Organizational Change WalkMe TeamUpdated December 8, 2021

The Complete Guide to Teleworking in the Digital Age

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The Complete Guide to Teleworking in the Digital Age

This guide will explore teleworking from top to bottom, covering teleworking policies, the pros and cons of teleworking, tips for improvement, and more.

Teleworking – often used interchangeably with telecommuting or remote working – can offer astounding benefits to employees and, as a result, their employers.

However, there are downsides and considerations to be aware of. Understanding these can help with the development of telecommuting policies and programs.

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Also, a look at the future landscape can tell us what the future holds for teleworking.

To start off, though, let’s define teleworking…

What is Teleworking and Why Does It Matter?

Teleworking is performing one’s job remotely, away from a physical office.

It’s a trend that has become very popular in recent years, thanks to the internet, mobile technology, and other internet technologies.

Teleworking is also popular because of the many benefits that it offers.

Studies have shown that teleworking:

  • Makes employees happier and more engaged
  • Can cut costs for both organizations and workers
  • Improves productivity and performance

However, teleworking does come with considerations.

If proper measures aren’t taken, teleworking can negatively impact the organization’s social environment and the culture.

To better understand the pros and cons of teleworking, let’s answer some of the most commonly asked questions about the topic.

Frequently Asked Questions (FAQ) About Teleworking

To start with, it’s important to understand the rationale behind teleworking policies in a bit more depth.

Why do organizations implement teleworking policies?

As mentioned, there are many benefits to teleworking:

  • Since commuting can cause stress, teleworking removes that by allowing them to work from anywhere, including their homes
  • Telecommuting cuts office costs by removing the need for paid office space
  • It provides flexibility for workers, many of whom want more flexible workplaces
  • It can improve work-life balance, boost retention, increase loyalty, and more
  • Teleworking programs can add flexibility for workers which can a layer of protection against external risks, such as natural disasters or illnesses

In some cases, individual employees may request teleworking arrangements. And organizations may implement those on a case-by-case basis. 

However, teleworking policies can also be applied generally, to large numbers of employees.

Either way, in order to maximize the value of a telecommuting policy, it is important to understand the value it can deliver to both the workforce and the organization.

At the same time, teleworking is not without its flaws, so its potential downsides should also be examined.

What are the challenges and drawbacks to teleworking?

According to Buffer’s survey of remote workers – who worked remotely at least part time – top struggles of teleworking included:

  • Collaboration and communication (20%)
  • Loneliness (20%)
  • Not being able to unplug (18%)
  • Distractions at home (12%)
  • Being in a different time zone than my teammates (10%)

Naturally, each of these problems would require a different approach. Some are also easier to solve than others.

A good telecommuting policy and program – one which educates workers about telecommuting effectively – can mitigate a great deal of these issues.

How do you design a teleworking program?

Telecommuting programs should have several agendas items, such as:

  • Provide skills training
  • Train workers on how to telework effectively
  • Set clear, achievable goals for the telecommuting program
  • Use metrics and KPIs to track performance

And implementing these programs will mirror the implementation of any other business process, following a set of stages such as:

  • Strategy
  • Assessment
  • Planning
  • Implementation
  • Monitoring
  • Ongoing Optimization

Next, we’ll explore these steps in more detail.

How to Implement a Teleworking Policy

When formulating a stance on teleworking, it is important to think strategically – that is, consider the potential benefits, then devise ways to overcome challenges and mistakes.


First and foremost, it is important to understand the “why” behind a teleworking proposal.

Namely, it pays to understand:

  • Benefits. The benefits covered earlier, such as increased job satisfaction and engagement, are all good reasons to begin a teleworking program.
  • Drawbacks. Understanding the challenges associated with teleworking can help managers educate employees on how to overcome those obstacles.
  • Employee needs. Do employees have the right skills, tools, mindsets, and setups? Employee surveys can be used to perform assessments (see below).

Once managers have a basic grasp of the rationale and underlying aim of the teleworking effort, it is time to brainstorm a strategic direction.


