What is one remote work compliance challenge your business has faced and your best tip to overcome it? 

To help employers with the tools for resolving remote work compliance challenges, we asked CEOs and other thought leaders this question for their best tips. From assisting employees to secure home occupation permits to creating a remote work policy guidebook, there are several recommendations that may help employers tackle compliance challenges that come with remote working these days.

Here are 12 best tips for resolving remote work compliance challenges:

  • Assist Employees to Secure Home Occupation Permits
  • Use Work Collaboration Apps To Standardize Communication
  • Employ Managed Accounting for Remote Employee Tax Compliance
  • Provide Clear Guidelines for Compensations and Benefits
  • Explore Third-Party Benefit Options To Stay Compliant
  • Reinforce Security of Private Company Data
  • Introduce Flexible Work Hours To Foster Productivity
  • Provide a Productive and Professional Work Environment
  • Schedule Time for employee Engagements
  • Choose a Platform for Posting Digital Notices
  • Find Reliable Time-Tracking Tools
  • Create a Remote Work Policy Guidebook


12 Tips To Help Employers Resolve Remote Work Compliance Challenges


Assist Employees to Secure Home Occupation Permits

A remote work compliance challenge we’ve had is the requirement of a local-level home occupation permit for some of our remote employees. Some states, cities, or counties require this permit to process payroll taxes, which becomes a problem for automated business processes if employees do not secure one. As such, we allowed our employees to take paid leaves to accomplish these requirements as soon as possible. It helped expedite the completion of these permits in our files and reduce disruptions to our automated employee management system.

Nunzio Ross, Majesty Coffee


Use Work Collaboration Apps To Standardize Communication

The challenge is guaranteeing that communication is available to all, and everyone participates in essential discussions. As a manager, you have to orient the workers beforehand to let them understand that their workload will remain the same whether they opt to go to the office or work from home. Work hours also apply, and being strict with this will lower the chances of blurring the lines between home and work for them, potentially compromising productivity. 

One of the best ways to ensure that communication is standardized is utilizing work collaboration software like MS Teams. This makes inter-company communications convenient and provides various other features helpful as you manage a remote team. For example, you can store documents or work on bookkeeping on their cloud storage services like OneDrive. You can also create communication channels for each team in the company. This will departmentalize communication and will keep everything organized.

Stephen Keighery, Home Buyer Louisiana


Employ Managed Accounting for Remote Employee Tax Compliance

I have remote writers and marketers across the country and abroad. Most of the time remote employees face problems with double taxation, one in the state where they live and the state where the employer operates. Because I don’t have in-depth experience in handling taxes, I had to seek an expert’s advice to comply with tax laws and regulations. I took advantage of managed accounting services, wherein the accounting firm handles all tax-related matters, including determining the applicable income tax for my remote employees.

James Parsons, Content Powered


Provide Clear Guidelines for Compensations and Benefits

Defining clear lines for the workers’ compensation is one remote work compliance challenge we have. Identifying work-related injuries can be challenging in a remote setup, which becomes an issue when employees demand or claim their benefits and compensation while working from home. To deal with this problem, we have strict guidelines on work hours and necessary conditions to ensure work-related claims are legitimate and within the scope of our compensation strategy.

Tory McBroom, Pond Academy


Explore Third-Party Benefit Options To Stay Compliant

One issue we struggled with was standardizing our remote work to be compliant with benefits. We hired full-time remote teams for our Sales and Marketing departments and switched their medical and mental health benefits to telehealth services to remain compliant with State and Federal law. By leveraging a third-party wellness service like Headspace for meditation and mental wellness services, you can avoid the red tape of trying to grant PT and FT employees compliant health benefits. Many remote workers are also expecting new and specific types of benefits as part of their contracts which are made much simpler by using third-party services as the in-between. 

As much as we want our employees to have the resources to access the best healthcare and other benefits we can offer, we must find creative workarounds that allow equitable access for all of our employees to use the same benefits in order to remain compliant with local and federal laws.

