Chat with documents across your file library

Bring PDF, Excel, PowerPoint, Word and Markdown files into one source library. Ask a specific question, then inspect the passages behind the answer. Ask Your Docs is designed for marketing and sales work where a useful answer may depend on more than one document.

One campaign question, three different sources

A price list tells you an amount. A presentation records a plan and its status. A policy explains the approval rule. Asking only one of those files can produce a plausible answer that misses a condition from another source.

The fictional Harbor exercise puts those distinctions into three downloadable files. It contains no customer information, real supplier offer or actual spending. The source passages below are manually checked examples of the evidence an answer needs; they are not a recorded response from an external assistant.

What we verified on September 5, 2026: a new account signed in to the live private library, uploaded this CSV, Markdown policy and PowerPoint deck, and reached AI-ready status. Separate searches returned the original price, approval rule and finance-pending passages from their respective files. The same test also uploaded and retrieved checked passages from our Word, Excel and PDF examples. This verifies source retrieval; the combined answer below is an authored example, not a measured ChatGPT or Claude response.

Ask for the price and the decision evidence together

What is the listed paid-ads price for Harbor, and can the ads launch now? Use the price list, presentation and approval policy. Name the source for each part, preserve approval conditions, and distinguish planning amounts from actual spending.

Authored example answer: The listed planning price is USD 10,000 per campaign package. The sources do not establish that paid ads can launch now: the presentation says finance is pending, while the policy requires both marketing and finance approval.

Check three pieces of evidence: the Paid ads row in the CSV, the channel table on slide 2 and the Channel approval section of the policy. The example does not need to recalculate a workbook or interpret a chart. It needs the right statements from three files and the relationship between them.

Download the complete exercise, including a separate four-question evaluation sheet. Keep that answer sheet outside the uploaded collection so it cannot become the source of the answer.

Upload, organize, connect and ask with sources

1. Upload a file. Sign in to the private workspace and add the supported source files. Wait for their processing state before asking about them.
2. Organize the references. Use clear names and collections for the same task. Keep the active version identifiable and unrelated examples separate.
3. Connect your AI. Follow the relevant setup under Connect your AI. Confirm the intended account and any workspace prerequisites.
4. Ask with sources. Run the question and open the returned passages. Authorization or a successful setup screen alone does not prove the assistant consulted your library.

The built-in Ask workflow and an external assistant are separate routes. Built-in answers use your configured personal Anthropic key; an external assistant uses its own account and available tools. Review the document processing explanation before introducing private material, and check the setup requirements for the route you choose.

Keep format support separate from interpretation

Different files preserve different evidence. A spreadsheet may contain formulas and saved values; a slide deck may place important context in images or speaker notes. Upload support by itself does not establish calculation, OCR or full visual understanding.

• PDF: use readable text for passage retrieval. Image-only scans may need a separate OCR step. See the PDF guide.
• Excel and CSV: verify values and row relationships. Retrieval is not workbook recalculation. Use the spreadsheet exercise when arithmetic matters.
• PowerPoint: the private library’s text extraction does not establish full image or speaker-note interpretation. Inspect the original deck for those questions.
• Word: preserve the original when layout, revision history or document structure changes meaning. The Word guide includes an approval exception.
• Markdown: maintain explicit source versions and upload required linked files. A relative link alone does not cause the library to fetch another file.

Test exceptions, missing facts and changed sources

Try a follow-up about an attributed customer quotation. The Harbor policy adds written customer permission and legal approval. A response that repeats only the channel approvals has omitted a separate requirement.

Then ask what was actually spent or what cancellation fee applies. Neither fact is supplied. A planning price is not actual expenditure, and an absent fee cannot be recovered by guessing. Record whether the answer identifies the gap and whether its source genuinely supports that conclusion.

When a source changes, make its version explicit and repeat the question in a fresh conversation. Inspect the passage returned rather than assuming the update has propagated. The internal knowledge base guide provides a maintenance process; the three example libraries offer other bounded tasks to practice.

Choose the workflow that fits your work

A native assistant project may be enough if you work in one assistant and its source and sharing controls fit. A separate library is worth evaluating when the same maintained references need to support different assistant workflows. Compare the setup, updates and actual source answers rather than choosing from a feature label.

Start with this harmless example, then apply the same checks to a small authorized collection. Keep approval decisions with the people responsible for them. A sourced answer can explain what a policy requires; it does not itself approve a campaign or authorize a spend.

Frequently asked questions