To help maximize the efficiency of a large-scale teleworking program, it is important to minimize obstacles and risk, while maximizing the chances of success.

Here are a few tips:

  • Set goals and objectives. The goals should typically be related to performance. Tracking changes to areas such as employee performance, employee satisfaction, and costs can be a good place to start. Ideally, goals would revolve around improving these metrics.
  • Ensure that employees receive skills training. To perform their jobs effectively, employees need to be digitally literate enough to work remotely. If they need to learn new software in order to work remotely, they should naturally receive training.
  • Teach employees about teleworking best practices. Since there are challenges and obstacles to effective teleworking, employers should explain how to overcome those difficulties. Experienced remote workers, for instance, have developed a number of tactics for combating feelings of loneliness. 

Once the general approach has been developed, it is time to perform basic assessments of the workforce.


Assessments should aim at understanding the current state of the workforce.

These analyses will help managers understand factors that can impact the teleworking program, such as:

  • Digital literacy levels. Digital literacy – that is, basic digital skills that allow one to operate in a digital work environment – are essential for the modern employee. And it often falls on the organization to fulfill digital training needs. Teleworkers must have a basic level of digital literacy, as well as digital literacy skills with software used in teleworking.
  • Available funding. All business programs cost money, though teleworking programs actually end up saving money rather than costing money. If an organization wants to further enhance the efficiency and productivity of its workers, then funding can be used to invest in software or employee training efforts.
  • Buy-in. Alignment is critical for the success of any business effort, including teleworking. If the appropriate business leaders – as well as the employees – are not aligned and supportive, then resistance can easily harm the teleworking program’s results.
  • Readiness. Readiness can include change readiness, digital readiness, and, more specifically, the readiness to evolve a program. How ready an employee or a workforce is for teleworking can help employers determine how much effort to put into the teleworking program. If an employee, for instance, is highly digitally skilled, then they may need little or no training when they begin telecommuting.
  • Sentiments. Employee sentiment refers to how employees feel about something. In this case, it is useful to gauge their sentiment towards teleworking. Employee surveys can be used to assess sentiment, and that information, in turn, can help when designing communication programs, change efforts, and teleworking programs.

That information then be used to design a concrete plan of action.


The plan will put the strategy into action, but not all teleworking plans are equal.

Since flexibility is one of the main aims of teleworking, when possible it also pays to make the teleworking program adaptable.

Here are a few program components that can help workers begin operating remotely:

  • Part-time teleworking
  • Full-time teleworking
  • Staggered schedules
  • Flex-time
  • Tools and technology
  • Policy

On the one hand, it is useful to create broad policies and guidelines that apply to the workforce as a whole. 

Implementation and Monitoring

Here are a few tips for implementing a teleworking program:

  • Pilot test the effort. A pilot test can provide useful information about the success of the telecommuting program, without investing too many resources. Once the program is modified as needed, it can be rolled out to the entire workforce. 
  • Individualize when possible. When and where possible, personalize teleworking programs to meet employee needs. This can involve adjusting the mix of on-site and off-site working, licensing new software to improve teleworking efforts, training employees on specific software, offering online education opportunities, and so forth.
  • Perform check-ins to assess progress. Since teleworking impacts different employees differently, HR staff or managers should check in regularly to ensure that employees are productive and happy. If needed, make adjustments to the hours or the arrangement.

Naturally, the teleworking program will not be perfect right from the start, which is why it should be continually optimized.

Ongoing Optimization

Programs should be undergoing continual improvement in order to keep them relevant and profitable.

Data sources can include:

  • Analytics and performance data. Naturally, employee productivity is a top concern for employers. In most cases, as we have seen, teleworking benefits employees. However, in some cases, performance can decrease – which signals that it is time to make a change.
  • Employee surveys. Employee surveys, polls, and one-on-one discussion can all be used to gain insight into the status of the program. These regular reviews should continue periodically throughout the life of the program. After all, not all problems will manifest themselves at the outset. In some cases, real issues may emerge in weeks, months, or longer.
  • Customer data and feedback. Since products and services can be affected by teleworking, it is also important to evaluate customer data and feedback. This is especially true if employees hold customer-facing positions – customer feedback can provide yet another lens into employee performance and productivity.

