How to have difficult conversations when working remotely - Deepstash
How to have difficult conversations when working remotely

How to have difficult conversations when working remotely

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Taking the time to address difficult issues

Taking the time to address difficult issues

Difficult conversations at work are inevitable, whether you're a leader addressing a team member's performance or an employee unhappy about a situation with your boss. Remote working adds another layer of difficulty.

Many people would rather leave than talk to their boss. However, if people had taken the time to address the issues, they may have had a different outcome.


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Be clear on your objective

You need to understand why you need to have the conversation. Decide if you should have the conversation in person or not.

For example, if you have a conversation with an underperforming employee, you may either want them to improve their performance or go through the steps to exit them from your organisation.


204 reads

Organise your thoughts

Create an outline and key talking points, including the desired outcome of the conversation, key messages or examples to share.

Take advantage of an online conversation by keeping your notes in front of you or on a second screen.


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Book time on the calendar

It's best not to have an impromptu conversation. Instead, schedule the call in advance.

For example, you could ask to have a conversation and set a date and time on your calendar. Ensure that you both have privacy despite fake Zoom backgrounds.


147 reads

Weigh the pros and cons of video

With remote working arrangements, a video conference may not always be the best choice. If you need to let someone go, a phone conversation can ease the psychological load.

When you want to work with someone to get to a resolution, a video conversation may be better as there is less room for interpretation and increased levels of empathy.


143 reads

Starting the conversation

The sandwich approach to delivering bad news may be unproductive. Instead, lead with your perspective.

For example, an employee who is micromanaged might say to their boss, " I have given it a lot of thought, and feel like I need to say that the way I'm being managed isn't working for me," followed by the reasons why.


155 reads

Ending a difficult conversation

When the conversation comes to an end, ensure both parties know how things will change going forward.

It's always good to ask the other party to tell you their understanding of what just happened. It may be that they didn't get what you were trying to say. At that point, you can be specific and say exactly what they need to do.


158 reads



Know your boundaries, let other people also know them.


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