.

Why We Avoid Difficult Conversations

Why are we afraid to face a conversation even if it has the potential to make things better for us? It’s because we fear what we might lose more than we want what we might gain. “It goes to the nature of who we are as human beings,” says Cornell professor Jim Detert, who has researched why employees are often afraid to speak up in organizations. “We have deep financial, material wellbeing concerns. We have deep, deep social concerns. Fear of ostracism is one of the biggest fears humans have. At the deepest level, that’s why people are afraid to challenge their colleagues.” We fear so much: losing the respect of our colleague, spiraling out of control in the moment, being proven wrong, getting pushed aside or fired for not going along with the status quo. Detert also says that it’s human nature to disproportionately remember times we’ve spoken up (or witnessed someone speaking up) and it’s gone wrong, amplifying that fear.

It can be so overwhelming that many of us try everything we can to put it off or avoid it altogether. Some people would rather change jobs than actually attempt to directly confront a colleague or manager about something that’s bothering them. But “while it’s completely human to have a tendency to delay,” observes INSEAD’s Jean-François Manzoni, “a delay is largely unproductive. The dynamic gets worse. You think you’re hiding your aggravation, but you’re not. The other party will sense something’s wrong, and that’s probably not going to help.”

But if you find ways to navigate difficult conversations, your colleagues will come to respect your candor and your ability to work through a problem without making it personal. And when you conduct difficult conversations, you’re contributing to an environment where having hard talks, offering different points of view, and giving honest feedback are accepted—and that is better for everyone and for your organization as a whole.

How to Have a Productive Conversation

There’s no one-strategy-fits-all approach to challenging conversations, but there are guiding principles. The process should proceed in two phases: the preparation you do, if you can, to set yourself up for success; and then the navigation of the actual conversation. If the two of you aren’t able to work things out on your own, there may be organizational resources you can lean on.

Prepare

Although most people might focus on changing how they feel and act during a confrontation, Manzoni says it’s more important to prepare before you have the conversation. “My experience is that 75% of the battle is fought before you walk into the room,” says Manzoni, who has conducted extensive research on conflict management. The most effective things you can do, Manzoni says, are to manage your own state of mind and consider how you’ll frame the conversation. To psych yourself up for a difficult, but positive, chat, follow these guidelines.

Manage the timing.

You want to avoid delaying a difficult conversation just because you dread it, but sometimes choosing not to have it is the right call, says Jeanne Brett, director of Kellogg School of Management’s Dispute Resolution Research Center. If you’re so angry that you can’t control your emotions, you’re not in a good frame of mind for a discussion. “In the heat of the moment, it’s important to recognize ‘I’m in no emotional shape to have this conversation,’” she observes. You’ll say the wrong thing, embarrass yourself or your colleague, or create awkward scenes for others. In those instances, she advises, it’s wiser to take time to cool down. Walk around the building. Change your surroundings, and work in a small conference room or head home to work in peace there.

If your colleague confronts you in the hallway after a meeting or walks into your office ready to explode, Brett suggests you do whatever you can to put off the conversation. “I see that this is a problem, and I’d like to take some time to think about ways to resolve it. I promise I’ll come by your office tomorrow to discuss it.” Acknowledge your colleague’s feelings—“I can see you’re really upset about this”—and then ask whether you can set a time to talk when you’re both calmer. “It’s tough not to be defensive in such a situation, especially if you were caught off guard,” Brett advises. (For more on confrontations, see chapter 13, “Managing Conflict Constructively.”)

When you’re ready, find a good time to talk to your colleague. Not first thing on Monday when you’re both coming in to a full inbox. Not last thing on Friday when you’re eager for the weekend to begin. Instead, find a time and place that are least likely to add tension to the meeting. Right after lunch in a neutral conference room? Over coffee at the local greasy spoon? Avoid “turf” settings; inviting people into your office for a conversation gives you home field advantage, because it’s filled with your professional mementos, you’re the one sitting behind a desk (and usually in a larger chair, signaling your higher power), and so on, Detert advises. Ideally you’ll find a time and place where you’ll both feel up to working through a healthy conversation.

Manage your message.

What do you want your counterpart to take away from the conversation? You’ll have a better chance of being heard if you define your message and decide how you’ll convey it.