James Shalhoub, Finn


Reinforce Security of Private Company Data

Remote work makes it difficult to track who gains access to company information. So to reduce the odds of data breaches, we’ve implemented multi-step security verifications to access all company files. Only team members with the relevant passcodes are authorized to handle different types of information. We’ve also included regularly scheduled verification checks to ensure that the person who entered our database a week ago is still the same one accessing it today. It’s not a matter of mistrust within our organization. But working remotely from a laptop means that devices can get lost or stolen. As a healthcare-related company, it’s only essential that we take measures to protect our clients and ourselves as professionals in the industry.

Stephan Baldwin, Assisted Living Center


Introduce Flexible Work Hours To Foster Productivity

Our productivity suffered during the initial phase of setting up a remote-based workplace. Employees found it hard to follow their schedule because of unavoidable distractions at home. Some slept during their break time through the end of their shift, not accomplishing any tasks at all. However, we rose above the occasion by being flexible. We modified our timetable and adopted the ‘set your own hours’ policy. We have granted our employees the freedom to work during their most productive time. All we ask from them is to preserve the quality of their work and complete their tasks before deadlines. Doing so enables us to redeem our productivity while ensuring that our employees are happy and satisfied.

Allan Stolc, Bankly.dk


Provide a Productive and Professional Work Environment

One of the challenges we faced is how to provide a productive and professional work environment for our contractors when we were not physically around. We solved it by ensuring our contractors were always motivated by setting proper expectations from the get-go. More often than not, it wasn’t a compliance issue but a lack of proper planning on our part. By keeping a good communication channel with our contractors, we were able to solve the problems as they arose.

Richard Morgan, Cyclone Computers


Schedule Time for employee Engagements

Disconnection is a top remote work compliance challenge among businesses today. Asynchronous work and remote meetings limit human interaction. Team members might find it difficult to run into side conversations with others or clarify matters in real-time as they would together in an actual office space. Intentionally schedule the time and platform for remote team workers to engage in discussions and water cooler conversations to resolve disconnection woes. Doing so can effectively boost good working relationships and improve team performance.

Douglas Ferguson, Voltage Control


Choose a Platform for Posting Digital Notices 

When working on-site, any notices you had would be posted in a visible area to everyone who arrived in the office. Once the switch to remote work occurred, we had to figure out a way to have these notices actually reach employees in the digital space. It’s not as easy as it may sound due to the fact that the digital space can be vast and overwhelming. The pro tip here is to cross-test multiple platforms for notice posting. HR has used emails with unconventional subject lines and coordinated with team leaders to ensure everyone reads them regularly. Team managers and HR would direct coworkers to a database where they’d simply put a checkmark next to their name for the week in question. When it comes to notifying people about the notice’s main points and reminding them to mark it as read in the database, HR would use a “notice board” Slack channel. With time, Slack has proved to be more effective than emails, so full notices started being posted solely through that platform.

Nicole Ostrowska, Zety


Find Reliable Time-Tracking Tools

Timekeeping has been a real challenge. I had to sort and compare the best time trackers to ensure my remote marketers and writers are paid according to their job hours. Because many of our team members come from different countries, we entrust time tracking to Hubstaff. This platform auto-generates time reports with corresponding currency values for the number of hours rendered, which we also use for computing taxes and bookkeeping.

Lorraine Daisy Resuello, Connection Copilot


Create a Remote Work Policy Guidebook

My business has faced the challenge of ensuring that all team members are remote-work compliant, meaning they have the proper equipment and training to work from home. The best way to overcome this challenge is to create a remote-work policy and procedures guidebook that outlines expectations for both managers and employees. This guidebook should include topics such as what equipment is needed, how to set up a home office, how to stay connected with coworkers, and how to take care of one’s mental and physical health while working remotely. 

Another remote work compliance challenge my business has faced is making sure everyone understands the company’s remote work policies. We’ve overcome this challenge by hosting regular training sessions and webinars on the topic. We’ve also found it helpful to post reminders of the company’s remote work policies in our internal communications channels.

Nathan Richardson, Bariatric Journal



Terkel creates community-driven content featuring expert insights. Sign up at terkel.io to answer questions and get published.