Plain-English Answers to 'What's Our Policy On…'
Stop re-reading the handbook for the same questions. A Project that answers policy questions in plain language, cites the source, and flags when something needs a human.
The same five policy questions, asked a hundred times, should not require you a hundred times.
PTO, remote work, expenses, leave — people ask, and you re-find the answer in a handbook nobody reads. Ground a Project in your actual policy documents and it answers in plain language with the citation, so you're only pulled in for the genuine edge cases.
When the answer is hard to find, people stop asking and start guessing — and guessing about leave or expenses is how small problems become compliance ones.
A policy only works if the answer is easier to find than to guess.
This answers from your documents; it does not invent policy. When a question isn't covered, the right output is 'this needs HR,' not a confident guess. Not legal advice.
| Complexity | Easy |
| Tools needed | Claude Pro or above, Claude Desktop → Cowork mode, on macOS or Windows, Claude Projects |
| Time to build | ~20 min first time · ~1 min per question after that |
| Best for | Founder or HR lead fielding the company's policy questions — Small companies with a handbook nobody reads |
What this solves
The same handful of policy questions interrupting you week after week — each one answered by re-finding the same handbook paragraphs.
The problem
“How much PTO do I have rolling over?” “Can I expense this?” “What’s the policy on working from another state?” You get these constantly, and the answers are all in the handbook — a document people find too long to search, so they ask you instead. You re-find the same paragraphs again and again. Worse, when the handbook is hard to navigate, people stop asking and just guess, and a wrong guess about leave or an expense can turn into a real problem. The knowledge is written down. It’s just not accessible in the form people need: a quick, plain answer to a specific question.
The fix is grounding Claude in your actual policies so it answers the routine questions accurately, cites the source, and escalates the rest.
Ingredients
- Claude Subscriptions — Cowork and Projects aren't available on the free plan
- Platforms & Modes — Cowork runs in the desktop app only — not on web or mobile. This recipe reads your policy documents and answers from them — file-grounded work that runs in Cowork
- Claude Projects — Your policies are the same for everyone who asks. A Project holds your real handbook so every answer comes from your documents, with a citation — not from generic knowledge of how companies usually do things
How it works
The questions repeat and the policies are shared. A Project holds your real handbook and your escalation rules, so every answer is grounded in your documents and consistent no matter who asks.
- Open Claude Desktop and click Cowork in the mode selector across the top (Chat · Cowork · Code).
- In the left panel, find Projects and click the + button.
- Choose Start from scratch. Name the project “Policy Answers” or “HR Help” and let Claude set up its folder.
- You’ll know it worked when the project appears in the left panel with its own folder and an instructions field.
Your project has a folder on your computer — that’s where your policy documents and the rules file live.
- Ask Claude, right in the project: “Create a file in this project’s folder called
answer-rules.md. Leave it empty — I’ll fill it in.” (Or create it yourself in any text editor and save it into the project folder.) - Fill in
answer-rules.mdusing the description below. - Copy your real policy documents — the handbook, policy PDFs or docs — into the same folder.
- Confirm Claude can see everything: ask “List the files you can see in this project.” The handbook and
answer-rules.mdshould both come back. If they don’t, see If It Doesn’t Work.
answer-rules.md
How you want questions answered: plain language, always cite the section, and — most important — when to refuse and route to a human instead of guessing.
Example: “Answer only from the documents in this folder. Always cite the policy section. Use plain language, no legalese. If the documents don’t clearly cover a question — anything about a specific person’s situation, anything legal, anything involving accommodation or termination — do not guess. Say it needs HR and stop.”
The handbook itself is the knowledge source. The Knowledge File Seeding guide can help if your policies are scattered and need consolidating into clean documents first.
Open your Project in Claude Cowork. Give Claude the specifics for this run, ask for the main output, then follow up for any additional pieces you want. The exact wording for each prompt — with what it’s asking for and why — is in What you actually type below.
Check three things, especially while you’re establishing trust in it:
- Every answer cites a real section. An answer with no citation is one you can’t verify and shouldn’t trust. Confirm Claude points to the actual policy text — and that the cited text really says what the answer claims. This is your guard against a confident wrong answer.
