How to Have Difficult Conversations With Remote Employees
Frustrated remote employee

How to Have Difficult Conversations With Remote Employees

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written on May 2020 by Marek Grygier

As a manager of a virtual team, things are always going to come up that you will have to deal with from time to time. You may even be an employee who is having to bring up an issue yourself. Team conflicts, project roadblocks, or even more sensitive conversations will unfortunately happen, and being remote doesn’t make them any easier.

In fact, they’re challenging enough when in the office when you can notice more visual cues, let alone tackling them from a virtual one. Although your approach is going to be different when you work remotely, it doesn’t have to be harder when you’re equipped with the right skills. You will need to focus more on communicating effectively with your team and making up for the gaps you have in other ways.  

You can’t just avoid having these difficult conversations online either. It may even seem easy to put off an issue when you’re not in the same office and can avoid it. But in fact 94% of managers are regularly having one on ones, and 48.5% of them are doing them weekly. While these might not all be for having difficult conversations, the skills you learn in dealing with people in closed conversations are transferable into your normal meetings and calls too.

So, you need to get out there and really grab the bull by the horns! We’ve got together some of the best tips that you can implement easily into your workflow, so let’s get right into it.

Preparing yourself for a successful conversation

Preparing yourself for a difficult conversation is just as important as having the conversation itself. There are a few things to think about, including the time that you organize your meeting and making sure you create an agenda to stick to.

Being well-rested is a must, as well as being in the right frame and mindset to have a potentially difficult conversation. Some of us naturally just aren’t morning people, so it’s best to try to schedule for a time you feel most comfortable.

Don’t forget, it’s not just you that needs to prepare for this. The other person (or people) should be allowed some time too. It’s as simple as sending off an email or dropping someone a message in Slack to make sure they’re notified with enough time. Think about providing some good written context into what you want to discuss so there are no nasty surprises either.

Leave your assumptions behind you

It’s easy to go into a meeting with a lot of presumptions and ideas of what the other party will want to say, and likewise for yourself. Preparing is of course key as we just discussed, but you shouldn’t just be preparing for the conversation you’ve been playing out in your head.

Pay attention to what is actually being said and discussed, and not just what you want to say. Assuming things can be dangerous, as a conversation may not always go the way you imagine.

Cultivate a sense of curiosity 

A conversation needs two-way interaction between the participants to really make it an actual conversation. This is why asking questions is so important, so that you can both find out more about the reasons behind the other person’s opinion.

Cultivate curiosity, and try to understand the other person’s point of view from their position. Having someone try to understand your point of view and feelings on a difficult topic is going to benefit both sides of the conversation.

Think about what’s happening below the surface

A conversation doesn’t just involve words… there’s a lot more going on to it than you think. Above the water you can hear and process all the words that someone is saying. Below the water though there is a lot going on with non-verbal cues and context that you should try to pick up on. While we all put forward our arguments, in fact there are probably feelings and emotions that aren’t being said. 

It’s difficult reading these non-verbal cues in a remote environment, so your best chance is to schedule a video call so that it’s easier to read the tone and emotion of the participants. You can really hone in by making sure that you are in a focussed state without any distractions. 

Ask questions to dig deeper and create true dialogue

Only by asking questions are you going to be able to have a more meaningful conversation during your meeting. It can be a bit tricker to come up with them on the spot, so you should try to think beforehand about some general questions that will help. You can start creating a true dialogue by asking more revealing questions like:

“Can you help me to understand?”

“Can you share an example?”

“What was the impact?”

These questions are useful in all difficult conversations, so you should try to get a couple in along with the specifics you might need to ask. Making sure of what you’ve heard and clarifying it will also help avoid to misunderstandings:

“To make sure I am understanding you correctly…”

“What I believe I heard you say is…”

“Did I get that right?

Refocus your conversation

Like any kind of meeting, it’s easy to get off-topic. You can begin discussing one thing and end up talking about something completely else. Some participants can become more reserved too as a conversation goes on.

Getting focus back on what matters is needed to get the most benefit out of your time. The agenda you created earlier now comes into such great use. Keep on track by checking it, and you’ll notice when you start to drift off topic. Refocus the conversation with points like these:

“It seems like we’re starting to talk about different things.”

“I am noticing that … (eg. you’re sharing less, we’ve stopped asking each

other questions).”

Use I & Impact statements to share your perspective

We can all sometimes struggle voicing our opinions precisely once we’re really into a conversation. But taking the opportunity to express what you want to say and how you feel is critical in steering the conversation on to the right path.

Making basic statements and structuring it around what you (or I in your case!) think will help you to easily express your perspective on matters. Think about phrasing it like this to really lay out how you and the other person in your conversation is feeling:

“When you said X, the impact it had on me was Y. I’m guessing you didn’t mean that. Can you share what you were trying to say?”

Thinking before you talk

Taking a look at what we’ve covered, it really shows that you shouldn’t go into a conversation empty-handed. Give yourself time to prepare, and try writing down what you want to say and some of the phrases we’ve given if you think it will help.

The more you have these conversations, the easier it really gets when you build up on these skills. It’s easily one of the more important skills in your remote toolkit. Now that more of us are having to experience remote work in some way or another, it’s important we try to think about how we can make the most out of the situation.

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