The Good, the Bad, and the Ugly: Ten Years as a Remote Worker

I’ve been a “Swiss Cheese” remote worker for over ten years. For the majority of my career I’ve been a full-time remote worker, but occasionally I accepted on-site or partially on-site roles. To put it lightly, I’ve seen the good, the bad, and the ugly. I’ve learned from both fantastic remote managers and, unfortunately, from some poor ones. I’ve worked in roles with an abundance of remote technology, and in roles without any support whatsoever. Today I’m going to take you through some of my experience in hopes that you can learn from it.

Entering the Remote World

I lucked into my first remote role early in my career. I happened to be sitting on an airplane working away, when another passenger asked what I did for a living. When I shared that I was (at that time) a technical writer, an individual sitting in the row ahead of me turned around and told me his company was looking for a tech writer. A few interviews and a couple of weeks later I entered the remote world. 

As a relatively green member of the corporate world, the freedom that came with a full-time remote position was huge. Fortunately, this company knew what they were doing. They worked to put policies in place that both provided structure for workers and also gave them the freedom they needed to thrive. 

What Worked

The company did a great job of setting guidelines around work hours. In an effort to provide some flexibility, their guideline was that they required every employee to work at least half of their work day between the hours of 8 AM and 5 PM. This ensured that you could find a time to collaborate, while still allowing employees to flex the work day for personal needs. 

To manage their remote work force, they used a company-wide project management tool. To ensure we all stayed on the same page, we had a weekly team meeting where we discussed what we had done the week before, what we were doing in the coming week, and any roadblocks we were experiencing. 

What Didn’t Work

The company used a bunch of different communications tools. We were each responsible for getting a phone line in our homes, through any provider of our individual choice. We also had Skype accounts associated with our personal email addresses, and business email addresses provided by the company. The disconnect between the three systems made it difficult to communicate seamlessly, especially because we only had the one weekly meeting. There wasn’t a company phone directory, which made it hard to learn how to get in contact with anyone. And if an employee left, the customer had the former employee’s personal phone number, not the company’s. 

What I Learned

Looking back, I realize that by walking the fine line of set work hours and flexibility in their remote policy, managers and employees alike learned to focus more on productivity than on exact hours. And it worked! While the weekly meetings that I attended seemed like just a quick team update, in reality they created a forum to work together, without micromanaging team members, which improved productivity.

The Hybrid Remote World

My next role transitioned my career into marketing as well as into an office, with an exasperatingly long commute through dense city traffic. Within a few months, to decrease commute time, I was offered the opportunity to shift into a hybrid on-site/remote role. I worked three days a week in office, and two days from home, switching off every other day. This was a great fit as it allowed me to collaborate with coworkers in person, but also to cut off commute time, with the added benefit of distraction-free work time at home. Eventually, this turned into a completely remote role. 

What Worked

On my first day in this role my manager told me that her management style was just like parenting a high school student. As long as you were an A+ employee, with good productivity and high-quality work, she would be a hands-off manager. You were rewarded with autonomy and could manage your role as you saw fit. If an employee started slacking, becoming anything less than an A student, the managerial team would start bringing in the structure, setting exact work hours, and requiring daily to-do lists in the morning with an afternoon check-in. The “high school student” strategy allowed employees to manage themselves but gave managers an opportunity to step in and provide guidance where needed.  

What Didn’t Work

The one gap in this company’s remote infrastructure was in their communications. This company relied heavily on email and chat. They didn’t have a phone system that you could take home with you; at best you could forward your desk phone to your personal phone—but only if you remembered to plan in advance. For those of us who ran virtual events, not having a work phone at home meant using our own resources. This added on a layer of complexity that negatively impacted productivity.  

What I Learned

My manager’s hands-off approach has stuck with me and impacted the way I work to this day. Sometimes, a little bit of space can go a long way for an employee’s well-being, as well as for their opportunity to problem solve and grow on their own. On top of that, communicating is important. It’s not only about interacting, it’s about having the infrastructure to do so. 

The Inexperienced Remote Manager

A few years later, I was approached by a recruiter about a 100% on-site role. I was incredibly torn; the role itself would be great for my career, but remote life suited me. My husband also held a remote job, which allowed us to work from anywhere, together. We were able to balance our careers and our life together beautifully. I found myself begrudgingly accepting the role, knowing that the company had a lot to offer in terms of experience and career growth. 

The company itself may have been somewhat open to remote work, but the head of my division was staunchly against it. Her reasons weren’t openly communicated, but it became clear that employing remote workers conflicted with her management style. She needed to see her employees at their desks, typing away, to believe that they were working. Seeing is believing, and all that. 

What Worked

As the team was only able to work remotely on snow days and other special, pre-approved occasions, there isn’t really anything to point to what did work. Unfortunately, this gap left a lot of opportunity for things not to work when remote work was necessary. And as we learned in 2020, it’s critical to have a good foundation in place to work remotely to failover to when the unexpected occurs.

What Didn’t Work

During my time in that role, there were many heavy snows in the area, forcing frequent remote work snow days. The rules on these days were strict. Every member of the team logged on at the latest at 8 AM and continued through 5 PM, at minimum. Every employee was required to send a list of what they planned to work on that day. At the end of the day you were required to email back a list of every task you completed and what you didn’t, as well as exactly why you didn’t. This probably helped them feel that they could carefully track productivity, much like watching an employee sitting and typing at their desk. For the one or two employees who struggled with remote work (it’s not for everyone, after all), the strategy worked. The rest of the team walked away from a remote day feeling stressed, distrusted, and discontent in their roles. 

