Many in tech have started questioning whether documentation is still worth the effort. Teams spend countless hours on documentation, only to realise it becomes outdated far sooner than expected. Every new feature release, system enhancement, or process change creates another round of updates, making documentation feel like a moving target that’s difficult to maintain.
Yet despite these challenges, documentation remains a critical component of product development, user experience, and internal knowledge sharing. In this article, we’ll explore the most common challenges teams face, why documentation often falls apart, practical ways to address these issues, and, importantly, why documentation still matters today.
Across teams and industries, documentation challenges usually fall into three major categories: productivity, maintenance, and organization.
Documentation isn't just plain text. It often includes:
And producing all of this clearly, consistently, and for multiple audiences takes time.
One company we interviewed spends around three hours producing a single knowledge base article. That includes writing instructions, taking and editing screenshots, and creating accompanying video walkthroughs.
Technical documentation often takes even longer because it requires a deep understanding of the codebase, clarity on who the audience is, and the ability to explain why things exist the way they do.
Smaller companies face an even tougher challenge: they often don’t have the capacity to hire a dedicated technical writer or freelancers. This leaves existing teams to take on the extra workload, which means:
With the rise of AI, many hoped documentation would finally become easier. But relying on AI alone introduces three major gaps:
Maintenance is arguably the biggest challenge teams face, and the most commonly neglected.
Few things feel worse than spending hours crafting a high-quality document, only to watch it become outdated within weeks. Broken links, inaccurate screenshots, outdated instructions, and inconsistent style all contribute to a poor user experience and internal confusion.
Documentation is supposed to serve as a source of truth, but it can’t serve that purpose if no one maintains it.
The uncomfortable reality is this:
unless you have technical writers, documentation is often no one’s core job.
Feature development takes priority. New launches take priority. Strategic initiatives take priority. Documentation slips through the cracks, not because it doesn’t matter, but because no one is explicitly responsible for keeping it accurate.
This is the dilemma many companies face, and it leads to a vicious cycle:
outdated documentation → eroded trust → even fewer people rely on or maintain documentation.
Documentation chaos often stems from one issue: it’s scattered everywhere. It lives across Confluence, Notion, Google Docs, shared drives, Slack threads, and old PDFs sitting in someone’s desktop folder. When documents are split across multiple platforms:
It’s often impossible to see when a document was last edited, who changed it, or why.
Without organisation, documentation can't serve as a reliable foundation, no matter how good the content is.
While documentation challenges are significant, they aren’t unsolvable. Here are practical strategies teams can adopt.
Use tools that automate the repetitive work
For step-by-step tutorials, several tools can automate screenshot capture and walkthrough generation.
Use AI as an assistant, not a replacement
AI tools like ChatGPT can help with:
However, ensure your organisation approves connecting tools to your GitHub or codebase before using them for developer docs.
Set realistic expectations
Even with AI, video creation and high-fidelity tutorials still require manual effort. Quality takes time, and teams should plan accordingly.
Make documentation part of the product release lifecycle, not an afterthought.
That includes:
Remember: documentation is often the first point of contact for prospective customers evaluating your product. Outdated or inaccurate documentation can damage credibility quickly.
Consolidate platforms
Ideally, store all documentation on one platform, or at least in one ecosystem, to reduce fragmentation.
Separate internal and external docs
Maintain two clear portals:
This prevents accidental exposure and ensures content is written for the right audience.
Define ownership and access control
Each document should have:
Using tools like Slack, Jira, or equivalent systems can help track doc updates alongside product changes.
Yes, documentation still matters. In fact, it matters more than ever.
Across product, engineering, and technical writing communities, a consistent theme emerges: teams struggle with documentation not because it lacks value, but because the process surrounding it is often broken. Documentation becomes outdated when no one owns it. It becomes irrelevant when it's not integrated into the development lifecycle. It becomes invisible when it's scattered across platforms.
But when done well, documentation:
Documentation isn't disappearing, it's evolving. And teams that invest in better processes, thoughtful ownership, and the right tools will find that documentation is not only worth the effort, but a competitive advantage.
Wikidoc is an AI-powered documentation platform that helps businesses easily capture, share, and preserve organisational knowledge.
