Questions to Ask Before Hiring a Lawyer

Hiring a lawyer is not just about finding someone with a license, finding someone who can do the job, or even finding someone who has done it before. It is about finding someone who has the right experience, communication style, strategy, and fee structure for your specific problem. You want to find the right fit. A good lawyer can clarify your options, manage risk, and guide a matter efficiently. Before hiring a lawyer, we at The Hamilton Firm would encourage you to ask questions that reveal experience, communication style, fees, strategy, and fit—not just credentials.
Below are some useful questions, the answers to which can provide highly salient information you can use to evaluate your options and make the right choice.

1. How much experience do you have with cases like mine?
“Like mine” means substantively similar matters, not just the same broad practice area. You are looking for someone who with the subject matter expertise for your case.
Follow-up questions
•           How many similar matters have you handled?
•           Were they litigated, settled, or resolved through negotiation?
•           What issues tend to decide cases like this?
•           What risks do clients in my situation often underestimate?
Why it matters: Specific experience usually produces better issue-spotting, more realistic expectations, and fewer surprises. A lawyer who regularly handles your type of matter will usually identify procedural traps, evidentiary issues, timing concerns, and realistic outcomes.
2. What is your assessment of the strengths, weaknesses, risks, and likely outcomes?
A trustworthy lawyer should be able to discuss both favorable and unfavorable facts. Be cautious if you hear only optimism or guarantees.
Look for:
•           Identification of the strongest evidence on each side.
•           Key legal issues and uncertainties.
•           Best-case, expected, and worst-case scenarios.
•           Estimated timelines and procedural milestones.
Why it matters: You are hiring judgment, not just advocacy. Realistic analysis is often more valuable than confident predictions.

3. How do you charge, and what will the total cost likely look like?
Legal fees are often the source of the biggest misunderstandings.
Ask for:
– Fee Structure Models   
– Billing model   Hourly, flat fee, contingency, hybrid, or phased billing?
– Rates    Attorney, associate, paralegal, and other staff rates.
– Retainer           Amount, replenishment rules, and refundability.
– Expenses          Filing fees, experts, travel, transcripts, investigators, e-discovery, etc.
– Budget range    Best estimate for the first phase and the entire matter.
– Triggers            Events that typically cause costs to increase.

Get clear answers on
•           Hourly rate(s) for everyone who may bill time
•           Flat fee vs. hourly vs. contingency
•           Retainer amount and replenishment rules
•           Minimum billing increments (e.g., 0.1, 0.2, or 0.25 hour)
•           Expenses billed separately (filing fees, experts, transcripts, travel, e-discovery, investigators)
•           Whether you will receive itemized invoices
•           Precisely how the Contingency fee works.
Why it matters: A lawyer who can explain fees clearly at the outset is more likely to manage the engagement transparently later.
How we do it: At The Hamilton Firm, we handle the vast majority of our cases on a contingency fee, meaning that you will not pay a fee unless you win. But, to the extent there are expenses involved in our representation, and while the amount of incurred expenses can vary from case to case depending on what is needed for a particular case, ultimately those will be charged back to you. Your lawyer should make that clear from the outset.

4. Who will actually work on my matter?
The lawyer you meet may not be the person doing most of the day-to-day work.
Ask: Who is the lead attorney? Will other lawyers or paralegals handle portions of the work? Who will appear in court, attend hearings, or negotiate? How is supervision handled?
Why it matters: You should know who is responsible and who is making strategic decisions.

5. What is your strategy, and what are the alternatives?
A lawyer should be able to explain a preliminary strategy for your case—not just any case in general—in plain English.
Listen for:
1.         The immediate next steps;
2.         What evidence or documents matter most;
3.         Whether early settlement is realistic;
4.         Whether motion practice is likely;
5.         What leverage exists for negotiation;
6.         What could force a change in strategy
Why it matters: This is your case. It is important for the lawyer to compare various strategies in terms of cost, time, and risk to enable you to meaningfully participate in your case as it progresses.

