It's no surprise that remote work affords both employees and employers many benefits. For example, those who work remote at least once a month are 24% more likely to feel happy and productive in their roles than those who don't or can't work remotely. However, work is still work, and even with a happier and more productive workforce, it's inevitable that sometimes you'll have to have challenging conversations.

There are all sorts of difficult conversations that are just an inevitable part of work -- whether that's delivering corrective feedback about a project, discussing changes that will impact a direct report's work-life, or letting them know they didn't receive a promotion or raise. These conversations are always challenging, and they're even more challenging if you're not face-to-face with the employee in the same room.

This post is written from the manager's perspective, but these lessons can be applied by anyone, whether their direct report works remotely or in the office. We won't cover delivering HR news like layoffs or termination, although many of the same principles will apply. In those cases, we recommend that you confer directly with an HR representative at your organization to make sure that you get the policy and legal aspects of the conversation right, too.


How to Have Difficult Conversations with Your Team


1. Create a culture of honesty and transparency.

It's always easier to tackle a problem when it's a small issue rather than a giant elephant in the room. To avoid this, managers should be proactive and get ahead of these small issues when they're first noticed. You can help make that possible by deliberately building an office culture of openness and radical candor. Create an environment where both you and your direct reports feel comfortable giving and receiving feedback on a regular basis, and not just during performance reviews. Here are a few suggestions for getting in the habit:


Incorporate feedback into your regular communication.

Sharing feedback in real time, both positive and negative, is hard but worth it. My boss loves to tee this up by saying, "Here's my in-the-moment feedback," and then sharing her honest opinion on how something has gone. Most frequently, this is an opportunity for praise or helpful suggestions, but it's created a space where it wouldn't be unreasonable for her to share constructive criticism, too.


Schedule regular opportunities to give feedback via video chat, in addition to in-person.

Does your company require regular performance reviews? If not, you should consider implementing more regular reviews, in addition to weekly or bi-weekly 1:1 conversations. Better still, set aside five or ten minutes in regular one-on-one meetings to share thoughts on an employee's performance. You may not use the whole time every week, but when the need to deliver corrective feedback comes up, you'll be glad that you've created space to do so.


Solicit 360-degree feedback.

An easy way to gain trust and build a culture of honesty is to invite employees to share their feedback equally. You want them to know that it's okay to be upfront about what's going well and what they find challenging. If you're trying to be proactive and get ahead of problems before they snowball, don't you want the same ability to get ahead of problems that you might be creating? Plus, it will engender trust with your direct reports if they feel that the relationship is equally vulnerable.


2. Avoid blindsiding employees with constructive criticism or corrective feedback.

Let your employees know what's coming, or at least that corrective feedback or bad news is coming, before delivering it to them in-the-moment. This isn't always possible. For example, if your company has decided to change a policy that will be unfavorable to your remote employee, you probably won't be able to tell them until the news is released to the wider company. Still, you can usually give some kind of advance notice that a tough conversation is coming down the road.

Be as clear and direct as you can be when you give the heads up. Nobody likes to hear that a tough conversation is coming, but at least with clarity, your employee can prepare. An email or a quick message on Slack can go a long way. For example, saying, "We need to discuss this project before noon today," is clear and direct, and will give your employee a chance to get their thoughts together.

But don't send this message too far in advance. Give a heads up as close to your desired meeting time as possible. No one likes hearing, "We need to talk," and then waiting all day to have that dreaded conversation. Don't leave your employees too long to stew in their thoughts. If their minds wander for too long, they might make incorrect assumptions, and your conversation won't be productive if they're overly anxious or angry.

Let them in on context clues that they might not get without being in the office if they work remotely. Are people grumbling because this employee's work has been slipping? Is there tension because two executives are having a public disagreement? Video conferencing can help people ready body language and get other context clues, but remote employees can't see everything that's going on at all times. If they're missing important context, fill them in so they can be better prepared in the future.


3. Be factual, concise, and compassionate.

Focus on the facts. "You missed a major deadline, and as a result, we have to delay our product launch by a month. In the future, I will expect you to share status updates more proactively and let me know sooner if you will miss a deadline so we can adjust plans as needed." When it comes to corrective feedback, focus on the facts -- not feelings. Making things personal won't help your employee hear the feedback you're trying to deliver or improve in the future. Instead, lay things out in a way that will help your employee fix the problem, rather than a way that puts them on the defensive.

Let your employee respond, and really listen to their feedback on the situation. You may not be able to change anything in that moment, but you can certainly be sympathetic and let your employee know that they are being heard. For example, you may not be able to change a new policy that remote employees have to travel to headquarters once a month, but you can let your remote teammate know that you hear their frustrations and know what they would want changed and why.

End the conversation with clear next steps to move forward. Are you expecting your employee to change their behavior in some way? Are you implementing new procedures that they will have to follow? Let them know. By being direct about next steps, you will show your employee how they can turn a bad situation around.


4. Follow up on progress.

Schedule a follow-up conversation after an appropriate amount of time to make sure you revisit the issue. You've already given concrete expectations about what should change between your initial conversation and the follow-up. Now, hold your employee and yourself accountable. Without accountability, the team member could grow even more alienated and wonder why they had to have an awkward chat for nothing. You can see how things could spiral from here; stay on top of the issue so that everyone involved feels like things are improving.

Make sure that your employee knows that you are available for follow up questions or concerns. They might want to talk prior to your official follow-up meeting. Encourage them to do so. This is how you can help them win.

Make sure they know what resources are available to help them improve or handle the situation. Do they need to improve a particular skill? Point them towards learning resources. Are they having a conflict with a co-worker that would benefit from some face-to-face time? Let them know if there's a budget available for them to travel for an in-office meeting if they work remotely.

Nobody likes having difficult conversations, but we hope that these tips can help you make the best of a tough situation and help move your business forward in a thoughtful way. To learn more, read our list of tools to use to support your distributed team.
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