Thoughts on Telework Transitions for the Organization

Mike Peluso
10 min readSep 4, 2023


I was in a leadership group at work. I absolutely love them, leadership groups I mean. I take part in them whenever I can and have been in many of them over the years. I don’t love them for what you learn. The content is always mixed. Some information is great and some is rather drab. What makes leadership programs so enjoyable to me has nothing to do with what you are supposed to learn. It’s the people in the groups. I love being around movers and shakers and they are usually the only people who volunteer to do extra work like taking part in a leadership program. They are also the only ones who get really engaged in conversations. That part is key to this narrative. One of the meetings at this latest work based leadership group was with the head of our fairly large organization. It was supposed to be a town hall style question and answer session. We got to submit our questions in advance and our president was supposed to answer some of them. I always take advantage of these types of situations and had submitted a litany of questions on various different subjects. Of the many questions I had submitted was a question about our organization’s new telework policy. I honestly thought it was a throwaway question and would be a one minute answer. I was wrong. I was blown away by how it resonated with everyone and the conversation it generated.

Why did I ask the question? In all honesty I was using it as an opening to ask another much more specific question about my personal wants. In my perfect fantasy telework world I would work one semester 100% telework and one on campus every day. In this scenario I would get to maintain the all important student, campus and community connections yet also get to maximize my flexibility as an instructor by spending half my year living in some exotic locale where I could really take in the local culture. I know we are years away from that kind of model, but I figured I’d nose around to see if it was something I could hope for in the future. What I wasn’t expecting was the litany of everyone in the leadership group engaging in the conversation before I could even begin to explore my thoughts.

The gist of the experience was that everyone had an opinion and the organization, one that had never really had to deal with telework in any meaningful way, had opened a Pandora’s box of cultural change with the new policy. Even though most of the rest of the business world had figured this out, my organization was just starting their struggle with the concept in the same way that the business world did decades ago. I had lived through those early years of telework adoption and as the old joke goes, the conversation I was hearing felt like “deja vous all over again.”

In the earliest days of telework, or what we would call field work, there weren’t groupware applications or real time cloud based business applications. In the beginning it was phone booths, very expensive candy bar cell phones, and an expectation that remote work was “on the road”. In my earliest days my productivity was measured by my gas and hotel bills. Bills I quickly learned to manipulate so I could have the flexibility to do whatever I wanted in addition to getting the job done. I loved this flexibility so I loved my job. The private sector eventually figured it out. Over time the organizations I worked for evolved from micro-management to project work to simply giving an employee so much work that they really didn’t have that much time to slack off. This was all cemented by ubiquitous broadband and groupware and cloud apps which made remote working so much more efficient for everyone.

Eventually the on the road model morphed into working from home, often so the employer didn’t have to pay for expensive office space. Ironically I learned that the best way to telework efficiently was to have my own dedicated office space. Being a man of extremes I took the concept of dedicated office space to the logical end point where I wound up building my own mini office building complete with a bathroom. Aside from an issue with how I designed the air conditioning, it was a great space and one of the better decisions I made in my life. From that point forward I have had dedicated space in my homes for work for both myself and my wife. I share this all because I think it gave me a unique perspective as I was hearing the telework conversation and understanding the concerns of everyone from management to rank and file employees including some who were not 100% on board with telework.

During the animated conversation with our president, one of the points brought up by someone unfamiliar with the telecommuting lifestyle was a concern that as telework got adopted more broadly they were going to lose the motivations, or energy as they referred to it, from office camaraderie. I personally know that’s not much of an issue because if you interact with a team, even remotely, over time bonds are developed that are as strong as those that are developed in the office. There are always lots of phone calls for work, and the conversations typically expand to where team members become each other’s support and motivation groups. On top of the telework, nearly all organizations have occasional in-person meetings for their teams, even those that are geographically distributed. These in-person meetings act like the professional equivalent of quality time together and really help bond the team members. I think this last part is the most important when considering telework versus a traditional on-site office. There is definitely something unique you get out of face to face and in-person engagement that can’t be replicated by a 100% telework experience. Still, to get those benefits, you don’t have to be even close to 100% in person.

It’s safe to say that that individual was in the minority, the tone from the rest of the group was one of accelerating telework. In a Post COVID-19 Pandemic world, where everyone got to sample it for a couple of years, telework is definitely the aspirational choice for many more than it used to be. In fact it was the genesis of the telework policy. I could also tell from the questions and the answers that the real topic of telework wasn’t one of identifying “more” or “less”, it was more about identifying where it could be implemented with minimal disruption to services. It was also about how managers, who have never had to deal with it before, now had to go through the process of becoming comfortable with managing a distributed workforce.

