We Shouldn't Be a Fan of Our Work

Last year, after almost a decade of circumventing rules at the day job to help people serve students better, I was moved out of the classroom and into a full-time development role to continue doing what I was doing as an instructor, but without all the cloak and dagger to make it happen. A lot of people were happy with the news, including myself. It meant that I could play a role in making something that colleagues all over the country might find value in, rather than something that just a handful of schools would use without really saying much to upper management about it. Over the last 15 months, though, I've come to dread going to work. I despise checking email. I want to be invisible on Skype all the time or, better yet, just shut the distraction down so that I can make it through the day without wanting to hurl a computer five stories to the pavement below1.

The problem is not with my colleagues. The problem is not with the endless complaints from people who storm into the little space where I do my work. Believe it or not, the problem is not even with the sound of silence from human silos within the organization who refuse to share their knowledge of the home-grown CMS my project must interface with. The problem boils down to a very fundamental issue that will never be resolved so long as I am working for someone else.

The issue is the result of an unsharable vision.

Steve Jobs and the First iPad

Way back in 2010, soon after Steve Jobs walked on stage and showed the world the iPad, I started thinking about how such a device could be used in education. By that time I had been teaching for almost three years and had the hubris to think that I could write software for a tablet that would make education easier for teachers, students, and all the support staff that are required to make a school function. Looking back at the early design sketches, I almost cringe at the naivety on display. The concepts I was dabbling with were far too similar to the way Microsoft approached tablet software in 1999.

Suffice it to say, the sketches went nowhere and I shelved the idea for a few years, revisiting the idea whenever I'd read an article about how tablets were being used in education.

Fast forward to 2013, I was asked to create a special kind of report for a new type of class that was being trialled in the area. Excel was a mainstay at the day job, and every report we gave to students or their sponsor came from this spreadsheet software. Me being me, I was one of the few people responsible for writing all of the reports in the region to ensure that every student and every sponsor would see a consistent message with consistent formatting and consistent quality. This new kind of report, though, needed something that Excel was not particularly good at without a complex series of macros. Instead, I used this opportunity to push through an idea that had been bouncing around in my head since the year before: build a data-collection website that is designed to be finger-friendly so that teachers simply tap-tap-tap their feedback and let the database do the heavy lifting.

Selling the idea was not easy, as people "just wanted an Excel report", but I used a long weekend to prototype the site and build some dummy reports. I presented it to the managers the following week, and they loved it.

This was shortly after my employer had rolled out iPads to all of the schools in a bid to make us seem more efficient and professional. Both counts failed and the project was bleeding money but, again, I had enough hubris to think that I could push through my own agenda while using company resources to solve company problems. Within six months the project had expanded to include several different types of reports, and people were generally happy with the system. A few times the project came close to being shut down when certain members of IT learned of the project2, but there was always just enough pushback from the local schools to keep the project alive.

In 2015, after a redesign of the iPad software teachers were supposed to use in class, a number of people gave up trying to use the tablets in the classroom. We still had to use them to record attendance, lesson goals, homework, and other details, but a large portion of the teaching staff gave up trying to use the tablets beyond the bare minimum. The problem was that the software was poorly designed for the job it was hired to do. The textbook application was nothing more than a frustrating PDF reader that stuttered and crashed every 15 minutes. The pedagogical tool was sluggish, hard to look at, and buried all of the student profile information, making it very difficult to learn more about students — or record updates — before walking into a classroom. Despite transitioning from paper to digital two years beforehand, people were pining for the day when we'd drop the iPads and go back to paper records. The older textbooks that made use of cassette tapes were easier to use and less embarrassing than the iPad software.

So I decided to do something about it.

Again, over a long weekend, I mocked up a new pedagogical system that would work on the tablets while making the system easier to use for teachers and staff. Information would be easier to find and filter. Textbooks would be searchable and come with custom lesson plans to help inexperienced or fatigued teachers. Reports — my specialty — would be built in to the pedagogical system meaning that teachers would spend less time writing them while students and sponsors received more data from them. In the space of four days the demo was ready and I started to show it around to people at the day job.

People loved it. Managers loved it. Even some of the students commented and said that it looked simpler. HQ, however, wouldn't hear of it. There were processes and procedures and hierarchies to obey, and I was bucking the system. They demanded it be shut down, even though there was zero student information in the system. I "conveniently forgot" to do so.

Then, in the fall of 2015, an interesting thing happened. The president of the company caught wind of these projects I was working on and asked to see them. He then asked why I "was being wasted". A week later I was approached with the opportunity to transfer to do software development in the IT department and, in March 2016, it became official. That 4-day design of the pedagogical replacement system is still being worked on and refined today, and people are generally happy with it … except when they aren't.

Back to the Problem

Earlier I said that my problem boils down to a very fundamental issue that will never be resolved so long as I am working for someone else, and this is completely accurate. I have been working quite hard on the problem of creating effective software for use in education for almost five years, the first four years of which was in near isolation where I was able to design and implement features and functions as I saw fit. When I would watch people interact with my software, I would find problems. These were often actions they would do that I never once considered, and I would go back and find a better way to support their goals while also ensuring mine were met. People would come at me with ideas or complaints, and I'd listen and find ways to make the system better for them, again ensuring that my goals for the system were not lost along the way. The way I looked at the tool was very simple: the UI is for the teachers, the printed reports are for the students, the database is for me.

By doing this I was able to create something that teachers actually liked to use. Students were happy. I had a nice database full of numbers from which to quickly answer questions from managers.

