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Add a file, then chat with it

Uploading a document adds it to your Library — the place where you upload documents, data, and other files to reference in your chats. Once a file finishes processing, you can ask Chief questions about it directly.

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Upload from the prompt bar

The Upload files command in the prompt bar plus menu
  1. In the prompt bar, click the + (plus) button to open the Command Center menu.
  2. Click “Upload files”.
  3. Pick the document from your computer in the file picker and confirm.
  4. Watch the “Uploading Files” progress window. You’ll see “Uploading 1/1 files” and a note that “You can close this pop-up. Your files will keep uploading.”
  5. When it’s done you’ll see “All files ready” and a “Chat with 1 files” button to jump into a conversation about it.

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Or drag and drop

The full-screen Drop files here zone that appears when you drag a file over Chief
  1. Drag a file from your computer over the Chief window.
  2. A full-screen dropzone appears reading “Drop files here” with “Upload your files to add them to the conversation”.
  3. Release the file to start the upload.
ℹ️ Good to Know: Chief accepts essentially any file type — documents, data, video, audio, or images. After upload, each file moves through stages: “Queued for upload,” “Processing your file so you can chat with it,” and finally “Ready.” Larger files take a little longer to process.
🚀 Pro-Tip: You don’t have to wait. Close the upload pop-up and keep working — your files keep uploading and processing in the background, and they become chat-ready on their own.

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FAQ

Files above the maximum size are rejected with that message. If your file is too large, split it into smaller files or compress it before uploading. (The exact maximum is enforced by Chief’s servers and shown in the error message.)
Most file types are accepted, but a few are rejected on the server. Convert the file to a common format (such as PDF or DOCX) and try again. If it still fails, use Get Help.
Yes. The upload view offers to let you try the file again, and a “Get Help” link if it keeps failing.