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My 20 Year Journey as a Remote Worker

Updated: Dec 15, 2020

20 years ago, I was hired to work with a group of consultants to develop a software product. We worked in a large office space in New York City overlooking Madison Square Garden. We had to collaborate with team members located in San Jose, North Carolina, and Bangalore. We did so by putting together every technology that would help us to collaborate over a long-distance. We used clunky instant messaging tools, e-mailing applications, webcams, and digital sketch pads to simulate a personal teleconferencing experience that wasn’t available at the time. Combining these off-the-shelf hardware and applications would often take longer to setup than the time we spent in the session, but it was better than trying to describe things over a phone call.

As the project progressed, the local team of consultants phased out and I was the only one left working out of New York. One cold day, as I made my commute from uptown to midtown Manhattan, I asked myself, “Why am I commuting at all?” I mean, I liked the free snacks at the office, but I wasn’t physically working with anyone at that location. The next day, I decided to stay in my apartment and work from home instead. That was the day I became a telecommuter.

I faced new challenges as I adapted to my new work environment. The following lessons became an important part of working effectively in my new environment:

Ensure everyone has access This was back in 1999. There were a lot of technical details to workout. First, I did not have VPN connectivity. That meant that I had to download the work to my laptop and reupload from the office once I completed my tasks. This meant going into the office at least once a week to update my work. We quickly figured out how to establish a VPN tunnel to access an agreed server that would become our code checking. Today, having a common repository that can be accessed from anywhere is an essential element for any distributed team. Currently, the trend is to migrate services to the cloud so that team members can access them from anywhere. In addition, most companies support VPN connectivity into the office and the standard laptops are equipped with VPN clients such as Cisco VPN.

Provide Communication Tools Something as simple as making and receiving calls also became a challenge. Normally we would call each other over our office line but working from home meant that I didn’t have access to the office line. I could check my voicemails remotely but by the time I received them, it was too late. Making phone calls created a similar challenge as I watched my long-distance phone bill skyrocket. So, we started depending on instant messages as the main form of communication for quick items. We would then agree to join a telephone conferencing session if the conversation went longer. This helped us communicate more synchronously and respond to change quicker. Today, unified communication services such as Microsoft Teams have teams covered. Using these services, team members can IM, call, or video conference from most devices, including mobile devices.

Enable Shared Collaboration I had to be able to work independently from the rest of the team. This meant that I signed up for a chunk of work at a time and would spend the week working on it. I would then check in the work and grab a new batch. The problem was that often, the work didn’t fit together. This is because the team had moved on with other solutions that did not quite fit the approach I had taken. We quickly learned that smaller batches and coupling tasks were a better way to avoid misalignment and improve collaboration. This meant that I would work closely with a set of individuals and share tasks. This allowed me to stay connected to the team and vice versa.

Create an Inclusive Culture We rarely think of inclusion as something that could affect remote workers. But team members can unintentionally discriminate against their remote counterpart. We had phone conferencing services, but it was difficult to schedule meetings and get everyone to attend since we did not have shared calendars. Meetings would normally happen at the office in North Carolina, but I would not be invited since they tended to occur in the spur of the moment. I was often out of the loop on the critical information that I needed to do my job. My team members were not trying to exclude me. It was just easier to walk into a room and start a conversation. I mitigated this by being very proactive and almost pushing myself into the conversations. Overtime, we grew comfortable recording meeting discussions so that others could listen and catch-up. This helped a lot, but it wasn’t perfect since my side of the conversation would be missing. Today, collaboration tools such as Slack allow all team members to be included in the conversation, no matter where they are located. Be sure to use it and be careful not to keep discussions in your local work group and unintentionally exclude others.

Increase Distributed Belonging I consider myself a very social person. In fact, I recharge when I’m around people. Working alone was not my idea of having fun. Actually, working remotely full time started to drive me crazy. I started to crave a crowded office and the water cooler conversations. I would have called the whole thing quits if it wasn’t for my wife reminding me of all the headaches she was facing commuting and being cramped in a cube. I needed a way to connect with people, so I created a routine that allowed me to do so. This included going out for lunch, (even though my fridge was stocked), taking a morning jog in Central Park and closing the day by meeting friends. In other words, I had to become more methodical about my social life and activities. This also helped me to strike a work-life balance that kept me from burning out. Today, Zoom Happy Hours are all the rage. These virtual social sessions, as overused as they might feel due to the current social distancing measures, go a long way at building the social capital that makes the difference between a group and a team.

We now live in the age of Zoom, Slack, and unified communication. Most services exist in the cloud. Many companies have now moved to flexible desk practices where they host a smaller number of seats than employees. Employees are actually encouraged to work from home and are given laptops with VPN connectivity to access company assets that aren’t on the cloud yet but are likely on the cloud migration roadmap. Telecommuting and working from home have not only become normal practice, but as the recent Coronavirus pandemic has shown us, telecommuting is now a necessity. Consider a few of these learned lessons to overcome some challenges you might be facing as you adapt to the new telecommuting business environment.



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