Prompt Ladder — Worked Example

Sade Strickland's Prompt Ladder

All 4 levels — built on the same real scenario, one upgrade at a time
👤 Sade Strickland
🏢 Assistant to the VP of Career & Technical Education (CTE)
🏛️ United Federation of Teachers
📌
Sade's Chosen Scenario
Drafting a communication to UFT CTE teachers about an upcoming professional development opportunity
This is the ONE scenario used across all 4 levels. Each level adds a new layer — the prompt is never deleted, only upgraded.
How to read this page: Each box shows the complete prompt for that level — color-coded to show exactly what was added. 🟡 Yellow = the core task  |  🔵 Blue = context  |  🟢 Green = Sade's role + format  |  🩵 Teal = persona  |  🟠 Orange = constraint. By Level 4, all five colors appear together.
1
THE BARE ASK
One sentence — no context, no role, no format
10 PTS
✍️  What's added: Just the raw task — nothing else
Sade's Level 1 Prompt
Write an email to CTE teachers about an upcoming professional development opportunity.
Task
⚠️
What the AI doesn't know: Which teachers. What kind of PD. Why it matters to CTE specifically. Who is sending it. How long it should be. What tone is appropriate. The result will be a generic, corporate-sounding email that could come from any organization — not the UFT, and not specifically about CTE.
Expected AI Output at this level A generic 3-paragraph email about "professional development." No UFT voice. No CTE specificity. Words like "Dear Valued Teacher" or "Please be informed." Requires heavy editing to be usable.
2
TASK + CONTEXT
Add WHO, WHY, WHAT must be included
25 PTS
➕  What's added: WHO the audience is · WHY this PD matters · WHAT must be included
Sade's Level 2 Prompt
Write an email to CTE teachers about an upcoming professional development opportunity. The audience is UFT members who teach Career and Technical Education in New York City public schools — programs like culinary arts, cosmetology, IT, health careers, and construction trades. The PD is a full-day workshop on integrating real-world industry standards into CTE classroom instruction. It is being offered in partnership with the UFT and is free for members. Teachers need to know the date (October 18th), the location (UFT headquarters, 52 Broadway), and that they must register by October 10th. Attendance counts toward their professional learning hours requirement.
Task
Context (WHO, WHY, WHAT)
📈
What gets better: The AI now knows the audience (CTE teachers, not generic educators), the specifics of the PD (industry standards, free, one day), logistics (date, location, deadline), and the incentive (PL hours). The email will be significantly more relevant and usable — but it still won't sound like the UFT, and the structure may be unpredictable.
Expected AI Output at this level An email with real details — date, location, deadline, benefits. Audience-appropriate. Still may use generic professional language ("We are pleased to announce...") and the structure (paragraphs vs. bullets) will be whatever the AI guesses. Better, but still needs a formatting pass.
3
CONTEXT + TASK + FORMAT
Add Sade's role + exact output structure
40 PTS
➕  What's added: Sade's professional role · A specific format instruction
Sade's Level 3 Prompt
I am the Assistant to the UFT Vice President of Career and Technical Education. I am drafting this communication on behalf of the CTE department to go out to all UFT CTE teachers across New York City public schools. Write an email to CTE teachers about an upcoming professional development opportunity. The audience is UFT members who teach Career and Technical Education — programs like culinary arts, cosmetology, IT, health careers, and construction trades. The PD is a full-day workshop on integrating real-world industry standards into CTE classroom instruction. It is being offered in partnership with the UFT and is free for members. Teachers need to know the date (October 18th), the location (UFT headquarters, 52 Broadway), and that they must register by October 10th. Attendance counts toward their professional learning hours requirement. Format the email with: a compelling subject line, a warm opening paragraph, a short bulleted section with the key logistics (date, location, deadline, cost, PL hours), one paragraph explaining why this PD is valuable specifically for CTE educators, and a clear call-to-action with a registration link placeholder at the end.
Task
Context
Sade's Role
Format
What gets better: The AI now knows it is writing on behalf of a specific person in a specific role — not anonymously. The format instruction means the output will have a subject line, a bullet list of logistics, a "why this matters for CTE" paragraph, and a CTA. This is now structurally ready to use. The remaining gap: it still doesn't fully sound like the UFT's voice and values.
Expected AI Output at this level A properly structured email: subject line, warm opening, bullet logistics, CTE-specific value paragraph, registration CTA. Very close to ready. Might need a light tone adjustment to feel more "UFT" — but this is the level where most people would actually use the output.
4
⭐ THE FULL PACKAGE — EXPERT
Full persona + constraint = work-ready output, first try
50 PTS + VOTE
➕  What's added: A full UFT CTE persona · Two guardrail constraints
Sade's Level 4 Prompt — The Full Expert Version
You are a professional communications expert supporting the UFT's Career and Technical Education (CTE) division. You have deep knowledge of NYC's CTE programs — including career pathways in culinary arts, cosmetology, health careers, information technology, construction trades, and business. You understand that UFT CTE teachers are unionized professionals who take pride in their trade expertise and their role in preparing students for industry careers. Your communications reflect the UFT's values: member-centered, empowering, solidarity-focused, and clear. You write in a voice that is warm, collegial, and motivating — never bureaucratic. I am the Assistant to the UFT Vice President of Career and Technical Education. I am drafting this communication on behalf of the CTE department to go out to all UFT CTE teachers across New York City public schools. Write an email to CTE teachers about an upcoming professional development opportunity. The audience is UFT members who teach Career and Technical Education — programs like culinary arts, cosmetology, IT, health careers, and construction trades. The PD is a full-day workshop on integrating real-world industry standards into CTE classroom instruction. It is free for members and offered in partnership with the UFT. Key details: Date: October 18th · Location: UFT Headquarters, 52 Broadway · Registration deadline: October 10th · Attendance counts toward professional learning hours. Format the email with: a compelling subject line, a warm opening paragraph, a short bulleted section with key logistics (date, location, deadline, cost, PL hours), one paragraph explaining why this PD is valuable specifically for CTE educators, and a clear call-to-action with a registration link placeholder. Constraints: Keep the email under 300 words. Use a warm, collegial tone — avoid bureaucratic language like "please be advised" or "please note." Do not use the phrase "Dear Teacher" — address CTE educators specifically. End with a sign-off from the UFT CTE Department, not a generic signature.
Task
Context
Sade's Role
Format
Persona
Constraints
🌟
What gets better: The persona tells the AI exactly who it is and what voice to use — UFT values, CTE pride, union solidarity, warm and collegial tone. The constraints eliminate the two most common AI failure modes (generic sign-offs, bureaucratic filler phrases) and set a word count that keeps the email actually readable. This output should be sendable with zero or minimal editing.
Expected AI Output at this level A polished, UFT-voiced email under 300 words with a strong subject line, CTE-specific framing, clean bullet logistics, a compelling "why this matters for your classroom" paragraph, and a proper CTE department sign-off. Colleagues will not know an AI wrote the first draft.
🏆 Bonus challenge: Try this same Level 4 prompt in both ChatGPT and Claude. Paste both responses to the Padlet. Notice how each AI's voice differs — which one lands closer to the UFT tone? That observation is your first step toward knowing which AI to reach for in the future.

📊 The Progression at a Glance

L1
The Bare Ask
Generic. Could be anyone. Heavy editing needed.
L2
Task + Context
Relevant details. Right audience. Still unpredictable structure.
L3
+ Role + Format
Properly structured. From Sade's desk. Light tone edit needed.
L4
+ Persona + Constraint
On-brand. UFT voice. Work-ready. Minimal to no editing.