6. What is a realistic timeline?
Clients often hear optimistic timelines that ignore court schedules, discovery disputes, expert deadlines, or appeals. The reality is that almost all cases take longer than you think they will take. There are many practical reasons for this that most folks have not thought about at the outset of their case. There are lawyers on both sides of any case and those lawyers have multiple cases going on at any given time. Often times scheduling events like depositions depend on when multiple busy people can attend. You want a lawyer who is willing to give you realistic, not aspirational, time estimates.
Why it matters: The goal is not get a promise on a specific timeline, but rather a reality-based range founded on experience and precedent.

7. What are the strongest and weakest parts of my case?
While different cases may have similar legal and factual issues, no two cases are perfectly identical. There is no perfect case. Every case has weaknesses. Every case has risks. Every case has knowns and unknowns, especially at the beginning. The unknowns create risk and when discovered can impact a case substantially.
A useful answer should identify things like:
•           Favorable facts and documents;
•           Unfavorable facts that cannot be ignored;
•           Witness credibility issues;
•           Legal uncertainties or unsettled law;
•           Evidence that is currently missing, that will need to be preserved, or that will need to be discovered.
Why it matters: You are hiring a lawyer for his or her judgment, not just advocacy. Realistic analysis is often more valuable than confident predictions.

8. What is a realistic goal for the outcome of my case?
Again, you are looking for a reality-based answer, not a guarantee, or an unjustified aspiration. Recoveries vary from case to case and depend on a number of different factors—some of which are known at the outset, but many of which are not; some of which are predictable, some of which are not. Any answer that does not take into account the knows and unknowns is less reliable.
Why it matters: Realistic expectations are crucial in an attorney-client relationship.

9. How often do your cases settle before suit is filed/how often do your cases go to trial?

The answer to this question will give you insight into your lawyer’s experience and overall philosophy. It will also give you insight into your lawyer’s assessment of your case. Cases that are more straight forward are more likely to be resolved quicker whereas more complex cases often need to be litigated so that the parties involved can assess the relative risks involved.
Why it matters: The answer to this question also has more practical implications. The more willing a lawyer is to take a case to trial can have a direct impact on a client’s recovery, as we have discussed here.

10. If you were in my position, what would you do?
Here’s something that you won’t hear too many lawyers say: Even if it is viable, not every case is one that should be pursued. A thoughtful lawyer will usually respond by distinguishing legal possibility from practical wisdom. They may tell you that a claim is viable but economically irrational, or that a quick settlement is strategically superior despite a strong legal argument.
Why it matters: The answer reveals judgment, not just knowledge. Below is a real life example of an email conversation where we addressed many of these same questions. It has been edited to keep personal information private.

From what I have researched – my car’s value if I were to buy ‘in-kind’ today, is anywhere from $10,500 to $11,500. This number does not include the 10% sales tax I would have to pay. In addition, considering my car is totaled, but the engine, catalytic converter, transmission and airbags are intact – my totaled vehicle has a value of $3000. Remember that the property damage is wholly separate. In Tennessee the proper measure of damages is either (1) the cost of repairing the vehicle to its pre-accident appearance, function, value; or (2) the difference in the fair market value of the property immediately before and after the wreck. Because the cost of repair is greater than the value of the vehicle, we go with option 2. The best way to determine the FMV of the 2016 Camry is to look at the Kelly Blue Book value and to look at any recent sales of similar vehicles. That is separate from the personal injury damages that would be available. [Insurance company] will handle that with you directly, so it will not be a part of any attorneys’ fees calculation.

Again, forgive my lack of knowledge on this – I was just curious to learn what amount you all would work to actually recovering, what your goal would be for me to walk away with and how confident you all are that is we pursue this it is worth your time and ours. That really depends on the case. Here, [Redacted legal advice and medical information] … then we would seek damages for the full cost of his treatment plus any follow-up, his lost wages from missing work, and the pain and suffering he had to go through. [Redacted medical information] …  I’m not the kind of lawyer who is going to recommend that a client go get treatment just to drive up “value” because the value of getting better is greater than any dollar figure.

