The Rise of the Remote Employee

The Rise of the Remote Employee

September 23

Just over three years ago, I pitched my boss on the idea of working remotely.

I planned to move to southern Utah, about 1200 miles away from the company headquarters located 20 miles south of Seattle. At the time, the company didn’t have a remote worker policy in place because we didn’t have remote employees.

Today, most large companies have an ever growing number of employees who work remotely. According to PGi, about 80% of U.S. knowledge workers are employed by companies that have a telecommuting program in place. “Telecommuting is rapidly becoming one of most attractive benefits a company can offer,” said Sean O’Brien, executive vice president of strategy and communications at PGi. “Our teleworking survey also revealed that 80 percent of employees consider the option a job perk.”

One of my favorite TED talks was given by Jason Fried, co-founder of 37 Signals, which became Basecamp. Jason is a big proponent of working remotely, and believes that a lot of work doesn’t happen in the office. He believes that people are trading in their workdays for a series of work moments, and he blames the distractions that come with an office job. His strong views are controversial, but they are thought-provoking.

Remote employees might perform work from home or coffee shops which introduce significant challenges to IT. This week I will look at how IT can work with management to create sensible policies that work for both remote workers and they company. MSPs and VARs are often in a similar spot where their services might cover both office and remote workers. Are there services they can provide that will help companies manage their remote workforce? Let’s take a look at some of the challenges as well as some solutions.

The Remote Worker

Today’s remote worker could be your boss, colleague or a direct report. The days are over when only specific positions were earmarked for remote work. I once worked for a company that only allowed graphic designers to work remotely. It was uncommon to have more than a couple of remote workers at a time, but that’s no longer the case at most companies.

The tech savvy remote worker has held an advantage by understanding what hardware and software is required to do the work. If a network setting needed to be tweaked, that wasn’t an issue like it would be for someone in accounting. But even with all the right technology in place, there are a lot of challenges that make remote work difficult for the company and worker. These issues are often punted to IT.


While IT will likely provide the hardware and software to remote workers, MSPs and VARs can make sure they are complying with company security policies, performing proper backup routines, and maintaining a safe work environment. Many IT groups may not understand how to best integrate these practices. For example, is it realistic to expect a remote worker to backup data in the same manner as an onsite employee? An MSP or VAR may consider offering premium services that help integrate the remote worker into these and other standard routines that often are out of the wheelhouse of corporate IT groups.

When I began working from home, I realized that not all the software I needed worked well outside company walls. It took some trial and error to determine which programs integrated well with software already in use at the office. I provided my own workstation, which contained a lot of sensitive material. I wasn’t part of the corporate domain so my data wasn’t backed up each week.

Each of these issues took time to work through. I work for a technology company in a technical capacity, and if we’re experiences these hurdles, you can be sure that other companies are too. MSPs and VARs can play a critical role in bridging the knowledge gap between company and remote worker by offering services that help both succeed.


The primary challenge I still face working remotely is timely communication.

I know it might sound cliche, but if communication hurdles exist, it will be difficult for the remote worker to succeed. “Communication is the number one component of managing a mobile workforce,” said Joel Frisch, founder of employee scheduling tool ReadySetWork. Most workers will default to email if other options are not in place, and that’s not always the best option. I’ve used email to provide status updates on my work and pass along minute details that work well over email. But email doesn’t do a very good job of facilitating casual conversations, and small issues can be dragged into mind-numbing threads.

For immediate and mostly casual conversation we use a mix of Skype and the open source XMPP chat server that employees access through Pidgin. These and similar tools provide a more casual space for employees to connect with those inside and outside the office.

Slack is a new breed of messaging tool built specifically to address corporate communication needs. Slack allows users to create communication channels based on project or department or a number of other variables. Groups can collaborate on projects and share files. And everything is searchable. I’ve used Slack as a team member for a complex project, and I loved how it reduced the number of emails and never-ending discussion threads. Slack largely solves one of the biggest fears of those working remotely: feeling disconnected. The mix of immediacy and intimacy of Slack discussions made me feel like a natural member of the team.

Another challenge that comes with having a remote workforce is tracking productivity. When working from an office, managers and coworkers usually have a good grasp on your work schedule and work ethic. It may not be fair, but working remotely can breed jealously among those who don’t have the privilege or whose work isn’t tailored to working outside the office. Making sure you have tools in place is critical to tracking and measuring success. Unfortunately, I haven’t found a lot of software that is designed around this goal. I’ve been utilizing a low budget solution that’s worked well for a couple of years. I created a spreadsheet in Google Docs and shared it with with my manager. Each week, I add those projects I’m working on along with a note to detail my progress. Every Monday we discuss this list which helps my boss recognize my contribution and allows me to re-prioritize my time based on his input. It’s not an idea solution, but it works. If you have a solution that works for you, please leave me a comment below.

The final challenge I want to mention is culture. When you go from having a team work alongside each other, it’s naive to think your company culture will not change when that same team is working remotely. I used to sit less than ten feet from an experienced technician, and I loved bouncing idea off him throughout the day. That I was able to overhear his conversations helped me when I was getting up to speed on technology that was new to me. Companies with a large contingent of remote workers such as Basecamp and WordPress gather their teams together at least twice a year. This allows them to feel connected to each other and feel like they are part of a larger cause.


Advances in technology have ushered in an era of remote workers. From high-speed internet to mobile and cloud services, the opportunities for employees as well as MSPs and VARs are endless. MSPs and VARs can help companies work through challenges such as software licensing, security and backup options. It might make a lot of sense to have a premium service tier that covers remote employee needs, starting with the challenges I listed above.

As a technologist, you might see everything as a technological problem, but that’s probably not how the manager or employees view it. The technology will change. New products will come and go. But the challenges of communication, tracking and culture will be around for a long time.

Solve even one of those issues and you’ll have a viable business.