- Edge cases get escalated, not guessed. Test it with a question your handbook doesn’t cover. The right response is “this isn’t addressed in our policies — check with HR,” not a plausible-sounding invention. If it guesses, tighten
answer-rules.mdto forbid it. - The language is genuinely plain. If the answer just quotes legalese back, it hasn’t helped. It should translate the policy into what it means for the person asking, while still citing the source.
Before you rely on it: policy answers can have legal weight, and this is not legal advice. Spot-check the answers against the source, keep the documents current, and route anything about a specific person’s situation — accommodation, leave, discipline — to a human every time.
What you actually type
Name your files explicitly the first few runs, and ask Claude to show its work on anything that matters.
“What's our policy on carrying over unused PTO at year end? Answer in plain language, cite the section, and tell me if any part of this isn't clearly covered.”
“Draft plain-English answers to our ten most common policy questions, each with its citation, that I can post to our internal wiki.”
A plain-language answer to the policy question, a citation to the specific section it came from, and a flag on any part the documents don't clearly cover. On a question the handbook doesn't address — or anything about a specific person's situation — the right output is a refusal that routes to HR, not a plausible guess. If an answer arrives without a citation, or quotes legalese back instead of translating it, it missed — don't pass it on.
- It's only as current as the documents in the folder. An outdated handbook produces confidently wrong answers — keeping the source current is on you.
- It doesn't handle individual situations. Accommodation, leave disputes, discipline — anything about a specific person goes to a human every time, however well the handbook covers the general rule.
- It's not legal advice. Policy answers can carry legal weight; spot-check against the source and keep counsel in the loop on anything consequential.
If it doesn’t work
- No Cowork tab in Claude Desktop — update the app to the latest version and confirm you’re on a paid plan; Cowork isn’t on the free tier. On Windows, Cowork also needs the Virtual Machine Platform feature enabled — if the tab still won’t appear, that’s the fix.
- Claude can’t see the handbook or
answer-rules.md— the documents aren’t in the project’s folder, or they’re in a different folder than the one the project owns. Open the project, check which folder it points to, and move the handbook and the rules file there. Then re-run “list the files you can see.” - Answers come back without citations — an uncited answer is one you can’t verify, which defeats the recipe. Ask: “Cite the policy section for that answer.” Then make “always cite the section” the first line of
answer-rules.mdand name the file in your prompt until the citations show up unprompted. - It guesses on questions the handbook doesn’t cover — test it deliberately with a question your documents don’t address. If you get a plausible invention instead of “this needs HR,” tighten
answer-rules.md— “if the documents don’t clearly cover it, do not guess; say it needs HR and stop” — and re-test until the refusal comes back. The refusal is the feature.
Extra credit
Small additions that pay back the next time you run it.
- Internal wiki — generate the cited plain-English answers once and publish them, so people self-serve before they even ask.
- Keep it current — when a policy changes, update the document in the folder; the answers update with it. An outdated source is the main failure mode.
- Shared, scoped access — if you put this in front of the team, keep sensitive HR docs out of the shared folder and limit it to general policy. See the Connectors guide on scoping access.
“Half of HR's interruptions are the same answer the handbook already gives — just somewhere nobody can find it.”
What this teaches you about Claude Cowork
The recipe is one application. The principles apply to everything you’d hand to Claude.
Grounding is what makes it safe. An ungrounded model will answer a policy question from how companies usually work — which is sometimes wrong for you. Pointing the Project at your real documents and forbidding outside answers is what turns a guess engine into a reliable lookup.
Citations make answers checkable. Requiring a source on every answer is the mechanism that lets you trust it — and lets the employee verify it. An answer you can’t trace is one you have to re-confirm anyway, which defeats the purpose.
Knowing when to refuse is a feature. The most important thing this recipe does is decline the questions it shouldn’t answer. A confident wrong answer about leave is worse than no answer. Storing the escalation rule is what keeps the routine handled and the sensitive in human hands.
Who this is for
Founder or HR lead fielding the company's policy questions in Small companies with a handbook nobody reads (15–150 employees).
The pain: The same five policy questions on repeat — and wrong guesses when people stop asking
The outcome: Routine questions answer themselves with citations; only genuine edge cases reach a human
Published June 24, 2026 · 0 views