Why You Hate Your “Productivity” Software

Tell me if this story sounds familiar. At your company, there is The Tool. Everyone is required to use The Tool. It is the central information hub for the entire company. Or at least it was supposed to be. In practice, it is where information goes to die.

The Tool can come in many guises: a wiki, document repository, database, or one of the legions of “project management” products. Whatever its form, it has a reputation for being slow, complicated, and difficult to navigate. No one likes it, so everyone avoids it. The easiest thing in The Tool is adding a new comment / task / card / document, so that’s what people do. The Tool becomes effectively write-only: post a comment on a document, toss a new card in the backlog. The Tool gets messier and harder to navigate. The real work of the organization splinters into ad-hoc communication channels such as email, chat, and meetings.

Eventually, complaints about The Tool reach a fever pitch. Surely anything would be better than the current mess. Approval is granted to seek out a New Tool. A months-long process ensues, with everyone campaigning for their favorite. Eventually, a choice is made. No one is fully satisfied, but everyone is thrilled to be rid of the Old Tool. The New Tool is so much faster, cleaner, and better organized.

Within a few months to a few years, the New Tool — by now just The Tool again — has developed a reputation for being slow, complicated, and difficult to navigate. The rumblings begin again.


— John Gall, Systemantics, found via @SysQuotes

Ever since computers were invented, a fundamental misperception has been repeated so often it has acquired the veneer of Truth: “Computers are good at organizing information.” Therefore, if you need to organize information, you need a computer.

In fact, computers are terrible at organizing information. Computers are good at storing data. When that data is structured and highly regular, computers are good at processing it. Humans, on the other hand, produce highly irregular, unstructured data, e.g., cards, stories, comments, documents.

Computers make things worse by offering virtually unlimited storage space for irregularity. A computer is like an infinite supply of post-it notes or a whiteboard that never has to be erased. In a multi-user system, there’s even a social incentive against erasing: That card/story/document represent’s someone else’s effort. You don’t want to destroy their work, do you? Better leave it, just in case it contained some vital insight.

So you have a system in which the natural behaviors are always create new things and never delete anything. But organization requires curation, which requires leaving things out. Few employees in a modern office are trained in the science of curating information. That responsibility has been outsourced to computers. And computers make a terrible job of it.

To err is human, to really foul things up requires a computer.

Bill Vaughan, probably

I often wonder if the best approach might be to eschew computers altogether and stick with physical media. After all, post-it notes and whiteboards remain popular despite the plethora of software products vying to replace them. Having worked remotely for most of my career, I often have no choice but to use software to communicate, but I always think of it as an inferior substitute for paper.

I think the attraction of software-based tools speaks to our discomfort with ambiguity. A table of tasks and dates, all neatly sorted and color-coded, gives the appearance of structure and organization, even if it has no bearing on reality. It may be a lie, but it’s a comforting lie. No one wants to admit that we don’t know how to keep track of our own work. Software lures us with the promise of a solution that doesn’t require any extra effort. When we fail, it provides a convenient scapegoat.