AI tools like ChatGPT, Claude, and Google Gemini can dramatically speed up your reselling workflow. But the quality of output depends entirely on how you ask. This guide teaches you to write prompts that get useful, actionable results.
The Prompting Mindset
Think of AI as a capable assistant who has no context about you or your situation. The more specific information you provide, the better the response. Vague questions get vague answers.
💡 Core Principle: Be specific. Include context. Give examples of what you want. The AI can't read your mind - spell out exactly what you need.
Prompt Structure That Works
Great prompts follow a pattern:
- Role: Who should the AI act as?
- Context: What's the situation?
- Task: What specifically do you need?
- Format: How should the response be structured?
- Constraints: Any limitations or requirements?
Writing Product Listings
Basic Prompt (Gets Basic Results)
Write an eBay listing for a vintage jacket.
Better Prompt (Gets Better Results)
Act as an experienced eBay seller who specializes in vintage clothing.
Write a compelling listing title and description for this item:
- 1970s Levi's Sherpa-lined denim trucker jacket
- Size Medium (chest 42", length 26")
- Made in USA, orange tab era
- Excellent vintage condition, minor fading consistent with age
- No rips, stains, or repairs
Requirements:
- Title: 80 characters max, front-load keywords
- Description: Highlight collectibility, include all measurements
- Tone: Knowledgeable but approachable
- Include relevant search terms naturally
Template: Listing Generator
Write a [PLATFORM] listing for:
Item: [DETAILED DESCRIPTION]
Brand: [BRAND]
Condition: [CONDITION WITH SPECIFICS]
Measurements: [ALL MEASUREMENTS]
Flaws: [ANY ISSUES]
Style: [Professional/Casual/Enthusiast]
Target buyer: [WHO WOULD BUY THIS]
Keywords to include: [RELEVANT TERMS]
Product Research
Identifying Items
I found a ceramic figurine with these markings on the bottom: [DESCRIBE MARKS]
It's approximately [SIZE], depicts [DESCRIPTION], and appears to be [AGE ESTIMATE].
Help me identify:
1. The manufacturer
2. Approximate age
3. What similar items sell for
4. Key terms to search for comparables
Authentication Assistance
I'm examining a [BRAND] [ITEM TYPE] and need to verify authenticity.
What I observe:
- [DETAIL 1]
- [DETAIL 2]
- [DETAIL 3]
What are the key authentication points I should check for this specific item? What are common fake tells?
⚠️ Important: AI can provide guidance on authentication, but shouldn't be your only verification. For high-value items, use professional authentication services.
Customer Service Messages
Responding to Issues
A buyer messaged: "[PASTE THEIR MESSAGE]"
Context:
- Item sold for: $[AMOUNT]
- Item was: [DESCRIPTION]
- My return policy: [POLICY]
Write a professional, empathetic response that:
- Acknowledges their concern
- Offers [SOLUTION YOU'RE WILLING TO PROVIDE]
- Maintains a positive relationship
- Keeps communication on-platform
Template: Difficult Buyer Response
Buyer message: "[THEIR MESSAGE]"
Write a response that:
- Remains calm and professional
- Doesn't admit fault if I'm not at fault
- Offers a reasonable solution
- Protects me if this escalates
- Is under 100 words
Bulk Processing
Generating Multiple Titles
Generate eBay listing titles for these items. Each title should be under 80 characters, front-load keywords, and include brand, size, and key features:
1. Nike Air Max 90 shoes, white/red, men's size 10, worn twice
2. Lululemon Align leggings, black, size 6, new with tags
3. Vintage Starter jacket, Dallas Cowboys, XL, 1990s
4. [ADD MORE ITEMS]
Format as a numbered list matching the input order.
