5 Ways to Make Difficult Conversations Easier on a Remote Team

Difficult conversations are just that: difficult. They are even harder in a remote business. Conversations via video can seem impersonal, and that can seem inappropriate for a difficult conversation. The key is to set up your remote culture so that difficult conversations via video will not seem impersonal.

Why difficult conversations are harder in a remote context

On a Zoom meeting or phone call, It is harder to notice when someone is struggling. In an office, when someone is having a down day (or several down days), it can be noticeable. Online, a person can put on an act for a video call. Body language is less obvious if you are only seeing a person’s head and shoulders or impossible if video is turned off.

Ways to make difficult conversations less painful; focus on connection first

1.Keep the video on. It is not perfect but it is better than not seeing the person. We had a client who started the rule that all video must be on during their weekly team meetings. Their productivity and accountability improved vastly. Who knows what people are doing while the video is off. They might be making their grocery list for all you know. Create the rule that video must be on and you will see a difference.

2.“I need to have a difficult conversation with you and it’s not going to be perfect”

I heard this nugget of advice the other day and love it. When you start a conversation with this lead, it defuses any tension within yourself and allows you to get to the meat of the issue. You may think it puts the other person on guard but knowing where you are going up front is better than waiting and guessing what you are going to talk about.

3.Leave time for personal conversations.In the “flesh world,” personal conversations happen at work all the time. In the remote world, they can seem frivolous. As a business owner, one may ask, why would I pay for people to just shoot the breeze? So we do not have meetings just to hang out. 

When it is all work all the time, you miss out on the personal connection that can tell you when something is wrong. Leave time during regular meetings or schedule a meeting specifically for people to share what is going on in their lives. That connection will go a long way when it comes time for a difficult conversation.

4.Have a safe word. When conversations with the team are always scheduled, it can be hard to bring up when something is not going well. Or they bring it up but it may not register with you how serious the issue is. 

Create a safe word where employees can essentially call a timeout. When someone says the safe word, that is code for putting your defenses down, stop thinking about other things, and listen. At Freedom Makers, our safe word is LUTA (let us talk about it).

5.Call people. Again, in a remote environment, most conversations are typically scheduled in advance. Pick up the phone and call someone out of the blue, simply to check in on them, to say hi, to let them know you are there for them.

Connection counts

From our tips, you can see that it is all about connection. Having a strong connection makes having difficult conversations easier. Leading with why you are having the conversation sets the tone for the rest of it and for the relationship going forward.

As we mentioned earlier, it starts with how you set up your remote culture. Let your employees know there is a safe word. Give yourself grace to know the conversation will not be easy or perfect. Be gentle all around. Difficult conversations will always be difficult, as they should be, but when they are handled appropriately, they can be more helpful to the people you are having them with.