Stop Fighting the Losing Battle of Manual Documentation

Imagine a complex distributed system as a massive cruise ship. Every few weeks, an unexpected issue arises or a pressing new requirement surfaces—forcing you to update or fix the ship mid-journey, without steering it off course.

No matter how thorough your testing is, how meticulously you discuss potential changes, or how many experts are involved, unforeseen issues and ripple effects are inevitable. Here’s why:

1. No single person knows how everything works. Each team member has different pockets of knowledge and quirks they understand.
2. No one can track all the changes. The sheer volume of modifications across the ship is impossible to fully catalog manually.
3. Changes cascade unpredictably. Tweaking one part of the ship often creates unexpected side effects elsewhere.
4. There’s no shared, accurate source of truth. Without reliable documentation, understanding the ship’s current state becomes a matter of guesswork and siloed information.

Communicating and sharing knowledge about a complex system is a challenge in itself, and teams have tried countless approaches to document systems—often with varying degrees of frustration and limited success.

Unfortunately, documentation is rarely a priority and it lingers on the backlog. Developers have to grapple with outdated diagrams, fragmented knowledge, and scattered notes. This creates a systemic problem in the software community: developers spend more time reading code and deciphering their systems than building and innovating.

It’s time we ask the hard question: Are humans simply incapable of keeping up with system documentation? And, if so, how can we leverage technology to do what we cannot—accurately track and document complex systems at scale?

We’ve Tried Them All

The ideal scenario for any engineering team is a persistent, authoritative source of truth for the entire project. The specific format—diagrams, documents, or something else—is less important than ensuring it’s always up-to-date and can be confidently referenced during any discussion.

Unfortunately, despite the best intentions, teams have struggled to achieve this ideal. Here’s a look at the most common approaches and why they fall short in practice:

Manually Created (and Maintained) Docs

Architecture diagrams are often the first example that comes to mind. They’re an invaluable tool for visualizing and communicating complex ideas in a digestible format. Diagrams help engineers understand, collaborate on, and evolve systems.

But here’s the reality: manually created diagrams are time-consuming, prone to human error, and almost always out of date.

How many times have you stared at a whiteboard sketch with “Do not erase” scrawled across it, knowing full well it no longer reflects the system’s current state?

Whiteboarding tools, even digital ones, have their place—especially for brainstorming or outlining new features—but they are not purpose-built to act as a real-time, reliable source of truth for complex systems with dynamic components, dependencies, and integrations.

The same challenges plague all forms of technical documentation: from Architectural Decision Records (ADRs) to software design documents and API specs. Documentation is only as good as it is current—and maintaining it takes significant effort.

The Myth of Self-Documenting Code

Many teams fall into the trap of believing that “the code is the documentation,” as long as developers follow best practices like writing clean code, adding comments, and using descriptive variable names.

While those are excellent habits to cultivate, they only provide a partial view of what’s needed to understand a system fully.

• Code may describe what the system does, but it often fails to explain why certain decisions were made, the trade-offs considered, or how various components interact.
• Reading code is harder than writing it—just think back to the hours you’ve spent trying to decipher another developer’s logic or reasoning.

Self-documenting code also doesn’t cater to non-technical stakeholders, who rely on documentation to align with the engineering team on business priorities and goals. And when it comes to legacy systems, messy and disorganized code can make understanding the system feel like deciphering an ancient text.

In short, no matter how clean the codebase, it cannot replace the need for detailed, accessible, and up-to-date documentation that captures the context, decisions, and rationale behind the system design.

Embedding Documentation in the Development Process

A common suggestion is to embed documentation tasks directly into the development workflow: developers are expected to document their code and decisions as they go. On paper, this sounds like a great idea. In practice, it’s a lot more complicated:

• Time-Consuming and Unpredictable: Writing documentation is not a trivial task, and the time required depends on factors like code complexity, required detail, and the company’s documentation standards.
• Procrastination is Inevitable: When deadlines loom, documentation often gets pushed to the bottom of the priority list.

What about hiring a dedicated technical writer? Sure, that helps—until the writer has to chase developers for context about what changed, why it changed, and which parts of the system need updates.

