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How to manage a remote employee who is struggling

When an employee is underperforming while remote, it’s tough to know exactly what to say and do. Here’s a path you can pursue to manage a remote employee who is slipping.

Manage a remote employee who is struggling

An experienced manager will tell you that it’s always easy to manage a remote employee when they’re performing well.

But what about when they’re not? What do you do when a remote employee is underperforming?

Answering this can feel complicated. Given the uncertainty and fear during these times of COVID-19, some of our team members might be experiencing greater mental burden and emotional distress than usual. Many employees are caretakers for others right now, and others may be having a difficult time coping with the social isolation and the precarious state of our world.

As leaders, we want to be sensitive and empathetic to the fact that these are indeed challenging times for us all – and yet at the same time, we have standards, expectations, and goals that we’re accountable to. It can feel hard to know precisely what to do…

But a path forward does exist. This is not an impossible quandary. You do not have to suffer in silent acceptance of a team member’s poor performance because your team is now remote. Nor do you have to cause undue hurtful stress on your team members by confronting their underperformance.

Rather, to manage a remote employee who is struggling well, you can approach the situation with care, positivity, and thoughtfulness. You can, in fact, help that person change their behavior for the better.

Here’s how…

#1: Emphasize your intention, not your own emotion.

Swap out “You’re messing up…” for “I want to help…”

When someone’s messing up, it’s easy to want to express our dismay or exasperation. “I don’t understand why this is late again” or “This is making my job really hard,” you’re tempted to say. But no matter how true those statements might be, starting the conversation that way shuts down the conversation. The other person will feel attacked, perhaps even ashamed, and immediately move into a defensive mode.

The minute someone moves into defensive mode, they aren’t going to want to change. They’ve hardened. You won’t be able to get through to them. Conversation over.

Instead, you’ll want to focus purely on the positive intent of your conversation. The #1 reason a person will become defensive is that they misread your intention. So if you can make your intention for why you’re sharing critical feedback about the performance, the less likely that person will be defensive to your comments.

For example, you could say: “There is nothing more I want than for you to be successful at your role. But I’ve realized that I haven’t done my part in helping you with that by not being as clear as I can. So I’d love to share as clearly as possible with you where I’ve observed expectations not met and areas of poor performance. It will feel critical, but it’s because I want you to be successful, and so I’d like to be as honest as possible with you.”

Notice that the example here does not mince words about performance being deficient. You should be as clear as possible that someone is not meeting expectations. But do so in the context of explaining why you’re being critical. Intention outweighs everything if you want the other person to truly change and to manage a remote employee well.

Have this conversation with our 1:1 Tool 💭
Ensure your 1:1 conversation makes your intention clear.

#2: Hone in on observable behaviors.

Swap out “You haven’t done X…” for “I noticed…”

When you’re describing what the other person needs to improve, you may find yourself wanting to say things like “You didn’t complete X…” or “I’m frustrated when…” or “You seem careless when…” However, those statements point fingers at the person. They may not sound accusatory to you – but there’s a more productive way for framing your descriptions that will make the other person more receptive.

Frame the areas of improvement as observations, instead. For instance, rather than saying, “You didn’t do Y…” try saying “I saw” or “I noticed” or “The team observed.” A useful self-check is to ask yourself: “Is it observable behaviors that I am describing?” You’ll also want to be as specific as possible. I recommend citing numbers and time frames, when applicable. For example: “For the past Z months, there have been at least YY times when I and others on the team have observed that you haven’t…” Another example: “I noticed YY number of XX that were not completed on time, that was a part of your role expectations.”

The more you can describe observable behaviors, the more probable it is that the other person will be able to see the situation as you see it.

#3: Ignore your instincts – and ask outward and inward questions.

Swap out “I think you’re stuck because…” for “How am I getting in the way of you making progress?”

You think you know. Someone is underperforming because they have a hard time doing detailed work. Or someone is underperforming because they’re missing the in-person social interaction with their team.

Whatever the reason is, be wary of the assumptions you project. You don’t really know why someone is underperforming unless you ask precise questions that help you reveal this.

Ignore what your instincts might be telling you and carve out space to ask questions that help you understand: What is exactly causing this person to not perform up to standards?

To get to the bottom of this, you’ll want to ask questions during a one-on-one meeting along two different axes: (1) Outward (2) Inward. Outward questions try to uncover what external factors on the employee’s side are hindering them. (“How is the employee themselves or the circumstance itself holding them back?”) Inward questions try to understanding what internal factors on your side as a manager are blocking the employees. (“How am I as a manager getting in the way?”)

Here are some examples of outward questions you can ask…

  • How have you been feeling about your own performance lately? Where do you see opportunities to improve, if any?
  • How is the remote work environment currently hurting or helping you in making progress on your work?
  • What are you most enjoying about the work you’re doing? What part of the work is inspiring, motivating, and energizing, if any?
  • What part of the work do you feel stuck? What have you been trying the “crack the nut” on, but it feels like you’re banging your head?
  • What part of the work is “meh”? What tasks have you felt bored or ambivalent about?
  • When’s the last time you got to talk to or connect with a customer who benefited from the work you did? Would you like more opportunities to do that, and should make that happen?
  • Do you feel you’re playing to your strengths in your role? Where do you feel like there is a steep learning curve for you?
  • Would you say you’re feeling optimistic, pessimistic or somewhere in the middle about the company’s future?

