How to Handle Difficult Conversations at Work

Author: Rebecca Knight

Difficult conversations—whether you’re telling a client the project is delayed or presiding over an unenthusiastic performance review—are an inevitable part of management. How should you prepare for this kind of discussion? How do you find the right words in the moment? And how can you manage the exchange so that it goes as smoothly as possible?

What the experts say

“We’ve all had bad experiences with these kinds of conversations in the past,” says Holly Weeks, the author of Failure to Communicate. Perhaps your boss lashed out at you during a heated discussion, or your direct report started to cry during a performance review. Maybe your client hung up the phone on you. As a result, we tend to avoid them. But that’s not the right answer. After all, tough conversations “are not black swans,” says Jean-François Manzoni, professor of human resources and organizational development at INSEAD. The key is to learn how to handle them in a way that produces “a better outcome: less pain for you, and less pain for the person you’re talking to,” he says. Here’s how to get what you need from these hard conversations—while also keeping your relationships intact.

Change your mindset

If you’re gearing up for a conversation you’ve labeled “difficult,” you’re more likely to feel nervous and upset about it beforehand. Instead, try “framing it in a positive, less binary way,” suggests Manzoni. For instance, you’re not giving negative performance feedback; you’re having a constructive conversation about development. You’re not telling your boss no; you’re offering up an alternate solution. “A difficult conversation tends to go best when you think about it as just a normal conversation,” says Weeks.

Plan but don’t script

It can help to plan what you want to say by jotting down notes and key points before your conversation. Drafting a script, however, is a waste of time. “It’s very unlikely that it will go according to your plan,” says Weeks. Your counterpart doesn’t know “his lines,” so when he “goes off script, you have no forward ­motion,” and the exchange “becomes weirdly artificial.” Your strategy for the conversation should be “flexible” and contain “a repertoire of possible responses,” she says. Your language should be “simple, clear, direct, and neutral.”

Acknowledge your colleague’s perspective

Don’t go into a difficult conversation with a my-way-or-the-highway attitude. Before you broach the topic, Weeks recommends asking yourself two questions: “What is the problem? And what does the other person think is the problem?” If you aren’t sure of the other person’s viewpoint, “acknowledge that you don’t know and ask,” she says. Show your counterpart “that you care,” says Manzoni. “Express your interest in understanding how the other person feels,” and “take time to process the other person’s words and tone,” he adds. Once you hear it, look for overlap between your point of view and your counterpart’s.

Be compassionate

“Experience tells us that these kinds of conversations often lead to [strained] working relationships, which can be painful,” says Manzoni. It’s wise, therefore, to come at sensitive topics from a place of empathy. Be considerate; be compassionate. “It might not necessarily be pleasant, but you can manage to deliver difficult news in a courageous, honest, fair way.” At the same time, “do not emote,” says Weeks. The worst thing you can do “is to ask your counterpart to have sympathy for you. Don’t say things like ‘I feel so bad about saying this’ or ‘This is really hard for me to do,’” she says. “Don’t play the victim.”

Slow down and listen

To keep tensions from blazing, Manzoni recommends trying to “slow the pace” of the conversation. Slowing your cadence and pausing before responding to the other person “gives you a chance to find the right words” and tends to “defuse negative emotion” from your counterpart. “If you listen to what the other person is saying, you’re more likely to address the right issues and the conversation always ends up being better,” he says. Make sure your actions reinforce your words, adds Weeks. “Saying, ‘I hear you’ as you’re fiddling with your smartphone is insulting.”

Give something back

If you’re embarking on a conversation that will “put the other person in a difficult spot or take something away from them,” ask yourself: “Is there something I can give back?” says Weeks. If, for instance, you’re laying off someone you’ve worked with for a long time, “You could say, ‘I have written what I think is a strong recommendation for you; would you like to see it?’” If you need to tell your boss that you can’t take on a particular assignment, suggest a viable alternative. “Be constructive,” says Manzoni. “Nobody wants problems.” Proposing options “helps the other person see a way out, and it also signals respect.”

Reflect and learn

After a difficult conversation, it’s worthwhile to “reflect ex post” and consider what went well and what didn’t, says Manzoni. “Think about why you had certain reactions, and what you might have said differently.” Weeks also recommends observing how others successfully cope with these situations and emulating their tactics. “Learn how to disarm yourself by imitating what you see,” she says. “Handling a difficult conversation well is not just a skill, it’s an act of courage.”

Principles to remember

Do:

• Take regular breaks during the day—the more calm and centered you are, the better you are at handling tough conversations when they arise

• Slow down the pace of the conversation—it helps you find the right words and it signals to your counterpart that you’re listening

• Find ways to be constructive by suggesting other solutions or alternatives

Don’t:

• Label the news you need to deliver as a “difficult conversation” in your mind; instead, frame the discussion in a positive or neutral light

• Bother writing a script for how you want the discussion to go; jot down notes if it helps, but be open and flexible

• Ignore the other person’s point of view—ask your counterpart how he sees the problem and then look for overlaps between your perspectives

Rebecca Knight is a journalist who writes about all things related to the changing nature of careers and the workplace. Her essays and reported stories have been featured in the Boston Globe, Business Insider, the New York Times, BBC, and the Christian Science Monitor. She was shortlisted as a Reuters Institute Fellow at the University of Oxford in 2023. Earlier in her career, she spent a decade as an editor and reporter at the Financial Times in New York, London, and Boston.