Skip to content

Business knowledge preparation guide · By Yes AI

ChatGPT with your files or a built knowledge search?

Published 5 min read

Many teams start by uploading a handbook to ChatGPT and asking it questions. That works for one person with a few files, and it breaks down when the documents change or many people need the same answers. This guide compares the main ways to use ChatGPT with company documents against a purpose-built knowledge search.

Quick answer

Uploading files to a ChatGPT project suits one person or a small team working with a few stable documents. A ChatGPT Business or Enterprise workspace with the SharePoint or Google Drive app connected reads files in place and follows existing permissions. A built knowledge search suits a defined document set that many staff rely on, where you need measured accuracy, refusal rules and control over updates.

Office coordinator uploading a staff handbook file from a laptop at a Perth office desk, printed handbook beside the keyboard
Uploaded files are copies, so someone has to replace them when the original changes.

What happens when you upload files to ChatGPT?

Uploaded files become copies attached to a conversation, project or custom GPT. OpenAI's help centre lists the limits: documents up to 512 MB per file, text capped at 2 million tokens per file, up to 40 files per project on Business and Enterprise plans, and up to 20 files as knowledge for a GPT. When the original policy changes, the uploaded copy stays as it was. Someone has to remember to replace it in every project and GPT that holds it, or staff keep getting answers from the old version.

How do the SharePoint and Google Drive apps differ?

Connected apps read files where they live instead of copying them in. OpenAI states that the SharePoint app only retrieves content the user's Microsoft account can already access, with SharePoint, OneDrive and Microsoft 365 group permissions still applying. Its SharePoint search supports .txt, .pdf, .docx, .pptx, .xlsx and .csv files up to 100 MiB each. Your Microsoft administrator may need to grant consent, and the ChatGPT workspace administrator decides which actions, such as creating folders or updating files, are allowed. Answers draw on whatever the user can open, whether or not it is the current version.

Is our data used to train OpenAI's models?

OpenAI says it does not train its models on business data from ChatGPT Business, Enterprise, Edu and the API platform by default. For Enterprise and Edu workspaces, administrators control how long data is retained, and OpenAI says deleted conversations are removed from its systems within 30 days unless it is legally required to keep them. Free and personal accounts are a different case. The OAIC recommends, as best practice, that organisations do not enter personal information, particularly sensitive information, into publicly available generative AI tools.

Where does a built knowledge search fit?

A built system indexes an approved document set, such as the current procedure library, and answers only from it. Because it is a shared service, the business can test it against real staff questions, set a threshold below which it says the documents do not cover the question, and require a citation for every answer. Updates flow from the source on a schedule, and documents marked as superseded can be filtered out. The trade-off is a build and an internal owner, which a ChatGPT workspace does not need.

What goes wrong with the do-it-yourself route?

Problems with this route tend to be organisational. Different staff upload different versions of the same document to their own projects. A departing employee's projects hold the only copy of a useful set of files. Nobody can say which answers came from which version. Personal accounts get used for work files because they are quicker to open. None of this shows up in a demonstration. If you take this route, put a few rules in place from the start.

  • Keep a register of shared projects and GPTs, with an owner for each.
  • Record which document version each one holds, and replace it when the source changes.
  • Allow work files only in business workspaces, never in personal accounts.

Which should you choose?

Use uploads for personal research and drafting with a few files. Use a business workspace with connected apps when staff need help across documents they can already open and your permissions are in order. Choose a built knowledge search when one approved set of documents must give consistent, checkable answers to many people, or when you need to measure accuracy before relying on it. Some businesses run both, using ChatGPT for drafting and a knowledge search for policy answers.

ChatGPT options compared with a built knowledge search

ApproachWhere documents sitHow it stays currentPermissionsGood fit
Personal account uploadCopies in one person's chats or projectsManual re-uploadOnly the uploaderAvoid for work files that contain personal information
Business workspace projectCopies in a shared project, up to 40 filesManual re-upload by the project ownerProject membershipA small team with a few stable documents
Connected SharePoint or Google Drive appRead in place from the sourceReads the live fileThe user's existing source permissionsStaff searching files they can already open
Built knowledge searchAn index of an approved document setScheduled re-indexing and archive filtersSource permissions carried into retrievalMany staff relying on consistent, cited answers

Practical checklist

  • Work files are allowed only in a ChatGPT Business, Enterprise or Edu workspace, not in personal accounts.
  • Each shared project or GPT has a named owner and a record of which document versions it holds.
  • Connected apps have been tested from an ordinary staff account to confirm what they can reach.
  • SharePoint or Drive sharing has been reviewed before connecting, because connected apps follow existing access.
  • Where your plan allows it, the conversation retention period has been set and recorded.
  • Questions that need a single approved answer have a defined source document, whichever tool is used.

Common questions

Can ChatGPT cite the page an answer came from?

Connected apps can search and reference the files they used, and you can ask for the passage to be quoted. How precise the reference is depends on the file and the tool. If staff need to open the exact clause or page to confirm an answer, test that with your own documents before relying on it, and include tables and scanned pages in the test.

Is a custom GPT the same as a knowledge search?

A custom GPT with knowledge files is closer to a shared upload. OpenAI allows up to 20 files as knowledge for a GPT, and those files are copies that someone must replace when the originals change. Measuring how often it answers correctly is up to you, so keep a list of test questions and expected answers if staff will rely on it.

Does the Google Drive app work the same way as SharePoint?

OpenAI provides a separate Google Drive app with its own setup instructions. Its connected apps guidance says app permission settings do not grant an app new access, and workspace controls still apply. Native Google Docs cannot be uploaded directly as .gdoc files; OpenAI says to export them as PDF or DOCX first. Check the Drive app's current limits before connecting.

What should we do about files already uploaded to personal accounts?

List them, move the work to a business workspace and delete the personal copies through the account's own controls. Check whether any of the files held personal or confidential information, and if so, consider whether your privacy obligations require further steps. The OAIC's guidance on commercially available AI products is a practical starting point.

Can we restrict ChatGPT's SharePoint access to certain sites?

OpenAI says workspace administrators can use a site-collection allowlist to restrict the SharePoint app, and that OpenAI enforces these restrictions on top of the Microsoft permissions, which they do not replace. Each user can still only reach what their Microsoft account can open. Use the allowlist to keep the app to approved sites, and fix oversharing in SharePoint itself.

Sources and further reading

Continue planning

Plan a useful knowledge-search pilot

Describe the documents your staff use, the questions they need answered and how uncertainty should be reviewed. We can discuss preparation and a bounded pilot. Keep source documents, customer records and confidential information out of this enquiry.