difficult conversations remotely

How to have difficult conversations remotely with your team

As leaders, we encounter all kinds of situations where we need to have difficult conversations with team members. It’s not easy at the best of times, but it’s even harder to have difficult conversations remotely. 

With more people than ever working from home thanks to the worldwide pandemic, many leaders are trying to figure out how to have an uncomfortable discussion when you can’t sit across the table from someone. 

Regular readers of this blog may remember that we shared strategies for turning difficult conversations into essential conversations. It helps to approach each situation with a more positive mindset than dread!

Here’s how to have a difficult conversation remotely:

Prepare to confront tough issues with courage, compassion and skill. 

It’s always better to start a conversation like this when you’ve taken time to prepare so that things don’t go wildly off track. Having an opening statement that names the issue (and gives an example of the behaviour or situation that needs to change), describes the effect this has and what’s at stake is important. So is acknowledging your own contribution to this situation, describing an ideal outcome and then giving the team member you’re talking with time to respond. 

That sounds like a lot but we created a free downloadable to help you prepare for having an essential conversation. It covers each step to PREPARE for the essential conversation (and these are the same steps to use to OPEN the conversation with your employee or peer). As a bonus, we cover some mistakes we see over and over again when clients practice this model — so you can avoid making these common errors.

Don’t delay having a difficult conversation.

It’s never easy to talk with someone about performance issues, and perhaps even more so when we know we ourselves and many of our team members have had a challenging few months. Being able to articulate your concerns with specific examples is important so the focus is on the issue or behaviour and not the person:

“I notice that you’ve missed the morning meeting the last three times” rather than, “You’re ignoring our regular morning meetings”

“There seems to be some tension between you and Sam in finance” rather than, “You’re always short-tempered and rude to Sam”

“Your contribution to the last few reports was not as detailed as required” rather than, “The quality of your work on the last few reports was substandard”

We’ve talked before about how to have performance conversations before things are completely derailed (that’s not fair to anyone!) or fester and erupt. When leaders are prepared and use a problem-solving approach, it can be much easier to approach job performance concerns objectively and with empathy. 

Check your assumptions before you have the conversation.

Sometimes we hold beliefs or make decisions about people or situations without even realizing that we’re assuming things to be true that maybe are not. We often make assumptions about the other person before we even start talking.

When we offer leadership workshops, our Ladder of Assumptions exercise always surprises and impresses participants. It’s a short activity that helps folks realize how each of us might say or think something or behave a certain way because of things we believe or have experienced that can then influence how the other person responds. (Pro tip: Click through to that blog post and you’ll find the free worksheet we created to walk through the ladder exercise before you undertake an essential conversation.)

Always have an essential conversation face-to-face.

Sure, it can feel really awkward and you might be tempted to just send a quick text message or email instead. Don’t! It’s very difficult to manage tone and intention in writing. 

A video call is the next-best-thing to meeting in person if you have to have a difficult conversation remotely. Failing that, a phone call at least allows you to communicate your tone — but if you can’t see each other then you’ll have to really make certain that you don’t sound as though you’re reprimanding but rather that you’re looking to resolve an issue and provide resources or support as needed. 

Pick a mutually convenient time.

The end of a long and stressful work week is probably not the best time to have a heartfelt discussion that could result in hard feelings! Similarly, some people aren’t morning people. These days, remote workers may well be juggling childcare or caring for elderly families while working from home. 

Ask the other person what timing works for them (accommodating time zone differences so you’re the one up extra early or working a little later if applicable) and give them a bit of information about what you need to discuss with them so they don’t feel completely blindsided. 

Focus on resolving the issue.

If you follow our guide to Essential Conversations you’ll see that the last step is “Invite Your Partner to Respond.” That’s because our guide walks you through preparing for the conversation and introducing the conversation in a way that sets a good tone and outlines everything that needs to be discussed. We can’t presume where the conversation will then go (see the Ladder of Assumptions paragraph above). So, once you’ve opened the conversation, outlined your concerns, provided an example and stated what’s at stake, give the peer or team member you’re talking with the opportunity to share what they think about the issue. 

If you’re one of our regular readers, you’ll know this point in the conversation is a time to listen with the intent to understand (not to respond!). When people feel seen, heard and understood, they’re less likely to get angry and defensive. 

It’s much better to have a heartfelt conversation than a fight over who is right. To do that, be curious about what the root cause for the behaviour or issue is and pay careful attention to body language because there could be stressors that you weren’t aware were a factor. What resources, supports or changes could help change what’s happening for the better? Ask for help to understand what’s happening and clarify what you’re hearing to make sure you’re both on the same page.

Keep the conversation on track if required.

Despite your best efforts and careful preparation, the conversation might take some unexpected detours. Different personalities deal with perceived criticism in different ways, so you may encounter some hostility, some deflection or some red herrings. 

Take the time you need to bring the conversation back to the main issue and re-focus as required on finding a solution. Work to keep frustration, anger and annoyance in check. You can suggest discussing other topics another day or point out when you’re getting off topic. Asking questions can also help you keep the conversation on task. 

Schedule a follow-up.

Having this essential conversation is just the first step in resolving the issue. It’s a big mistake many of us have made: to breathe a sigh of relief after this awkward and difficult conversation is over and then assume it’s all taken care of going forward. You’re not done yet! The next step is to follow up to discuss whether things are improving or if there’s a need for more support or action. 

You can check in casually to see how things are going, but it’s also good to re-assess things with a scheduled conversation before too much time elapses. This way, it’s clear that your expectation is that things are going to get better.

Coach’s Questions

What is the biggest challenge for you with having difficult conversations? What can you do differently or better to prepare for an essential conversation? What steps could make having a difficult conversation remotely better for you and the other person? What conversation needs to be had?