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Common Prompting Mistakes (and How to Fix Them)
Even seasoned advocates occasionally make simple mistakes when interacting with AI assistants. Understanding these common pitfalls will save your firm hours of frustration and protect the quality of your legal output.
1. Being Too Vague
- ❌ The Mistake: "Write a contract." or "Draft an agreement."
- ⚠️ Why It Fails: The AI does not know if you need an employment agreement, a commercial land sale, a joint venture partnership, or an NDA. It will generate a generic template that fails to address your client's commercial goals.
- ✅ The Fix: Specify the document type, the parties, the governing law, and the key financial deal points:
"Draft a 2-year Independent Consultancy Agreement for a senior marketing specialist under Kenyan law, with monthly retainer billing and strict client non-solicitation."
2. Missing Case Context
- ❌ The Mistake: "Help me with this case." or "Can we win this land matter?"
- ⚠️ Why It Fails: The AI cannot read your mind or inspect the paper physical file on your desk. Without dates, title numbers, and the adversary's claims, it cannot assess legal viability.
- ✅ The Fix: Give a 3-sentence factual summary of the dispute and the specific legal question you need evaluated.
3. The "Everything at Once" Prompt
- ❌ The Mistake: "Research this case, draft written submissions, write an email to the client, summarize the witness statements, and tell me our chances of winning."
- ⚠️ Why It Fails: Overloading five complex tasks into a single prompt forces the AI to summarize excessively, resulting in shallow, low-quality work across all five areas.
- ✅ The Fix: Break complex instructions into manageable sequential steps:
- Step 1: "First, review these witness statements and extract the 3 main factual contradictions."
- Step 2: "Now, based on those contradictions, outline the legal arguments for our submissions."
- Step 3: "Finally, draft a short email update to the client explaining the next steps."
4. Contradictory Instructions
- ❌ The Mistake: "Draft an aggressive, threatening demand letter, but keep it warm, cooperative, and conciliatory so we don't damage our friendship with the other side."
- ⚠️ Why It Fails: AI models struggle when asked to adopt mutually conflicting tones or contradictory legal positions in the same instrument.
- ✅ The Fix: Be clear on your firm's strategic objective. If you want a firm without being overly contentious, specify:
"Draft a professional, courteous, but legally firm reminder notice that maintains a business relationship while making it clear that formal legal action will commence if payment is not remitted within 7 days."
5. Assuming the AI Knows Facts You Didn't Provide
- ❌ The Mistake: "Draft the affidavit for John's case."
- ⚠️ Why It Fails: The AI does not know who "John" is, which court he is in, or what facts he wants to depose to.
- ✅ The Fix: Provide the name, ID number, and specific factual points that John intends to swear to.
6. Treating AI Output as Final Without Review
- ❌ The Mistake: Copying text directly from the AI screen into court filing paper or sending it directly to a client without reading it.
- ⚠️ Why It Fails: The AI might miss a local court practice direction, include an outdated statutory reference, or misinterpret a subtle factual detail.
- ✅ The Fix: Always conduct a thorough professional review. Edit the tone, verify the names, and ensure the document reflects your firm's standards.
7. Blindly Trusting Citations Without Verification
THE MOST CRITICAL MISTAKE IN LEGAL AI
Never copy and paste an AI-generated judicial citation or statute section into formal court pleadings without looking it up in an authoritative law report (e.g., eKLR / Kenya Law Reports).
AI models predict words based on statistical probability. An AI can fabricate a citation that sounds completely authentic (e.g., Mwangi v. Equity Bank [2021] eKLR), even when no such judgment was ever delivered.
Courts worldwide have penalized practitioners who filed submissions containing hallucinated AI citations. Always verify before you file!