How To Work With Your Lawyer (Or Hire One)

I was eleven at my grandfather’s funeral. Afterward I walked past a side room at the funeral home. The men who ran the place were laughing, talking about dinner, talking about a football game. My grandfather was gone. It was the worst day of my life. For them, it was Tuesday.

I never forgot it. Years later I sat across from a criminal defense lawyer with my freedom on the line and thought about it again. Was I in his side room? Would he go home that night, eat dinner, watch Jeopardy, and forget my name was attached to a government file on his desk? In other words, “did he really care?”

I never asked him. That’s the first thing I got wrong about how to work with your lawyer.

The problem

Most people facing a federal case land in one of two spots with a lawyer. Either they haven’t hired yet and don’t know what to ask, or they already hired someone, feel ignored or dismissed, and believe there’s nothing left to do because starting over costs money they don’t have.

Both spots come back to the same twelve questions. Whether you’re hiring someone new or figuring out how to work with your lawyer you already have, the questions are the same. Ask them before you sign. Or use them today, on the lawyer sitting across from you right now.

Someone in our community said this to their lawyer after ten days of silence: “If I were your son, is this how you would advise me? Not calling me back for ten days. Making me feel like an inconvenience. Telling me you don’t want to push the U.S. attorney anymore.” That question changed the relationship. The lawyer started calling back.

The lesson

One. Is this just a job to them?

Go back to the funeral home. The men working there weren’t cruel. They did this every day, and every day becomes routine. Before you hire, ask why he does this work. Listen for whether the answer sounds rehearsed. If you already hired someone and it feels like he’s going through the motions, say it: “I need to know you’re still invested in this, not just processing it.” Watch what he does with that.

Two. Can you speak to a few people he’s represented?

At our company, if someone considers hiring us, I offer to connect them with people we’ve worked with. Do your own vetting. It’s in my interest to tell you we’re great. Get the version from someone with nothing to gain by lying to you.

Here’s what happens when you skip this. A lawyer told me, “Justin, I think we can beat this case.” I asked how much. I wrote the check before he finished the sentence. It didn’t work. I went to another lawyer. He said something similar. I wrote another check. I never asked anyone about his actual record. I wrote checks based on what I wanted to hear.

If you already hired someone, it’s not too late. Ask: “Can you connect me with someone you represented in a case like mine?” Whether he can produce anyone tells you something about the lawyer you’re already paying.

Three. Hourly or inclusive, and what does winning look like?

An inclusive rate means you know the number before you sign. One figure, covers the case start to finish. An hourly rate means the number depends on how the work unfolds, and sometimes on how many lawyers sit on one call at seven hundred fifty dollars an hour apiece.

I had an hourly agreement once. When the bill arrived, I poured half a glass of wine before I could open the envelope. I knew it would be bad. I had no idea how bad until I looked. Ask upfront: what’s the inclusive rate, is there a payment plan, and if it’s hourly, can associates or paralegals handle some of the work at a lower rate.

If the hourly bills already cost more than you can carry, ask this week whether he’ll move to an inclusive arrangement. Whether you’re hiring or already stuck, ask what winning looks like, in his own words, with a date attached.

Four. How well do they write, and how persuasive are they?

Ask to see a recent motion or filing. In a criminal case, look at where the judge landed. If the government asked for fifty-one months and the defense asked for thirty-three, where did the sentence fall, and how much of that gap closed because of the writing.

If you already hired someone, ask to see the actual draft of anything going to the judge, not a summary. If you’ve never seen an actual draft, ask why.

Five. Who else in the firm does the work, and what is he actually working against?

Some lawyers close the deal, then hand your file to someone in the firm you’ve never spoken with. Get in writing exactly who handles your case day to day.

If you were sold by one lawyer and only hear from someone else, ask who’s responsible and request a call with that person. At the same time, learn what he’s working against: court schedules, a prosecutor’s timeline, other cases on his desk. None of that moves at the speed of your anxiety. Knowing his real constraints doesn’t mean accepting silence. It means you can tell a broken promise from how the system moves.

Six. Have they had issues with the state bar?

The state bar website is public in every state. Type in the name. Check for complaints, sanctions, trust account issues. Give the lawyer a chance to explain anything you find. If you already hired someone, check now. It won’t change who you hired. It tells you what you’re working with.

Seven. Will they send status reports, and are you keeping your own record?

