How to Handle Difficult Conversations as a Manager of a Remote Team

Your direct report Joe has been missing deadlines.

You’ve looked at the situation from all angles. You’ve made sure Joe’s missed deadlines were a regular occurrence, not a one-off fluke. You’ve communicated your expectations. Still, the deadlines are being missed.

It’s time to talk. But how? When? What if he gets angry? What if I’m missing something?

And the biggest question: How do I hold this difficult conversation remotely?

As a manager, you’re responsible for coaching your employees to success — even if that means having difficult conversations, and even if that means having those conversations remotely. Doing so helps Joe become better in his job. It also helps your team become more effective and you become a stronger leader.

This article shows you how to handle difficult conversations remotely.

Before having a difficult conversation

Set the stage for an effective conversation by following these two rules beforehand.

Rule #1: Never avoid difficult conversations, but don’t rush into them either.

Familiarize yourself with the instances that need a difficult conversation. To do so, ask yourself:

  • 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 the answer is yes, you need to have a talk. First, spend time identifying and confirming your assumptions. Prepare for the conversation as you would an interview: Draft your talking points and your ideal outcome.

Rule #2: Make sure you have a trust and emotional bank account.

Having mutual trust and respect with your employee is your ‘emotional bank account.’ It helps ensure that your difficult conversation kicks off on the right foot.

Earning that mutual trust and respect will look different for each employee. Joe, for instance, appreciates chatting about things other than work via messaging, phone, or video. The remote company Zapier, in another example, gathers remotely for weekly team hangouts. Sometimes the team discusses new projects or shows demos, sometimes the team simple chats through an idea. Whatever happens, it’s a chance for everyone to build rapport across time zones.

Having a difficult conversation

Have It ‘In Person’

Don’t have difficult conversations over messaging or email. Talking on a video call is ideal — remote company Invision recommends Zoom. It will make the conversation feel as ‘in person’ as possible. A phone call is a solid second option if bandwidth issues are making your video conferencing spotty.

Consider Time Zones

Joe works on the West Coast, three hours behind you on the East Coast. You’re planning to schedule your call during Joe’s working hours — no one wants to hear difficult feedback at 7 a.m. If someone has to wake up a little early or stay online a little last, it should be you.

Overcommunicate Your Intentions

The point of having a difficult conversation is not to chastise your direct report. It’s to show that you care about his success and are here to help. In person, you can rely on body language, tone, and facial expressions to drive that point home.

You don’t have the luxury of body language, tone, and facial expression on a call. So drive your point home by overcommunicating your intentions. Recognize that this conversation is more difficult over video or phone. Reaffirm your intentions in having this conversation a few times.

Keep The Conversation Structure the Same

Structure a virtual difficult conversation the same as you would in person. Focus on these best practices:

  • Give feedback on the behavior, not the person. For example, you’ll tell Joe “I’ve noticed these three projects have all finished after the deadline” instead of saying “You’re disregarding my deadlines.”
  • Reiterate your intentions. You plan to tell Joe that you’re “here to help Joe complete projects and reach deadlines as successfully and efficiently as possible.”
  • Ask for input. Now, turn it over to Joe. Ask broadly “what do you think about all this?
  • Coach. The remote company Aha recommends using feedback as a teaching opportunity. Work with Joe to identify what needs to change and how.

Follow Up

If you had this conversation in person, you’d be able to observe your direct report after the conversation. How do they seem to be absorbing the feedback? Do they seem annoyed? Have they put your next steps into action?

Check in by scheduling a follow-up chat sooner than you normally would. You want to keep this conversation active — you’ll show your direct report that you’re invested in helping them address this feedback.

Managing a remote team comes with a variety of challenges — having difficult conversations is one of them. Follow these tips to keep the process smooth. You’ll find that holding these difficult conversations helps your direct report, your team, and you improve.

To learn more about remote management, join us on December 11th for our webinar on Developing and Engaging Distributed Teams with executives and HR leaders from InVision, Dashlane, CultureIQ. Click here to register.

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