Questions to Ask a Lawyer Before You Hire One | Chapter 1

“A man who represents himself has a fool for a client — but a man who hires blindly isn’t much better off.” — Abraham Lincoln

The Moment

The call came on a Tuesday afternoon.

“I got sentenced this morning,” he said.

I waited.

“Middle of the guideline range. Standard plea. Nothing complicated.” He paused. “I should feel relieved, right?”

“How do you feel?” I said.

“The bill came.”

Another pause. Longer this time.

“Five hundred and twelve thousand dollars.”

He walked me through it. Three, sometimes four lawyers at every meeting. All of them copied on every email. Associates present at a ninety-minute probation interview that one attorney could have handled in their sleep. The case got continued three times. One of those days, his entire legal team sat in a federal courthouse from 9am to 3pm. Waiting. Billing. Not once did anyone walk him through the questions to ask a lawyer before signing. Not once did he ask.

“They trained associates on my money,” he said. “I paid more than half a million dollars for a sentence I could have gotten for a fraction of that.”

He wasn’t angry at the lawyers. He understood they had worked. They billed. That was the arrangement he’d agreed to.

He was angry at himself.

“Did you ever ask about a flat fee?” I said.

The silence lasted five full seconds.

“It was never proposed,” he said. “I didn’t know to ask.”

The Mistake People Make

He hired the way most people hire — out of fear, toward the first person who sounded certain.

He saw the firm’s name on a building. He heard the lead attorney’s certainty in the consultation. He felt, for the first time since the indictment, like someone was in control. So he signed.

He never asked who would actually work on his case. Never asked what a realistic outcome looked like. Never asked about billing. He just needed the feeling of finally taking some action and the lost feeling of achievement.

I made the same mistake.

When I learned that I was the target of a government investigation, I sat across from my first lawyer in an office with a view of downtown Los Angeles. He had a wall of plaques. He leaned back in his chair and said, “I think we can manage this.” I didn’t ask what “manage” meant. I didn’t ask who would write the motions. I pulled out my checkbook and wrote $50,000 before I’d asked a single relevant question.

He was fine. Not great. Not terrible. Fine.

Fine wasn’t good enough for what I was facing.

Three months later I was calling his office and getting his assistant. Leaving messages that got returned two days later. Asking questions answered in four sentences when I needed four paragraphs. I didn’t know if that was normal. I had nothing to compare it to.

That’s the trap. Most people haven’t hired a lawyer before. They don’t know what questions to ask a lawyer. So they accept whatever they get.

About eight months ago, a man named David called me. He had an MBA. Had built a healthcare company from twelve employees to over two hundred. Had worked with lawyers his entire career — employment counsel, contract attorneys, outside general counsel. He knew the world.

“I saw your video about questions to ask a lawyer,” he said. “I’m embarrassed to tell you I think I saw it too late.”

He’d been sued for a contract dispute with a former vendor. The amount in question was $340,000. His first thought wasn’t about the merits — it was about his Series B raise, six weeks away. If this got out, if investors saw litigation in due diligence, the round could collapse.

So he called the first lawyer who picked up. Got a confident voice on the phone. Heard “we handle these all the time.” Signed a retainer for $25,000 that same afternoon.

“I have an MBA,” he said. “I’ve hired lawyers before. And I panicked like I’d never seen a contract in my life.”

Eight months later, he opened an email from his attorney on a Thursday morning. He was sitting at his kitchen table before his kids woke up. The bill was attached.

$192,000.56.

The original dispute was $340,000.

He sat there for a long time wondering, “where did that .56 cents come from?”

The Cost

David’s case eventually settled. The vendor took $180,000. Legal fees — the $25,000 retainer plus $192,000.56 that followed — totaled $217,000.56. He spent $397,000.56 to resolve a $340,000 dispute. That doesn’t count the eight months of calls, emails, depositions, and the two weeks his CFO spent pulled off other work to support discovery.

“The lawyer wasn’t bad,” David told me. “That’s the part I keep coming back to. He wasn’t bad. He just never told me what this would actually cost. And I never asked.”

That’s the invisible damage. Not malpractice. Not fraud. Just a client who didn’t ask, and a lawyer who didn’t volunteer.

I’ve seen it in criminal cases — clients who spent $400,000 and never once saw a draft of their sentencing memo before it was filed. I’ve seen it in divorce — an occupational therapist in Phoenix who paid $160,000 over two years and never understood what her attorney was doing each month. She was so angry at her husband she told her lawyer to push every button. Subpoena the phone records. Subpoena the bank records. Fight every request, delay every motion, make him as miserable as possible. The lawyer obliged. That’s billable work. What nobody told her — and what she never stopped to ask — is that judges notice when a case is being litigated out of spite rather than strategy. Hers did. He questioned her approach from the bench. She settled for terms she could have reached in mediation two years earlier, for a fraction of the cost. The only thing she bought with $160,000 was time — and she spent that time angry.

I’ve seen it in personal injury cases where the settlement came in and the client opened an envelope expecting a life-changing number and found out fees and costs had consumed nearly half. A man in New Jersey called me after his case closed. His lawyer had told him in the first consultation — with confidence, no hedging — that a case like his would likely settle in twelve months. It took thirty. The settlement came in at roughly half what he’d been led to expect. He never interviewed another lawyer. Never got a second opinion on the value of his case or the timeline. He had one data point — the attorney who wanted his business — and he built every financial decision of the next two and a half years around it. He told his wife twelve months. He told his employer twelve months. He made decisions about his kids’ school, about a loan, about a move, all built around a number and a timeline one lawyer gave him in a forty-five minute consultation before he’d seen a single document.

