Questions for Your Client

October 11th, 2023 / By

In my last two posts, I explored the ways in which GPT-4 could help a new lawyer identify legal issues in a client problem. Most law graduates are fairly adept at issue spotting, but they can still benefit from GPT’s advice. In this post I consider a task that fewer graduates have a chance to hone while in law school: questioning a client to obtain key facts related to the client’s problem.

The Uncle, the Guest Room, and the Fentanyl

I outlined the basic facts of this client problem, drawn from a sample bar exam question, in my first post. The client was staying in a guest room at his uncle’s house. While the client was away from the house, police knocked on the front door of the house and asked the uncle if they could search the house. The police offered no reason for the search, other than that they were investigating a noise complaint, but the uncle consented to the search. Police found fentanyl in the guest bedroom and charged the client with possession. The new lawyer wants to file a motion to suppress the fentanyl.

In my first post, GPT-4 helped the new lawyer identify possible issues to raise in this motion. In the second post, GPT-4 responded to a request to narrow those issues to the two most promising ones. Those issues were the client’s standing to challenge the search and whether the uncle’s consent was valid. I continued my dialogue with GPT-4, asking it to give me the most important questions to ask my client with respect to those two issues. GPT-4 responded:


When focusing on the two central issues of standing to challenge the search and the validity of the consent to search, here are the most important questions you would want to ask your client:

1. Standing to Challenge the Search:

a. Nature of Stay: – How often have you stayed in the guest bedroom at your uncle’s house? – Have you stayed there regularly or was this a one-time event? – How long was your stay? Was it just for the night, or did you have an extended stay?

b. Personal Belongings: – Did you leave any personal belongings in the guest bedroom? If so, what kind of belongings (e.g., clothes, luggage, personal documents)? – Were any of these belongings visible to anyone entering the room?

c. Expectation of Privacy: – Did you have any conversations with your uncle or any other resident about the privacy of the room during your stay? – Were you given a key or any means to lock the guest bedroom? If so, did you lock the room when you left?

d. Knowledge of Prior Guests: – To your knowledge, had other guests used the room shortly before or after your stay?

2. Consent to Search:

a. Uncle’s Understanding: – Do you know if your uncle understood what he was consenting to when he allowed the police to enter? – Is there any reason to believe your uncle might have felt pressured or coerced into giving consent?

b. Relationship with Uncle: – How would you describe your relationship with your uncle? (This can provide insight into whether the uncle might have any reason to allow or disallow a search.)

c. Prior Conversations: – Had you discussed with your uncle the possibility of police or others searching the room or the house? – Were there any explicit or implicit understandings about the privacy or security of the guest room between you and your uncle?

d. Presence of Contraband: – Were you aware that the fentanyl was in the guest bedroom? – If so, why was it there, and who had access to the room during your stay and after?

The answers to these questions can provide crucial information to determine the viability of a motion to suppress. They can also help in formulating a defense strategy beyond the suppression motion.


This is an excellent list of questions to begin fleshing out the motion to suppress. The new lawyer might think of additional questions while talking with the client, but GPT-4’s outline offers the new lawyer a strong starting place. If the new lawyer has never interviewed a client to uncover the facts of a dispute, GPT-4’s list will help the lawyer through that initial interview. Even if the lawyer is fairly experienced, GPT-4 generated this list in less than 30 seconds. Rather than type out their own questions (which will take much longer than 30 seconds), efficient lawyers can start with GPT-4’s list and supplement the questions as needed.

I wondered if GPT-4 could help with more interpersonal aspects of client interviews, so I entered another prompt: “Thank you for this list of questions to ask my client. What if my client answers the last question by saying that he didn’t know the fentanyl was in the bedroom–but I think he’s lying. How should I handle that situation?”

GPT-4 responded with a detailed discussion of how to handle the ethical challenge of representing a criminal defendant who might lie on the stand. The advice was sound, including a reminder that the new lawyer could seek guidance from senior colleagues, ethics hotlines, or the local rules of Professional Conduct. GPT-4’s performance on this question suggests that it can be an important sounding board on ethical issues. As with other questions, it may not give a full answer–but it is advice that a lawyer can obtain quickly and confidentially.

