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Managers: 15 Questions You Should Ask Remote Employees

Ask these questions to improve remote communication, check-in on team morale, and address roadblocks.

Virtual one on one meeting

Remote work has never been as common as it is now. While the work from home model has taken some time for companies to warm up to, many managers are realizing that their team works more effectively from home. Managing remote employees takes some getting used to and there are certainly adjustments that need to be made to see a productive team output. 

To make your transition to managing remote teams an easier adjustment, Fellow has outlined 15 questions to ask your employees to help with managing remote employees. 

What is remote work?

Remote work is any work that is done outside of a traditional office environment. It is often referred to as working from home (WFH) or telecommuting. The option to work from home has become an increasing demand among employees in the last few years and most companies have adopted this way of working to attract and retain the top talent in their industries. Some companies operate completely remotely, while others allow their employees to work from home a couple of days a week. 

One of the main benefits of remote work is that it enables individuals to successfully complete their daily responsibilities without needing to commute into work every day. Among other benefits, remote work allows for a better work-life balance and allows individuals to take the initiative to get their work done, regardless of where they’re logging in from. 

Woman working from home couch

Why is it important to follow-up with your employees when working remotely? 

One of the most common challenges for remote workers is lack of communication and social connection. As a manager, it’s really important to check-in with people on your team on an ongoing basis and ensure that they have the tools and resources they need to do their job well. Checking-in and following-up with remote employees is an important way to understand how they are feeling and if there’s anything you can do to support them.

As the Harvard Business Review’s guide for remote managers explains:

“Managers need to understand factors that can make remote work especially demanding. Otherwise high-performing employees may experience declines in job performance and engagement when they begin working remotely, especially in the absence of preparation and training.” 

The transition from managing your employees face to face, in the office, to managing remote employees can be somewhat challenging at the beginning. Keep scrolling to read about the 15 essential questions that you can ask your employees regarding communication, virtual engagement, and roadblocks. 

15 Questions to ask remote employees

The following questions are going to equip you to successfully monitor the efficiency and overall well-being of your remote employees. 

Questions about remote communication

Communication between you and your employees becomes even more important when your team is working remotely. It takes some time, trial and error to determine which means of communication is the most effective for you and which remote collaboration tools will be the most beneficial for your employees working from home. 

Ask the following questions about communication to uncover how to improve the way you interact with your remote team:

  1. What do you think could help us improve daily communication?
  2. Are you clear on your role and what you should be working on? What aspects aren’t very clear?
  3. Do you think our decision-making processes include those that work remotely? 
  4. What can we do to improve the way we communicate company updates and decisions? 

In asking these questions about communication, you are gaining valuable insights from your remote teams. You can then use the information that you gather in order to facilitate more effective team meetings, reconsider the collaboration tools that you’re using and to make improvements where they’re necessary. 

By compiling the answers to these questions from each team member, you can then consolidate the most frequent answers and pinpoint what you need to work on to make your team’s communications stronger than ever. 

Questions about employee well-being

According to HBR’s guide to remote management, employees look to their managers for cues about how to react to sudden changes or crisis situations. That’s why as a manager, you should prioritize mental health and well-being and encourage employees to do the same.

“Especially in the context of an abrupt shift to remote work, it is important for managers to acknowledge stress, listen to employees’ anxieties and concerns, and empathize with their struggles.”

Here are some questions you can ask about your remote employees’ well-being:

  1. Do you feel the company supports remote staff effectively? How can we support you more?
  2. When have you felt stressed or overwhelmed in the past month? What can I do to prevent that?
  3. What part of your job is the most energizing?
  4. What part of your job is the most draining?
  5. What do you normally do to recharge your energy?

Questions about engagement and roadblocks

Working remotely definitely has its advantages but there are still several challenges that come with working from home that need to be addressed with your team. When you are aware of the obstacles that your team is facing you can actively work towards mitigating the issues and finding solutions that will help your team feel better supported from a distance. 

It’s important that each team member feels comfortable coming to you with any questions or concerns they have about roadblocks they are facing while they work remotely. 

Here are some great questions that will prompt valuable insights from your employees working at home:

  1. Are there any obstacles that prevent you from doing your best (obstacles at work, or if you want to talk about it, personal)?
  2. Is there anything right now that is slowing you down or blocking you?
  3. What are some challenges you’ve faced recently? How can we work them out together?
  4. If you had to point to something that was holding you back or slowing you down in achieving your goals, what would you say that would be?
  5. How do you manage distractions during the day? Is it a challenge for you?
  6. Is there an aspect of your job that needs more help or coaching?

You can opt to use these questions at your regularly scheduled one-on-one meetings or use them in team meetings to facilitate an open discussion about how you can ease some of the issues that your team is facing.

Pro Tip

Show your direct reports that you care by remembering what they said during past meetings. With Fellow, you can see a history of every 1-on-1 conversation you’ve had and ensure that you’re staying focused on important decisions and action items.

One on One Meeting Tool

There is always room to learn and to grow collectively, as a team. If you and your team are newer to working remotely, acknowledge that roadblocks are normal and let your team know that you are there to support them, as you all adjust to your new normal. 


Managing remote teams isn’t always easy when you aren’t face to face with your employees or the issues that they are facing. Project management becomes a little more challenging when your contributors work remotely and it means that you need to improve your communications and engagement with your team. 

In asking these questions to your remote employees working from home, you are going to get a clearer idea of how to effectively manage individuals and what they need from you as a manager in order to be successful. 

Refer back to this guide anytime you need to check-in with your remote team and understand their level of engagement!

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