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.
Remote work is no longer an emergency workaround. It is an operating model leaders choose, tune, and govern. The question for HR teams and executives is not just whether people can work from home. It is whether the business has the policies, communication norms, security practices, and workflows to make the transition work.
That decision still matters because remote work has settled into normal business life. The U.S. Bureau of Labor Statistics reported that 22.6% of workers teleworked in March 2026, and many remote-capable teams now operate somewhere between fully remote and hybrid.
If your company is considering a shift to remote or hybrid work, use these questions before you change policies, tools, or expectations. In this Process Street post, we’ll be covering:
- What is remote work?
- 15 questions to ask yourself before the work from home transition
- Is the work from home transition right for your team?
Let’s jump right in!
What is remote work?
Before we get into the specific questions you should ask yourself, let’s start from the beginning: What is remote work?
Remote work software supports a working style where employees do not need to be in the same office to complete their work. The model can be fully remote, hybrid, flexible, or distributed, but the operating requirement is the same: people need clear policies, documented processes, secure access, and reliable handoffs.
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.
- Improves business continuity when offices, travel, or local conditions change.
- 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 choosing a remote working strategy for your company, define the model before you pick tools or policies.
Fully remote
In a fully remote model, employees work outside a company office by default. This can widen your hiring pool, reduce office overhead, and support people who need location flexibility. It also raises questions about time zones, equipment, tax rules, data security, and how managers keep work visible without watching people constantly.
Hybrid work
Hybrid teams split work between home and an office, customer site, or coworking location. This is often the most practical model for teams that need some in-person collaboration but do not need everyone on-site every day. The hard part is deciding which days matter, who is eligible, how meetings work, and whether remote employees get equal access to decisions.
Flexible work policies
Flexible policies give employees some choice over where or when they work. They are useful when roles vary by department, but they need clear guardrails so flexibility does not turn into inconsistent treatment.
Distributed workforce
A distributed workforce has people spread across locations, sometimes with one or more offices and sometimes without a central office at all. This model can work well, but only if documentation, communication, onboarding, and approvals are designed for people who are not in the room.
How should you decide which type of remote work is right for you?
Remote work isn’t for everyone or every company. Be honest about which roles can work remotely, which decisions need real-time collaboration, what security controls are required, and whether your managers are ready to lead by outcomes instead of proximity.
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 GitLab 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 GitLab 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?
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’s How to Make Remote Work Part of Your Team’s DNA session is still a useful resource. The practical lessons hold up because remote leadership is less about location and more about clarity, trust, and follow-through.
Here are a few topics to work through with your own managers:
- The sustainability of running a remote or hybrid 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, which is different from being in the office.
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, start with the operating jobs your tools need to support: communication, documentation, recurring workflows, approvals, secure access, onboarding, and performance visibility.
Chat tools like Slack help people communicate quickly, but chat alone does not create a remote operating system. You also need a place where recurring work is documented, assigned, approved, and tracked.
Process Street is a remote work software option for teams that need repeatable workflows instead of scattered messages. Docs gives teams a governed place for SOPs and policies, Ops turns those procedures into assigned workflows with approvals and audit trails, and Cora helps monitor execution so remote work does not depend on memory or manual chasing.
For example, you might pay for company-wide communication tools, give managers workflow and documentation systems, and reserve specialist tools like time tracking for teams that need billable-hour reporting, project costing, or explicit time approvals.
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?
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 logistical, cultural, legal, and operational questions to answer before a work from home transition is feasible for your company.
But remote and flexible working conditions can still be a meaningful advantage when they are designed deliberately. Work through the questions before you make the change. Decide the model, document the policy, choose the tools, and build the workflows that make remote work sustainable.
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!