A bill for nine thousand dollars arrives and you’ve spoken to your lawyer twice all month. Ask for weekly or biweekly updates in writing before you sign.

If you already hired someone, ask for this now, and start your own log: date of every call or email, what was discussed, what was promised, by when. When you feel ignored, you won’t rely on a feeling. You’ll have a page. Bring him a fact instead of a complaint: “It’s been ten days since our call on the fourteenth. You told me I’d have an update by the seventeenth.” That’s harder to wave off than “you never call me back.”

Eight. Ask about a case that didn’t go well, and tell him what you need.

Nobody is perfect. Ask him to walk you through one that didn’t, and what he’d do differently now.

Whether you’re hiring or already in it, ask what he needs from you to move the case forward, documents, answers, decisions, on what timeline. A lawyer working with someone who shows up prepared moves faster than one working with someone who stays quiet. This runs both ways.

Nine. Do they offer payment plans?

If the work stretches across months or years, don’t hand over the whole fee on day one. Ask for a payment plan tied to the actual stages of the work, in writing. If your current agreement doesn’t allow this, ask this week if it can change. Circumstances change. Lawyers adjust more than people assume.

Ten. Does the retainer require a fixed balance in trust?

A man came to me after hiring a criminal defense lawyer for one hundred thousand dollars up front, against an hourly rate of seven hundred fifty dollars. He hadn’t read the agreement closely: the trust account had to stay at one hundred thousand dollars at all times. The first month burned through sixty thousand in fees. He thought he had a cushion. Instead he got a bill for sixty thousand more, because the balance had to be refilled every time it dropped. That’s standard practice, not deception. Read that page before you sign, or reread your own agreement this week.

Eleven. Are the online reviews real?

Look for a first and last name on every review. Lawyers have asked me to post five-star reviews when I was never their customer. A page of “Joe M.” and “Mary Q.” proves nothing. This won’t change a decision you already made. It tells you how much weight to put on what brought you here.

Twelve. Can this lawyer be reasoned with?

We’ve interviewed federal judges, including Judge Bennett, who talk about how little weight a lawyer’s words carry at sentencing compared to the defendant’s own. I’ve had lawyers dismiss judges like that outright: “that judge doesn’t know what he’s talking about.” A man who’s sentenced thousands of defendants apparently knows less than a lawyer who’s been doing this for thirty years.

Thirty years doesn’t make it right. For three and a half years before I surrendered, I sat on the couch every day eating bonbons, cookies, and donuts, chewing tobacco, running the same routine with discipline. Doing it every day didn’t make it a good idea.

Before you hire, ask how he responds when he’s shown he’s wrong. If you’re already stuck with someone, this question matters most. Bring him a fact, a strategy, a piece of evidence. Watch whether he engages or shuts it down because it didn’t come from him. If it’s always his way no matter what you or the record show him, say so. You may not change him. You’ll know exactly who you’re paying.

A word on the four who gave me a chance

When I came home from prison, most lawyers wouldn’t give me the time of day. They assumed I was a consultant playing lawyer, offering guarantees I had no business offering, negotiating plea agreements that weren’t mine to negotiate. I told them: I’m not a lawyer, I don’t do that work. The more I pleaded my case, the worse it went.

Four lawyers gave me a chance: Alan Eisner, Mark Werksman, Diane Bass, Peter Hardin. I’ve worked alongside all four for years. Our legal directory is being rebuilt right now to feature them alongside hundreds of others, based on how much our community has asked for it. I’ll share it soon.

The assignment

Pick the lawyer relationship you’ve been avoiding a hard conversation about. This week:

Start a written log of every communication going forward, even the ones you already remember. Dates, what was discussed, what was promised.

Pick the one question from the twelve above you’re most afraid to ask, or the one fact from your log you’ve been sitting on.

Send it. Email, not a vague text. Put a deadline for a response in the message itself.

If you haven’t hired a lawyer yet, pick three of these twelve questions and write out, word for word, how you’ll ask them in your first meeting.

Closing

I didn’t ask these questions before I hired my lawyer. I wrote checks instead, because someone told me what I wanted to hear and I was too scared to ask anything harder. I regretted it more than once.

You don’t need a new lawyer to learn how to work with your lawyer you already have. You need the log, the question, and the email you send this week.

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About the Author

Hi, I’m Justin Paperny. I am committed to creating content that will help you prepare for the best outcome. To succeed, however, you must do more than read or watch my videos: do not be a spectator. Get engaged and start creating!