Before you sign a retainer agreement with a liability lawyer, you need to know one thing above all else: have they actually handled cases like yours, and what happened in those cases? This is not a rude or intrusive question. It is the single most practical way to separate a competent attorney from someone who will learn on your dime. Liability law covers a wide range of situations, from slip-and-fall injuries to product defects, car accidents, and professional malpractice. A lawyer who excels at defending insurance companies in auto accident cases might be useless when you are suing a manufacturer for a faulty machine part. So you have to ask directly about their track record with claims that share the same legal theory, the same type of defendant, and the same general facts as your own.

Start by asking them to describe three or four comparable cases they have handled in the past five years. Do not accept a vague answer like “we handle personal injury” or “we have a lot of experience in liability.“ Demand specifics. What was the nature of the claim? Was it a premises liability case involving a broken stairwell, or a product liability case involving a defective power tool? Who was the defendant? Was it an individual, a small business, or a large corporation? What stage did the case reach—settlement, summary judgment, or trial? And most importantly, what was the financial outcome for the client? You are not looking for a guarantee, because no ethical lawyer can promise a result. But you are looking for a pattern. If every comparable case they handled ended in a lowball settlement or a dismissal, that tells you something.

You also need to ask about the lawyer’s role in those cases. Some attorneys are “name partners” who bring in business but hand off the actual work to junior associates. Others are solo practitioners who do everything themselves. Neither is automatically better, but you need to know who will be doing the heavy lifting on your file. Ask specifically: “In those similar cases, did you personally take depositions, argue motions, and negotiate with opposing counsel, or did someone else in your office do that?“ If the lawyer you are interviewing will not be the one handling your case, then you need to interview the actual person who will. Do not let a firm’s marketing department or a friendly paralegal distract you from this core question.

Another critical angle is to ask about the lawyer’s experience with both settlement and trial in liability cases. Many liability claims settle before trial, and that is often the right outcome. But you want a lawyer who is genuinely prepared to go to trial if the other side refuses to offer a fair number. Ask how many liability cases they have tried to verdict in the last three years. Then ask how many of those verdicts were for the plaintiff versus the defendant. A lawyer who has never taken a liability case to trial is essentially a negotiator, not a litigator. That might be fine if the case is straightforward, but if the defendant’s insurance company senses that your lawyer will cave at the sight of a courtroom, your settlement value drops significantly. Conversely, a lawyer who tries every case and rejects reasonable settlement offers is a risk. You want someone who uses trial readiness as leverage, not as an ego trip.

Do not forget to ask about the outcomes in cases that went against them. Every liability lawyer has lost cases. How they talk about those losses is very revealing. A mature, honest lawyer will tell you clearly what happened, why it happened, and what they learned. A lawyer who claims they never lose is either lying or does not try hard cases. Ask specifically about a comparable case that did not go well. What was the weakest part of the plaintiff’s evidence? How did the jury or the judge respond? What would they do differently? This question does double duty: it tests the lawyer’s self-awareness, and it gives you insight into potential weaknesses in your own case that you might not have considered.

Finally, ask about client feedback from those similar cases. While confidentiality rules prevent a lawyer from sharing names without permission, most will let you talk to a former client who has signed a release. If a lawyer hesitates or makes excuses when you ask for a reference from a comparable case, treat that as a red flag. A confident lawyer with a solid track record will gladly connect you with someone who can describe the experience, the communication, and the final result. Listen carefully to what that former client says about how the lawyer handled surprises, whether the lawyer returned phone calls, and whether the lawyer explained each step in plain language. That level of practical information tells you more than any billboard advertisement or peer award ever will.

In the end, hiring a liability lawyer is a business decision, not a popularity contest. You are paying for judgment, skill, and specific experience. Asking pointed questions about their track record with similar claims is not impolite. It is exactly what a smart client does before committing to an attorney who will hold your legal and financial future in their hands. Get those answers in writing, compare them across multiple candidates, and choose the lawyer whose past performance gives you the clearest picture of how your own claim will be handled.