Context

Systems evolve faster than shared understanding, and without a way to preserve intent, teams end up rediscovering old decisions the hard way. This framework offers a durable model, supported by documentation patterns and LLM agents to keep essential knowledge accessible as your system grows.

The Problem

Engineering teams accumulate knowledge the way legacy systems accumulate complexity: gradually, invisibly, and without a deliberate structure. Much of this knowledge resides in the heads of a few experienced engineers who remember why a timeout was set to a particular value or why a seemingly harmless refactor once took down an entire region. When those people step out of the room whether for a weekend or for good, the organization loses not just memories, but operational stability.

I’ve seen this pattern repeat across wildly different scales. At ShareChat, a fast-growing startup serving 300 million users, tribal knowledge emerged organically as teams scaled faster than documentation could keep up. At Airbnb, a mature organization with established processes and robust documentation practices, it still existed. The difference wasn’t whether tribal knowledge existed, but how it manifested. Company size matters. Engineering culture matters. Investment in tooling matters. But none of them eliminate the problem entirely.

Tribal knowledge rarely manifests as missing documentation alone; it distorts the system’s behavior in subtle ways. When the "why" behind a design decision is not captured, engineers are forced to reconstruct intent from code that reflects only what the system does, not why it behaves that way. As systems mature, these gaps compound: architectural trade-offs, incident learnings, and historical limitations accumulate faster than shared understanding.

A simple example illustrates the point:

# What the code says:
client = ServiceClient(
timeout=1000  # 1 second timeout
)

At face value, this appears to be an arbitrary constant. But often the real story looks more like this:

# What the code doesn't say:
# WARNING: Do not reduce this timeout!
# In Q3 2022, we tried 800ms and it caused cascading failures
# across region-b when the payment service was under load.
# See incident report: INC-2847
client = ServiceClient(
timeout=1000  # 1 second timeout
)

The second is the tribal knowledge that exists only in the head of the engineer who debugged that incident at 3 AM.

In this write-up, I explore a model for treating knowledge as part of the system architecture. The approach combines decision records, living documentation, explicit technical principles, and a searchable repository: all augmented by LLMs that help maintain coherence as systems change. The goal is not to eliminate tribal knowledge entirely, but to constrain its blast radius so teams can move faster without depending on who remembers the last incident.

Documentation Entropy

Documentation rarely breaks in a single moment. Instead, it drifts quietly and predictably as the system evolves. This drift is documentation entropy: the natural tendency for written knowledge to become inaccurate or incomplete unless continuously aligned with the system it describes.

Several forces accelerate entropy:

• Rate of Change: Dozens of code changes may occur before anyone revisits a document. The narratives fall behind the system’s reality.
• Local Knowledge: Engineers understand the part they touched, but not always how it interacts with the wider system. Documentation lacks these global updates.
• Incentive Misalignment: Shipping code has immediate value; updating documentation pays off slowly and invisibly.
• Fragmented Knowledge Sources: Decision logs, Slack threads, PR discussions, incident reports, and individual memory all evolve independently unless deliberately synchronized.

These forces manifest across different types of documentation each drifting in its own characteristic way:

Category	Examples	Typical State
Decision Docs	ADRs, Design docs, Post-mortems	Written once, rarely updated if decisions changes mid-way
Code-Level	Docstrings, PR Comments, README, PR descriptions	Hit or miss
Living Docs	Wikis, API docs	Stale after few months
Executable	Tests (unit, integration)	Best maintained
Informal	Code walkthroughs videos, Slack threads, Peoples’ heads	Never organized

The pattern is consistent: the further a document is from the code and the less feedback it receives, the faster it decays. Entropy accumulates until the team no longer trusts the documentation, at which point it stops being a tool and becomes background noise.

Controlling entropy starts by recognizing it as an expected property of evolving systems, not a failure of engineering discipline. The goal is not eliminating drift but designing workflows that reduce its slope.

The natural question, then, is not how do we write more documentation, but how do we create mechanisms that continuously capture, structure, and update the knowledge a system depends on?