This company also lacked a comprehensive communications set. They relied on desk phones and email for the entirety of their communications. The phones didn’t sync with computers or mobile phones. As remote work days were always unplanned due to weather, employees didn’t have an opportunity to forward their desk phones before working from home. 

What I Learned

The feeling of being stressed, distrusted, and discontent following a day of remote work bled into the entirety of my feelings about my role. Most of the other people on the marketing team felt the same way. Providing a bit of trust to your team can go a long way in empowering them and helping them to stay engaged with their job. I think that if the head of the division had embraced a solution that provided additional communications tools and reporting, they would have felt more comfortable with remote work. Employees would have been able to communicate more readily both in office and at home, and, in my experience, would have felt empowered to work hard without being micromanaged. I believe the head of the department would have been able to relax using reporting to gain insight into team productivity when employees weren’t in the immediate vicinity.   

Remote Roles Done Well

After some time in my on-site role (where, as I had guessed, I had the opportunity to learn and grow) I was contacted by Vertical Communications about a completely remote role. I’m sure that my enthusiasm about the role was glowing through the screen when I responded to the original email. I had been hoping to move back into a remote role at some point, and to have the opportunity fall into my lap felt like it was a dream come true.

When I joined the Vertical team, many team members had been remote for years, while others had more recently transitioned. Despite my deep experience in remote roles, Vertical still changed the way that I work remotely, adding to my skill set as well as to my appreciation for the telework life. 

What Worked

Vertical is successful with a remote strategy because they have the remote trifecta: a foundation of communication, supporting technology, and experienced remote managers. 

Tackling Communication

Vertical strives to keep all of their employees in the loop all the time. They don’t use a sniper approach for this. Instead, they go for a shot gun blast approach, with internal email communications, monthly internal newsletters, an internal knowledge base, and quarterly company-wide calls. Everything that occurs is communicated more than once to make sure that every employee is in the know. 

Supporting Technology and Technology Engagement

Not only does Vertical have a comprehensive communications system, it’s also part of the company culture to utilize it. Vertical uses a Unified Communications (UC) tool that is integrated with our Outlook application. Every employee can communicate from within a single application, using the tool that fits their personal preference and is appropriate for the individual situation. And if we’re away from our desks, we can answer calls from our mobile phone or laptop, too. Ensuring that we can always communicate from a single application ensures we’re always in communication and productive, no matter where we’re at.  

Vertical also focuses heavily on engagement with their communications tools. This helps to set the standard that the entire company uses the tool, keeping every employee engaged. For example, at one point Vertical rolled over to a new UC system. To ensure engagement with the new system there was an internal campaign, as well as an effort to regularly create company-wide and team-wide chats, etc. Various teams ran engagement competitions to encourage that employees to use the tool. Leaders company-wide embraced the technology, which helped their team member’s transition as well. 

Experienced Remote Managers

When I joined Vertical, they were already a well-oiled remote team. On top of that, my direct manager had worked remotely for many years before he joined Vertical and had already managed a remote team for a decade. He knows how to expertly manage a remote staff, as does the rest of the leadership team.  When I joined the Vertical team, they started with a certain amount of structure. There were a few of us who started at the same time and Vertical worked hard to get us all on the same page. Vertical is very good at walking the fine line of structure in a workday with flexibility for personal needs. For instance, on the first day, we scheduled a daily stand-up (good structure) but we worked together to select a time that worked best for everyone’s work style (flexibility). Obviously, not every remote manager is experienced with a remote team. Simply providing new remote managers with the tools and guidelines to do it well is a great step toward success. 

What Didn’t Work

Vertical does remote work very well, but there’s always room for improvement. Despite my love of a remote lifestyle, I think some Vertical employees could get together with their local team members more often. Prior to the pandemic, I saw my local team once or twice a year, and I know other employees in other states did the same. Doubling that amount could go a long way in creating strong relationships. 

From time to time I’ve also seen some siloing between divisions. While communications are sent company-wide to keep us all on the same page, I don’t always experience the same thing between divisions and am taken aback when I learn something that the marketing team needs to know. In an office, it would be easy to walk by and see what other teams are doing, or talk around the water cooler about projects. Remotely, that can be harder to tackle. 

What I Learned

A remote work strategy isn’t a sprint, it’s a marathon. To be successful, you need to create the infrastructure to be successful (A.K.A., the remote work trifecta), and then you have to continuously train, build, and tweak it. Next, having a foundation of communication is absolutely critical to success. And finally, a communications foundation is a two-part equation: 1) giving your team the right communication tools and 2) creating a culture of communication. With only half of the equation, you can’t find success with a remote strategy. 

What’s Next?

Transitioning to a remote strategy isn’t seamless. There’s a lot of trial and error. Vertical made the change years ago, carefully strategizing and removing obstacles along the way. If you’re considering moving your business to a remote workforce for the long term, Vertical can help. We’re happy to share our experience with you and help you avoid the obstacles we ran into along the way.