31 Questions to Ask Remote Employees to Better Support Them

Supporting remote employees is different, and in some ways harder, than employees in the office. But the right questions during your 1 on 1s can go a long way to helping them thrive. Read on to learn specifically crafted questions to ask remote employees on your team.

Remote management is the same as managing people in an office with you, right?

Not quite. According to Buffer’s State of Remote Work report, remote employees face many unique challenges:

31 Questions for Better Supporting and Managing Remote Employees - Buffer report image
Very few of these also affect people in an office.

As a manager, it can be hard to understand what your remote workers are going through, especially if you’ve never worked remotely yourself. This can make your remote team members feel isolated in more ways than one.

Remote employees are separated from the rest of the office, so it’s easy for them to feel out of the loop of normal office communication that happens organically.

However, that’s not the only difference. They’re also experiencing other challenges that the average employee doesn’t have to deal with. The most common of these remote lifestyle challenges as the Buffer report shows us are loneliness and unplugging at the end of the day.

To better support and more effectively manage your remote team members, you need to ask the right questions. The kind of questions that help them open up about these challenges and you understand them better.

Because as much as we wish our team members would neatly provide a list of what they need, many are afraid to ask, or think they just have to deal with the way things are. Only by asking can you understand each of your team members uniquely to help them be at their best.

questions to ask remote employees are key for managers

31 Questions to Ask Remote Employees to Better Support them

Asking the right questions can unlock insights that help you break through issues and better support your team. That’s why we want to share some great questions you can use today to uniquely understand and support your remote employees.

The key is focusing on the specific challenges of working remotely.  Your team may not volunteer information about these issues, but addressing them can improve their work life and the performance of your team as a whole.

Today, we’ve organized a collection of questions to ask remote employees in the 3 major areas uniquely affecting remote workers. This includes:

Within each section, we’ve provided context to help you understand the purpose of the questions and how they allow you to help remote workers facing those particular challenges.

Starting things off, here are 31 questions to ask remote employees.

31 Questions for Better Supporting and Managing Remote Employees - Buffer report image

1) Remote lifestyle

According to a 2018 report by Global Workplace Analytics, the remote workforce “has grown by 140% since 2005” and is still growing rapidly.

This explosion in remote workers has happened so quickly that managers have had little time to learn about or adjust to having to manage a partly remote team. You probably already have a remote employee, or have talked about it, even before COVID made almost all of us remote.

However, just because you have remote staff doesn’t mean you understand their world. If you work in an office, you have a set of typical routines:

  • Your commute
  • Your office environment surrounded by colleagues
  • Lunch either in the kitchen or outside the office
  • Meetings throughout the day
  • Then your commute home

But for a remote employee, their day can be completely different:

  • Working from a home office, coffee shop, or at a nearby co-working space (where, even then, many of those people may remain strangers)
  • Communicating usually through chat, where understanding context is difficult without non-verbal cues
  • Only interacting with others face-to-face over video
  • And ending the day at a set time only enforced through self-discipline

Given those differences, it’s no surprise that your remote employees may face different challenges than your typical office worker.

Questions to Ask Remote Employees

Remote lifestyle questions

The questions below will help you understand how their day is structured and identify ways you may be able to help them. (For example, obtaining a budget for them to improve their home office or get a co-working space.):

  • 1) What’s your favorite part about working remote? (Understand what drives them)
  • 2) What’s your daily routine like for working?
  • 3) What’s the highlight of your day? (Look for signs of loneliness, encourage socializing, or routines to encourage)
  • 4) What’s most challenging for you in your daily work routine? (Help troubleshoot)
  • 5) What do you do to recharge each day?
  • 6) What’s your setup like for working?
  • 7) What’s one thing we could get for you that would make your work easier or better?
  • 8) What’s the most important thing we do to help you be successful working remotely?
  • 9) How do you manage distractions during the day? Is it a challenge for you?
  • 10) Have you explored or regularly use a co-working space? What are the benefits that make you go?
  • 11) How long have you been working remotely? What were the most challenging and surprising things when you first started?
  • 12) What helps you feel connected to others and counteract the potential loneliness of working remotely?
  • 13) Why did you start working remotely?
  • 14) Do you think you can fully disconnect at the end of the day or when you’re on vacation? What helps you do so?

With these questions, you’ll accomplish two key things:

First, you’ll build empathy by understanding how they feel about working remotely and their average work day/routine.

The second is you will uncover issues by understanding better what some of their challenges they’re facing by working remotely.

Both will help you work with them to help them have a great experience working remotely. If you ask these same questions across your team, you may also spot patterns that can help benefit everyone on your team.

2) Info dissemination

One of the biggest challenges of working remotely is communication. Particularly, all the ad hoc conversations they miss out on that happen in the office.

Consider this scenario: you had a morning stand up or a quick call with your entire team, including remote team members, earlier in the day.

31 Questions to Ask Remote Employees to Better Support Them

Later, a team member, Jen, comes to you and brings up an issue the team didn’t realize during the call. After that, another team member, John, comes to you and explains that he and Jen figured out a solution. You tell them it looks good and to run with it.

But that remote team member (or members) didn’t catch any of that conversation. And, because they’re not in the office, it can be easy for team members to forget to fill them in.

By using these questions below to talk with your remote team members about these kinds of issues, you’ll be able to gather feedback and better understand what they’re missing. Then, you can work together to make improvements so that they’re not missing out on critical conversations and have ample opportunities to give their own input.

