ChatGPT, which has some key differences from Claude that we can leverage.
Key Differences with ChatGPT:
Memory Feature: ChatGPT can retain context within a conversation and has “Memory” that persists across conversations (if you have it enabled) Custom Instructions: You can set up permanent instructions that apply to every conversation GPT Builder: You can create custom GPTs specifically for this assessment purpose
Option 1: Using ChatGPT’s Memory Feature (Easiest)
Step 1: Enable and Set Up Memory
Go to Settings → Personalization → Memory and turn it on. Then start with this prompt:
I want you to become my personal learning coach for AI integration in course creation. Please remember these details about me:
LEARNING GOAL: [Your specific goal]
ASSESSMENT START DATE: [Today's date]
CURRENT TOOLS I USE: [List them]
MY BIGGEST CHALLENGE: [Be specific]
Please remember our assessment conversations and track my progress over time. I want honest feedback based on evidence, not just encouragement.
For today's initial assessment, ask me scenario-based questions to reveal my actual skill level vs. what I think I know. Start with one realistic scenario I'd face in course creation.
Step 2: Let ChatGPT Build Your Profile
ChatGPT will automatically remember key details from your conversation. After the assessment, tell it:
Please save to memory: My current skill assessment, the 3 priorities we identified, and my commitments for the next 2 weeks. Next time I check in, remind me of what I said I'd do and ask for evidence of what actually happened.
Step 3: Regular Check-Ins
Start new conversations with:
Hi, I'm back for my learning progress check-in. Remind me what I committed to last time, then ask me specific questions about what I actually did vs. what I intended to do.
Option 2: Custom Instructions Method
Step 1: Set Up Custom Instructions
Go to Settings → Personalization → Custom Instructions:
“What would you like ChatGPT to know about you?”
I'm a course creator learning AI integration. I want you to act as my learning coach, tracking my progress over time. Ask scenario-based questions, not theoretical ones. Focus on evidence of actual progress, not just good intentions. Challenge me when I'm overconfident and identify blind spots I don't see.
“How would you like ChatGPT to respond?”
Be conversational but direct. Ask follow-up questions that reveal the gap between what I think I can do and what I actually demonstrate. Help me set realistic, measurable goals. Always ask for specific examples and evidence when I claim progress.
Step 2: Start Your Assessment
I want to do a skills assessment for AI in course creation. Instead of asking what I know, give me realistic scenarios and help me discover what I'm missing based on how I'd handle them.
First scenario: I need to create a complete course outline for "Productivity for Remote Workers" in 2 hours using AI. Walk me through exactly how I'd do this, and you tell me what gaps you notice in my approach.
Option 3: Create a Custom GPT (Most Powerful)
Step 1: Build Your Assessment GPT
Go to “Explore” → “Create a GPT” and use this configuration:
Name: “My Learning Coach”
Instructions:
You are a personalized learning assessment coach. Your job is to:
1. Track a user's learning progress over time through regular check-ins
2. Use scenario-based questions rather than knowledge-based quizzes
3. Identify gaps between confidence and actual competence
4. Provide evidence-based feedback, not just encouragement
5. Adjust learning priorities based on real-world results
For assessments:
- Start with realistic scenarios they'd actually face
- Dig deeper with follow-up questions based on their responses
- Look for what they're NOT considering in their approach
- End with specific, measurable next steps
For check-ins:
- Ask about specific commitments from last time
- Require evidence of what they actually tried
- Identify patterns of avoidance or overconfidence
- Adjust priorities based on real progress
Always be conversational but direct. Focus on practical application over theoretical knowledge.
Conversation Starters:
- “Let’s do your initial skills assessment”
- “Time for a progress check-in”
- “Test my skills with a challenging scenario”
- “Help me analyze what’s working vs. what’s not”
Step 2: Use Your Custom GPT
This GPT will remember your conversation history and can reference previous sessions automatically.
Step 3: The Check-In Process (All Methods)
Every 2-3 weeks, use these specific prompts:
For Progress Review:
It's been [X weeks] since our last check-in. Before we assess new areas, let's review what I actually did vs. what I committed to:
COMMITMENT 1: [What you said you'd try]
WHAT ACTUALLY HAPPENED: [Honest report]
EVIDENCE: [Specific examples, time saved, results]
COMMITMENT 2: [What you said you'd try]
WHAT ACTUALLY HAPPENED: [Honest report]
EVIDENCE: [Specific examples]
Based on this evidence, what should I focus on next?
For Skill Testing:
I think I've improved at [specific skill]. Test that assumption by giving me a scenario that's slightly harder than what I've been doing. Let me walk through my approach, then tell me what gaps you still notice.
For Pattern Recognition:
Looking at our conversation history, what patterns do you notice about:
- Things I consistently avoid or struggle with
- Areas where I overestimate my abilities
- What's actually working vs. what I just think is working
- Whether my goals are realistic
What should I adjust in my learning approach?
Pro Tips for ChatGPT Success:
Use the same conversation thread when possible – ChatGPT maintains context better within a single conversation
Reference previous sessions explicitly – “Last time you told me to focus on X” helps trigger the right memory
Be specific about timeframes – “It’s been 2 weeks since…” helps ChatGPT contextualize your progress
Save important insights – Copy key assessments to a separate document as backup
Use the Memory feature strategically – Periodically ask ChatGPT “What do you remember about my learning goals?” to see what it’s retaining
The Custom GPT option (#3) is probably your best bet if you have ChatGPT Plus, as it creates a dedicated coaching environment that remembers your specific context and goals.
Which approach feels most manageable for your current ChatGPT setup?