This leads us to a set of practical frameworks lightweight enough for real teams, yet durable enough to survive system evolution that help constrain tribal knowledge and reduce the blast radius of entropy.

Frameworks for Capturing Tribal Knowledge

Preventing tribal knowledge outright is unrealistic; systems evolve faster than teams can document them. The practical goal is to create lightweight mechanisms that continuously capture the intent behind decisions and make that knowledge discoverable long after the original authors have moved on. The following frameworks are not silver bullets, but together they establish a structure that reduces drift and preserves institutional memory.

1. Engineering Decision Records (EDRs)

Most organizations already use some form of decision artifact: ADRs, RFCs, architecture proposals, design notes. Here, EDR serves as an umbrella term: any artifact that records a decision with long-term architectural or operational consequence.

EDRs counter one of the primary forces of entropy: loss of intent. They capture the reasoning behind decisions, the alternatives considered, and the expected consequences. Useful EDRs are concise, linked to the code or component they influence, and updated when the decision materially changes.

Appropriate scope includes:

• Architecture or protocol changes
• Production incidents and the decisions that followed
• Cross-team integrations
• Deprecations and migrations
• Feature decisions that create durable constraints

2. Living Documentation

If EDRs explain why a system is the way it is, living documentation explains what it currently is. It evolves automatically with the system-schemas generated from code, diagrams produced from architecture scans, API references produced from interface definitions.

Living documentation reduces code–narrative drift, the most predictable source of documentation entropy. It works especially well for fast-changing surfaces such as APIs, internal service boundaries, and platform contracts.

The core idea is simple: where accuracy matters and drift is expensive, let machines generate the documentation.

Adoption patterns include:

Auto‑generated API references

Example Tool: Swagger[3]

What it does: Generates API documentation directly from machine‑readable specifications, keeping endpoints, schemas, and error definitions in sync automatically. Ideal for precision‑critical surfaces; it ensures correctness but doesn’t capture design intent.

Self-updating wikis

Example Tool: DeepWiki[4]

What it does: Links documentation pages to code artifacts (modules, files, classes). Automation keeps links valid; engineers add the narrative. Great for onboarding and architectural insight. Code-linked wikis align closely with the codebase, but they overlap with EDRs and tend to provide only partial context; they surface structure, not the full narrative behind architectural decisions

Self‑Updating Integration guides

Example Tool: Mintlify[1]

What it does: Monitors code changes, surfaces documentation‑impacting updates, and drafts revisions. Engineers review and merge the docs in the same PR that changes the code, keeping explanatory guides aligned with implementation.

Adoption

Anthropic auto-publishes brand-aligned, scalable documentation without adding engineering overhead: the system lets engineers and collaborators update docs alongside code changes, significantly reducing friction for content updates.

3. Constitution (Technical Standards)

A constitution defines the non-negotiable engineering principles for a system such as naming rules, layering constraints, approved libraries, testing expectations, compliance requirements, and so on.

Constitutions limit unnecessary variation, which in turn reduces entropy. When engineers operate within a predictable set of constraints, decisions become easier to document, align, and automate.

A good constitution:

• Is short enough to be memorable
• Is specific enough to constrain behavior
• Is updated deliberately rather than casually
• Reflects real architectural intent, not aspirational ideals

Overly prescriptive constitutions become bureaucracy; overly vague ones provide no guardrails. The strength lies in striking a stable, enforceable middle ground.

A Parallel Approach

Microsoft’s Spec Kit[2] reflects the same principle: well-defined engineering guardrails reduce variation, making architectural intent easier to preserve as systems scale.

4. Decision Repository (Tribal Knowledge Hub)

A repository provides coherence. It is the single place where EDRs, constitutions, and key design references live. Without a central store, tribal knowledge simply migrates from heads into scattered artifacts.

The repository should be:

• Lightweight enough that teams consistently use it
• Structured enough to support search and linking
• Stable enough to integrate with future LLM agents

Avoid placing this exclusively in Git. While Git excels at versioning, it performs poorly as a day-to-day knowledge tool: editing friction is high, search is limited, and contributions depend on PR workflows that slow updates.