What if we enforce documentation as a mandatory step in the development cycle? That might work in theory, but let’s be honest: tasks like “Write/Update documentation” are the first to land in the backlog and stay there indefinitely.

Even with fantastic tools to streamline documentation workflows, the root issue remains: someone still has to manually track and update the information. And with the pace of modern development, it’s nearly impossible to keep up.

Why it’s a Losing Battle

Manually documenting your software system is an uphill—and often unwinnable—battle. While cultural factors (such as a lack of emphasis on documentation) or individual habits (like procrastination) may contribute, the core issue is that constant change erodes traditional documentation.

Modern software systems are vast, interconnected, and complex. There’s no upper limit to how intricate they can become. Engineers often find themselves working on poorly understood systems, which only grow more convoluted as they evolve. This makes the task of maintaining accurate documentation not just challenging but fundamentally unsustainable.

Here’s why:

1. You can’t document everything at once.With large systems, you must prioritize what to document, leaving significant portions uncovered.
2. The system evolves faster than you can document it.Changes occur even as you document, creating a perpetual game of catch-up.
3. All documentation has an expiration date.Without constant updates, any document—no matter how thorough—will eventually grow stale.

Moreover, relying on individuals—whether software architects, technical writers, or developers—to maintain documentation introduces human error, inconsistencies, and gaps. Even with the best intentions, people are fallible, and the manual process is inherently flawed.

Compounding these challenges is the prevalence of poor practices:

• “Check-the-box” documentation: Documentation created to satisfy process requirements rather than to add real value often results in subpar quality.
• “Busy-work” documentation: Produced merely to appear productive, this kind of output rarely benefits the team or improves system understanding.

When systems grow exponentially in complexity and teams face mounting pressures to deliver, it’s no wonder traditional documentation methods fall short.

The Solution: Automation

As Kent Beck famously observed, “nobody wants to write documentation.”

Documentation exists to address a fundamental need: information. Whenever you’re working on anything even moderately complex, there are countless moving pieces that take time and effort to fully understand. Engineers need a clear view of their systems and the context required to make informed decisions.

But here’s the problem: documentation is a costly and brittle solution to this need. It demands significant time and effort to create and maintain, and it often doesn’t keep pace with the system itself. In many teams, maintaining accurate documentation feels like a luxury rather than a practical reality.

In his article, “The Documentation Tradeoff,” Kent proposes several strategies to address the challenges of documentation:

• Simplifying systems and reducing unnecessary complexity
• Socializing: pairing, whiteboarding, and storytelling
• Testing (beyond QA)
• Improving code quality

These are excellent practices, and we wholeheartedly endorse them. But there’s one critical piece missing: leveraging modern tools to auto-document and understand your system.

Current automation tools can create architecture snapshots or generate some documentation, but they often require significant maintenance and offer limited practical value for day-to-day development.

That’s where OpenTelemetry and LLMs come in. These technologies have the potential to fundamentally transform the documentation process. By automating much of the work, they free up teams to focus on what truly matters—building robust, efficient, and maintainable systems.

At Multiplayer, we embrace this philosophy. Our system auto-documentation feature is designed to reduce the burden of manual documentation, providing an up-to-date, accurate, and centralized view of your system architecture. And this is just the beginning of what automation can do to eliminate overhead and simplify system understanding.

The Impact on Engineering Teams

Documentation is an essential yet often undervalued part of software engineering. Unfortunately, the manual practices we’ve relied on for decades are fundamentally flawed: humans simply can’t keep up with the pace and effort required to document continuously evolving and expanding systems.

The solution is clear: automate system documentation. By doing so, teams can save time, improve accuracy, and ensure their documentation remains relevant and useful over time.

The benefits are transformative:

• Efficiently manage legacy systems, making sense of outdated or undocumented code.
• Debug complex distributed architectures with ease and precision.
• Preserve institutional knowledge even when team members leave.
• Collaborate on system designs with real-time visibility and shared understanding.

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With Multiplayer’s Auto-Documentation:

• Developers gain clarity and confidence, enabling better and faster decision-making.
• Teams collaborate seamlessly using a shared, always-accurate source of truth.
• Onboarding becomes effortless, empowering new hires to quickly understand the system without endless searching.

Take the first step toward painless documentation and experience the difference for yourself. Start your free 1-month trial today.