Can you walk me through exactly how the contingency fee is calculated? Sure. Let’s say that the total recovery is $100.00 (just to make the percentages easier for me). Our fee would depend on the stage of the case [note that our contingency fee structure at The Hamilton Firm is typically staggered by pre-suit settlement, recovery after suit is filed, and recovery once trial begins]. That fee comes out of the total first. Then, you would pay THF (The Hamilton Firm) back for any expenses it fronted for the case (like a filing fee, the cost of retrieving medical records, etc.). Next, to the extent there are any liens outstanding (for instance, unpaid medical bills), those would have to be satisfied. The remainder is what you all would put in your pocket, so to speak.

Are expenses deducted before or after attorney fees? After.

If we lose the case entirely, do I owe litigation costs out-of-pocket? Yes, but this is about as remote of a possibility as I can imagine. The odds of “getting zero’d” on a case of undisputed liability like this one are effectively 0.

Will you negotiate medical liens and bills after settlement? Yessir.

If I terminate representation, how would the fee actually work in practice? We would have a lien against the ultimate recovery. The amount of that lien would depend on a number of things, but mainly how close to the finish line we got you before you actually crossed it. So, let’s say that [Insurance company] offered you a settlement of $100.00 and you fired us before accepting. If you accepted that offer the next day, then our fee would be per contract + our actually incurred expenses (at least that is what we would ask a court to award). But, if you decided you wanted hire us, and then decided it wasn’t a good fit before we incurred any expenses or did much of any work, then our lien would be for much less (IF WE PURSUED IT AT ALL). The same would be true if we terminated representation — although that is something I have never done in nearly 19 years.

Who will actually handle my case day-to-day? Mainly me. This is the difference between our shop and many other firms you might see advertise on television. THP is not a “volume firm,” meaning that we don’t accept cases just because someone calls. Generally, we handle much more complex cases with greater damages. Now, to be sure, we have paralegals that will help with various different aspects of the case and you will get to know them throughout the case because they’ll contact you if/when needed and you can always contact them, but I will be involved and hands-on at every turn.

The way I look at any case is that you are hiring me and it is my name on it as the lawyer, so you are going to get me and I am going to have created everything that is submitted (sometimes with help, but never without my final approval).

How often do your cases actually go to litigation or trial? This is one of those questions where the answer is more involved than you’d think. A small percentage of my cases actually go to trial and a small percentage settle prior to having to file suit. Over my nearly 19 years, I have averaged between 1 and 2 trials per year. That doesn’t sound like many, I’m sure, and it’s really not. But, it is still more than I would bet 95% of the lawyers in this area. The same is true for my partners.

We treat every case as though it will be tried right up until it isn’t. That’s the only way I know how to do it. That generally has the effect of making our recoveries greater for our clients because the lawyers and insurance adjusters on the other side of our cases realize that we are very involved and invested and that we are not simply trying to turn over as many as we can as quickly as we can. To be sure, though, this is all very case dependent, because as I said, I handle more cases that are fairly complex and less straight forward.

Who has final authority to accept settlement? YOU. Let’s be very clear (all caps clear) about that from the jump. YOU have the final say on any offer that is made. Strategic decisions are mine. But, when it comes to accepting or rejecting a settlement offer, YOU make that call. I must and will communicate every settlement offer to you, which is an obligation I take very seriously. Even if you have told me: “Bill, you don’t have to call and tell me what they’re offering. Unless and until they get to $x, I am going to reject it.” I’m still calling to talk to you about it and discuss how we respond.

My job is not to make that decision (and I never will). My job is to give you all of the information and (hopefully) perspective that you need to make it. You also won’t have to wonder what I think about any offer. I’ll tell you and I’ll tell you plain. If I think it is a good offer, I will tell you and I will tell you why. If I think it is a bad offer, I’ll tell you that, too. But, regardless of what I think, the decision is YOURS and I’ll back your play whether it’s the play I would have run or not.

Written By: William J. Rieder