Any areas of the program can be modified, such as employee training efforts, the quantity of remote hours, and so forth.

Tips, Best Practices, Do’s, and Don’ts

Let’s look at a few tips and best practices that can help organizations and employees both make the most out of teleworking:

Keep employees at the center of the teleworking program

In other words, telecommuting policies should be designed around employee needs, at least insofar as they improve the workplace.

The idea is that by improving the employee work experience, organizations will be better able to increase output and performance. In turn, the organization’s performance will improve.

To create teleworking programs that better serve employees:

  • Focus on the employee experience
  • Offer flexible, personalized work options
  • Continue to collect and optimize with data

Naturally, teleworking should be designed to maximize profit for both parties – employees as well as organizations.

Since a better teleworking experience results in improved employee output and productivity, enhancing that experience is one of the best places to start.

Develop the right culture

As discussed below, organizational culture can be affected by teleworking.

That’s why it is important to take the right steps in order to cultivate, maintain, and communicate the proper culture to employees.

This means:

  • Clearly articulating the corporate culture and mission
  • Selectively recruiting candidates that fit with that culture
  • Create a digital culture that is teleworking-friendly

This is not to say that a company should become virtual and become completely digital.

However, since a great many positions can be worked remotely – and since there are so many clear benefits to a teleworking arrangement – there is little reason to at least incorporate some teleworking into the business.


Personalization means creating an experience that is customized to fit the needs of an individual.

In this case, it means offering teleworking options that are flexible and suited to the individual employee.

This means finding a teleworking option that is suite for that person, while also meeting the organization’s needs.

Here are a few ways to do that:

  • To the extent that it is feasible, offer employees options around the design of their teleworking program
  • Provide online digital training options that are personalized and automated
  • Evaluate employees’ work efforts on an individual level and provide guidance if necessary

Some organizations may feel that such measures are unnecessary.

And given the fact that most HR staff have enough to worry about, these measures may seem superfluous.

However, if the telecommuting trend continues to accelerate, it is important that organizations take it seriously and do all they can to ensure that the workforce continues to operate effectively and efficiently.

Become a more digitally mature organization

Digital transformation, the process that leads to digital maturity, is no small feat.

However, organizations that are more digitally mature will have a much easier time adopting teleworking measures.


There are several points to consider when evolving the digital workforce:

  • The digital workplace. Organizations should rethink their approach to the workplace. Rather than merely augmenting existing workflows with digital technology, to stay competitive, businesses must rethink their entire strategy. To this end, many organizations are transforming their business processes, IT infrastructures, entire technology stacks, and the workplace. Teleworking is one area that can help workplaces become more digital and more efficient in the digital era.
  • Tools and technology. Without the right tools, an organization cannot become digitally mature. And since the right tools – when those digital tools are fully adopted – can deliver significant competitive advantages, it should go without saying that the adoption of these tools is a prerequisite to becoming digitally mature.
  • The remote workforce. Having a remote workforce or remote working options is another hallmark of digital maturity. If a business employs remote workers, then it is a sign that the organization has achieved a certain level of digital maturity – at least enough to support remote workers. It also means the organizational culture is more digitally-friendly, digitally literate, and forward-thinking. On the one hand, a remote workforce can help cut costs and improve employee productivity, as mentioned above. But it can also help attract remote workers that might otherwise be averse to working on-site in an office.
  • The digital skills gap. One of the first areas to address on the road to digital maturity is the digital skills gap. Today, there is a continually widening gap between knowledge workers and their tools. The typical office worker will often use a wide variety of tools to complete a task. And the more that an organization adopts new technology, the more necessary it is for employees to keep learning. 
  • Digital adoption and digital training. The best way to close the digital skills gap is by creating a comprehensive digital adoption program. This program should aim at streamlining onboarding, training, and the entire adoption process. It should involve the use of digital adoption platforms, since they can automate training and facilitate the integration of adoption tools into day-to-day business workflows.

