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October 8, 2020

How to Have Difficult Conversations Online – Your Top Tips!

Rosie Robinson


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Few of us relish the prospect of difficult conversations. Delivering bad news can be stressful for those giving and receiving it, particularly those fearful of confrontation.

Go in too strong and you could cause offense. But try to sugarcoat bad news, and you may not get your message across.

If that wasn't tricky enough, remote working means that many of these difficult conversations have now moved online. So, how do you ensure that they remain constructive and supportive when you can't speak in person?

We asked you, our social media friends and followers, for your top tips on how to handle difficult virtual conversations. Here's a selection of the best responses!

Plan Difficult Conversations

Many of you agreed that difficult conversations require a calm and organized approach. Rather than winging it and risk saying the wrong thing, you need to plan ahead.

You stressed the importance of gathering relevant materials or evidence ahead of your meeting. When Facebook friend Alex Fullerton is gearing up to a potentially contentious conversation, he ensures that he has relevant source material and links to hand. But he also believes that it is important not to bicker. He says, "If they remain unconvinced, I typically move on."

Preventing arguments is important but ensure that you're not silencing the other person simply because you don't like their viewpoint.

Operations specialist Vijayalakshmi Vasudevan suggests sending out a "detailed agenda to ensure focus." This can prevent the person you're talking to from feeling cornered or attacked, and instead demonstrate a willingness to collaborate. This is especially helpful for online discussions when you can't provide reassurance in person.

However, particularly delicate or serious conversations may not permit an agenda. In which case, be prepared to explain why and give the other person time to ask questions.

Stay Focused

According to Twitter follower @BeireannBuanBua, it's important not to "get distracted or obsessed by the fact that [the conversation] is online." Approach the topic as you would an in-person discussion, and focus on the task at hand. Chances are, the recipient will feel vulnerable, so your undivided attention is vital for supporting them through this difficult time.

Vijayalakshmi offers a helpful reminder that awkward conversations are "equally difficult" for everyone involved. As such, keep an open mind and use active listening to understand all sides of the situation.

Honesty Is the Best Policy

LinkedIn follower and researcher Joti K. Dhillon believes that "it's important to be as transparent as possible."

Concealing the truth to protect someone's feelings may seem like a good idea at first. But this can create confusion and cause further harm down the line if you're found out.

Instead, opt for an open and honest conversation. Joti added that it’s easy for your message to "get lost when communicating online." Clear communication is key to avoid potentially damaging misunderstandings.

Make the Most of the Distance

Virtual meetings don’t have to be all doom and gloom. Well-being expert Louise Levell points out that remote working can offer much-needed distance and perspective during difficult conversations. She says, "Reading and typing gives us time to re-read, ask for clarification, digest, breathe, and compose a response and edit if necessary. There's more 'space.'"

Whether you must let an employee go, deliver a performance appraisal that's less than positive, or call a team member out for bad behavior, difficult conversations are inevitable from time to time. But with a clear and organized approach, you can help to take the sting out of painful conversations and handle even the most awkward situations.

Tell Us What You Think

Thank you to everyone who shared their tips and thoughts. If you have any ideas about how to handle difficult conversations online, make sure to leave a comment, below. And follow us on LinkedInFacebook or Twitter!

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2 comments on “How to Have Difficult Conversations Online – Your Top Tips!”

  1. I agree - it’s helpful to focus on how the space created by remote conversations might actually be helpful for difficult conversations. I’ve been running workplace mediations online during lockdown and noticed that people seem to be able to manage their emotional response to what they hear far better in the safety of their home. Subsequently they are quickly able to make progress without getting hijacked by strong emotions. Both parties still need to pay attention to their emotional intelligence but the space can help rather than hinder.

    1. Thank you Clare for sharing you experiences. I find it fascinating that you have noticed people are managing their emotional reactions more effectively in the virtual environment. In addition to being in the safety of their home, any thoughts as to why that might be?

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