Since moving into a role with IT this has changed. People at HQ are accustomed to working with software that fights you every step of the way. Want to record someone's attendance? You'd best have 3 minutes to spare, because what used to be a circle or an X on a piece of paper needs to be infinitely more complex in the name of "security". Want to know what textbook your student will be using after they finish their current book? Go ask one of the school's support staff, because the teaching software will not let you know that information without a fight. This is the state of corporate software in the world, and the previous solutions for the iPad and schools all came from this group of people. My software with it's opposite approach to the same problems is completely alien to the way they think about the job. This isn't a criticism or a disparagement. It's a fact. They're looking at problems as A⇢B⇢C⇢…⇢Z, and I'm looking at problems as A⇢F⇢Z.

It's no wonder there is a great deal more confusion at head office than at the schools. It's no wonder that when members of the various departments in Tokyo report "bugs" in my software, it's because they're not accustomed to software understanding a person's job and performing a bunch of steps transparently on their behalf. From a big picture point of view, I completely understand this. In the heat of the moment when I'm reading that email or new issue on GitHub that has nothing to do with an actual bug and everything to do with making the software harder to use, however …

Flip that Table!

I'm too close to the project. I've invested a great deal of time and effort into making something that is designed to be used by people who really couldn't care less what the corporate interests are. That's why I invested so much time into making the UI for the people who would actually use the software rather than the people making snap decisions months after the initial decisions had already been made. This is why I call people people instead of using the same language as other people in the corporate structure. The whole thing has been designed to serve the people at the bottom of the totem pole. HQ wants things changed to serve their interests3, and I am growing tired of pushing back.

There are, of course, a lot of people that I've worked with over the last year at HQ who do understand the goals of this project and have gone to bat on my behalf more times than I can count. A lot of very smart people with very sharp insights have helped take a rough idea hammered out in 4 days through to the state it's in today. Many of them are just as frustrated with the various emails, non-issues, and Friday 5:30pm deployment cancellation calls as I am. But there's not much that can be done to change this. The vision of the project is simply too foreign at the moment for people, and the sole developer is too angry all the time to cast it in a positive light. I really need to take a step back …

… and another step …

… and one more.

Because it really doesn't make much sense to continue dreading going into work. There is a lot of good about going in, too. I like a lot of my colleagues. I like the ridiculous amount of freedom I have within the organization. I like seeing people use my software without realizing they're doing more in 30 seconds today than they did in 5 minutes last year. It's a great feeling! I just need to stop being so attached to this specific project.


  1. This would be especially bad, given that I'm using my computers at the day job.

  2. these are the same people I work with now

  3. 15 months into the project, mind you …

I Need To Be Chris

Between 2002 and 2007, I worked at a medium-sized company in Canada that was best known for its calendars and other print materials. I started in the warehouse and, over the course of 3 years, moved into different roles that culminated in a position as a software developer and worked with a number of very smart people who taught me a lot about software development, and a lot about how to ask the right questions to find out what people want the software to do, rather than making the wrong assumptions and delivering something that isn't at all what they're looking for. The person I learned from the most, however, was a man named Chris1.

Chris had a rather wide range of knowledge on just about every technical subject, no matter how obscure the tools might have been. His knowledge on certain subjects would often run circles around others, even when it was their area of focus. And, while he most certainly did complain when he was called in to fix somebody else's problem, he tried to make education part of the solution. There really isn't any point being "the only person who knows X" in a company, because that doesn't benefit anybody in the long run2. The guy seemed to know everything he needed and then some, and was honest enough to say "I don't know" when he really didn't know right before investigating whatever needed to be learned so that he wouldn't answer the same question the same way later.

I learned a lot from him in the two years or so we worked together, and would be happy to work with him again if the opportunity arose.

The way Chris handled situations was often incredibly efficient, and it's something I really need to work on myself. The last few weeks at the day job have been incredibly stressful as I attempt to do four very different tasks simultaneously in order to deliver a project that should have started limited trials back in August. I've recently complained that I shouldn't be doing four very different tasks if bugs and enhancements are going to be resolved by arbitrary deadlines, but complaining about reality will rarely resolve the problems one faces.

I've been incredibly fortunate over the last two decades to have worked with a lot of very different technologies and worked in a lot of very different roles. This sort of make me a little like Chris, in that I can look at a problem from different angles, apply lots of experience to find a solution or — at the very least — know how to find a solution, and have the capacity to do it without necessarily asking for a great deal of help. What I need to learn is how to make common distractions from various groups into learning experiences rather than seeing them as work blockages. When people have questions about databases, I need to guide rather than brusquely answer. When people have questions about X over Y, or the alternatives to Z, I need to outline the gist and provide some basic links to sites with more in-depth answers. The people I work with are not fools. They genuinely want to do a good job and go home knowing they accomplished something, and this is the same goal I have at the end of every day. The question I have now, though, is how to do this without coming across as dismissive or as though I'm "mansplaining"3 something.

Having spent the better part of 8 years working in a classroom, you'd think this would be natural. That said, the teacher-student dynamic doesn't work with peers, nor do I want to have that dynamic with my colleagues. So how does one turn a work-stoppage into a learning opportunity while also meeting all of the arbitrary and constantly shifting deadlines that managers are all to happy to create?


  1. He had a last name, too, but I'll just use his first one here.

  2. Seriously. You don't want to be the person to receive a 3:00am phone call when things go bad … especially if it's with something that isn't technically your responsibility.

  3. I hate this pseudo-word like you wouldn't believe … but it seems to be part of the lexicon, now.