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Your Top 10 Teleworking Questions Answered

Updated: Apr 22, 2021

Now that restrictions are easing, some people want to work from home full-time. In fact,80% of employees are interested in teleworking at least part of the time

If you’re considering hiring teleworkers or setting up a telecommuting-friendly workplace, here are the top questions I answer the most often.

Q: Does my company need to supply all of the office supplies for a teleworker?

A: This answer varies. If you’re going to be expecting a certain level of support, such as with computer and network devices, it’s best that your company supplies those items. If you’re hiring an experienced teleworker who already has their home office set up, then you may consider a small stipend to help defray any setup costs for your position.

Q: How do I communicate with my remote workers?

A: Now more than ever, you have a plethora of ways to communicate with your workers. Whether your employee is in the office or across the country, you can choose many options. The best plan of action is to determine how you want to communicate and then how often you want to check-in. You can use the following methods:

  • Email

  • Instant messenger

  • Text messaging

  • Voice messaging (such as walkie-talkie app Voxer)

  • Video meetings (such as Zoom or Microsoft Teams)

Remember that this process may also be a work in progress. You should start out with one or two main ways of communicating with a set minimum number of “check-ins” with each other. This is a good place to start, but you may need to change things up as you continue.

Q: What does my HR department need to do differently to manage staffers who work from home?

A: The simple answer is—not much really. Your employee has to abide by all the same rules and expectations you have for those who work in the office. The only difference can be that it’s advisable to create a telework agreement. This should go into more detail about the expectations for someone who’s working away from the office.

Q: How do I know if the remote workers are actually working, instead of surfing social media?

A: There are many ways to check in and know that your employees are actually putting time into their projects. Ultimately, you won’t know what your staff’s doing every moment. That’s probably very likely the case at the office, too: You never know what every employee is doing every minute of their workday. Instead, you should create expectations, set communications standards and have periodic check ins on projects and work. If all that is met, you needn’t worry.

Q: Do I need to create a telework policy?

A: Yes. You need one both for your protection, and for your employees to know and understand the expectations you have. Legally, it’s in your best interest to have a document that spells out the privacy and confidentiality required from remote workers.

Q: How do I ensure everyone can work together and collaborate on work and projects?

A:  You’re in luck. Today, there are so many options for collaboration. Right now, the two most popular options are ProofHub and FlowDock. These integrated apps can help keep your staff connected. You can also check out this list of collaboration software for other options.

Q: Does productivity suffer when the company has teleworkers?

A: No. Many studies have found productivity to improve. One study from Stanford showing a massive 13% increase in productivity was a pleasant surprise. At first, during a transition to remote work, productivity may suffer while you work out the basics (communication, getting collaborative software set up, etc). This happens with any new work setup—it takes a while to get everything on track, but once you do, it’ll run smoothly. Once you define your work protocols and put them in place, you can ensure productivity stays the same or improves.

Q: Is there anything I can do as CEO or leader in my company to create a good remote work experience for everyone?

A: Yes! Just reading this shows you’re interested in doing what is best and being prepared. Research as much as you can on the subject. While managing is hard enough with employees in the office, it can present a bit of an extra challenge managing remotely. The main thing? Communicate with your employees. Make sure everyone knows what’s going on and what your expectations are for them.

Q: How do I know if my teleworkers are happy?

A: Great question. The key here is open communication. If your employees are having difficulty, they should be able to identify the issue and quickly discuss it with a supervisor or an HR rep. Being able to address problems as they come up instead of letting them simmer will greatly alleviate stress and unhappy workers. Usually, these problems are small issues that can be easily handled. But if they go on without resolution, these small issues will build into problems and lead to unhappy workers. Bottom line: lowered morale and sinking productivity.

Q: Some staff have to work in the office due to their position in the company. How do I prevent employees at the office from feeling left behind by their teleworking counterparts?

A: It’ll be incredibly important to be transparent through the process of hiring or transitioning remote workers. It should be apparent that certain positions can’t work from home due to the nature of their work. It’s imperative that you let office employees know their position is very important and can’t be done at home. Also, you should make sure that staffers who telework need to be available to those in the office during specified hours.

If you want to add teleworkers to your staff, there are aspects you need to consider ahead of time before making the addition. If you follow these guidelines, you’ll make sure it’s a positive experience with a smooth transition.


Richard Flynn has led virtual teams for the past 20 years. It works!

If you need help with a business issue, I can provide you with the professional advice you need to make an educated decision. Contact me for a FREE 30-minute consultation with me today.

#virtualjob #freelance #virtual #telework #workfromhome

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