Documentation Debt is Destroying Your Team

"We decided to change the API spec last month. Do you remember why we made that decision?"

"Hmm... I think we discussed it on Slack, but I can't remember exactly."

"The person who led that discussion, A, has left the company... I don't think anyone knows."

It was an important technical decision, but it wasn't documented anywhere. The Slack messages disappeared due to the 90-day limit on the free plan, Figma comments are buried deep in files, and the key person who participated in the decision has already left the team. This is 'Documentation Debt.'

1. What is Documentation Debt?

Technical Debt vs Documentation Debt

Technical Debt is a well-known concept. When you compromise quality for speed, you pay the price later through refactoring or bug fixes.

Documentation Debt works the same way. When you skip recording for quick execution, you pay the price later through information gaps, repeated questions, and poor decisions.

The difference is that technical debt is visible in code, while documentation debt is invisible because it's the 'absence' of something. That makes it more dangerous.

Scattered "Verbal Communication" in Collaboration Tools

Documentation debt accumulates in places like:

• Slack messages: "Let's prioritize this feature this sprint" (disappears after 3 months due to message limit)
• Figma comments: "We decided to change this component style" (buried deep in files, nobody can find it)
• GitHub PR discussions: "The reason we implemented it this way is..." (nobody reads it after the PR is merged)
• Meetings: "Okay, let's go with option A!" (no meeting notes, nobody knows who chose option A or why)

Everyone 'discussed' but nobody 'documented.' Decisions were made, but context disappeared.

2. Why Documentation Debt Accumulates

The "I'll Do It Later" Psychology

The meeting is over. Several important decisions were made. The PM says:

"I'll organize today's meeting notes and upload them to Notion later."

But 'later' never comes. Right after the meeting, an urgent issue arises, there's another meeting to prepare for, and the quarter-end deadline approaches. Writing meeting notes keeps getting pushed down the priority list until it's forgotten by everyone.

Fast Execution vs Documentation Dilemma

The faster the team moves, especially in startups, the more documentation takes a backseat.

"Let's just build it first. Documentation can wait." "Instead of writing meeting notes, I'd rather write another line of code."

Documentation isn't an immediate deliverable, so it's always classified as 'something to do later.' But postponing documentation is borrowing from your future self and teammates.

The Hassle of Documentation

Honestly, writing documentation is tedious. A 10-minute discussion on Slack takes 20 minutes to transcribe to Notion.

"Everyone saw it on Slack, do we really need to write it in Notion too?"

But the assumption that 'everyone saw it' is the problem. What about people who weren't in that channel? Those who were on vacation? New hires joining next week? Your future self wondering 'why did we do it this way?' in 3 months?

3. Three Problems Created by Documentation Debt

1. Knowledge Loss and Context Disappearance

The most serious problem is the loss of context.

Looking at code from 3 months ago, you think: "Why was this written so complexly? This simpler way would work."

But there was a reason back then. It could have been due to a specific browser issue, performance concerns, or customer requirements.

Without documented context, you repeat the same trial and error, or worse, recreate previous problems.

2. Repeated Questions and Time Waste

In teams with accumulated documentation debt, the same questions repeat.

Questions you see weekly on Slack:

"How do I use this API?" "Why was this feature built this way?" "What's the deployment process?" "Is this the latest design file?"

Senior developers, designers, and PMs waste time answering the same questions repeatedly. If it were documented once, "Please refer to the documentation" would be enough.

3. Repeating Failed Decisions

People suggest methods that were tried and failed in the past.

"How about trying this library?" "Oh, we tried that last year but removed it due to performance issues."

Without documented decisions and reasons, the same experiments are repeated and fail for the same reasons. It's a waste of time, money, and opportunities.

4. Hidden Costs of Documentation Debt

Delayed Onboarding for New Hires

A new team member joins. You provide onboarding documents, but there's actually more that's not documented.

"Why is it done this way?" "Well, I'm not sure why... but that's how we've always done it."

"Doing something without knowing why" is the worst way to learn.

Without proper documentation, it takes months for new hires to work independently. Meanwhile, seniors are constantly bombarded with questions.

Increased Dependency on Key Personnel

Teams with severe documentation debt have lots of 'knowledge only that person knows.'

"Ask B about this. Only B would know." "C is on vacation, we'll have to wait until C comes back."

High dependency on key personnel means that person's vacation, sick leave, or resignation paralyzes the entire team. The bus factor is 1.

Knowledge Gaps When People Leave

The most critical moment is when key personnel leave the team.

All the knowledge in that person's head—decision contexts, lessons learned from trial and error—disappears. Undocumented knowledge is personal assets, not company assets.

Remaining team members must guess "why did they do it this way?" when looking at the departed person's code. Reverse engineering becomes routine.

Solution: Paying Off Documentation Debt

1. Make Documentation Part of the Work

Documentation shouldn't be 'extra work' but 'part of the work.'

Add documentation to Definition of Done: A feature isn't finished when code is merged, but when related documentation is also updated.

Mandatory meeting notes: Important meetings must have documented notes that all attendees review. Reserve the last 5 minutes of meetings for writing notes.

2. Reduce Documentation Burden with Automation

But honestly, manually documenting everything is difficult. That's why automation is necessary.

Automated solutions like Daigest:

• Automatically collect all discussions and changes from Slack, Figma, GitHub, and Notion
• AI identifies and summarizes important decisions, decision contexts, and technical discussions
• Delivered via email every morning, providing a quick overview of what happened in the past 24 hours
• Saved for future search, making it easy to find past context

Without setting aside separate time for documentation, the traces left while working are automatically organized.

Documentation debt accumulates quickly but is hard to pay off. However, with automation tools, you can slow the accumulation and prevent loss of important knowledge.