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How to have difficult conversations when working remotely

These six steps will help ensure you still have a productive conversation.

How to have difficult conversations when working remotely
[Source photo: Olezzo/iStock]

Whether you’re a leader who needs to address a team member’s performance or you’re an employee who is unhappy about a situation with your boss, difficult conversations happen at work. Fortunately, these kinds of talks aren’t a daily occurrence, but that doesn’t make them any easier.

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Avoiding them can have consequences that make the situation worse, says Roberta Matuson, author of Can We Talk? Seven Principles for Managing Difficult Conversations at Work. “We’re seeing a surge in employee turnover,” she says. “A lot of people believe, ‘Why bother talking to my boss?’ You wonder if people had taken the time to try to talk things out whether that might have had a different ending.”

Conversations are hard enough, but remote working arrangements add another degree of difficulty. There are some things you should do when you need to have a difficult virtual meeting.

Get Clear on Your  Objective

The first step is to understand why you need to have the conversation, says Matuson. This is a step to take whether you’re having the conversation in person or not.

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“For example, if you’re having a conversation with an employee who is not performing at the level that you need them to perform, are you having that conversation because you want to help them improve their performance or are you going through the steps to exit them out of the organization?” she asks. “Those are two very different conversations, so it’s important to get clear on what you want to happen at the end of this conversation.”

Organize Your Thoughts

Preparation is key for difficult conversations, says Amy Mosher, chief people officer at isolved, provider of workforce management software solutions.

“Whether it’s an employee needing to talk to their manager or a manager needing to talk to their employee, having an outline and key talking points is critical,” she says. “The outline should include the desired outcome of the conversation, any questions or key messages they want to relay or examples they have to share.”

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One of the positives of the remote environment is being able to have all your notes handy, adds Mosher. “Tape it on your second screen or put them in front of you on your desk,” she says. “None of us want to be scripted, but take advantage of no one but you knowing you’ve plastered notes everywhere.”

Be careful, though, that you don’t use notes to the point where you are not actively listening, says Mosher. “Hearing the other person out is important,” she says.

Book Time on the Calendar

Whether you’re talking to your boss, a coworker, or your employee, it’s best not to have the conversation impromptu. Instead, schedule the call in advance.

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“You can approach them by saying, ‘I’d like to have a conversation with you. Do you have a time on your calendar where you can speak candidly with me?'” says Matuson. “The challenge with remote work is that we all have these gorgeous, fake Zoom backgrounds, and you have no idea if the person’s spouse or kids are in the room, too. A lot of these conversations are of a sensitive nature, and you want to make sure that you both have the privacy you need.”

Weigh the Pros and Cons of Video

When everyone is in the office, difficult conversations are usually done in person. With remote working arrangements, it’s natural to assume a video conference is the best choice, but that’s not necessarily the case. If you need to let someone go, for example, a conversation over the phone can ease the psychological load, says Betty Johnson, PhD, author of Making Virtual Work.

“Camera use requires emotional energy expense,” she says. “Camera use requires visual focus, robbing energy from information processing. An unfocused gaze, such as looking at the wall instead of at another person’s face, is, for many, necessary to process complex information, such as that in a difficult conversation.”

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If you want to work with someone to get to a resolution, Tara Lilien, chief talent officer for the communications and marketing firm Peppercomm, recommends turning the video on.

“We’ve found that face-to-face conversations have been the most beneficial for difficult conversations—they leave less room for interpretation and increase levels of empathy and understanding,” she says. “Face-to-face conversations have also proven to result in a faster and easier-found solution to the conflict or problem at hand.”

Starting the Conversation

You may have heard of the sandwich approach to delivering bad news—say something nice, then deliver the news, and end with something nice. Matuson says it’s the wrong approach.

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“I think this gets managers in trouble,” she says. “It doesn’t make sense to say something like, ‘You’re the strongest member on my team. However, I’m going to let you go. But I enjoyed working with you.'”

Instead, lead with your perspective. For example, an employee who has a micromanager boss might say, “I’ve given this a lot of thought, and I feel like I need to tell you that the way I’m being managed isn’t working for me and here’s why.”

“Nobody can tell you that your feelings are wrong,” she says. “This is better than saying, ‘When you do this, it pisses me off.’ Instead, you’re taking it on yourself, and you’re sharing your observations.”

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But be direct, adds Lilien; skirting around an issue will only allow it to fester. “This is even more important in a remote work situation where you can’t read verbal and physical cues as well as you can when you see someone each day at work,” she says. “Often, you will find the receiving party appreciates the directness, as it provides clarity and gets to the point much quicker than if you are dancing around a situation.”

Ending a Difficult Conversation

At the end of a conversation, make sure you both are on the same page about how things will be different going forward.

“It’s always good to say to the other person after the conversation, ‘Tell me what your understanding is of what just transpired,'” says Matuson. “If you’re telling them that they need to be more of a team player and they think you’re talking about improving their tennis game, you’re on different planets. At that point you can bring them back and say, ‘Okay, I probably wasn’t clear enough; let me be specific and tell you exactly what I need you to do.'”

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While no one likes confrontation, it’s best to take a timely approach, says Matuson. “It’s easy to put things off, and some people hope the problem will magically just go away, but that doesn’t usually happen,” she says. “The longer you wait to have a discussion, the more difficult and complicated it can get.”

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