Right when a deal is gaining speed, a security questionnaire turns up, and nothing moves until it is done. Most of what it asks we have answered many times: how we encrypt, who can access what, how we handle data, which policies we follow. The catch is the packaging. One buyer sends a SIG, the next a CAIQ, another a spreadsheet of their own design, and each must be filled in using its own layout.

So we let an agent on Machine write the first draft, using only our vetted knowledge base. Below is how we handle our own security questionnaires, along with what it connects to and the limits we set.

The problem

We already hold most of the answers. Encryption at rest, SSO, incident response, data retention: the same topics appear on almost every questionnaire, and we have approved wording for each. But no two questionnaires share a format. Someone has to go through every question, find the approved answer that fits, and paste it into the vendor's chosen layout, whether that is a SIG workbook, a CAIQ or a homemade spreadsheet.

The usual fixes only go part of the way. A shared answer library still needs a person to match each question to it by hand. Recycling the last deal's answers can sneak in one that no longer applies. A general-purpose AI writer with nothing to anchor it will happily produce confident answers that are not our approved ones, and on a security document that is exactly the thing you cannot allow.

What we built

On Machine, every questionnaire that arrives sets off an agent. It gets its own session, a fresh cloud computer (a sandbox) for that questionnaire alone, with access to our knowledge base of approved answers and policy documents. The agent splits the document into questions and matches each one to our approved answers and policies. It writes the responses in the vendor's own format, whether SIG, CAIQ or a custom spreadsheet, and marks for a person anything it cannot answer with confidence. What comes back is a completed draft that security reviews before it is returned.

How it works

The pattern

Each incoming questionnaire is a trigger that opens a session with narrow connectors to the document and our knowledge base. Approved answers and policies live in its skills and memory. The agent drafts and flags, and security signs off before anything leaves.

Guardrails

What this agent writes is a security document built from our own approved answers, so its reach is narrow and its output stays contained:

• Isolation. Each questionnaire gets its own sandbox, used for that one task. The session reads the incoming document and the knowledge base it was given, and the filled draft is the only thing it sends out.
• Scoped secrets. Keys for the questionnaire source and the knowledge base are stored encrypted in the Secrets Manager and only handed to the agents you grant them to.
• Human approval gate. Security checks every completed draft before it goes back to the prospect, and any uncertain question waits for a person rather than getting a guess.
• Everything is code. The agent's setup, skills and permissions are files in the repo. They carry version history, and changes go through a reviewed change request instead of a dashboard toggle.

The outcome

Questionnaires now come back as completed drafts in whatever format the buyer used, each answer pulled from our approved knowledge base and the uncertain ones flagged. Security spends its time on review and on the tricky questions instead of hunting and pasting, and no prospect receives anything until a person has signed it off.