• Articulate your goal. Ask yourself what you’re trying to achieve with the conversation, suggests Manzoni. Does what you want make sense? Is it realistic? If not, let it go and set your sights a little lower.
• Identify a constructive frame. Considering how you’ll approach the conversation—literally what you’ll say and won’t say—will set you up to succeed. View it as a presentation: What information does your partner need to hear? Identify the key points you’d like to make, highlighting mutual benefits when possible.
• Consider your colleague’s point of view. Before (and during) the conversation, try to get a sense of what your colleague might be thinking. She made her choices or behaved in a certain way for a reason. What might that reason be? How might she respond to your approach? Also ask yourself whether there’s any other explanation for what’s bothering you. Is your take on the situation fair? Ask a colleague for his interpretation of the events to see whether your conclusions are reasonable. Paint the situation for him as neutrally as you can. Cataloging every fault and misstep will probably get you sympathy but not constructive feedback, so focus on the problem.

With your emotions and thoughts collected, and an appointment on the calendar, you’re ready to talk.

During the conversation

Whether your discussion happens unexpectedly or it’s something you’ve scheduled, these guidelines will help you as you conduct it.

• Make it two-way. Maintain the most positive, open, and constructive mind-set you can. “Don’t assume that the other party is unreasonable,” advises Manzoni. Walk into the room “as present in the moment as possible. Be prepared to listen to what is being said—or not being said.” If you have something to say that might not be easy for others to hear, recognize that there are other points of view, while presenting your thoughts as part of a conversation. In this way, people will be far more likely to hear you rather than shut down. According to Detert, using language that acknowledges that everyone’s view, including your own, is a “partial view”—such as “I understand the current thinking is X, but I’d like to share my view and hear yours”—is far more conducive to an open, nondefensive conversation.
• Focus on the problem, and not the personalities. You may feel as though someone repeatedly disrespects you, but just airing that isn’t likely to solve your disagreement. When you focus on the problem, and not the person, you’re less likely to get your colleague’s defenses up and so you’re more likely to have a good outcome. Camille may never read your reports even though you worked hard to write them well and on time, but the larger problem is that when she fails to read the reports, she isn’t up to speed on what your group is doing, and that could lead to conflicts or mistakes down the line. Highlighting the impact of her behavior is a better approach than telling her it annoys you: “I’m adding a lot of details that you might not be aware of in my reports to you. I’m concerned that if you aren’t finding time to read them routinely, then you and I aren’t in sync. Is there a better way for me to keep you informed?”
• Accept responsibility. Americans, in particular, says Brett, tend to want to point to factors beyond their personal control when something goes wrong: “Liam’s team never responded when I asked for updates.” But that’s the last thing any boss wants to hear. You’re more likely to infuriate him and suggest that you can’t handle responsibility. If you are part of the problem, say so up front. Even if it’s not really your fault, “own” the problem: “I know you wanted this to come in on budget, but I didn’t manage to make that happen.” Your boss may well be angry with the news—and in fairness, you have to allow him the opportunity to express that anger—but there’s little for him to stew on if you’ve clearly accepted responsibility and addressed concerns so that it won’t happen again.
• Propose solutions. Don’t merely scratch at a problem. Flag it, and then show up at the meeting with ideas on how you can fix whatever is going wrong. Be a problem solver: “I know we ran over budget, but I have two ideas for how we can cut costs on the next phase of the project to help mitigate that. And I’ve discussed with the other team members how we can avoid the problem next time.”
• Forget winners and losers; stay in neutral. Conversations that depend on one party admitting complete defeat—“You’re right, I was totally wrong”—aren’t likely to be successful. “People think difficult conversations have winners and losers, so they try to win,” observes Holly Weeks, author of Failure to Communicate: How Conversations Go Wrong and What You Can Do to Right Them. But a better outcome is for both parties to win. To do this, set a neutral tone from the beginning. “I might say, ‘Karen, I have something difficult to talk about. It’s hard for me, and I think it’s going to be hard for you because it’s something we haven’t talked about yet,’” suggests Weeks. This is a problem identification and problem solving conversation, and not a battle. “Neutral is a nice, easy formula. Clear content, neutral tone, tempered phrasing.” Your face, your body, and your voice should shift into (or stay in) neutral. Don’t yield to the temptation to escalate, respond in anger, or give in to your colleague unnecessarily.

