Early Case Assessment: Twelve Questions Before You Litigate

The merits, honestly

1. What does winning actually look like?

   A judgment is not money, money is not always the goal, and an injunction you can’t police is paper. Define the business outcome — collected dollars, a terminated contract, a defended market position, a precedent avoided — and test everything that follows against it.

2. What do the documents say — starting with the bad ones?

   Read the worst five documents first, the ones the other side will blow up on a screen. Cases are won and lost on documents that existed before anyone called a lawyer; know yours before you commit.

3. Who are your witnesses, and will they hold?

   Do the key people still work for you? Will they in two years? A departed, disgruntled, or deposition-fragile witness can flip the value of a claim. Note who needs an interview now, while they’re friendly and memories are fresh.

4. What’s the realistic range — fees included, both directions?

   Best case, expected case, worst case, each with rough probability and each net of your own fees and any fee-shifting exposure. If the expected case net of fees is close to the walk-away number, that’s the answer, however the merits feel.

The battlefield

1. Where will this be fought?

   Forum-selection clause, arbitration clause, likely venue, the judge pool, the jury pool, the appellate backdrop. The same case is worth different amounts in different rooms.

2. Who pays the lawyers if you win? If you lose?

   A fee-shifting clause changes settlement math from day one — it makes small-dollar claims viable for them and marginal defenses expensive for you. Know whether one exists before setting any strategy that assumes American-rule economics. Fee exposure can also arise without a clause — through prevailing-party statutes, offer-of-judgment rules, and bad-faith or sanctions doctrines — and the American-rule baseline itself varies by forum, so confirm the rule where you would file.

3. What can they bring back at you?

   Counterclaims, setoffs, audits of your own performance, and discovery into corners of the business you’d rather keep boring. Suing someone hands them a courthouse; assume they’ll use it.

4. What does discovery cost the business — not just the budget?

   Executive depositions, document collection across systems, engineers pulled off projects, the dispute as a standing agenda item. For some companies this burden, not the verdict risk, is the real exposure. Price it honestly.

The exits

1. Can you actually collect?

   A judgment against an insolvent or judgment-proof counterparty is a receipt for your own fees. Check assets, insurance, guarantors, and parent-company exposure before spending a dollar chasing one.

2. Is there insurance or indemnity — on either side?

   Their policy may be the real defendant; your policy may fund the defense; an indemnity clause somewhere in the contract stack may move the whole loss. This question is worth an hour with the broker before strategy is set.

3. Does this case set a pattern?

   Will settling teach every counterparty that demands work? Will fighting signal the opposite at ten times the price? Serial plaintiffs, copycat claims, and reputational ripples belong in the assessment, not in the post-mortem.

4. Where are the exit ramps, and when?

   Early mediation, a dispositive motion, a season when the business relationship could absorb a deal. Mark them on the calendar at the start — cases that pass their off-ramps tend not to see another one until the courthouse steps.