The Ultimate Guide to Managing Difficult Conversations Remotely

The Ultimate Guide to Managing Difficult Conversations Remotely

Your managers are responsible for coaching your employees to succeed. While we wish that just entailed sharing positive feedback and putting employees up for promotions, managers must also ensure their employees meet performance standards. Unfortunately, that often requires your people leaders to manage difficult conversations.

To add a layer of complexity, managing difficult conversations is no easy task in person, let alone remotely.

When you’re in the same room with someone, you can read their body language and facial expressions more easily to understand how they’re reacting to your feedback. Unfortunately, these indicators are less clear in a virtual environment, leading to misunderstood intentions and harm workplace relationships. Still, as the modern workplace becomes increasingly pro-remote work, the odds your managers will have to have a difficult conversation with an employee virtually are increasingly high.

The Ultimate Guide to Managing Difficult Conversations Remotely

That said, difficult conversations must be approached gracefully and tactfully to ensure employees don’t become overly defensive and understand what their managers are trying to say. From reviewing how to share constructive feedback to reminding managers to lead with empathy, we’ve put together a few key points you can use to train your managers to share input remotely. 

Here are a few best practices to help you connect with your managers and employees in a meaningful way while managing difficult conversations virtually: 

The Golden Rules of Managing Difficult Conversations Remotely

1. Tackle Difficult Conversations Head-On

Difficult conversations are just that… difficult. While our natural insights might encourage us to avoid confrontation, avoiding these crucial conversations can cause more harm than good.

If employees aren’t aware of issues, they will continue behaving the same, blissfully unaware that their actions are affecting others. Or, refusing to address the minor problems when you first notice them can cause them to balloon up and cause even considerable challenges for your team.

Instead of avoiding difficult conversations, encourage your managers to address issues immediately as they arise proactively. What initially might seem like a significant issue might only take 5-minutes of candid conversation to resolve.

2. Don’t Rush It

When managing difficult conversations, remind your managers to take their time to get their facts straight. They should never rush to confront an employee but take the time to process the situation and their emotions. This allows them to come prepared with a plan and approach the conversation with a level head.

When your managers discover an issue, teach them to step back and take a breath. Then, have them ask themselves these questions:

  • Is this employee failing to meet the expectations outlined for their role?
  • Is this employee failing to act by our company values?
  • Is this employee making others uncomfortable?
  • Does this employee seem unhappy, unmotivated, or disengaged?

If they answer predominantly yes, then it’s time to talk.

Next, instruct managers to identify and confirm their assumptions with facts. Your managers should never have a conversation based on rumors or gossip. Managing difficult conversations requires the same preparation as an interview: your managers must draft their talking points and ideal outcome to get the most out of a conversation and focus on clearly communicating their main issues and intentions to their employees.

3. Establish Trust

Having mutual trust and respect with your employee is your “emotional bank account.” This process takes time and needs to start long before a candid conversation.

Still, a solid manager-employee relationship makes managing difficult conversations so much easier. Your employees will immediately respect their manager’s opinion, understand they want to see them succeed, and want to improve their performance. 

It’s important to note that mutual trust and respect will look different for each employee. For example, some employees might want a more hands-on manager, while others might thrive when given more space.

The best ways to support each employee as a manager are critical to managing difficult conversations. Train your managers on a few management and conflict resolution styles so they can choose the best way to approach each of your employees and ensure their feedback lands positively. 

How to Give Feedback that Lands

A team lead sitting at her desk managing difficult conversations
Photo by Ekaterina Bolovtsova on Pexels

How Managers Should Handle Difficult Conversations Virtually

To help you train your managers to have difficult conversations remotely, we will look at how one manager might help their employee, Joe.

Our manager’s direct report, Joe, has been missing deadlines for a few weeks.

Our manager has looked at the situation from all angles. Joe’s missed deadlines are a regular occurrence, not a one-off fluke. Our manager has communicated their concerns and detailed their expectations. Still, Joe continues to miss critical due dates.

It’s time to talk. But how? When? What if he gets angry? What if our manager is missing something?

And the biggest question is how Joe’s manager can manage difficult conversations remotely.

Here’s how we recommend our manager approach the difficult conversation about Joe’s performance and act with empathy to find a resolution – as well as how you can adapt these lessons for your workplace:

1. Have It ‘In-Person’

Don’t let managers have difficult conversations over e-chat or email. Talking on a video call is ideal and can help make the conversation feel as “in-person” as possible. In addition, a phone call is a solid second option if poor WiFi makes your video connection unstable or spotty.