Creating Item Specifics
For this item: [DESCRIPTION]
Generate all eBay item specifics in this format:
- Brand:
- Size:
- Color:
- Material:
- Style:
- Pattern:
- [ADD CATEGORY-SPECIFIC FIELDS]
Pricing Research
I need to price this item: [DETAILED DESCRIPTION]
Based on your knowledge, what factors affect the value of this item? What should I research to determine fair market value? What would make this example more or less valuable than average?
💡 Note: AI doesn't have real-time pricing data. Use it to understand value factors, then verify with actual sold comps on eBay, Poshmark, etc.
SEO & Keywords
Keyword Generation
Generate search keywords for: [ITEM DESCRIPTION]
Include:
- Primary keywords (most searched)
- Long-tail keywords (specific phrases)
- Common misspellings buyers might use
- Related terms and synonyms
- Style/aesthetic terms (cottagecore, Y2K, etc.)
Format as comma-separated list.
Learning & Research
Understanding a New Category
I want to start reselling [CATEGORY]. I'm a complete beginner.
Teach me:
1. What makes items in this category valuable
2. Common brands/makers to look for
3. Red flags for fakes or reproductions
4. Where to find inventory
5. What to avoid as a beginner
6. Expected profit margins
Common Mistakes to Avoid
❌ Too Vague
Write a good listing.
✅ Specific and Detailed
Write a Poshmark listing description for a women's Theory blazer, size 4, black wool, excellent condition. Emphasize work-to-evening versatility. Target professional women. 150-200 words.
❌ No Format Specified
Tell me about vintage Pyrex.
✅ Clear Output Format
Give me a quick reference guide to vintage Pyrex patterns. Format as a table with: Pattern Name | Years Produced | Rarity | Typical Price Range
Advanced Techniques
Chain Prompting
For complex tasks, break them into steps:
- First prompt: "Help me identify this item..."
- Second prompt: "Based on that, write a listing..."
- Third prompt: "Now suggest a pricing strategy..."
Role-Playing for Better Results
You are an expert vintage clothing authenticator with 20 years of experience. A seller is asking you to examine photos of a supposed 1950s Hawaiian shirt. What specific questions would you ask them? What details would you examine?
Getting Multiple Options
Give me 3 different listing title options for: [ITEM]
Option 1: Focus on brand recognition
Option 2: Focus on style/aesthetic
Option 3: Focus on specific features
I'll choose the best one.
AI Tools for Resellers
| Tool | Best For | Cost |
|---|---|---|
| ChatGPT | General writing, research | Free / $20/mo |
| Claude | Detailed analysis, long content | Free / $20/mo |
| Google Gemini | Image analysis, research | Free / $20/mo |
| Copy.ai | Marketing copy | Free / $49/mo |
| Jasper | Brand voice, bulk content | $49+/mo |
Image Analysis (Vision AI)
Some AI tools can analyze photos. Upload an image and ask:
Look at this image of a vintage item. Help me identify:
1. What is this item?
2. Approximate age/era
3. Any visible maker's marks or labels
4. Condition issues you can see
5. Suggested search terms for research
What AI Can't Do Well
- Real-time pricing: AI doesn't know current market values
- Definitive authentication: Use professionals for valuable items
- Platform-specific rules: Policies change; verify current rules
- Guaranteed facts: AI can be wrong; verify important information
Quick Reference: Prompt Templates
Listing Title
eBay title, 80 chars max, for: [BRAND] [ITEM] [SIZE] [CONDITION] [KEY FEATURE]
Description
Write a [PLATFORM] description for [ITEM]. Include: [MEASUREMENTS]. Tone: [STYLE]. Target: [BUYER TYPE]. Length: [WORDS].
Customer Reply
Professional reply to: "[MESSAGE]". Offer: [SOLUTION]. Keep under 50 words.
Research
What makes [ITEM TYPE] valuable? List top 5 factors.
Practice Makes Perfect
The best way to improve is to experiment. Try different approaches, see what works, and save your best prompts for reuse. Build a personal library of templates that work for your specific business.