Skip to main content

​
Add a file, then start a task with it

Where a file goes depends on its type. A PDF or image (PNG, JPEG, GIF, or WebP) you add from the prompt bar attaches to your next message, so Chief reads it with your question. Every other file type uploads to your Library, the place where you upload documents, data, and other files to reference in your tasks. Once a Library file finishes processing, you can ask Chief questions about it directly.

​
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”. A panel of five tiles opens: Upload files, Upload images, Paste content, Add a URL, and Record an audio file.
  3. Click the “Upload files” tile, then pick the document from your computer in the file picker and confirm.
What happens next depends on the file:
  • A PDF or image appears as a tile above the text in the prompt bar. Type your question and send it; the file goes with that message. The Library icon in the tile’s bottom-right corner also saves the file to your Library when you send. It’s on by default for PDFs and off for images. You can attach up to 5 files per message, with images up to 5 MB and PDFs up to 32 MB.
  • Any other file opens the “Uploading Files” progress window, with a note that “You can close this pop-up. Your files will keep uploading.” When it’s done you’ll see “All files ready”. Click “Start task” on the file’s row to jump into a conversation about it. When you upload several files at once, a “Start a task with” button at the top (for example, “Start a task with 3 files”) covers them all.

​
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. Drop it over the prompt bar and a PDF or image attaches to your message, as above. Drop it anywhere else and it uploads to your Library.
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,” “Uploaded. Processing your file so you can work with it,” and finally “Ready.” Larger files take a little longer to process.
Pro-Tip: You don’t have to wait for Library uploads. Close the upload pop-up and keep working — your files keep uploading and processing in the background, and they become task-ready on their own. An attached PDF or image is different: you can’t send the message until its tile has finished uploading.

​
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. For a Library upload, the upload window offers to let you try the file again, and a “Get Help” link if it keeps failing. If an attached PDF or image fails, its tile gets a red border and a warning icon, and the message can’t be sent. Click the x on the tile to remove it, then attach the file again.