Thoughts on Work Tracking Software

One difficult problem to deal with as a career software engineer is that planning and tracking work, especially at a large scale, is pretty hard. Worse yet, it's important. When working with other people, agreeing on what to do and the plan to accomplish it is unavoidable, and lack of planning can lead to wasted time, effort, and hard feelings all around. Furthermore, there are countless religious¹ debates about the philosophical framework under which you should be working, which then shape your day to day practice.

In the software industry, naturally, many B2B SaaS products exist to help you organize your work and track what's being worked on. Unfortunately though, they all suck. This is to be expected, because work tracking software has to balance a lot of competing interests. Here are a few, in no particular order:

"I only want one piece of software to do my work in!"

Negotiating software sales contracts is annoying, and lawyers are expensive. Your boss wants "results damn it!" not a new tool. You already have a Microsoft 365 subscription (the analysts needed Excel, and we couldn't possibly make slides outside of PPT) so why spend more to get Slack when Microsoft Teams is free? And by the way, why can't I see my Google Calendar when I'm inside my Gmail inbox? Fuck it, let's add Google Meet directly into the Gmail app. I'm already in Gmail, why do I have to change apps to make a call? What do you mean it's confusing to start a video call from your email client on mobile? You want me to convince my boss' boss to pay for Zoom and Google Workspace? Are you out of your fucking mind?

Put another way: "a restaurant for everybody is a restaurant for nobody," to quote my coworker Luke. Attempting to make software cover all use cases means that it will never be good at any one of those use cases. But seemingly inevitably, large enterprises attempt to consolidate into as few pieces of software (or suites thereof) as possible to make procurement and staffing/hiring "easier." The cost of this consolidation, like a lack of market competition, is that the customer experience gets worse without individual recourse. Nobody stops to quantify the cost of having poor internal wiki software, but everybody freaks out at the idea of paying for a good one separately from your existing software suite. This naturally leads to...

Vendor Lock-In

Do I think that the Microsoft Teams developers set out to make a bad piece of software? No, of course not. But does Microsoft have any incentive to make Microsoft Teams good? Also no. Software developed to round out a wider portfolio, or to prevent competition, has no reason to exist except to smooth sales contract negotiations, or to convince your customers (or yourself, or your investors) that you aren't abandoning a vertical. Of course, you might still be abandoning a vertical, but you might have to pretend not to for regulatory or disclosure reasons. Again, Trello is a good example here: Atlassian makes their money on selling the Atlassian suite, not on any part of it being particularly good. Now that they own Trello, they can soft-abandon it and recover the cost of maintaining it, and over time convince your company to just use Jira instead. But maybe you're an idealist. You set out to make the best new work tracking software², to prove everyone wrong. Inevitably, you will encounter a new problem...

Making Money

Capitalism, no free lunch, etc.. It costs money to host software, it costs time (and thus money) to improve it, and generally people like to make a little extra on top for beer, car repairs, and gambling on crypto. Ultimately, any good software product which desires to become a profitable enterprise will be forced to contort itself to satisfy the demands of "the market" even if those demands actively detract from the original vision. Example: Google search. Search results are now halfway down the page, beneath sponsored links and AI content, in the interest of adding marginal revenue/getting some VP promoted. This process, where something good becomes bad to make more money, is known as enshittification. Trello's acquisition³ and subsequent "integration" to the "Atlassian Suite" is another example of this and the aforementioned vendor lock-in problem.

I Want It To Stop

Me too.

But I think that the root of all of these has to be the lack of respect for non-financial performance metrics in western business, which itself is a symptom of the overall financialization of culture.⁴ If businesses measured developer/PM happiness and job satisfaction, and really, truly adjusted their behavior based on the results, maybe better work tracking software would win on its own merits. Additionally, with more aggressive pro-competition legislation, it's possible that there would be significantly less of a market for "workspace" products that include shitty, half baked work tracking software as an offering. I think higher market competition would also reduce enshittification of work tracking software, as it would be easier to start and sustain competitors with narrow focuses or uses cases (and thus lower profit margins.)

Will we see that? Probably not in the next four years. But it's also possible that the overall consolidation of the enterprise SaaS market, and thus lack of good options, means there will be room for smaller startups to invent something better.

Footnotes:

1: Agile, Waterfall, The Hybrid Method, The Toyota Way, etc. etc.. These are all, practically speaking, religions. They help you frame the world and the decisions available to you, and different people believe different ones. Holy wars are often fought between true believers of one practice or another, and many are atheists and believe none of them. And of course, we won't know which one is right until after we're dead.

2: This will prove ironic later. Foreshadowing!

3: In the author's opinion, an anticompetitive move that flew under the radar.

4: Once I get some more life experience I'd love to write about this more. As of right now I don't know how complete my thoughts would be.