By addressing these areas and becoming more digitally mature, the workforce and the organization will both benefit.

In some cases, this may mean hiring digital transformation consultancies or similar firms … and naturally the scope of this process will extend well beyond teleworking itself.

But the point is worth making: teleworking is only one among many digital-first processes that organizations must begin adopting.

Test teleworking programs first, then roll out across the organization

To minimize potential difficulties and challenges, telecommuting programs should be tested prior to rollout.

Depending on the scale of the telecommuting program, this can mean:

  • Testing an individual’s program for a few months, then evaluating the results
  • Testing out part-time telecommuting, staggered schedules, flex-time, and similar hybrid options
  • Allowing a small group to test teleworking first, then allowing the whole organization to test

A test-driven approach is aimed at minimizing risk.

Since only a small number of people – or a small amount of time – is at stake, mistakes will have smaller impacts.

At the same time, the data collected from these efforts can be used to make improvements to the teleworking program before full-scale implementation.

Take a structured approach to change management

Teleworking programs are relatively small-scale changes compared to other organizational changes, such as restructuring or digital transformation.

However, the discipline of change management can be informative and useful when implementing any new business process.

This is especially true since teleworking is a process that has such a large impact on the individual employee.

Though less effort is required for managing this type of change than more complex projects, it is still useful to:

  • Communicate why the change is occurring. Employees are much more likely to support a change project if they understand the reasoning behind it. If changes occur unannounced and with no explanation, employees will be more confused and frustrated. And since they see no rationale behind the new program, they will be more likely to resist the new program.
  • Motivate employees by promoting the benefits of teleworking. One way to build support and keep employees engaged is by selling them on the specific benefits of the teleworking program. Earlier, we covered plenty of benefits, such as the freedom to work from anywhere – or the ability to spend time with family – or the lack of a commute. However, these benefits can be further enhanced by overcoming common objections and challenges, such as feelings of  loneliness. Training is a means of doing just that.
  • Ensure that they have adequate training and skills. Training programs should focus on digital skills, both for job-specific tools, as well as teleworking tools. Additionally, as mentioned, it is important to teach employees how to be effective when working remotely. With a multi-pronged educational curriculum such as this, telecommuting programs will experience fewer problems and they will also yield greater benefits.
  • Continue to manage engagement, track performance, and optimize the program as needed. If an organization is initiating a large-scale telecommuting program for the first time, then it will likely run into speed bumps, at least in the beginning. With a data-driven, analytical approach, such problems will be easy to overcome.

Again, for individual employees, a great deal of oversight is not necessary. But the larger the teleworking program, the more risks are involved. 

Implement the right software

It is important to remember that, to be successful, teleworkers must use the right software.

That is, teleworkers should use tools such as:

  • Video conferencing apps. Video conferencing apps, as the name suggests, allows people to hold video-based conferences in real-time, entirely online. Zoom, Google Hangouts, Skype, and a number of other tools are being used to stream digital conferences in real-time. These are invaluable for workers who regularly take part in online conferences.
  • Chat apps. Chat apps, such as Slack, are widely used by organizations that need to collaborate virtually. These are excellent ways to keep in touch with a wide variety of work groups and teams.
  • Project management tools. Project management tools help project managers coordinate projects, track performance, collaborate with teams, and more. These tools prove invaluable when working with remote workers, since they are entirely cloud-based – and designed for online use.
  • Workflow and task management tools. Task management tools are similar to project management tools. But these are designed to manage a specific series of repeated tasks. Trello, for instance, allows users to create kanban boards for virtually any time of business activity.
  • Digital training software. Workers still need to be trained, regardless of whether they are working on-site or remotely. Digital adoption solutions, mentioned above, are ideal training solutions for businesses of any scale. They can operate automatically, without human intervention, and train users on any number of software workflows and tasks.

In other words, like any other business process, teleworking requires its own “technology stack.”

That should be taken into account when developing a teleworking plan and, when necessary, managers should provide employees with training on that stack.