• Take the temperature. During your difficult conversation, pause for a moment to check your view of where things are. This isn’t a time for sweeping characterizations: “I know we’re really far apart on this.” Rather, Weeks advises stopping to take stock in a sincere and collegial way: “Here’s where I think we’re more or less on the same page” and “Here’s where I think we’re not.” Giving yourselves a moment to assess where your disagreement stands may well speed things along.

Explore organizational resources

You don’t want to escalate a dispute too quickly, but sometimes people get so entrenched in their positions, or situations get so heated, that you can’t work it out on your own. If that happens to you, don’t give up hope just yet.

Consider recruiting a neutral third party—maybe a manager or a respected colleague. Explain the conflict, indicate the impact on your group or the organization, and ask whether your colleague is willing to get involved. You’re not after that person to pick sides, but rather to provide a neutral space and time for the two of you to talk more rationally. Your neutral colleague could approach the other party, at your request, to organize a private sit-down: “Look, I know you and so-and-so have been wrestling with this issue. Can we sit down in my office and talk about it? It’s starting to affect the entire department.”

Your company may also provide low-key solutions for difficult conversations. Are there in-house mediators? Will HR staff act as sounding boards? What organizational rules or aspects of your company culture can help you work through your difficult conversation? If your company is mission driven, can “quality in everything you do” help you and your partner refocus your argument? Is there a company ombudsman who can listen and offer a neutral perspective without its becoming an official conversation?

Difficult Conversations in the Real World

It helps to have guiding principles to call on when you need to work through something difficult. But the context of your discussion also matters. Do you need to take a stand on something? Deliver bad news? Do you have time to prepare, or are you caught off guard? Here are some specific tips for navigating common scenarios.

If you have to deliver bad news . . .

No one likes to deliver bad news, especially to your boss. While your instinct might be to try to soft-pedal the news or hide it, experts say that’s the worst possible thing you can do. Here we see the power of problem solving in defusing an unpleasant conversation.

The wrong way.

Avoid the conversation. Or e-mail the boss after work hours, when she can’t come and find you: “I just wanted to update you that we made a mistake in the printed edition of the magazine. It’s too late to fix it.”

A better way.

Admit that there’s a problem, figure out what went wrong, take responsibility, and propose a solution. “When I was editor of a prestigious trade magazine, I realized that we had stupidly published a provocative letter to the editor from a very famous person—that turned out to be a completely fake letter,” recalls a journalist. “We only realized this when we got an angry call from that famous person. And my boss was a notorious hothead. This would be a major embarrassment for the magazine.”

What did the editor do? Precisely what the experts suggest: “I figured out exactly how the mistake had happened. My assistant was supposed to confirm all the letters, but she was new and she didn’t know how to contact the famous person. So she didn’t.” Then the editor designed a new procedure to guarantee that such a mistake wouldn’t happen again. She went into her boss’s office to tell him as quickly as she could so that he didn’t hear about it from other channels. He blew his stack, but then they were able to have a good conversation. “I took complete responsibility—it was ultimately my fault. I let him blow steam at me. And then I presented him with a solution.” The boss was mad, but the conversation ended in that one session.

If you’re mad about a decision that affects you . . .

We’ve all had white-hot reactions to news that affects our jobs. But nothing good comes from launching from your chair to give your boss or colleague a piece of your mind: You’ll lose the argument before you open your mouth. But waiting until you’re calm, and framing how the decision is bad for the company—and not just you—will put you on a more productive path, says Brett.

The wrong way.

“I just found out that Peter got double the raise I got. Are you kidding me? I work three times as hard as he does! WTF?”

A better way.

Take a broader view of the issue. If you’re unhappy about a decision, might others be, too? If so, why? What’s the larger issue for your team or organization? Brett advises framing the conversation as, “I’ve observed something that’s not good for the company, and I’d like to help address it” rather than “I’m really mad this decision has been made about me.” After discovering that her peer received a much larger raise, a young partner in a law firm successfully employed Brett’s approach of framing the problem as an organization-wide challenge. Although the young partner was upset, she recognized that it wouldn’t be wise to complain about her colleague’s raise or ruminate about the injustice. The firm hadn’t deliberately set out to slight her; another partner had just made a more convincing case for raising her colleague’s pay. So the aggrieved lawyer approached the senior partner, making clear that she didn’t begrudge her colleague’s raise, but framed the issue as one of lack of transparency: “We don’t have a clear, fair system for raises in this firm.” She volunteered to do some research on how other firms handled the same challenge so that her organization could create a better process. Eventually that research led to a new, fair, transparent system, one the partner was happy with. Although she didn’t get a salary correction immediately, she improved her situation for the future—and created a better process for everyone.

