Claude does not keep previous chats in memory so you’ll have to create an updated document.
Step 1: Create Your “Learning Profile” Document
First, create a simple document (Google Doc, Notion page, or even a text file) that will serve as your learning context. Here’s the template:
MY AI LEARNING ASSESSMENT PROFILE
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TOPIC: [e.g., "AI Integration for Course Creation"]
GOAL: [e.g., "Reduce course creation time by 50% while maintaining quality"]
ASSESSMENT START DATE: [Today's date]
CURRENT SELF-PERCEPTION:
- What I think I'm good at:
- What I know I struggle with:
- Tools I'm currently using:
- Biggest challenge right now:
ASSESSMENT HISTORY:
[This section will grow over time]
COMMITMENTS & ATTEMPTS:
[Track what you said you'd try vs. what actually happened]
EVIDENCE OF PROGRESS:
[Concrete examples, not just feelings]
Step 2: Your Initial Assessment Prompt
Start a new Claude conversation with this prompt:
You are my personal learning coach and assessor. I want to do an honest skills assessment for AI integration in course creation, and I'll be coming back to you regularly to track my progress over time.
Since you won't remember our previous conversations, I'll always provide you with my learning profile context at the start of each session.
For today's INITIAL ASSESSMENT, please:
1. Ask me scenario-based questions (not just "do you know X") to reveal my actual skill level
2. Help me discover blind spots I might not be aware of
3. Give me a realistic assessment of where I actually am vs. where I think I am
4. Suggest 3 specific next steps ranked by priority
5. Help me set measurable goals for the next 2 weeks
Ask me one question at a time, and dig deeper based on my responses. Start with a realistic scenario I'd actually face in my course creation work.
Ready to begin?
Step 3: Go Through the Assessment
Answer Claude’s questions honestly. After each exchange, Claude will dig deeper based on your responses. This might look like:
Claude: “You want to create an outline for a 10-lesson course on productivity. You have 2 hours. Walk me through exactly how you’d approach this using AI tools.”
You: [Give your honest answer]
Claude: “Interesting – you mentioned using ChatGPT for brainstorming. How do you ensure the outline matches your teaching style and your students’ actual needs rather than just being generic content?”
You: [Another honest answer revealing more about your actual process]
Step 4: Document Your Results
After the assessment, ask Claude:
Based on our conversation, please create a summary I can save to my learning profile that includes:
1. My actual skill level (be honest about gaps you identified)
2. The 3 specific things I should focus on next
3. Measurable goals for the next 2 weeks
4. Questions I should ask myself when I check back in
Format this so I can copy-paste it into my learning profile document.
Step 5: Set Up Your Check-In System
Two weeks later, start a NEW Claude conversation with:
You are my learning coach. Here's my learning profile from our last session:
[PASTE YOUR ENTIRE LEARNING PROFILE HERE]
It's been 2 weeks since my last assessment. Please:
1. Ask me specific questions about what I actually tried vs. what I committed to
2. Look for evidence of real progress (not just good intentions)
3. Identify what's working vs. what's not
4. Adjust my learning priorities based on actual results
5. Set goals for the next 2 weeks
Start by asking me about one specific thing I was supposed to try from last time.
Step 6: The “Reality Check” Follow-Up Prompts
During your check-ins, use these follow-up prompts to go deeper:
For evidence-based assessment:
I said I was going to [specific commitment]. Let me show you what actually happened:
- What I did: [specific actions]
- Results I got: [concrete outcomes]
- Problems I ran into: [honest obstacles]
- What I learned: [real insights]
Based on this evidence, what should I focus on next?
For gap identification:
I think I'm getting better at [skill], but I want you to test that assumption. Give me a realistic scenario that's slightly harder than what I've been doing, and let me walk through how I'd handle it. Then tell me what you notice about my approach.
Step 7: Track Patterns Over Time
After a few sessions, add this to your check-ins:
Looking at my learning profile history, what patterns do you notice about:
- Things I consistently avoid or skip
- Gaps between my confidence and actual results
- Areas where I'm actually making progress vs. just spinning my wheels
- Whether my goals are realistic or if I'm being too ambitious/conservative
What adjustments should I make to my learning approach?
Pro Tips for Making This Work:
Be brutally honest – The system only works if you tell Claude what really happened, not what you wish had happened.
Keep your learning profile updated – After each session, copy Claude’s summary into your profile document.
Set calendar reminders – Regular check-ins (every 2-3 weeks) work better than sporadic ones.
Use specific examples – Instead of “I’m getting better at prompting,” say “Here’s the prompt I used and the result I got.”
Track time and outcomes – “This used to take me 4 hours, now it takes 2 hours” is better than “I’m more efficient.”
The beauty of this system is that it forces you to be accountable to evidence rather than just good intentions. And because you’re maintaining the context manually, you get the benefit of longitudinal coaching even though Claude starts fresh each time.
Want to try the initial assessment prompt right now, or do you have questions about setting up the system first?