Why should managers opt for a video call instead of an email? A video call lets them read their employee’s body language and connect with them more personally. In addition, it’s harder to deflect the topic over video chat, so it can help them lead a more meaningful conversation.

2. Come With a Plan

Remind managers never to “wing it.” When managing difficult conversations, your managers need to come prepared with a list of talking points and specific examples to help guide their discussion and ensure they get your point across. Here are a few best practices for managing difficult conversations remotely:

  • Give feedback on the behavior, not the person. For example, instruct managers to tell Joe, “I’ve noticed these three projects have all finished after the deadline,” instead of saying, “You’re disregarding my deadlines.” Sticking with the facts can make it harder for employees to dispute or dismiss your comments. 
  • Reiterate your intentions. Remind managers of their conversation’s goal: to help their employees succeed, not reprimand them. In our example, the manager would tell Joe, “I’m here to help you complete projects and reach deadlines as successfully and efficiently as possible.”
  • Use the conversation as a coaching opportunity. Giving feedback can be a teaching opportunity. Encourage managers to work with their employees to identify what needs to change and how.
    New call-to-action

3. Let Them Share Their Side

When managing difficult conversations, don’t forget to let an employee speak. Encourage managers to ask questions like, “What do you think about all this?” or “Is there anything I should know about that has been impacting your behavior recently?”

Hearing the employee’s side of the story might give your managers additional context to help both parties reach an agreement. For example, when our manager asks Joe if there is anything that might be keeping him from meeting deadlines, he reveals that on top of his day job, he’s been taking care of his ailing mother for the last few weeks.

He often has to step away from his work during the day to help her and hasn’t been sleeping well because he’s been worried about her. All this, he says, has been wearing on him and causing projects to slip through the cracks.

Now that our manager knows about Joe’s situation, they can lead with empathy and work to find a resolution together with Joe. For example, our manager might tell Joe to work flexible hours to help his mother in the middle of the day or suggest he take paid time off or family leave to care for her. By presenting these options, our manager shows Joe they are listening to his concerns and trying to accommodate his needs so he has what he needs to get back on track.

A manager comes prepared with notes and an agenda for a tough conversation with an employee
Photo by Katerina Holmes on Pexels

4. Be Mindful of Time Zones

Managing difficult conversations isn’t all about what you say – when you say, it also matters.

Say Joe works on the West Coast, three hours behind our manager located on the East Coast. Make sure you remind your managers to schedule conversations during Joe’s regular working hours — no one wants to wake up early to hear challenging feedback at 6 a.m. It should be your manager if someone has to wake up early or stay online a little last.

5. Over-Communicate

The point of having a difficult conversation is not to chastise direct reports. Instead, it shows that your managers care about their success and are here to help. In-person, we can rely on body language, tone, and facial expressions to drive that point home. However, on a call, we don’t have those luxuries.

Instruct your managers to drive their point home by over-communicating their intentions. They can recognize that this conversation is more difficult over video or phone and take the time to reaffirm their choices for this conversation a few times to assure their direct report that they’re here to help.

When managing a difficult conversation, your managers should want their employees to understand that they’re on their side. After all, they’ll need to work together to come to a resolution that works for everyone. 

6. Follow Up

Once your manager and their employee have found a resolution together, train your managers to close the meeting by recapping the commitments, obligations, and agreements they made.

In our example, maybe Joe’s manager has promised to remind Joe of deadlines sooner than a day before the project is due. Or, maybe Joe has decided to take time off he needs to help his family. Or, Joe has vowed to raise his hand when he needs help or thinks he will miss an approaching deadline. 

When managing difficult conversations, remind your managers they can’t just make these commitments and then wash their hands of the conversation. Instead, they need to schedule a follow-up chat or address the plan in existing 1-on-1 meetings shortly after their initial discussion to chat on progress, see if the issues remain unresolved, and decide if the solution is or is not working.

Your managers should want to keep this conversation active — that’ll show their direct report that they’re invested in helping them address this feedback and have a successful career at your company.

New call-to-action

Overseeing a remote team comes with various challenges — managing difficult conversations is one of them. Follow these tips to keep the process smooth and see great results. You’ll find that holding these difficult conversations helps your employees grow and improve individually, improving employee performance, helping your team become more effective, and making your managers stronger leaders for your business.

Are you interested in learning more about managing difficult conversations remotely or leading a dispersed team? Speak to one of our L&D experts to get a brief demo of Hone and to learn more about some of our most popular remote management classes, like Manage Remote Teams or Communicate Powerfully Around Change.

Develop universal skills and drive growth with practical, real-world insights.