One point that went through my mind over and over was that a great majority of the population we serve, i.e. our customers, prefer telework options. In some cases, they express their opinions militantly and they see it as a right. The irony is that often they really need in-person engagement to succeed which is probably why we were moving so slowly. Organizational change for all stakeholders is hard.

The questions and ideas continued to flow but one point was clear, the trend of telework was going to expand. It will expand much more slowly than those who wanted complete adoption immediately but it will become more the norm than in-person as time goes by. You can’t have the majority of a community made up of service providers, and the individuals they serve all wanting telework, without it becoming woven into the fabric of an organization or even an industry. Everyone wants it because, from a life perspective, the flexibility that goes hand and hand with telework makes life more convenient, and as I have argued, convenience always wins. [change when this posts to after convenience article?]

I would be remiss if I didn’t discuss the benefits of working at the office. I relearned them after over two decades of telework when I got my first ‘office job’ with my current organization. Due to some health issues I was very nervous about going into a regular office with regular people every day. Fortunately everything turned out well. I did get to know my co-workers, folks I may not have been as close to if we were all teleworking together. There was a very formal dress requirement in the office and I wound up spending many years wearing suits. I learned that there is something fun in dressing up. Also, I was shocked to learn how different people treat you when you are wearing a tailored power suit. I think I would have enjoyed the whole office and dress up experience more if I didn’t have a yo-yo weight problem. It did get to the point where I dreaded having to put on my dress shirts because I would feel like I’m choking. Even though it was fun it was definitely not convenient. It was also expensive. These two elements, inconvenience and higher costs, together explain why, if we can have more telework, we will. It definitely explains the rapid adoption by the private sector wherever it makes sense, and it also explains why the government affiliated organizations are just now changing. Typically government organizations are about thirty years, or one generation of employees behind the private sector when it comes to newer models of getting anything done. As an example, we are just now seeing governments try to embrace the 401K as a retirement program, ironically just as the world is figuring out that a 401K based system is an abject failure.

The adoption of telework by an organization is a long and slow cycle where all the issues have to be figured out. That’s one of the big points of this narrative. As an example, college courses that are 100% online have a huge huge loss of students where students who are in the exact same class but in an on-campus seated section have much higher retention rates. The colleges of today haven’t quite figured out how to eliminate that gap. It’s one of the reasons why they are proceeding so slowly. Yes, there are many students who excel in online courses. You always have those. They typically get the course done very early. Others don’t. It’s all about personal discipline. I witnessed this first hand with a student who simply didn’t have the discipline to work remotely. No work was ever done and she was weeks behind. When I got her into the classroom, and sat her down, and really micromanaged her, she got her work done and done well. It took years for the private sector to figure out how to properly manage the employee version of these students. Now the public sector has to do it.

When I put it all together, telework is complicated and messy because people are complicated and messy. It works great out of the box for those who have a strong work ethic and innate discipline, it doesn’t work as well for everyone else . Tools and techniques need to be adopted for the various types of personalities that don’t acclimate to a completely remote environment.
Telework won’t ever be the only way we work. If your in the business of connecting with people on a personal level like with healthcare or education then big chunks of your industry will be in-person, at least partly, for a long time. For anything else that can be done well via telework, it will mostly be done that way, eventually. It’s too much of a win-win for everyone. For people they get to enjoy all the convenience flexible telework brings. For organizations it lowers costs and keeps people mostly happy. It’s not going to happen overnight because the transition is so cultural in nature. I think this is why we saw some organizations really push to get people to come back to the office after the worst of the pandemic. They still were fundamentally structured around an in-office population of workers even though they had operated for over a year with remote teams. I made the cultural transition which is why for most of my adult life, I saw home office space as a mandatory requirement for any house I have ever purchased. Now I get to watch my organization do it. It’ll be fun to watch but I do hope they get very comfortable with it soon. I don’t mind going on campus but I’d love to be teaching IT classes from a villa in Tuscany Italy for six months one year, and from a Caribbean beachfront bungalow for six months the next year. Now that would be a great life and I wouldn’t even have to be creative with my zoom backgrounds, I could just sit with my back to the window.

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Mike Peluso

Mike Peluso writes is about the collision between the professional world and life. Read more at or listen to the Peluso Presents Podcast