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The 7 Most Important 1-on-1 Questions to Ask Remote Employees

Ross Simons

Ross Simons

Director of Inbound Marketing

Have you ever spent any time on a deserted island? I have. I’ve spent seven long years on the Isle of WFH.

If you’ve done a lot of remote work, you probably felt at times like you were on a deserted island. There are times when remote employees feel isolated and on their own.

And there are times when you feel separated from your remote employees, wondering how they’re adjusting, whether they’re happy and if they’re hitting their work objectives.

The standard way of evaluating employees is the “Annual Performance Review,” but that’s a little outdated these days. Not only do your younger generations of employees prefer more regular feedback (and praise), but your remote staff needs it.

Imposter syndrome (where people worry that they don’t belong and are mere moments away from being found out and fired) is a major issue in remote work. The best way to combat this is by frequent check-ins. HBR surveyed 1100 remote workers and found that 46% of them said the best characteristic of their favorite remote managers were ones that checked in frequently and consistently.

Your first order of business is to have more meetings with your remote employees, and, once you have those scheduled, it’s all about using those discussions to their full advantage.


What type of questions should you ask remote employees?

It starts with your goals. What are you trying to accomplish in your one-on-one? Are you trying to understand them? Motivate them? Support them? Enable them?

It’s probably some combination of all of the above, so below, we have seven high-impact questions that will try to help you take advantage of these one-on-one moments.


1. How are you adapting to working remotely?

This question is trying to understand the strengths and weaknesses of remote work within your organization. If your employees are adapting well, you’ll hear good news here. It should also give you lots of areas of growth to improve the experience of your remote staff. The challenge is that your employees probably love the flexibility of remote work, so they may be worried about talking about the downsides and losing the flexibility. You must ask follow-up questions to get to the areas that employees are less happy about.


Follow-up questions:


What do you like best and least about working remotely?

Is remote work better or worse than office work?


2. What is your daily routine like?

This question is trying to ensure that they keep a daily routine. One of the central challenges of remote work is the blurring of the boundary between work and home. Maintaining rituals and routines is one of the best ways for remote employees to remain productive during their work hours and actually be able to “sign off” at the end of the day.


Follow-up questions:


• Do you hold similar work hours every day? What are they?

• Do you feel like you’re able to disconnect at the end of the workday?

• Do you stay consistent with taking breaks?


3. What is blocking you from being the best version of yourself?

This question is trying to uncover what you can do to enable and support them. You may have some ideas — but there’s a good chance your employee knows what’s blocking them. But it’s helpful to direct the conversation to cover all the bases.


Follow-up questions:


• Are there areas of education you need support with?

• Are there people we can connect you with?

• Do you feel like you have the same technology or resources you’d expect from an office environment?


4. What makes you feel appreciated?

This question is trying to learn how your employees show and feel appreciation. Different employees will “speak different languages” here. Some will feel most appreciated by simply hearing that they are appreciated. Others will respond well to gifts, like bonuses or gift cards. And still, others will feel most respected when you roll up your sleeves and take something off their plate.


Follow-up questions:


• How do you show appreciation to other people?

• What have other managers previously done that worked?


5. Are our WFH policies clear?

This question is trying to make sure that employees understand the policies and protocol around remote work at your company. This is especially relevant for hybrid models where employees will spend only some of their time working from home.


Follow-up questions:


• Do you know the process for taking a WFH day?

• Do you have an understanding of communication expectations while working from home?


6. What is your home setup like?

This question is trying to learn how you can enable your employees to work productively because of their setup, not despite it. Research has shown that remote employees are often more productive than those in the office. But, when they’re not, there’s usually a familiar culprit: their home setup is lacking. Remote employees may be moving from a dedicated desk or office with a multi-screen setup to a laptop and a kitchen table.


Follow-up questions:


• Lead with empathy. Not every employee will have a secluded home office, multiple screens, a live-in au pair, and infallible wi-fi. Sometimes the connection will drop, the mic won’t work, or their children will decide the best time to stop by for a visit is right in the middle of that Zoom meeting. Remember, few employees will be able to navigate remote work without ever feeling isolated, disconnected, or invisible.

• Be approachable. Set Zoom office hours, be proactive and try to recreate that “my door is always open” vibe.

• Learn what your employees are looking for. When your employees complain, know when to listen vs. when to solve their problems. (And when you figure this out, tell the husbands of the world.)


7. What can I personally do to improve your remote work experience?

This question is trying to help you figure out what you can do to support this employee. This is a powerful question if you do have resources (aka budget) at your disposal. The answers you get here could be diverse: sometimes it’s about connecting them with the right people. In other cases, it’s giving them the right technology. Sometimes, it’s a change to your benefits package.


Follow-up questions:


• Do you have a separate and suitable workspace?

• What technology did you have in the office that you don’t have now?

• If you could change one thing about your environment to improve your setup, what would it be?


Ask these seven questions, and your workplace will improve.

If you ask these questions (and variations) consistently, you’ll see improvement in productivity, engagement, and retention for your remote employees. And the answers you get from them just may help you improve the work experience for all of your employees.

These questions can be transformational to your workplace. Asking them puts you in a mindset where you’re focused on breaking down barriers, removing blockers, and actively supporting and enabling your workers to be the best version of themselves.

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