How to Create Assessment Questions from Files Using AI
- Tara Ellison
- May 15
- 3 min read

Creating effective assessment questions can be time-consuming, especially when you’re trying to align with local standards, differentiate by grade level, and keep things engaging. But what if there was an easier way? At TeachShare, we've designed a powerful, teacher-friendly tool that helps you generate high-quality assessment questions from any file in just a few clicks. Whether it’s a PDF, a lesson handout, or a reading passage, AI can optimize and speed up the process for you.
Here's how you can use TeachShare (and other AI tools like ChatGPT and Gemini) to turn your teaching files into customized, ready-to-go assessments.
Step-by-Step: Creating Assessment Questions with TeachShare
TeachShare is built with educators in mind. Our intuitive interface and smart enhancements make it the easiest and most effective way to generate assessments from your existing resources.
Open TeachShare
Start by logging into TeachShare. If you’re new, it only takes a minute to sign up.
Launch the Creator
From your dashboard, select “Launch Creator.” This is where the magic happens.

Choose “Create any resource”

Write Your Prompt
In the prompt box, tell TeachShare what you want.
For example: “Create a set of [number of questions] assessment questions” . And what's amazing about TeachShare is that it will offer you the option to enhance your prompt and make it more specific and effective (simply click the tab button).
Customize Your Assessment
Fill out the details to tailor the assessment to your needs:
Grade level
Standards
Lesson phase
Boosts (add-ons like higher-order thinking prompts or scaffolds)
Upload Your File
Here’s the key part: under source, upload the file you want to use. (TeachShare also supports YouTube links and websites, but for this article, we’re focusing on file uploads.)
Click the Arrow to Generate
Once everything’s set, click the arrow, sit back, and let TeachShare generate your customized assessment.
Chat & Tweak
Want to make changes?
Use the Options panel to adjust complexity, individualization, standards, or add boosts.
To add even more customization?
Or use TeachShare’s built-in AI Chat to:
Revise questions or activity formats
Add differentiation or scaffolding
Include Bloom’s Taxonomy levels or student-friendly language
You can also use the Reset Chat option to start fresh or return to an earlier version anytime.
Receive an Auto-Generated Teacher Guide
Pro Tip: TeachShare will automatically generate a Teacher Guide along with your resource that you created
This includes:
Classroom tips and usage ideas
Time estimates for each activity
Differentiation strategies to support all learners
Full answer key
Export and Share Your Worksheet
Once your worksheet and Teacher Guide are complete, we offer multiple flexible options to share or assign your resource:
Assign Online (Recommended):
Instantly generate an interactive student link.
Pro Tip: Enable TeachShare Autograder to get instant grading, no manual corrections needed!
Post to Google Classroom:
Turn your worksheet into a Google Classroom assignment with just a click.
Download as PDF:
Export a clean, print-ready version, perfect for in-person classes or offline learning.
And voilà! You’ve got a classroom-ready assessment from your uploaded file in minutes.
What About ChatGPT and Gemini?
While TeachShare is designed specifically for educators and includes built-in education features, general-purpose AI chatbots like ChatGPT and Gemini can also help you generate assessment questions from files. Here's how to do it:
Using ChatGPT-4o
Open ChatGPT (ensure you’re using GPT-4o for file upload capabilities).
Start a New Chat and upload your file (PDF, DOCX, etc.).
Prompt Example:
"Please read this file and generate [number] [question type, e.g., multiple-choice, true/false, open-ended] questions for [grade level] [subject], aligned to [standards or framework].
Review and Revise
You can ask follow-up questions to adjust tone, difficulty, or format.
Copy and Paste
You’ll need to manually format and export the questions to your preferred platform.
Using Gemini (by Google)
Open Gemini
Start a New Prompt and click the + sign to add files
Enter Your Instructions:
"Please read this file and generate [number] [question type, e.g., multiple-choice, true/false, open-ended] questions for [grade level] [subject], aligned to [standards or framework].”
Edit and Copy
Gemini will generate questions, but you may need to tweak the output and format them manually.
So, Which One Should You Use?
While ChatGPT and Gemini are powerful, they aren’t tailor-made for classrooms. TeachShare, on the other hand, was built by educators, for educators. From standards-aligned customization to export-ready formats, it’s the most teacher-friendly and fastest way to turn your files into assessments. So next time you’re staring at a lesson PDF and wondering how to turn it into a quiz for your students, sit back and let TeachShare help you
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