15 Questions to Ask Yourself (& Your Team!) Before the Work From Home Transition

work from home transition

This is a guest post from Katie Stearns, PR and outreach manager at BeeBole Timesheet. She’s a digital marketer who loves monitoring management and leadership trends to create more valuable B2B content for managers. Katie is particularly interested in helping the world become a more productive place.

For many HR professionals and company executives, 2020 has turned out to be rather stressful (to say the least). Many of us started off the year with a twinkle of hope in our eyes, but the current pandemic has proven to be more challenging than we imagined.

For many companies, switching to remote work was required, but they never considered if remote work was right for their teams. As company executives decide whether they want to return to the office or continue to work from home and move their operations online, employers are likely asking many questions.

If you and your company are considering a shift to remote work, here are some tips to help you get started on your journey. In this Process Street post, we’ll be covering:

Let’s jump right in!

What is remote work?

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Before we get into the specific questions you should ask yourself, let’s start from the beginning: What is remote work?

Remote work is a working style that allows employees to get out of the office and work from wherever they feel most comfortable (usually their home or a coworking space). Companies that have a robust remote work policy are ahead of the curve and attract top talent globally.

Why do companies choose remote work?

There are a variety of reasons why a company might choose remote work.

Remote work:

  • Lowers overhead costs, like the price of an office space.
  • Allows companies to recruit the best talent, no matter their zip code.
  • Helps companies deal with safety precautions (like a global pandemic).
  • Improves the carbon footprint of an organization due to reduced commute times.
  • Gives employees a better work/life balance and allows them to live in cities with a lower cost of living.

What types of remote work are there?

If you are looking to pick a remote working strategy for your company, here are some ideas to get you started.

Fully remote
If you’re thinking about remote work, you might already be familiar with the fully remote model. In this model, your company goes remote first; you don’t have the overhead of an office; your employees can work from anywhere, although you might want to find workers staying in a similar location to where your company’s virtual headquarters are.

If you intend to go fully remote, you might want to think about digital nomads. A digital nomad is a type of remote worker who works from wherever they have an internet connection. Most remote workers stay put in their homes or apartments, but you might run across a type of remote worker who likes to travel a lot. You might want to put some extra safeguards or security measures around these remote workers to ensure they handle the information they have about the company and customers properly.

Flexible work policies
For some companies, a fully remote experience just isn’t possible. Instead, they might allow employees to work from home a few times a week or month. These companies aren’t able to be as open with who they hire because they require time in the office. You might be able to look further outside your city to look for talent, though.

Distributed workforce
A distributed workforce is a mixture of a fully remote workforce and a company with flexible work policies. You might have a central office or a few sub offices. Employees will be free to work from those locations while you have some employees who live and work far away from them.

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How should you decide which type of remote work is right for you?

Remote work isn’t for everyone or every company. You have to be honest with yourself and your team about what works best for them. You also need to consider the world at large, which, at the moment, doesn’t allow us to work in an office.

15 questions to ask yourself before the work from home transition

Whether you need to look into remote work as a viable option for your team, or you simply want to play with the idea of it, here are some questions that will help you best understand if remote work is right for your team.

1. How will you measure success as a remote team?

Measuring success as a remote team is a lot different than in an office. You or your team may be dealing with personal issues, like taking care of a family, isolation, and depression, making it difficult to focus on work.

Before you switch to remote work, sit down with your team, so they understand what is expected of them while working from home.

2. How will you maintain your company culture remotely?

Translating company culture from in-person to online can be challenging, especially as you start to bring in new hires remotely. One of the best things you can do is create a culture statement. When you boil everything down, what does your company stand for? What defines the experience your employees should feel (even if they never set foot in an office.)

For example, a foundational statement to life at GitHub is “Everyone can contribute.” They build their work around that statement, and it’s a mission that drives their entire organization. People coming to work at GitHub understand how important this is, and it builds a healthy work culture at their company.

3. How will you communicate with your team? Through what channels? And how often?

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Consistent communication is vital at work. If you don’t take time to communicate, you’ll find many hurdles popping up at work.

Here are some things to keep in mind:

  • How many meetings will you have each week? What’s the timetable for those meetings? Thirty minutes or an hour?
  • What applications will you use to communicate on the go? Slack or text?
  • When is the appropriate time to message each other? When you work in different time zones, this can be a challenge. Is it expected that you will go off one time zone? Will you let people communicate whenever but expect messages to be returned during specific windows?

4. How will you handle disagreements or heavily charged conversations remotely?

Disagreements can be hard to overcome when you can’t talk it out face-to-face. Animosity can grow over time, and it will affect the work being done.

Set ground rules for how disagreements are settled remotely, so that you and your team can move past any arguments and do great work.

5. Will you want to bring the team together for some activities? How will you pay for that?

Many companies who work remotely come together for quarterly or yearly meetings. Remote work is convenient for many employees, but spending time together can fulfill the soul and tighten bonds with employees.

