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Legal Technology

Managing the teleworking office

Conrad J. Jacoby, Esq.  Founder / efficientEDD

· 7 minute read

Conrad J. Jacoby, Esq.  Founder / efficientEDD

· 7 minute read

Teleworking is a proven way to help provide workplace flexibility while maintaining business productivity, but managing remote workers can be a challenge

Over the past four months, and with only limited advance preparation, organizations all over the United States embarked on an unprecedented experiment in distributed, remote work as a means of staying operational in the midst of a global pandemic.

The speed with which our nation’s massive telework experiment was executed has meant that many supervisors and managers received limited (at best) training in how to best manage their remote staff. While many have adapted well to managing a fully distributed workforce, other managers have encountered challenges in exercising effective oversight in a purely virtual workplace. Fortunately, several basic principles — communication, focus, and flexibility — offer a framework for developing constructive and consistent ways to manage teleworking employees.

Provide effective communication

Communication within an organization or individual business units is critical to effective management and quality work product. That basic principle holds true whether employees are working together in a common physical location or working remotely from multiple locations.

From a technical perspective, communication between managers and remote employees is easier than it has ever been. In addition to the traditional telephone, Microsoft Skype and Teams software is bundled with Office 365 subscriptions, and, outside of the Microsoft suite of products, tools like Adobe Connect, Apple FaceTime, Cisco WebEx, Google Meet, and Zoom — to mention only some of the more popular platforms — are available within most organizations. Each of these solutions supports text and video conferencing, in addition to audio; some also support joint editing and other collaboration functions. Technology is rarely the problem.

A larger and more subtle challenge, however, is how managers are using these tools — i.e., the frequency and substance of their communication, rather than the methodology. At one extreme, some managers are concerned that their employees aren’t working their full duty hours and are reaching out to staff much more frequently “to check on them” than when everyone was in the same physical office. At the other end of the spectrum, some managers have taken the more relaxed view that as long as work is done in a timely manner and to an appropriate level of quality, little communication is needed.

Neither of these approaches is really a best practice.

The speed with which our nation’s massive telework experiment was executed has meant that many supervisors and managers received limited (at best) training in how to best manage their remote staff.

Working remotely can be challenging for workers. Unscheduled, casual conversations prompted by seeing someone in the hallway at work simply do not occur. Prior to the COVID-19 pandemic, multiple studies showed that full-time teleworkers felt isolated and their contributions overlooked by their employers, even when their work was used in organizational work product. Workplace interaction is a key way of remaining tied into a team; and for a manager, it’s also a critical way to learn about potential issues or challenges that need to be addressed.

Managers should not rely on their staff to initiate all conversations. While a manager may think that this sends the message that they are confident in the ability of the employee to work independently, it could just as easily (and is more likely to) send a message that they are being ignored. At the other extreme, requiring remote workers to inform managers every time they start or stop work and performing spot checks to see if they are at their computers provides limited management benefit and adds a new level of micromanagement that is unlikely to be appreciated.

Keep employees focused

A better approach would improve not only communication, but also help keep employees focused is to establish a frequency of interaction similar to what took place in the physical office via a mix of scheduled and unscheduled interaction. Because of fewer opportunities to see one another in person, it may make sense to increase the frequency of scheduled team or staff meetings, even if these are only short touch-base sessions. In addition, it may be helpful to encourage staff to use the technological tools at their disposal to send quick questions, reports, and other interactions as they might have done by physically walking to someone’s actual office.

For managers, it can also be very helpful to schedule weekly one-on-one meetings with each of the employees they manage. Even if these meetings are only 5 to 10 minutes long, these sessions provide employees with an opportunity to speak up about any concerns they may have that they might not feel comfortable sharing in front of the entire team. Further, it ensures that no team member is overlooked.

Because of fewer opportunities for unscheduled physical interaction when teleworking, managers may benefit from spending a bit more time up-front in explaining assignments and performance expectations. Ensuring greater clarity at the start of a project will help an employee ask more focused questions as issues arise, and it may help compensate for any communication lags that might occur.

Managers may consider sending an e-mail message that contains a clear written summary of each significant assignment, including expected work product, due date, and additional resources if needed. This type of rubric has worked very well in academic settings for some time; it can be equally effective in the workplace.

Encouraging management flexibility

Telework is appropriate for many reasons and in varying degrees, meaning that no single implementation fits all situations. Different workplace situations may support ad hoc telework, scheduled partial telework, or, as is the case with so many organizations currently, full-time telework. In turn, employees may telework from their homes or from other locations such as remote offices or vacation lodgings. Each of these variations may be highly effective remote work strategies; and it is appropriate for employees to cycle through multiple flavors of telework, depending on their personal situations.

Managers should remain flexible when working with teleworking employees, keeping in mind that their ultimate responsibility is for their business unit to remain productive and operating in compliance with governing labor laws. Managers may have an unconscious bias that their teleworking team members should telework the same way that they do, but they should resist this temptation and focus instead on the quality of the work and the ability of a teleworking employee to perform their work.

This may mean allowing some additional flexibility with the hours when work is performed. It may even mean re-prioritizing assignments for a teleworking employee. Flexibility does not, however, mean excusing non-performance of assigned work in the absence of mitigating circumstances.


Geographical distance does not mean social distance, nor does it make it impossible for knowledge workers to successfully complete their work. Our nation’s experiment with widespread telework has proven remarkably successful, and it may challenge ways that some organizations will do business going forward, well after the current health crisis is resolved.

Continued focus on consistent, clear communication, matched with strong helpful outreach by management, will help keep teleworking employees focused, working effectively. and feeling like they remain part of a larger team and organization.

This article represents the personal opinions of Mr. Jacoby and does not constitute an official position held by any of Mr. Jacoby’s clients or employers.

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