Case Strategy Prompts for Lawyers
Strategic prompts for thinking through case weaknesses, settlement decisions, discovery planning, and leverage assessment before you commit to a direction.
When You Need to Find the Weaknesses in Your Case Before Opposing Counsel Does
"I need you to tear apart my case and find every weakness before the other side does.
My theory of the case: [your story in 3-4 sentences]
The key facts supporting me: [your strongest evidence]
The facts I wish were different: [the problems]
The legal standard I need to meet: [the test/elements]
Opposing counsel's reputation: [aggressive? thorough? lazy?]
Ask me: If you were opposing counsel, where would you attack? What discovery would you request to expose my weak spots? Then tell me which vulnerabilities are fixable and which ones I just need to prepare for."
Why this works: Forces you out of advocacy mode into skepticism, identifies what you can fix vs. what you must manage, prepares you for their strategy.
When You're Trying to Decide If Settlement Math Actually Makes Sense
"Help me think through whether this settlement offer is actually smart or if I'm just tired of the case.
The offer: [specific terms]
Best case trial outcome: [what we'd win]
Worst case trial outcome: [what we'd lose]
Cost to get to trial: [fees, time, expenses]
Trial risk factors: [bad facts, difficult judge, unpredictable jury issue]
What client thinks: [their position]
What my gut says: [your instinct]
Ask me: What am I not accounting for in this analysis? What's the real probability of best case vs. worst case? Then help me run the actual expected value calculation and see if this offer is as good/bad as it feels."
Why this works: Separates emotion from math, quantifies risk properly, exposes motivated reasoning, gives you a framework to explain to client.
When You Need to Plan Discovery Strategy (Not Just Fire Off Everything)
"I need a discovery plan for [type of case] that actually gets me what I need without burying me in irrelevant documents.
What I need to prove: [the elements/story]
What I already know: [facts established]
What I suspect but can't prove: [theories]
What they'll fight giving me: [expected resistance]
The judge's discovery philosophy: [liberal? restrictive?]
Budget constraints: [realistic limits]
Ask me: What's the one document or admission that would win this case? Then work backward to create a discovery plan that gets me there without requesting everything that might possibly be relevant."
Why this works: Focuses discovery on case-winning information, avoids wasting money on CYA requests, creates a strategic sequence.
When You're Deciding Which Motions Are Actually Worth Filing
"I'm considering filing [type of motion] and need to think through whether it's strategic or just making myself feel better.
What the motion would argue: [your position]
Probability of winning: [realistic assessment]
What it costs to file and argue: [time, money, attention]
What I gain even if I lose: [creating record? other benefits?]
What it does to the case timeline: [delay? acceleration?]
This judge's track record on these: [how they usually rule]
What opposing counsel will do in response: [their countermove]
Ask me: Am I filing this because it's smart or because my client expects me to fight? Then help me decide if this motion is actually strategic or just expensive theater."
Why this works: Forces honest assessment of win probability, considers opportunity cost, distinguishes substance from optics, thinks three moves ahead.
When You're Evaluating Whether to Take a New Case
"I need to think through whether this potential case is actually worth taking or if I'm just seeing dollar signs.
The case: [basic facts]
Potential recovery: [damages/value]
Legal issues: [claims and defenses]
Client's credibility/appeal: [how they'll come across]
Evidence quality: [what exists, what's missing]
Likely defense strategy: [how they'll fight it]
My capacity right now: [realistic bandwidth]
Why I'm hesitant: [the red flag]
Ask me: What would make me regret taking this case in six months? What am I not seeing because I want the case? Then give me the honest assessment of whether this is a good case or just an appealing client."
Why this works: Surfaces the red flags you're ignoring, checks your optimism bias, considers opportunity cost, forces realistic assessment.
When You Need to Figure Out What Evidence You're Actually Missing
"I feel like I have a good case but something's missing and I can't figure out what.
My theory: [how you win]
Evidence I have: [what supports it]
The element/issue I'm worried about: [the gap]
What opposing counsel will argue: [their attack]
What the judge/jury needs to believe: [the key finding]
Ask me: Walk through my case element by element and tell me what I'm missing. What do I have to prove that I don't actually have evidence for? What assumptions am I making that aren't supported?"
Why this works: Systematic gap analysis, exposes assumptions masquerading as evidence, identifies what discovery you actually need.
When You're Stress-Testing Your Theory of the Case
"I have a theory of how this case works but I need to poke holes in it before I commit.
