“Documentation” is a Dirty Word

I just skimmed through another 20 page planning document, written in old-school “requirements specification”-ese with a hefty dose of ambiguity. You know, things like “the Project Manager shall…” and “the technical team will respond to bugs.” Sigh.

There’s a lot of good content in there. It’s not easy to get at, though… for each page I want to understand, I can expect to spend between ten minutes and an hour deciphering what’s going on. (That’s half a week of work, and I have a lot of other work to do this week. Is it even worth it?)

Also, this document is boringand there’s a lot of filler (like “package X is useful, flexible, and open source” – OK, that’s great, and factually correct, but not very informative).

The whole document could have been condensed into 4 or 5 slides of diagrams plus annotations. If that had happened, I’d be looking at a 10 to 30 minute commitment overall to get my brain into this particular company’s context… and then I’d be able to make some useful contributions. (As it stands, I’m weighing whether it’s worth my time to go spelunking in that 20-pager at all. Probably not.)

Unfortunately:

  • The bulk of technical documentation that I’m forced to read is unintelligible or lacks sufficient meaning. I have three decades of exposure to this stuff, so if I can’t understand something that’s written… I feel super sorry for the early career people who might interpret the obfuscation as their own lack of understanding.
  • Nearly all of the technical documents I read are uninteresting. And tech is interesting!!

99 times out of 100, technical documentation is dull and dysfunctional. While it’s supposed to help people and teams quickly establish a shared understanding of a system or a process or a concept, it just ends up looking really impressive and convincing you that the authors know a lot more about this topic than you do. It doesn’t help you learn much, if at all, and certainly not quickly.

And as a CTO, CIO, or VP of Engineering, I don’t want to pay for crappy documentation. This particular document that triggered my current rant probably cost me between $32K-50K, and that’s just the tip of the iceberg… because it doesn’t account for the incremental costs of the future people who will attempt to decipher it – which could be 10-100x more over the lifetime of that document. Although the person or team that wrote the 20-pager probably knows what’s going on (at least a little bit), the artifact itself is going to cost other people time and take them away from more value-adding tasks.

Don’t write things that COST other people time. Write things that SAVE them time by helping them learn quickly.

The sheer volume of information we’re required to wade through to gain understanding – without the assurance that it will lead us in the right direction, or even in any direction at all – is probably what’s led to the disease of devaluing documentation

A lot of managers think documentation isn’t value-adding, and shouldn’t be done, because… in most cases, people do it so badly that it wasn’t worth the investment in the first place.

Dear tech workers: can we fix this, please? I know it will take a whole generation to effect meaningful change, but… I’m ready to roll up my sleeves.

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I’m Nicole

Since 2008, I’ve been sharing insights and expertise on Digital Transformation & Data Science for Performance Excellence here. As a CxO, I’ve helped orgs build empowered teams, robust programs, and elegant strategies bridging data, analytics, and artificial intelligence (AI)/machine learning (ML)… while building models in R and Python on the side. In 2025, I help leaders drive Quality-Driven Data & AI Strategies and navigate the complex market of data/AI vendors & professional services. Need help sifting through it all? Reach out to inquire – check out my new book that reveal the one thing EVERY organization has been neglecting – Data, Strategy, Culture & Power.

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