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How to Handle Difficult Conversations at Work

How to Handle Difficult Conversations at Work
How to Handle Difficult Conversations at Work
Difficult conversations, whether you’re telling a client that a project is behind schedule or giving a sluggish performance review, are an inevitable part of managing. How should one prepare for this kind of discussion? How to find the right words at the moment? And Handle Difficult Conversations at Work?

What the experts say

“We’ve all had bad experiences with these conversations in the past,” says Holly Wicks, author of The Failure to Communicate. Perhaps your boss lashed out at you during a heated argument; or your direct report started crying during the appraisal; maybe your client hung up on you. As a result, we tend to avoid them. But this is not the correct answer. After all, difficult conversations are “not black swans,” says Jean-Francois Manzoni, professor of human resources and organizational development at INSEAD. The key is to learn how to deal with them in a way that will give you “the best 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 out of those difficult conversations while keeping your relationship going.

change your thinking

If you’re preparing for a conversation you’ve described as “difficult,” you’re more likely to be nervous and frustrated ahead of time. Instead, try to handle “word it in a positive, less binary way,” Manzoni suggests. For example, you don’t give negative performance reviews; you have a constructive conversation about development. You don’t tell your boss no; you offer an alternative solution. “handle Difficult conversations tend to go better if you treat them like normal conversations,” Weeks says.


“The calmer and more focused you are, the better you will be able to handle difficult conversations,” says Manzoni. He recommends: “taking regular breaks” throughout the day to practice “conscious breathing.” This will help you “refocus” and “enable you to take any hit” that comes your way. This method also works well at the moment. If, for example, a colleague approaches you with a problem that could lead to a difficult conversation, apologize (have a cup of coffee or take a walk around the office) and collect your thoughts.

Plan but don’t write

It can be helpful to plan what you want to say by taking notes and key points before speaking. However, writing a script is a waste of time. “It’s unlikely that everything will go according to plan,” Weeks says. His colleague doesn’t know “his lines”, so when he “steps away from the script, he has no forward movement” and the exchange “becomes oddly contrived”. Your conversation strategy should be “flexible” and contain “a repertoire of possible responses,” says Wicks. Your language should be “simple, clear, direct and neutral,” he adds.

Acknowledge your interlocutor’s point of view

Don’t engage in difficult conversation with a “my way or the highway” attitude. Before moving on to this topic, Weekes recommends asking yourself two questions: “What’s the problem? And what, according to the other person, is the problem? If you’re not sure about the other person’s point of view, “admit you don’t know and ask,” she says. Show your opponent “that you care,” says Manzoni. “Express your interest in understanding how the other person is feeling” and “take the time to process the other person’s words and tone,” she adds. As soon as you hear this, find common ground between your point of view and the point of view of your interlocutor.

Be compassionate

“Experience tells us that such conversations often lead to [tense] working relationships that can be painful,” says Manzoni. Therefore, it is desirable to approach sensitive issues from a position of sympathy. Be careful; Be Compassionate “It may not necessarily be pleasant, but you can deliver difficult news with courage, honesty, and fairness.” In the meantime, “don’t worry,” Weeks says. The worst thing you can do is “to ask your interlocutor to sympathize with you,” she says. Don’t say things like, “I feel so bad for saying this” or “It’s really hard for me,” she says. “Don’t play the victim.”

Slow down and listen

To prevent tension from flaring up, Manzoni recommends trying to “slow down” the conversation. Slowing down and pausing before responding to the other person, he says, “gives you a chance to find the right words” and tends to “decrease negative emotions” in your interlocutor. “If you listen to what the other person is saying, you’re more likely to get the right questions, and the conversation always ends better,” he says. Make sure your actions back up your words, adds Wicks. “Saying ‘I hear you’ while playing on your smartphone is offensive.”