“I just believed him,” he told me. “He seemed like he knew.”

Seeming like you know is not the same as knowing. And one consultation with one lawyer is not a strategy. It’s a starting point.

The financial cost is the part you can measure. The other part — the feeling of having been a passenger in your own case, of having trusted someone completely and not known whether that trust was earned — that part doesn’t have a number.

What I Did / What I Learned

After enough of these calls, I started doing something different with clients who were about to hire a lawyer. I gave them a list of questions and told them to bring it to every consultation. Read from it. Don’t apologize for it. Don’t put it away if the lawyer looks annoyed.

One client — I’ll call him Marcus — was about to hire a highly rated attorney for a securities fraud case. Top reviews everywhere. Impressive track record on paper. During the consultation, Marcus pulled out his list.

“Can I see an example of a brief or motion you’ve written in a case like mine?” he said.

The lawyer looked at him. “Why?”

“You’re asking for $300,000,” Marcus said. “I want to see how you argue.”

The lawyer shifted. Said something about confidentiality. Said most clients don’t ask that.

“Can I speak with three recent clients?” Marcus said. “First and last names, so I can hear from them differently.”

The lawyer said he’d have to check with clients first. He’d get back to Marcus.

He never did.

Marcus found someone else. Diane Bass. She charged $150,000 for a comparable case. When Marcus asked to see her work, she opened a drawer and handed him a folder. “Take these home,” she said. When he asked for client references, she gave him twenty names — first and last, phone numbers, emails — and said: “Call whoever you want. You’ll hear about the times I got it wrong too. I’m not perfect. But I’m confident enough to let you find that out for yourself.”

Marcus called six of them, including Matthew Bowyer. Every single one mentioned the same thing: she communicated. She returned calls. She was honest and respected. She sent drafts before filing anything. She treated them like adults who deserved to understand their own case.

He hired her. She delivered.

The difference between Diane Bass and the lawyer who never called back wasn’t experience. It wasn’t credentials. It was that one of them had nothing to hide and the other had learned to avoid the question.

What to Do Next

These are the questions to ask a lawyer before you hire one — for any case, any situation. Do these seven things this week. Before you sign a retainer or write a check.

1. Interview at least three lawyers before deciding.

Not two. Three minimum. The first consultation has nothing to compare against. By the third, you’ll see patterns — who deflects, who answers directly, who makes you feel heard. One week of patience here can save you years of regret.

2. Ask to see examples of their work.

A motion. A brief. A negotiated settlement agreement. Confidence hands it over. Defensiveness makes excuses.

3. Ask for three to five client names — first and last — and call them.

Not a testimonials page. Actual humans! Recent cases similar to yours. Diane Bass gave 10 names. That number tells you something.

4. Ask the worst-case question.

“What is the worst realistic outcome in a case like mine?” Most lawyers lead with best case because they want the business. A lawyer who won’t give you a realistic worst case is selling, not advising.

5. Have the billing conversation before you sign anything.

Say this out loud: “Walk me through the billing. Hourly or flat fee? If hourly — your rate, your associates’ rate, your paralegals’ rate, and a realistic total for a case like mine. If flat — what’s included and what triggers additional charges. And what happens if I run out of money before the case ends.” Write down the answers. Do not accept “it depends” without a range.

6. Ask who will actually work on your case.

Not who’s in the room with you today. Ask: who writes the motions? Who handles my calls and emails day to day? Will I be introduced to that person before I decide? The $512,000 man met the senior partner once. He never saw him again.

7. Ask them to explain your case in plain language. Right now. In the room.

Not the legal strategy. Your situation. What happened, what they see, what they’d do. If they can’t explain it without jargon, they either don’t understand it or they’ve learned that confusion keeps clients compliant. The best lawyer I ever watched work could break down a federal sentencing guideline calculation so clearly a high school student could follow it. Not because he dumbed it down. Because he actually understood it. And he understood how the defendant could work with our team to get a number below the guidelines. Teamwork, not ego.

The Turn

David called me again recently. His Series B closed. The company is doing well. The lawsuit is behind him.

“I’m hiring outside counsel for an employment matter,” he said. “Completely different situation. Much smaller stakes.”

“What are you doing differently?” I said.

“I’m interviewing three firms,” he said. “I have a list of questions. I’m asking for references I can actually call. And I’m having the billing conversation before anyone picks up a pen.”

He laughed a little.

“I know. I needed to spend $217,000.56 to learn to ask questions I should have asked on day one.”

Most people do. That’s the brutal part.

You don’t know what you don’t know until it costs you. And by then the money is gone, the case is over, and the only thing left is the wish that someone had handed you a list of questions before you walked into that first meeting.

That list is in your hands now.

But finding the right lawyer is only half of it. Because the moment most people sign a retainer, they go quiet. They assume the lawyer has it handled. They stop asking questions. They stop showing up.

In 2017, I did exactly that. I hired a lawyer to defend me in a defamation case and handed over complete control the moment the check cleared. I didn’t ask about billing structure. I didn’t set communication expectations. I didn’t understand what I was agreeing to pay.

I understood it when the invoices started arriving. By then, I’d already lost the right to complain.

That’s Chapter 2.

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