In this situation, however, I was looking for something different. I explained to GPT-4 that I wasn’t yet worried about representing this client at trial; very few criminal cases proceed to trial. Instead, I explained that I was seeking “a gentle way in which I can encourage my client to be more open.” GPT-4 responded:


Certainly. Building trust and creating an environment where the client feels safe and understood is crucial. Here are some gentle approaches you can use to encourage your client to be more open:

  1. Reiterate Attorney-Client Privilege: Remind your client that everything they share with you is protected by attorney-client privilege. This means that you cannot and will not share their information with others (with very limited exceptions). This can reassure them that their disclosures will remain confidential.
  2. Express the Importance of Truth: Gently explain that for you to defend them most effectively, you need to know all the facts, even the uncomfortable ones. You can phrase it in a way that emphasizes strategy: “The more I know, the better I can anticipate the prosecution’s moves and build a strong defense.”
  3. Non-Confrontational Approach: Instead of directly confronting them about a potential lie, ask open-ended questions that give them an opportunity to provide more details or correct any previous statements.
  4. Empathy and Active Listening: Make sure you listen actively and show empathy. If your client feels you are genuinely trying to understand and aren’t judging them, they may be more willing to open up.
  5. Refrain from Showing Doubt: If you show disbelief or doubt, your client might become defensive or more closed off. Even if you have doubts, try to maintain a neutral and understanding demeanor.
  6. Share General Information: Sometimes, sharing general anecdotes (without breaching confidentiality) about how honesty from past clients helped their cases can encourage your client to be more forthcoming.
  7. Reassure Your Commitment: Let your client know that regardless of the details they provide, you’re there to defend their rights and interests to the best of your ability.
  8. Ask About Their Concerns: Sometimes clients have specific fears or concerns about disclosing certain information. By directly asking about their concerns, you can address them and potentially alleviate their fears.

Building a strong attorney-client relationship based on trust is key. Over time, as you work together and your client sees your commitment and advocacy on their behalf, they may become more open and forthcoming.


This is a good answer: It would remind the new attorney (or teach them for the first time) about some ways to gain a client’s trust. And like the ethical counsel, this advice is available quickly and confidentially. I was disappointed, however, that GPT-4 didn’t recommend an approach that I often found successful with clients facing criminal charges. I continued my conversation with GPT-4 by asking: “What about saying to the client: ‘The prosecutor will try to build as strong a case as possible. Can you think of any evidence the prosecutor might offer that would show that you knew about the fentanyl? Or that the fentanyl belonged to you?'”

GPT-4 liked my approach and offered reasons why it would work:


That’s a strategically astute way to approach the situation. By framing the question this way, you’re not directly accusing or doubting your client. Instead, you’re positioning the conversation around preparing for the prosecutor’s potential strategy.

This approach accomplishes a few things:

  1. Strategy Focused: It shifts the conversation from a potentially confrontational one about honesty to a strategic discussion about anticipating the prosecutor’s moves.
  2. Empowerment: It empowers the client to be an active participant in their defense by thinking proactively about potential evidence.
  3. Indirect Confirmation: If the client does provide insight into potential evidence, it may give you a better understanding of the actual situation without having directly challenged their earlier statements.
  4. Building Trust: This method shows the client that you’re on their side and preparing for all possibilities, which can further cement trust in the attorney-client relationship.

Using this approach, you can gather potentially important information and gauge your client’s reaction, all while fostering collaboration and trust.


Here’s what I learned from using GPT-4 to prepare for this client interview:

  • For this problem, GPT-4 did an excellent job generating relevant factual questions for the client. A conscientious lawyer would want to consider additional questions, especially if the legal issues are more esoteric than the ones listed here. But GPT-4 can at least jump start the process of brainstorming questions.
  • GPT-4 may serve as a useful sounding board on ethical issues. In my experience, lawyers sometimes ignore red flags or feelings of unease. GPT-4 offers a quick, confidential way to check those feelings. Of course, lawyers should always follow up by checking the Rules of Professional Conduct, calling a hotline, or talking with more senior colleagues (as GPT-4 itself suggested). But GPT-4 may offer a useful resource on ethics. I plan to explore that possibility further in a future post.
  • GPT-4 can offer basic advice on the interpersonal aspects of client interviewing. But knowing what to do isn’t the same as doing it. In a world increasingly dominated by AI, good interpersonal skills may distinguish excellent lawyers from mediocre ones.
  • It is fun to suggest approaches to GPT-4 and get its feedback. I don’t know yet if GPT-4 is a “yes bot” who will approve any approach I suggest. That’s another avenue to explore in a future post.
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