Writing

On documentation that writes itself — and on the organizations that need it most.

• Engineering and security leaders

  AI documentation tools: what to check before you give one your repo

  Seven questions to ask any vendor that wants read access to your codebase, and what the honest answers sound like.

• Architects and engineering leaders

  As-built documentation, for software

  Construction has a word for documentation of what was actually built rather than what was designed. Software needs it more and has no word for it.

• Anyone whose documentation is out of date

  Automated documentation: what it actually means

  Automated documentation generates docs from artifacts you already have rather than asking people to write them. What it covers, where it works, and where it does not.

• Platform and engineering leaders

  Event-driven documentation: docs that rewrite themselves on merge

  Documentation regenerated by the change that invalidated it. What event-driven documentation means, how to wire it, and why nightly jobs are not enough.

• Engineering teams shipping with AI

  How to keep on top of AI slop

  AI agents generate code faster than any team can document it. Here is how to keep documentation current when the codebase changes every day.

• Private equity, corp dev and QofE providers

  Operational due diligence when the target has no documentation

  You have three weeks and the target's processes exist in people's heads. How to produce defensible process documentation inside a diligence timeline.

• Services and shared services teams

  Process documentation when your process lives in Excel

  The spreadsheet is the process. Here is how to document a workflow that exists as a workbook, a macro and three people who know not to touch column R.

• Technical diligence teams and acquirers

  Technical due diligence when the architecture diagram is 18 months old

  The diagram in the data room describes a system that no longer exists. How to get a true picture of a target's architecture without a six-week engagement.

• Services businesses and shared services

  Tribal knowledge is a single point of failure

  When one person is the only one who knows how a process runs, that is not seniority — it is concentration risk. How to get it out of their head without a six-month project.

• Operations and compliance teams

  How to write an SOP from a meeting recording

  A recording of people doing the work is better raw material than a blank SOP template. How to turn one into a procedure somebody can actually follow.