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A Lawyer’s Top 14 Tips for Asking Better Questions

A Lawyer’s Top 14 Tips for Asking Better Questions

November 24, 2016 | By Mandy Marksteiner | 2 Comments

A Lawyer’s Top 14 Tips for Asking Better QuestionsLike lawyers, B2B copywriters make persuasive arguments using evidence. But where does the most persuasive evidence come from?

To find out, I asked B2B copywriter Sheldon Lazarow, who is celebrating his 40th year practicing law, during AWAI’s Bootcamp.

“I’ve spent my life in a courtroom,” said Lazarow. “I have learned over the years that the case is won at the deposition stage.”

A deposition is an informal session where lawyers can ask a witness everything they know about the case. It is the best opportunity to gather evidence to be used in the courtroom, so asking better questions can lead to critical discoveries.

Depositions are a lot like interviews. Depending on how the questions go, you will either have everything you need to win the case… or pages and pages of transcript with nothing you can use.

Lazarow has interviewed thousands of people during his career and knows how to get people to open up and tell him helpful information.

Get more convincing proof by following Lazarow’s 14 tips:

Have a goal. You have to know what you are after and your goal has to be fairly specific. With each interview, you have to know the area you really want to go after. If you don’t have that goal, you are going to have a diluted interview. You are not going to have any information that you can really use.

Research the person you are going to interview. Most people don’t want to be questioned about anything. You have to find out as much as you can about that person’s life in advance. If you know about that person, you can get them to open up to you. Find out about the good things they did. It softens the person up, so when you get to the interview they are ready to talk.

Research your topic. Interviewing someone without researching the topic first will be a waste of time because you’ll never get what you want. You won’t know what to ask, and you’ll wind up asking general questions that will get you nowhere.

When you research your topic, you can start to hone your goal and think of questions that zero in on the most interesting pieces of information.

Be respectful, and make people comfortable. If the person is not comfortable with you, doesn’t like you, or doesn’t like the idea of being interviewed, you are not going to get what you want.

Don’t write down the questions… do this instead. Writing down all the questions is a very common mistake. It reduces your flexibility, and makes it hard for you to listen and think.

Instead of pre-thinking your specific questions and writing them down, you should pre-think your issues, and write down one or two words that will remind you of those issues. That way you can use your head.

Go beyond open-ended questions. Everyone knows that you should avoid asking questions that can be answered with one word, but even open-ended questions can be answered that way.

You ask your kids what they did at school today, and they can say “nothing.” It’s an open-ended question with a one-word answer. You have to know how to get a real answer.

Here’s how.

Open-ended questions start with who, what, when, where, why, and how. The problem is that asking these questions will normally only get you the bare facts. That doesn’t necessarily make for a good interview. So…

Ask about feelings and opinions. Get the person’s feelings about the facts and the person’s opinions about those facts because those are important as well.

Find out where their beliefs and assumptions come from. When you ask people questions much of what they say is assumptions or opinions. You need to get to the bottom of that, and you need to do it in a way that doesn’t put them off.

If the interviewee is assuming something you can say, “How did you come to that assumption? Did you read it in a book or an article, or have you talked to somebody who told you that?”

Ask about their sources.

Find out their true feelings. For example, maybe they have come to disagree with what they originally said, but they don’t want to admit it because it will look bad. If you can find out their true feelings and reasons, you will get into a discussion.

Listen. The biggest problem in interviewing, the reason people can’t get to the bottom of things, is that they don’t know how to listen.

What I see people do, especially when they are nervous, is think about the next question while the person is answering the previous question. When you do that, you won’t be listening to the answer.

It is important to genuinely hear the answer — even if you are taking notes. You can write down one or two words to remind you what he is saying instead of trying to write down everything he says.

Notice everything. Listen attentively. Look intently. You are not only listening to the words. You are listening to the tone of the answer. You are listening to the vocabulary being used. If you can see the person you are talking to, look at their face and their expressions. Watch them breathe. All these things together will tell you something about that person and that answer.

When you find a gem, dig deeper. When you are really paying attention, you might find an interesting little gem in their answer. Follow that gem. Ask more questions about that item. It will lead you to some very interesting things.

Feel comfortable with silence. An open-ended question requires people to think about their answer. While they are thinking all you get is silence, and you have to be comfortable with the silence. Just let it be. Something will come sooner or later. You have to let them think.

Never interrogate people. There are some people who shoot machine gun questions at people without really listening to the answers. They don’t care about the person they are questioning. They don’t care about their feelings. They don’t care about their answers. They are not empathetic to anything, and they are annoying. (It is annoying to have one question after another shot at you without any indication that your answers have been heard.)

Those are poor questioners. You don’t want to interrogate, because then people just clam up and get stubborn.

Be a nice person. Know a lot about the person. Know a lot about the information. Be genuinely interested in their answers and in how they came to those conclusions. Be interested in how they learned what they did and in what mistakes they made on the way.

Use these tips for asking better questions next time you interview a client (or their customer) for a B2B project and see what gems you can uncover. It could make all the difference in the success of your copy… and help you make your client very happy!

If these tips have helped you, let us know, and if you have one to add, please share it in the comments below.

About the Author

Mandy Marksteiner

Latest in B2B Copywriting


  • All very good tips and I can tell they would be helpful in all types of interviewing situations. One other that I try to follow, sometimes with difficulty, is to go into the interview with no preconceived assumptions or biases.

  • Well done Mandy and Sheldon. I’ve been a lawyer for 30+ years, and while I haven’t spent all of that time in a courtroom, I’ve spent enough of it in courtrooms and depositions to completely agree with Sheldon. I’ve often thought about the parallels to copywriting, but not this specific topic, and not in this way. I will now!

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