What you'll accomplish
By the end of this guide, you'll have a systematic ChatGPT Plus workflow for writing recommendation letters — including how to upload student brag sheets and data files so the AI can reference specific details without you copy-pasting anything, reducing each letter from 90 minutes to 20 minutes of personalized editing.
What you'll need
- A ChatGPT Plus account at chat.openai.com ($20/month — cancel after recommendation season if budget is a concern)
- Student brag sheets or summary documents (even basic Word docs or Google Docs exports work)
- A list of students with their college/program focus
- Time needed: 15-20 min setup, then 20-25 min per letter including editing
- Cost: $20/month (ChatGPT Plus)
How-To Guide: ChatGPT Plus for Recommendation Letter Season
Step 1: Set up your ChatGPT Plus account and enable file uploads
Go to chat.openai.com and upgrade to Plus if you haven't already. The key feature you need is file upload — the ability to upload a student's brag sheet document and have ChatGPT read it when writing the letter.
In ChatGPT, start a new conversation. You should see a paperclip (📎) icon in the message bar — this is the file upload button. Click it to verify it works.
What you should see: The ability to attach files to your messages. ChatGPT Plus can read Word documents, PDFs, and Google Docs exports. Troubleshooting: If you don't see the attachment icon, you may be on the free tier — upgrade to Plus or use the "Upload file" option from the plus (+) button.