Give something in return

If you’re starting a conversation that will “embarrass the other person or take something away from them,” ask yourself, “Is there something I can give in return?” Wix says. If, for example, he fires someone he’s worked with for a long time, “he might say, ‘I wrote what I think is a strong recommendation for you; do you want to see?’ If you need to let your boss know that you can’t take on a particular task, offer a viable alternative. “Be constructive,” says Manzoni. Nobody wants trouble.” Offering options “helps the other person find a way out and also shows respect.”

meditate and learn

According to Manzoni, after a difficult conversation, it’s worth “thinking after the fact” and thinking about what went well and what didn’t. “Think about why you had certain reactions and what you could have said differently.” Weeks also recommends watching how others successfully handle such situations and emulating their tactics. “Learn to disarm yourself by imitating what you see,” she says. “Knowing how to have a difficult conversation is not just a skill, it’s an act of courage.”

principles to remember

• Take regular breaks throughout the day; the calmer and more focused you are, the better you can handle difficult conversations when they come up

• Slow down the pace of the conversation – this will help you find the right words and let the other person know that you are listening.

• Find a way to be constructive by suggesting other solutions or alternatives.

Do not:

• Mark the news you need to report as “difficult talk”; frame the discussion in a positive or neutral light instead

• Take the time to write down how you want the discussion to go; take notes if it helps, but be open and flexible

• Ignore the other person’s point of view: Ask your interlocutor how they see the problem and then look for coincidences in their points of view.

Example #1: Be clear, direct, and emotionless

Tabatha Thurman, founder and CEO of Integrated Finance and Accounting Solutions, a financial firm with clients in the public and private sectors, knew she was having trouble with an employee. “She was a good person and worked long hours, but his productivity was a problem,” she says. “He was not fit for his position.”

She and her team tried a number of interventions, including working with a professional trainer, but six months later she needed to act. “We kept kicking the can down the road, but I realized I had to be the bad guy.” She will have to fire him.

Tabata was afraid to break the news. “I really liked this man,” she says. “We are a small company and everyone is very close: you meet people’s families and hear about their vacations. At the same time, everyone plays their part in the team and one weak link can destroy it.”

To prepare for the conversation, Tabata referred to her 20 years of experience as an Army officer. “I grew up in a military environment where there is no bluffing,” she says. “When you’re at work, you’re at work. You have to be strong with the people around you and get rid of your feelings.”

Her words were simple. She told the clerk that she “didn’t fit in.” She explained that the company would keep him on the job until the end of the month, and then went into detail about severance pay. Tabata says that although the employee “wasn’t happy,” he accepted the dismissal “like a soldier.”

Although she didn’t show her emotions during the meeting, Tabata still says that the conversation “stayed” in her head today. “I still feel bad that it didn’t work, but it was wrong,” she says. “We had to move on.”

Case Study #2: Get in the mood and show empathy

As the human resources director for Booz Allen Hamilton, Betty Thompson is used to difficult conversations. Recently, for example, she had to tell a successful long-term employee that her position was being eliminated.

“Over time, his role has become less important to the organization,” she says. “There were also problems of proximity: his team was on one side of the country and he was on the other. It just won’t work anymore.”

Betty decided that the best way to get the message across was not in one conversation, but in a series of numerous discussions over the course of a couple of months. “I didn’t want to rush things,” she says. “It was a process.”

Even before discussing the subject with a co-worker, she reminded herself of her good intentions. “You have to have the right energy to go for something like this. If it comes from frustration, which can happen, we’re only human, this is not going to be a constructive conversation. You should be thinking, “What is the best way for this person to hear the message?”

Her first step was to sit down with an employee and ask her how she thought things were going. “I wanted to know what his frustrations were,” she says. “I wanted him to look in the mirror instead of poking him in the eye.”

After her speech, she offered her point of view on the problem. She was defensive at first, but when they spoke a second time, she came to her senses and agreed there was a problem.

From her last conversation, the employee had decided to leave the company. They had a great conversation and even ended the conversation with hugs. “He knew I cared,” she says.