If you need to make critical comments in a public forum . . .

Speaking up is challenging enough. But speaking out in front of everyone in your company? It’s fodder for nightmares. Still, it doesn’t have to be. Preparing thoroughly, framing the issue with a company focus, and positioning yourself as a problem solver will help make the daunting task of raising concerns at a large meeting, such as a board meeting or all-staff meeting, more palatable and productive.

The wrong way.

It’s unwise to make a statement like this in front of everyone: “I think this is a stupid idea for the company. If we keep proceeding down this path, prepare for a death spiral!”

A better way.

Before you stand up, prepare to take some heat. Making a critical comment in a public forum is likely to generate anger in people who don’t agree with you. So say explicitly that you’re trying to do what you think is best for the company. But also recognize, Brett says, that you’re probably not alone: “In every case, you’re not likely to be the only person who has these concerns.” If possible, find a like-minded colleague before the meeting who might be prepared to back you up.

To start the conversation, say something like, “I know everyone thinks we can manage the potential conflict of interest between these clients, but I feel very strongly that if we start down this path, we’ll find ourselves managing all kinds of conflicts that will be destructive to our customers down the line.” But don’t stop there. Identify potential solutions to the problem you’re raising. “I know this will delay our work for the client, but I’m happy to spend the next few days discussing some alternative paths forward with other folks.” Hopefully one or two of your colleagues will join you in voicing the importance of alternative paths and volunteer to study the issue with you.

If a colleague goes postal on you . . .

Do not respond to raw anger. Let your colleague’s words wash over you. See whether the scene will wind down. Here’s where managing your thoughts and emotions will help you navigate this challenge successfully. “Most people reciprocate other people’s behavior,” Brett says. “It takes discipline not to get angry in response. But it’s effective.”

The wrong way.

“What are you talking about?! You have no idea what work went into this project! Next time I’m not going to bother to ask your opinion!”

A better way.

You don’t need to go all the way to the other extreme and cower, or apologize for something you didn’t do, but you can simply choose not to engage in the battle. If your colleague is so emotional that you can’t get a word in edgewise, sometimes merely labeling the situation helps deescalate the tension: “Listen, we can trade threats and insults here, but that’s not going to solve our problem. We’re not getting anywhere this way.” You’re much better off removing yourself from a situation than trying to fight back. Suggest you meet later to discuss the problem. Do whatever you need to do to stay calm and avoid having an emotional conversation.

But because you can’t always dictate the timing—and trying to do so can make some people even angrier as they stew about the problem—it helps to respond in the most neutral way possible without conceding or escalating. Neutral in this case sounds like this: “I don’t know what to say. This is unexpected. What shall we do next?” suggests Weeks. You haven’t placated the person, you haven’t conceded; instead, you have calmly acknowledged that your colleague is angry. The conversation may not be pleasant after that, but you haven’t made anything worse for either of you. You’re now thinking together, rather than just reacting.

On the other hand, if you are in the wrong, and you know it, apologize immediately, says Weeks. “I’m sorry. I meant that to be funny.” That’s it, you’re done. Don’t keep piling on the explanation. Just own it.

It’s not (often) possible to magically make a difficult conversation fun and happy and easy. That’s why they’re challenging. But you can make them more productive by preparing yourself to get through them better. The only way you’re going to get better at navigating difficult conversations, says Weeks, is to have them. “You’re not going to get more skillful if what you do is step aside from the issue,” she says. And worse, the issue that you think you’re sidestepping isn’t likely to go away, setting up you or your colleague for a disproportionate blowup. Difficult conversations are difficult, says Weeks. But that doesn’t mean you can’t get better at them by preparing, staying neutral, and focusing on a solution that’s not only better for you but also better for the company.