Background documents

The detail that doesn't fit on a CV — turned into interview-ready material.

What it is

Background documents let you upload career artifacts that are too detailed for a CV — project retrospectives, postmortems, case studies, promotion packets, performance reviews. Upskiller reads each one, summarizes it, tags its themes, and extracts STAR-shaped stories (Situation, Task, Action, Result). Those stories then ground the AI's output, so your counselor answers and interview cheat sheet draw on real experience instead of generic fill-in.

When to use it

Once your profile is in good shape and you want sharper, more personal AI output — especially before generating a cheat sheet or prepping for behavioral interviews. It's one of the highest-leverage things you can do after completing your profile.

How to use it

1. Click the upload zone (Click to upload) or drag a file in. PDF or DOCX, up to 10 MB.
2. Optionally edit the Title (it pre-fills from the filename).
3. Click Upload & extract. You'll see Parsing document… while we read it.
4. When the status badge turns Ready, click the document to expand it and review:
   • a short Summary
   • Themes (for example: leadership, ambiguity, technical depth)
   • Extracted stories in STAR format
5. Remove anything you don't want with the trash icon.

Tips & best practices

• Narrative beats bullet points. A project retro or a 360 review gives us far more to work with than a one-line summary. The richer the story, the better the interview material.
• Upload before you generate. Add your documents before generating a cheat sheet or running mock interviews, so the AI can use them.
• Cover the range. A win, a setback, a leadership moment, and a tricky cross-team project together answer most behavioral questions.
• Review the extracted stories. They're a strong first draft of your STAR answers — skim them so you can tell each one confidently.

Troubleshooting / FAQ

• "Please upload a PDF or DOCX file." Other formats aren't supported — convert to PDF first.
• "File too large. Maximum size is 10MB." Split the document, or export a lighter PDF.
• Status shows "Failed." Expand the row for the reason, then try a smaller or simpler document.
• Where do these actually get used? As context for the career counselor, your interview cheat sheet, and other AI features that benefit from concrete examples.
• Is my upload private? Yes — your documents are tied to your account and used only to personalize your output.

Related features

• Interview cheat sheet — prefers your real STAR stories over invented ones
• Career counselor — answers with your documents in context
• Your profile — the foundation these documents build on