If this is something you’d be interested in providing, consider details like:

  • How often will you bring the team together for meetings?
  • Who pays for these events? Do you reimburse or prepay for these expenses?
  • Do you get together as the entire team, or break it down by department?

6. How will you ensure company security?

Company security is imperative. Your employees and customers are trusting you with a large amount of private information.

The team at Remote takes security very seriously. They have clear and concise communication about company security available in their public handbook. Creating clear policies like this will help you and your team understand what’s expected of them to keep company information safe.

7. How will you make the employee experience a priority?

We spend a lot of time mapping the experience of customers, but we don’t spend as much time understanding the experience we’d like our employees to have. Understanding your employee experience helps you cut down on employee turnover.

Sit down with your team to write out the experience you want your employees to have. How will you make sure that happens when your team members are across the country and the world?

8. How will you adapt as a leader?

Being a great leader is even more important now that your team isn’t going into the office every day. You need to connect and bring your team together, even when you are communicating via the internet. Strong leaders understand that communication over the internet can leave a big gap. They know that they need to be clear, concise, and ask their employees for confirmation on their communication.

If you’re interested in strengthening your leadership in a remote team, BeeBole Timesheet is hosting a How to Make Remote Work Part of Your Team’s DNA webinar on Thursday, December 10, 2020.

Remote managers from Slack, GitLab, Workfrom, & Help Scout will share their tips for successfully leading remote teams.

Here are just a few of the topics to be covered:

  • The sustainably of running a remote team;
  • How to create a remote work policy;
  • Why results-based tracking is crucial;
  • How management skills differ for a remote team;
  • The ins and outs of virtual communication (it’s different than in the office!)

Save your spot today!

9. How will remote work change your hiring practices?

Having a remote company broadens your hiring capabilities. In theory, you could select employees from all over the world, but that also comes with time zone discrepancies.

How will you handle international applicants? Will you concentrate your hiring efforts in your state or country even though you have a remote business?

10. Will you change how you compensate employees based on their location?

There has been a lot of talk recently on how much remote workers should be paid if they move out of expensive areas. In particular, Silicon Valley companies have been at the center of this debate.

Some companies have chosen to pay employees less if they leave big (and expensive) tech cities like San Francisco. Moving to a less expensive city may mean that your employees can take less compensation, but you need to discuss this with your employees. You shouldn’t make significant changes to compensation without consulting your employees.

11. If you choose a distributed model, how will you make remote employees feel included?

Living across the country when most of your coworkers live close to each other can feel isolating. You need to make sure that your remote employees feel just as close as your in-office employees.

One of the best ways to ensure that your remote employees feel included is to simply talk to them openly. Let them know that you are genuinely interested in understanding their experience at your company and want to know how you can make them feel like they are part of the family.

Once you have that information, act on it, and let those employees know what changes you are implementing to make them feel more connected.

12. What tools will your employees need to work from home effectively and efficiently?

As you switch to remote work, you might want to invest in specific tools to help your team work from home effectively. Some examples include communication and project management/planning tools.

Figure out which tools your team needs to work together effectively. From there, figure out how to best pay for those tools so that your team has access to them.

For example, you might want to pay for a license to a tool like Slack for everyone in your company. Some tools may only require a few licenses that are shared across the company.

13. How will you handle time and productivity issues?

Working from home isn’t easy. Your employees’ lives may bleed into their work experience, which causes them to be late to an event or miss a deadline.

How will you handle this experience as an employer? What will you expect from remote employees when it comes to time and productivity? Do you want them to use a time tracking system? Do you want them to be on the computer at a particular time every day?

14. How will you educate employees who are new to remote work?

Many of your employees might be used to working in the office, and they might have minimal experience working remotely. If that’s the case, you should start by training those employees on remote work.

Make sure that they understand what’s expected of them and how they can best show up. Ensure they know what the differences are between working in an office and working online.

15. How will you deal with potential employee mental health issues due to isolation?

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Some people feel significant isolation when working from home (especially if they’re used to working in an office). This primarily affects extroverted employees, but it can affect introverts too if they are forced to be inside for long periods due to events like the current pandemic.

Here are some things you might want to consider:

  • Invest in a better health insurance plan that covers mental health.
  • Work on putting together a few meet-ups for people who live close by.
  • Offer to compensate your employees if they want to use a coworking space.
  • Schedule weekly or monthly activities with your coworkers via Zoom.
  • Create a self-care plan with your employees to make sure that they are taking care of themselves.

Final thoughts: Is the work from home transition right for your team?

Remote work can be a complicated experience for employers and employees alike. There are many things to work out logistically before remote work can be feasible for your company.

But at the same time, remote and flexible working conditions can make a fantastic benefit for any company. It’s worth the time and effort of working through these questions, to be able to create a remote experience that you and your employees love.

Have you recently switched to remote work? What tips would you give to others considering making the change? Let us know in the comments below!

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Oliver Peterson

Oliver Peterson is a content writer for Process Street with an interest in systems and processes, attempting to use them as tools for taking apart problems and gaining insight into building robust, lasting solutions.


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