Info dissemination questions

  • 15) What do you want to learn more about our team / the company? (Harder to learn when you’re not around the office)
  • 16) Have you been surprised by any news announced at an all hands? What was it?
  • 17) Do you feel included in our team decisions? Why/why not?
  • 18) Do you feel the company supports remote staff effectively? How could we improve?
  • 19) How are the tools we use as a team working out for you remotely? (i.e.- Are they handicapped by poor audio on hangouts or the like?)
  • 20) What challenges do you feel you have compared to those in the office?
  • 21) Are there any tools that we should try out that could help us improve our remote culture?
  • 22) Are our meetings friendly to remote folks like you? What could we improve?
  • 23) Do you think our decision-making process works effectively while also supporting our remote culture? Have you seen a decision drag out for too long lately? (Decision making is hard and usually longer in remote teams and is worth constantly monitoring the pulse on)

It’s hard to always recognize who isn’t in the room. Remembering to keep remote team members in the loop is a problem that requires a consistent, intentional effort and doesn’t always work out perfectly.

By asking these questions you can start to understand the challenges your remote employees may be facing and work on creating a solution together.

3) Connection

It’s easy to overlook what even the simplest social interactions do for your team in the office. Even simple day-to-day banter can build strong bonds for teams.

31 Questions for Better Supporting and Managing Remote Employees

This often happens naturally when you’re working in close proximity. But when you’re not working side by side every day, that can be a lot harder.

Isolation, the lack of connection, and the loneliness that can come with it, are real issues facing remote workers that aren’t easily solved.

However, it’s not just a lack of opportunities to bond face-to-face. One of the greatest challenges of working remotely is the lack of context.

A lack of context makes connecting with remote team members difficult

Most of the information we take in from a conversation is non-verbal. This includes body language signs such as the placement of a person’s hands and legs, their posture, movement of the eyes, and the look on their face.

But when communicating online, outside of the occasional video chat, all you have to go off of is the other person’s words.

one on one31 Questions for Better Supporting and Managing Remote Employees meeting questions to ask remote employees

Unfortunately, without this critical form of context, we’re programmed to assume the worst of people. According to former FBI instructor and author of It’s Not All About Me: Ten Techniques for Building Quick Rapport With Anyone, Robin Dreeke, this conditioning has been wired into us over thousands of years:

“These concepts are genetically coded in each of us (to varying degrees) because of our ancient survival instincts (ego-centrism) as well as our need to belong to groups or a tribe (tribal mentality for survival and resources).”

Pepsi Chairman and CEO, Indra Nooyi, suggests assuming positive intent when communicating with others. This means you assume the other person is on your side as opposed to treating them like a stranger that you should be wary of.

31 Questions for Better Supporting and Managing Remote Employees

We tend to do this naturally with those we know well. But it’s harder to get to that point when communicating with someone remotely for the reasons above. By assuming positive intent with remote team members, you’re able to build bonds with them easier and create an environment where remote team members feel more accepted.

Connection questions

Use these questions to ensure your remote employees are building bonds and connecting with the entire team:

  • 24) How well do you feel you know your coworkers?
  • 25) Which of your coworkers do you wish you had more of a connection with? How do you think that would help?
  • 26) You visit the office X times a year. Do you feel like that’s too much, not enough, or just right?
  • 27) How could I better support remote staff like you?
  • 28) When you have a creative idea or epiphany, what do you do with it? (The kinds of things that would get openly discussed in an office could be missing for them)
  • 29) Do you feel like you have opportunities for “water-cooler” type discussions with the team to help you spur on ideas? What ideas do you have for how we could create more of them?
  • 30) Do you feel supported by the team so that you could go to anyone asking them for help? (In remote teams, this can be a problem. Ideally, you want everyone to feel like they can go to anyone and ask them about something)
  • 31) Do you feel like you’re a full member of the team? What makes you feel connected/disconnected?

With insights from the above questions, you can start to improve any connection-related issues in a variety of ways:

  • Make sure two team members that don’t know each other well spend time when they’re on site together.
  • Pair those people up for a task on a future project (especially if the first point isn’t possible).
  • Or set up peer-to-peer one on ones to improve key relationships.
Questions to Ask Remote Employees

Help your remote team members be their best

You don’t know if you don’t ask. Managing remote employees has unique challenges. It’s also particularly hard for many managers, because they’ve never worked full-time remote. If you haven’t done it yourself before COVID, you may not realize the challenges your remote team members are facing.

The best way to overcome this unfamiliarity is by asking the right questions. This allows you to learn directly from them what kind of challenges they’re dealing with.

Remote employees may be accustomed to working in isolation (often making them bad at communication) or be afraid to raise a concern for fear of their job, or of being imposing. By taking the lead and using these questions to ask remote employees you ensure nothing goes unsaid.

You never know what you might learn until you ask.

[Ed note]: Want to organize everything you need for leading remote teams in one place? Download our free 1:1 meeting template now.

1 on 1 meeting template

Further reading for improving your one on ones and managing remote employees:

Looking for more questions to ask remote employees during 1 on 1s? Here’s some of our most popular 1 on 1 question guides:

And if you want to learn more about managing remote employees, these posts were written to specifically help you:

And here’s tips for you to help support your remote employees during the specific challenges presented by COVID:

More on supporting your teams and being a better manager:

Want the best of both worlds? Then sign up for a free trial of Lighthouse. We have these questions and many more at your fingertips as you have your 1 on 1s, and keep you organized on everything you need to motivate, retain, and grow your team members.

Start your free, 21-day trial now here.

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