Stop Staring at the Blinking Cursor

You know AI could help. You've heard the hype. You even opened ChatGPT or Claude. And then... nothing. Your mind goes blank. "What am I supposed to ask this thing?"

This is the dumbest problem to have, and yet every lawyer has it.

You spend all day solving problems, asking questions, thinking through scenarios. But put an AI chatbot in front of you and suddenly you can't think of a single thing to say.

Here's why: You're treating it like a search engine when it's actually a conversation partner.

You wouldn't open Google and type "help me with my case." That's too vague. So you've trained yourself to think in keywords: "motion to dismiss standard" or "discovery objections california."

But AI doesn't work like that. It works like talking to a smart colleague who asks follow-up questions. Except you're not used to asking that colleague for help, so you freeze.

The Fix: Real Situations, Real Prompts

Stop thinking "what should I ask AI?" and start thinking "what problem am I dealing with right now?"

Below are prompts organized by actual situations you face. Not "AI use cases." Not "marketing strategies." Just the stuff that's annoying you today.

How to use these:

Find the situation that matches your current problem
Copy the prompt
Fill in the bracketed parts with your specifics
Let AI ask YOU questions before it answers
Have a conversation, don't just fire off one question

The pattern you'll see repeated:

Every good prompt has the same structure:

Context (what's happening)
Your goal (what you need)
The complication (why this is tricky)
"Ask me questions first" (makes AI actually helpful instead of generic)

Now stop overthinking it and try one.

When You're Dealing With Clients

Client freaking out about timeline
Client wants you to do something they saw on TV
Need them to actually do something
They're mad at you (but it's not your fault)
Need to fire a client professionally
Reality check about their weak case
They want you to "destroy" the other side
Explaining your bill
They're making it worse on social media
Bad settlement offer vs. their expectations

Full post: Client Communication Prompts

When You're Dealing With Opposing Counsel

Want to call them an asshole (but need to stay professional)
They're ignoring your emails again
Their "emergency" motion is pure drama
Nasty letter copied to your client
Proposing something ridiculous with a straight face
Need to fact-check them without calling them a liar
Suddenly being nice and you don't trust it
Overbroad discovery requests
Accused you of not conferring (but you did)
You actually screwed up and need to fix it

Full post: Opposing Counsel Communication Prompts

When You're Drafting Documents

Demand letter that doesn't sound like a template
Discovery responses that aren't overkill
Motion that matches your judge's preferences
Settlement agreement that covers your ass
Client engagement letter they'll actually read
Witness prep outline for a nervous client
Deposition outline that finds the gaps
Opposition brief when their argument is bad
Status update email that doesn't invite micromanaging
Closing argument structure

Full post: Document Drafting Prompts

When You're Planning Case Strategy

Finding weaknesses before opposing counsel does
Analyzing whether settlement math makes sense
Planning discovery strategy
Deciding which motions are worth filing
Evaluating new client intake
Identifying what evidence you're missing
Stress-testing your theory of the case
Planning for bad facts you can't avoid
Deciding when to push vs. when to fold
Figuring out what the other side actually wants

Full post: Case Strategy Prompts

When You're Managing Your Practice

Delegating work to junior lawyers
Writing procedures so staff stops asking the same questions
Evaluating which cases to take
Pricing consultations and flat fees
Hiring interview questions that actually reveal problems
Marketing that doesn't make you feel gross
Practice area expansion analysis
Time management when everything's urgent
Explaining to your assistant what you actually need
Getting reviews without begging

Full post: Practice Management Prompts

Stop Waiting to Think of the Perfect Question

You don't need the perfect prompt. You need to start the conversation.

Pick one situation from above that's annoying you right now. Use that prompt. See what happens. If the answer sucks, tell AI why it sucks and ask it to try again.

That's it. That's the whole skill.

The lawyers winning with AI aren't doing anything magical. They're just willing to have a messy conversation instead of staring at a blank screen waiting for inspiration.

New to AI? How to Actually Get Good at Using AI - Start here if you're still figuring this out

Start here: Client Communication Prompts - 10 prompts for when clients are driving you crazy