Why Most Technical Documentation Gets the Difficulty Curve Backwards

There’s a pattern I’ve noticed in technical documentation across the industry, from scrappy startups to global technology companies. It shows up so consistently that I’ve come to think of it as the default failure mode of technical writing: the difficulty curve is backward.

Here’s what I mean. Open almost any software documentation, and you’ll find exhaustive coverage of the easy parts. For example:

• Installation instructions that hold your hand through every click.
• Configuration sections that explain every option, including those nobody ever changes.
• Getting-started guides that spend three pages on prerequisites before the user has seen a single interesting thing your product can do.

Then your customers hit the hard parts:

• The main concept, which requires genuine understanding to use correctly.
• The edge case that will bite you in production if you don’t know about it.
• The architectural decision that shapes everything downstream.

Unfortunately, in many cases, the same documentation that just spent 2,000 words telling you how to click through an installation wizard gives you two paragraphs and a link to a GitHub issue from 2015.

This issue isn’t the result of laziness. It’s a failure of perspective, and it’s almost understandable once you see where it comes from.

Why it happens

Technical writers—and engineers writing their own docs, which is a whole separate problem (yes, I’m a real person who just happens to love em-dashes)—tend to write from the inside out. They know the product intimately. Installation is trivial to them. Configuration is obvious. So when they sit down to document it, they document what they see, not what the user experiences.

The hard parts feel hard to document precisely because they’re hard to explain. So writers spend time on the parts that flow easily, and skim the parts that require the most careful thought. The result is documentation that’s thorough where thoroughness doesn’t matter, and thin where it matters most.

I’ve seen this produce some genuinely painful outcomes. I once worked with an engineering team at a Single Sign-On company whose documentation included a meticulous installation guide, complete with screenshots, for an installation wizard that never failed. The same documentation had a single paragraph describing how to configure FIDO2. This paragraph ended up being the source of most of the team’s support tickets. Nobody within the company had connected those two facts. When I pointed it out, the response was immediate recognition. Of course! It was obvious in retrospect. It always is.

What the difficulty curve should look like

Good documentation is proportional not to how much there is to say about a topic, but to how much users need help with it. That requires the writer to think like a user who doesn’t yet understand the product, which is harder than it sounds when you’ve been living inside it for months.

To mitigate and hopefully eliminate this issue, here are some questions I ask before writing any section of documentation:

• What is the conceptual prerequisite for this feature?
• What are the consequences of getting this wrong?
• What will the user try first, and why won’t it work?
• Where do users get stuck?
  • What support tickets exist regarding this section of the product?
  • Are there any online forum posts demonstrating user frustration on this topic?
  • Are there any related issues in your GitLab repository?

The question “What is the conceptual prerequisite for this feature?” helps me focus on the feature’s foundational concepts. Every product contains features that are hard to use correctly, not because the mechanics are complex, but because the underlying concept requires genuine understanding first. Skipping the concept and jumping to the mechanics is a hand-holding recipe for customers who can follow the steps but don’t know what they’re doing. However, without adequate documentation, your customers will fail the moment anything deviates from the happy path.

The question “What are the consequences of getting this wrong?” helps me focus on the risks customers face should they make a mistake. The higher the stakes of a mistake, the more attention the documentation deserves. This seems obvious, but documentation rarely reflects it. Configuration options that will silently corrupt data in edge cases deserve more than a one-line description. Authentication flows that have security implications deserve more than a pointer to an example repository.

The question, “What will the user try first, and why won’t it work?” helps me focus on documenting recovery paths for the customer. The most useful thing documentation can do is anticipate failure. Not just describe the correct path, but acknowledge the wrong turns; the things that seem like they should work but don’t, and why.

The question “Where do users get stuck?” and its child questions are a goldmine for technical writers. If the same question appears repeatedly, that’s where the documentation has failed. That’s where the words should go.

The invisible cost

The consequences of backward documentation are real and measurable, even if companies rarely measure them directly.

Support volume is the most obvious impact. Every question your support team answers is a question your documentation failed to answer first. When I’ve helped teams audit their support queues against their documentation, the correlation is almost always the same: the most common support questions correspond to the thinnest sections of the docs.

Developer adoption is subtler but equally significant. Developers talk to each other. A platform with documentation that wastes their time gets a reputation for having documentation that wastes their time, and that reputation travels faster than any marketing campaign. Conversely, documentation that respects a developer’s intelligence and actually helps them succeed becomes a genuine competitive advantage. It becomes the thing developers mention when they recommend your platform to their colleagues.

There’s also a trust dimension that’s harder to quantify but very real. Documentation that fails users on the hard parts that actually matter signals something about how much a company respects its users. Users notice, even if they can’t always articulate what they’re noticing.

Getting it right

The solution isn’t complicated, but it requires a discipline that’s harder than it looks: write for the reader’s experience, not your own knowledge. This is close to what the Diátaxis framework calls separating reference from explanation.

Getting it right means starting with where users struggle, not where the product starts. It means spending more words on complex concepts than on simple procedures. It means treating the difficult parts of your product as opportunities for documentation rather than burdens.

Success also means being willing to say hard things clearly. Acknowledging that a concept is genuinely complex, that an edge case exists and matters, that the obvious approach won’t work, and here’s why. Users don’t need documentation that pretends everything is simple. They need documentation that helps them succeed with what isn’t.

That’s the standard I hold every document we produce at Inkwright, Inc. to. It’s not always comfortable, because clients sometimes push back on the time it takes to get the difficult sections right. But it’s the only standard that produces documentation worth having.

If your documentation is generating more support tickets than it resolves, or your developers are struggling with integrations that should be straightforward, the difficulty curve might be worth a look. It usually is.

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Inkwright, Inc. provides technical writing and ghostwriting services for technology companies. Get in touch.