Centralization is not about control; it is about creating a coherent memory layer that the organization and AI systems can reason over.

Automating Tribal Knowledge: LLMs as Your Documentation Co-pilot

Once the foundational structures are in place: EDRs, living documentation, a constitution, and a decision repository, after this, the natural next step is automation. LLM agents can operate as continuous observers across the codebase and communication channels, reducing the manual effort of maintaining explanations, rationales, and architectural intent.

Below are five automation flows that reflect how real engineering teams can integrate LLMs into their knowledge ecosystem.

1. Drift Detection Flow

Goal: Detect when the system and its documentation diverge.

Trigger: A pull request modifies APIs, schemas, configuration, or system boundaries.

LLM Actions:

• Analyze the diff and detect changes that carry semantic meaning (e.g., new field, removed endpoint, tightened constraint).

• Compare the change against feature specific EDR & constitution rules.

• Surface mismatches such as:

• EDR contradicts new behavior

• Code violates a constitutional rule

Outcome: Engineers receive a notification indicating what needs to be updated and why, similar to how Mintlify flags doc-impacting PRs.

Why this matters: It shortens the feedback loop: entropy is corrected before it compounds.

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2. EDR Synthesis Flow

Goal: Capture intent at the moment decisions are made.

Trigger: A design discussion in Slack, a long PR comment thread, or an architectural meeting.

LLM Actions:

• Monitor relevant channels (within configured boundaries).

• Identify discussions that contain decision-making intent.

• Draft a structured EDR containing:

• context

• decision

• alternatives considered

• consequences

• Link the draft to related code artifacts and existing decisions.

• Submit the EDR as a review item for human refinement.

Outcome: Decision records are captured as they happen, not retroactively when memory has already faded.

Why this matters: It preserves the why, not just the what.

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3. Living Documentation Update Flow

Goal: Keep explanatory documentation aligned with code changes.

Trigger: A build, deployment, or merge event.

LLM Actions:

• Understand the code change in context (diff + historical patterns).

• Identify which documentation surfaces are affected:

• integration guides

• onboarding pages

• conceptual overviews

• Generate draft updates or callouts, preserving the doc’s tone, structure, and intent.

• Create a documentation PR with suggested updates.

Outcome: Narrative documentation evolves with the system: no stale examples, no forgotten instructions.

Why this matters: It bridges the gap between generated accuracy (Swagger) and human-authored intent.

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4. Knowledge Retrieval & Cross-Linking Flow

Goal: Make the repository searchable not by keywords but by meaning.

Trigger: A developer asks, "Why is this timeout set to 1 second?"

LLM Actions:

• Parse the query semantically.
• Search across EDRs, constitution, living docs, codebase, and documentation.
• Assemble an answer that references authoritative sources.
• Suggest related documents or decisions that should be linked for better future retrieval.

Outcome: Knowledge becomes discoverable, not just stored.

Why this matters: LLMs turn the repository into a living knowledge graph, not a static library.

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The Honest Truth

Even with disciplined practices and well-designed systems, some tribal knowledge will still slip through the cracks. Not every insight becomes an EDR, not every conversation contains enough signal to justify capture, and not every architectural nuance can be inferred from code or surfaced by an LLM agent. Real organizations operate under deadlines, shifting priorities, and the unavoidable asymmetry between how quickly systems evolve and how slowly shared understanding catches up.

The goal is not perfect preservation; it is controlled loss. If a team can reliably capture 70–80% of meaningful intent: decisions, constraints, lessons from incidents, integration patterns that is usually enough to prevent rediscovery, reduce operational fragility, and keep the architecture coherent as it evolves.

References

1. Mintlify: Modern documentation platform that keeps docs in sync with code
2. Spec Kit (Microsoft): AI-powered specification management with constitution-based guardrails
3. Swagger: Auto-generated API references
4. DeepWiki: Quickly grok and understand complex code.