How Are Your Remote Workers Doing?

Hana LaRock

by Hana LaRock

5 min read
How Are Your Remote Workers Doing?
Managing Teams Guides Inspiration Productivity Wellness
We’ve compiled 6 essential questions great managers should be asking their remote employees.

Managers of remote employees know that mental health and job satisfaction can significantly affect work performance and productivity. World events or situations at home can hamper an employee’s ability to concentrate on work. As a result, a growing number of people are focusing on self-care and on just how much their employers do or do not care about their mental well-being. In fact, according to a study published by Telus International, 80 percent of workers say they’d consider quitting their job to work for a company that cared more about their mental health.

If your goal is to increase your awareness and acknowledge the importance of your employees’ mental health, regularly checking in with them can help. We’ve compiled a list of questions to help you gauge how your team members are doing as they work in their own spaces.

1. How are you feeling?

It’s a simple question of common human decency, but it’s effective nevertheless. Clearly, even when employees seem really “on it” workwise, they may be dealing with all sorts of troubling things. According to SHRM president and CEO Johnny C. Taylor Jr., although it may be routine to ask team members how they feel about specific circumstances, sometimes just asking how they feel in general can be a productive way to open the door to fuller discussions. That’s especially true if you ask with genuine concern and take the time to listen and affirm the answers.


Follow-up steps: If most of your employees say they are doing okay, then perhaps they are. However, if you notice someone indicating signs of extreme stress, anxiety, or depression, then you may want to revise your question to dig a little deeper. Try to get to know your employees better and get a lens into their daily life, Business Marketing Engine suggests. This can help you be more compassionate to employee needs and offer assistance whenever possible. Providing helpful resources and reminding employees that they are entitled to a mental health day are other great ways of showing support.

2. What expectations do you have of me at this time?

Just because you’re the boss, that doesn’t mean you’re not human. Even those in leadership roles may have trouble managing employees working from sites all over the state, country, or world. As Harvard Business Review points out, “Creating successful work groups is hard enough when everyone is local and people share the same office space. But when team members come from different countries and functional backgrounds and are working in different locations, communication can rapidly deteriorate, misunderstanding can ensue, and cooperation can degenerate into distrust.” It’s a lot easier, therefore, to manage your employees’ expectations once you know what those expectations are.

Follow-up steps: Regularly checking in to get feedback from your employees can help you determine whether the relationship is working for both parties. Also, meeting with them before, during, and after a major project or assignment can help reveal opportunities for growth, according to Corporate Finance Institute’s tips on how to be a supportive manager.

3. Do you have the tools and resources needed to be successful at work?

Let’s face it, not every home is equipped to adapt to a work-from-home environment. One of the key things a manager can do to support their remote employees is to get the infrastructure right, advises Harvard Business Review. Functioning technological systems are imperative when people work from home, no matter the circumstances. If your employees are showing up every day with their equipment ready but your cloud storage is a disorganized mess, then you need to be aware of their frustrations and be prepared to address the issues that can lead to long-term burnout. Asking your workers to honestly tell you if they feel they have the tools and resources they need to do their jobs can help you understand any added stressors contributing to their workloads. You can be a better advocate with better information.

Follow-up steps: Resolving technology and infrastructure problems can be a lot more complex than simply referring employees to the IT department for support. As a manager, it’s your job to make sure your employees have what they need without having to navigate other departments. Be sure to follow up when employees express concerns about technology or other functions that are preventing them from doing their jobs properly.

4. What challenges are you facing?

Buffer’s report on the state of remote work says that the top three struggles for remote workers are: unplugging after work, loneliness, and collaboration and/or communication. Though you may be generally aware that working remotely has its challenges, knowing what each of your employees is facing will help you accommodate their needs that much more. Be sure to communicate at the group level when you’re addressing problems that affect all or the majority of your team members.

Follow-up steps: As long as it wouldn’t cause more stress for your employees, Kin suggests that regularly holding individual meetings to address any specific issues can be very powerful. This should be done in a safe space so that each worker can comfortably discuss with you the challenges they are facing. Even though some of these challenges may be felt by more than one employee, take care to not put anyone in the uncomfortable position of speaking for others.

5. How is your work-home balance?

Working from home involves good days and bad days, just like at the office. And though your employees may theoretically be able get more done at home, home has now become where they work. At an office, it’s actually easier to leave their work at work—the job stays at a physical building. But that’s not so easy at home, so remote workers sometimes struggle with finding a work-life balance. Directly asking about that balance can lead you to jointly implement strategies that can make remote work easier for them.


Follow-up steps: Providing occasional rewards and days off can empower employees to recharge their batteries. Consider ways you can enhance your employees’ work-home balance. For instance, allowing flextime, which lets remote employees choose the time spans that most accord with their own schedules, can translate to getting the best work from them when they’re at their best.

6. Are you checking in with yourself?

Part of being among the top 18 percent of good managers is asking your employees the five questions above. But to make sure that everyone involved is feeling good and doing okay, you need to check in with yourself too! By asking yourself these same questions—sometimes even before you pose them to your team—you’ll get an idea of how things are going overall. For instance, if you’re feeling overwhelmed, chances are your employees are as well. If so, maybe you can address things at the source before issues spill over onto your workers. But either way, conducting self-checks can only help you empathize with them better.

So whether you’re asking yourself or your employees, use these prompts to stay focused on essential areas:

  • How are you adjusting to working from home?
  • What are your biggest challenges?
  • What changes need to be made?
  • How can I help?

Follow-up steps: It’s no secret that it’s easier to bring negative vibes into the workplace than positive vibes. Integrative mental health experts agree that human beings feed off one another’s energy. And since we’re all humans whose equilibrium can suffer at times, checking in with yourself will help you detect when it’s time for your own mental health day. You may even want to consider working with a performance coach or therapist, because a healthy, well-balanced boss leads to healthy, well-balanced employees.


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