Ask Your Dev Team about their documentation

Here’s the minimum bar for documentation: at the end of any phase or milestone, another developer should be able to onboard and contribute on day one.

If that’s not possible, documentation is lacking. Period.

This ties directly to what we covered in issue 19 about contract endings. Documentation is the prerequisite for a clean handoff. Without it, you’re not just dependent on your current developer. You’re trapped.

What stakeholders should receive

You don’t need to understand every line of code. But you do need to know the basics of how your product works at a systems level. At minimum, your developer should provide:

• Where the code is stored. Which repository, which accounts, how to access it.
• Where it’s hosted. What cloud provider, what services, what the infrastructure looks like.
• How it’s deployed. The process for getting code from the repository to production. This should not live in someone’s head.
• A stack document. What languages, frameworks, databases, and third-party services your product depends on. This is vital. It’s the map of your product’s technical landscape.

Beyond the basics, entity-relationship diagrams and sequence diagrams are great additions. They help anyone, technical or not, understand how data flows through your system and how different components interact.

Living documents over perfect code comments

Some developers obsess over inline code comments. Comments have their place, especially for complex logic that isn’t self-explanatory. But a codebase full of comments and no high-level documentation is like a book with footnotes and no table of contents.

Prefer living artifacts. Documentation that’s maintained and updated regularly is worth more than a perfectly commented codebase that nobody reads. Frequently updated docs reflect the current state of the system. Stale docs are worse than no docs, because they mislead.

How good teams document

Some developers use source control itself as documentation. Pull requests describe what changed and why. Release notes capture what shipped. Commit history tells the story of how the codebase evolved. This is a valid approach, and it’s low overhead because it’s built into the development workflow.

At Cuttlesoft, we maintain a product requirements document in the project wiki alongside meeting notes and discovery artifacts. Diagrams live in the codebase itself, written in Mermaid and Markdown so they stay version-controlled and up to date. Every project includes runbooks and playbooks for common operations.

That’s our process. Your developer should have their own. The specifics matter less than the fact that they have one.

What to ask

1. “What does your documentation process look like?” A real answer involves specific artifacts and a cadence for updating them. A bad answer is “we comment our code.”
2. “Do you maintain runbooks or playbooks?” These are step-by-step guides for common tasks: deploying, rolling back, debugging, onboarding. They’re essential.
3. “If your team was unavailable tomorrow, could another developer get up and running from your documentation alone?” This is the test. If the answer is no, the documentation isn’t good enough.
4. “How do you keep documentation current?” Documentation that isn’t maintained decays fast. Ask how they prevent that.

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Expect better. Build better.