Don’t apply teleworking programs universally

This is especially true for businesses that have a predominantly traditional workforce.

Many prefer working in traditional office environments because they are more stimulating and more socially active.

In such situations, widespread teleworking can actually have a detrimental impact on the social climate and the workplace culture.

As mentioned elsewhere, employees each have their own needs, and full-time teleworking is not necessarily the answer to budget constraints or creating a digital workplace.

Instead, implement more personalization, allowing allows for flex-time, a mixture of full-time and part-time teleworking, and other flexible options. After all, on-site work can be an effective remedy for too much remote work.

The Future of Teleworking

In the coming years and decades, how will teleworking change?

There are a number of trends that experts predict will impact the world of remote working.

These include:


There are a number of technology that are impacting teleworking and will continue to do so for some time to come. 

These include:

  • AR. Augmented Reality (AR) uses digital technology such as googles, glasses, or even smartphones to overlay digital media on top of the physical one. According to AR company Magic Leap, its AR technology differs from VR or even smartphone-based AR apps: “It’s a spatial computer” that can project images around the user and “seamlessly understand the space that it’s in. It can even look you in the eye.” In time, we can expect to see this technology leveraged in teleworking through conferences, meetings, and other communication software.
  • VR. While AR is designed to overlay digital imagery into the physical world, virtual reality (VR) is designed to create an entirely virtual experience. Virtual reality goggles completely shut out the outside world and transpose user actions into a virtual 3D space. As with AR, VR will enable totally new levels of workplace collaboration and communication.
  • IoT. The Internet of Things (IoT) refers to the merging of the internet’s capabilities with physical devices. Sensors, for instance, can be installed in a wide range of devices, which can provide data and information from the real world. There are many remote working possibilities that open up with IoT. For instance, integrating AR and VR with IoT can allow workers to interact in complex 3D space. One teleworking application: allowing employees to operate robots remotely.
  • Automation. Automation technology can help teleworkers in a variety of ways. Digital adoption platforms (DAPs). These platforms layer themselves atop other software, allowing users to learn directly inside an application. Automating software training allows employees to learn anytime, anywhere, helping them to continue their skills training, even when working from home.

Given these trends, we can certainly expect remote working to become more popular, effective, and seamless in the coming years and decades.


Telecommuting automatically removes people from the physical office space, which will have an impact on the organization’s culture.

The more isolated that workers are from one another, the more difficult it will be for them to form strong relationships and a strong workplace atmosphere.

As mentioned, productivity can improve dramatically, but steps should be taken to maintain a strong culture.

One of the best places to start, says Deloitte, is by clearly articulating a culture and purpose.

With that grounding, it will be easier to screen new hires and teleworkers before bringing them on board. Over time, this approach can help to shape the organizational culture into one that better fits the organization’s stated mission and purpose.

The Workforce

The workforce will also continue to evolve, will will likely have an impact on what teleworking looks like in the near future.

  • People. In the coming years, employees will certainly begin making more and more teleworking requests. This will – if it hasn’t already – make it more difficult for organizations to attract and retain top talent. Though not everyone prefers telecommuting, many do. So we can expect to see more virtual, remote-only businesses.
  • Mindsets. Mindsets will also continue evolving. Workers will become more and more digital-friendly, and digital literacy will become more and more common. Cultures, workplaces, and organizations will all become more digital, until “digital” itself becomes the norm for all businesses.
  • Amount of remote working. We can certainly expect teleworking to increase in popularity, even among traditional on-site workforces. Part-time teleworking, part-time teleworkers, per diem contract workers, and full-time remote working will all become more common.
  • Workforce composition. The actual composition of the workforce, noted by Deloitte in the link cited above, will also change. This shift will impact organizational culture, the efficiency and effectiveness of the business, and more. 

Ultimately, every organization decides for itself whether and how to implement teleworking. 

However, given the changing demands of modern workers – as well as the clear benefits of teleworking, such as improved employee satisfaction – it is a good idea to investigate teleworking as an options.

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