Here are some examples of inward questions you can ask…

  • Is it clear what needs to get done? How can I make the goals or expectations clearer?
  • Is there any part of the way we’ve set up the remote work environment that feels burdening, stifling, or that simply isn’t working for you?
  • Is the level of quality that’s required for this work clear? What examples or details can I provide to clarify the level of quality that’s needed?
  • Am I being respectful of the amount of time you have to accomplish something? Can I be doing a better job of protecting your time?
  • Do you feel you’re being set up to fail in any way? Are my expectations realistic? What am I asking that we should adjust so it’s more reasonable?
  • Do you have the tools and resources to do your job well?
  • Have I given you enough context about why this work is important, who the work is for, or any other information that is crucial to do your job well?
  • What’s irked you or rubbed you the wrong way about my management style? Does my tone come off the wrong way? Do I follow-up too frequently with you, not giving you space to breathe?
Get 100+ 1:1 questions like these 💡
Use our One-on-Ones Tool in Know Your Team.

None of these questions ask, “What do you think you’re doing wrong?” They’re not “trick” questions that attempt to get the person to incriminate themselves when you look to manage a remote employee. It’s about creating a mutual, shared understanding. You’re trying to build a moat, not walls, with these questions.

#4: Co-create a path forward.

Swap out: “Do you have any questions?” for “How can we work together to improve things?”

Once you’ve (1) shared your intention in the conversation, (2) objectively shared what you’ve noticed needs to improve, and (3) asked questions to better understand the root cause of underperformance, now comes for the last piece: (4) Looking ahead.

You want to co-create a path forward. To do this, you’ll want to avoid abruptly ending your conversation with “Do you have any questions?” Instead, share some words that help clear the slate, and indicate that you want to get better together

For example, you could say something like: “I’m sure this is difficult to hear – and that’s our fault for not sharing these things earlier. But I’d love to start fresh, to be honest with one another, and support each other. Again: I want you to be successful in this role. And I’d love your help in trying to figure out how to build a path to that. I’m keen to understand from you: (1) Do you believe these are areas you can improve on? And, (2) How can we work together to improve on these things? Let’s work on this together.”

This path forward may result in adjusting the goal itself, so it’s more reasonable. You may even consider moving the person to a different project. Most frequently though, this will result in you implementing a performance improvement plan (PIP). I’ve written extensively about the factors to consider in a PIP here.

Whichever next steps you decide, keep in mind it is a step you’re taking together – and that you as a manager want to support this person in their attempts to improve. The shared responsibility is an important part to manage a remote employee well.

Deliver via video chat and then follow-up in writing

In lieu of having this conversation in-person, in a remote work environment, you’ll want to have this conversation via video chat. This way the other person can see your facial expression and hear your tone of voice when you say things like “I want you to be successful”. Then, if you find it prudent, you can share a write-up that confirms: “Here’s a summary of what we talked about and what we’ve agreed on as next steps.” This way, your path forward is documented, and the expectations are crystal clear.

For this video chat, here’s how you might structure the conversation and the one-on-one meeting agenda:

  • Catching up (10 – 15 min.)
    • How is your energy level these days?
    • Cook anything good lately?
  • Performance (30 min.)
    • My intention of this conversation
    • My observations
    • Inward + outward questions
      • How have you been feeling about your own performance lately? Where do you see opportunities to improve, if any?
      • How is the remote work environment currently hurting or helping you in making progress on your work?
      • What part of the work do you feel stuck? What have you been trying the “crack the nut” on, but it feels like you’re banging your head?
      • Am I being respectful of the amount of time you have to accomplish something? Can I be doing a better job of protecting your time?
      • Do you feel you’re being set up to fail in any way? Are my expectations realistic? What am I asking that we should adjust so it’s more reasonable?
      • Is it clear what needs to get done? How can I make the goals or expectations clearer?
  • Looking forward (20 min.)
    • How can we work better together? What tactical steps should we both take?
  • Takeaways / Next steps (5 – 10 min.)
Use our 1:1 meeting agenda templates ⚙️
It’s all in our One-on-Ones Tool in Know Your Team.

Whatever you do, don’t sit on it.

What you do not want to do is tolerate the behavior. Secretly hoping that your direct report “gets the hint” or that they magically wake up one day illuminated by the idea that they need to change something…

That never happens. If anything, the employee will become frustrated, and even angry, that you didn’t say anything, to begin with. The last thing you want is a team member who feels blindsided by their own performance.


The true indication of effective management is not merely in how you support your team members who are already doing a great job – but how you address, coach, and manage a remote employee who is slipping.

Do this well, and you’ll have learned to manage a remote employee well.

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Written by Claire Lew

CEO of Know Your Team. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.

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