My theory: [your narrative of what happened and why you win]
The facts supporting it: [your evidence]
The facts that complicate it: [inconvenient truths]
Opposing theory: [their narrative]
Which theory is simpler: [honest assessment]
What I need jury/judge to believe: [key inferences]
Ask me: What if I'm wrong about [key assumption]? Does my whole theory collapse or does it still work? Then tell me if I have a coherent theory or if I'm forcing facts into a story that doesn't quite fit."
Why this works: Tests resilience of your theory, identifies load-bearing assumptions, forces you to consider alternative explanations.
When You Have Bad Facts You Can't Avoid
"I have [bad fact] in my case and I need a strategy for dealing with it that isn't just hoping they don't notice.
The bad fact: [what it is]
Why it's bad: [how it hurts you]
Whether they know about it: [if it's discoverable/obvious]
The context that makes it less bad: [mitigation]
My best spin on it: [most favorable framing]
If I bring it up first vs. wait: [the tactical choice]
Ask me: Is this actually case-killing or does it just feel that way? Should I address it head-on or minimize it? Then give me a strategy for handling this that doesn't involve pretending it doesn't exist."
Why this works: Distinguishes real disasters from manageable problems, forces proactive strategy, considers timing and framing.
When You're Deciding Whether to Push Hard or Fold
"I'm at a decision point where I can [aggressive move] or [conciliatory move] and I don't know which is smarter.
The aggressive option: [what it is]
The conciliatory option: [the alternative]
What I gain if aggressive works: [upside]
What I lose if aggressive backfires: [downside]
What conciliatory preserves: [relationship/options]
What conciliatory costs me: [leverage/momentum]
Client's preference: [what they want]
My read on opposing counsel: [how they'll respond]
Ask me: What am I really optimizing for here - winning this battle or winning the war? Then help me think through which move is actually strategic vs. which one just feels satisfying."
Why this works: Separates tactics from strategy, considers second-order effects, checks ego-driven decisions.
When You Need to Figure Out What the Other Side Actually Wants
"I need to understand what opposing counsel/party is really trying to accomplish so I can figure out if there's a deal to be made.
What they're demanding: [their stated position]
Why that doesn't make sense: [the illogical parts]
What they might actually care about: [your theory]
What they've rejected: [previous offers]
Their client's situation: [pressures on them]
Their lawyer's reputation: [their typical strategy]
Ask me: What would explain their behavior if they're being rational? What non-monetary thing might they value? Then help me figure out what they actually want so I can test whether a deal is possible."
Why this works: Looks past stated positions to interests, opens creative settlement options, helps you test theories through tactical offers.
When You're Planning Your Case Timeline and What to Do When
"I need to plan the sequence of moves in this case and I'm not sure what order makes strategic sense.
Where we are now: [current posture]
Available moves: [motions, discovery, settlement discussions]
External deadlines: [trial date, filing deadlines]
Judge's case management style: [how they run cases]
What I need to accomplish: [goals at each stage]
Resources/bandwidth: [realistic constraints]
Ask me: What move sets up the next move? What has to happen before something else makes sense? Then create a timeline that sequences these strategically, not just chronologically."
Why this works: Thinks in strategic sequences not just deadlines, considers how each move sets up the next, accounts for practical constraints.
When You're Trying to Evaluate Your Leverage
"I need an honest assessment of what leverage I actually have in this case.
My leverage points: [what gives me power]
Their leverage points: [what gives them power]
My client's tolerance: [how long they can fight]
Their client's tolerance: [how long they can fight]
The risk of going to trial: [who's more scared]
Time pressure: [who needs this resolved faster]
Reputation/relationship stakes: [what else is on the line]
Ask me: Am I overestimating my leverage because I'm emotionally invested? What leverage do I think I have that might not actually matter to them? Then give me a realistic assessment of the bargaining power on each side."
Why this works: Checks overconfidence, identifies asymmetric pressure points, helps you calibrate settlement expectations.
When You Need to Decide If You're Being Too Aggressive or Not Aggressive Enough
"I need a gut check on whether my approach to this case is appropriately aggressive or if I'm either overdoing it or being too soft.
What I'm doing: [current strategy]
Client's expectations: [what they want]
Judge's temperament: [their preferences]
Opposing counsel's style: [their approach]
The stakes: [what's actually at risk]
My natural tendency: [your default mode]
Ask me: Is this strategy driven by what the case needs or by my personality/client pressure? Then tell me if I should dial it up, dial it down, or if I'm in the right zone."
Why this works: Separates case requirements from personality defaults, checks for client-pressure-driven decisions, considers judge's perspective.
Want more prompts for lawyers?
- Client Communication - when they're panicking, ignoring you, or making it worse
- Opposing Counsel Communication - when you want to call them an asshole but need to stay professional
- Document Drafting - demand letters, motions, and the hard parts of forms
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