How Legal Professionals Can Ask AI the Right Questions

As legal professionals delve into the world of artificial intelligence (AI) with tools like ChatGPT, the ability to harness accurate and reliable information becomes paramount. This lesson titled “How to Ask AI Questions” focuses on mastering the art of prompt engineering for legal scenarios.

Learning Objectives:

By the end of this lesson, you will be able to:

  1. Understand the nuances of prompt engineering tailored for legal scenarios.
  2. Craft refined prompts to elicit accurate AI responses.
  3. Recognize and rectify less than optimal AI outputs by modifying prompts.
  4. Apply strategies to enhance AI’s reliability and specificity in legal contexts.

The Art of Prompt Engineering

What is Prompt Engineering?

Prompt engineering refers to the practice of refining and optimizing the way you phrase questions or commands to AI, ensuring the output is aligned with the desired outcome. Given AI’s vast capabilities, the way a question is framed can significantly influence its response.

Example 1: Legal Definitions

Suboptimal Prompt (GPT-4)
					What's copyright?

Copyright is a legal concept that grants creators of original works exclusive rights to their intellectual property for a specified period of time. This means that the creator (or copyright holder) has the exclusive right to use, distribute, perform, reproduce, and display their work, or to authorize others to do so.
Refined Prompt (GPT-4)
					Provide an in-depth definition of copyright, its implications, and how it differs from trademarks and patents.
Absolutely. Let's delve into copyright, its implications, and how it contrasts with trademarks and patents.


Copyright is a form of intellectual property protection given to creators of original works of authorship that are fixed in a tangible medium. This includes literary, musical, dramatic, and certain other intellectual creations.


Exclusive Rights: Copyright grants the creator exclusive rights to reproduce, distribute, perform, display, or license their work. Others cannot do these things without the copyright holder's permission.

Automatic Protection: Upon creation and fixation of a work, copyright is automatic. Registration, while not mandatory, can offer additional legal advantages.

Duration: The length of copyright protection varies by jurisdiction. In many places, it lasts for the life of the author plus 70 years.

Limitations: Copyright has several limitations, such as "fair use", which allows for the limited use of copyrighted material without obtaining permission.

Transfer of Rights: Copyrighted works can be sold or licensed to others. The creator can also transfer their rights entirely.

Infringement: Unauthorized use of copyrighted material without the permission of the copyright holder may result in legal action.

Difference from Trademarks and Patents:

Nature of Protection: Copyright protects original expressions of ideas (like books, songs, or movies). Trademarks protect brand identifiers (like logos, brand names, and slogans). Patents protect inventions or processes for a set period.

Purpose: Copyright encourages creativity by ensuring creators can benefit from their work. Trademarks prevent consumer confusion by differentiating products/services of one entity from another. Patents stimulate innovation by granting inventors exclusive rights to their inventions.

Duration: Copyright often lasts for the life of the author plus 70 years. Trademarks can last indefinitely as long as they're in use and defended. Patents generally last for 20 years from the filing date.
Registration: Copyright arises automatically upon the creation of a work, but registration provides additional benefits. Trademarks require registration to gain maximum protection, and patents always need to be applied for and granted.

Use of Symbols: Copyrighted works can be marked with the © symbol, patented items with "Patent" or "Pat. Pending", and registered trademarks with ®.


Trademarks are symbols, names, or slogans used to identify goods or services from one party and distinguish them from others. The main goal is to prevent consumer confusion in the marketplace. Trademarks don't expire as long as they're in use and their registrations are maintained.


Patents are exclusive rights granted to an inventor for a specific period, typically 20 years. It gives the patent holder the exclusive right to produce, sell, and use the invention. In exchange, the inventor must publicly disclose the details of the invention, so society can benefit from this knowledge.

In summary, while copyright, trademarks, and patents are all forms of intellectual property protection, they serve different purposes and protect different types of intellectual assets.

Troubleshooting Inaccurate Responses

Why Do Some Prompts Fail?

AIs, including ChatGPT, are trained on vast datasets but might not always have the most recent information or may interpret prompts differently than intended. It’s essential to recognize that AI output can vary based on:

  • Ambiguity in the prompt
  • Lack of specificity
  • Over-reliance on previously fed information

Example 2: Legal Terminology

Suboptimal Prompt (GPT-4)
					What's consideration in law?


Consideration in the context of contract law refers to something of value that is given in exchange for something else. It is one of the fundamental elements required for the formation of a valid contract. Essentially, it represents the "bargain" or the "price" for which a promise is bought.


The response is correct but doesn’t offer in-depth understanding.

Refined Prompt
					Explain the concept of consideration in contract law and its significance in contract formation.


Consideration in Contract Law:

Consideration in contract law refers to a crucial element required for the formation of a legally binding contract. It represents the mutual exchange of value or the "bargain" between the parties involved.

For a contract to be valid and enforceable, each party must give and receive something in return. This reciprocal exchange is known as consideration. It solidifies the parties' intention to enter into a genuine and enforceable agreement, rather than a mere casual promise.

Significance in Contract Formation:

Mutual Exchange: Consideration ensures that both parties are offering something of value, making the agreement more than just a one-sided promise. This mutual exchange creates a sense of balance and fairness in the contractual relationship.

Evidentiary Function: The presence of consideration often serves as evidence that the parties have a genuine intention to be legally bound. It indicates that the parties have consciously entered into an agreement, understanding the implications of their promises.

Deterrent Function: By requiring an exchange of value, consideration ensures that individuals do not enter into contracts lightly. Knowing that they have to give up something of value often makes parties more deliberate in their decision to form a contract.

Economic Function: Consideration ensures that resources are allocated efficiently. By requiring both parties to provide value, contracts based on consideration promote transactions that are beneficial to both sides.

Types of Consideration:

Executory Consideration: A promise made in exchange for another promise. For example, A promises to deliver goods, and B promises to pay for them upon delivery.

Executed Consideration: When one party makes a promise in exchange for an action by the other party. For instance, A promises to pay B upon B's completion of a specific task.

Past Consideration: Refers to a past event or action that cannot be used as consideration for a current promise. For a contract to be valid, consideration must be present or future, not past.

Limitations and Exceptions:

Adequacy: Courts usually don't assess whether consideration is "adequate" or whether what's being exchanged is of equal value. The focus is on its existence, not its amount.

Pre-existing Duty: If someone is already obligated to do something, doing that thing isn't valid consideration for a new contract.

Promissory Estoppel: In some jurisdictions, even if consideration is absent, a promise can be enforced to prevent injustice if one party has relied heavily on the promise of the other.

In summary, consideration is a foundational element in contract law, ensuring a genuine and mutual exchange in contractual agreements. Without it, a contract might lack the binding force that characterizes legal agreements, leaving parties without recourse should disputes arise.

Enhancing Reliability

Understanding that AI systems may sometimes provide outputs that are not entirely accurate is crucial. You can enhance reliability by:

  • Breaking complex queries into simpler prompts.
  • Providing explicit context.
  • Asking the AI to think step-by-step or verify its sources.

Example 3: Understanding Contract Clauses

Suboptimal Prompt (GPT-4)
					What's a non-compete clause?


A non-compete clause, also known as a covenant not to compete (CNC), is a clause commonly found in employment contracts, partnership agreements, or sale of business contracts. It restricts one party from engaging in direct competition with another party, usually after the relationship between the two ends.
Refined Prompt (GPT-4)
					Explain the implications and enforceability of non-compete clauses in employment contracts in New York.

					Certainly! Non-compete clauses in employment contracts have been the subject of scrutiny and legal challenges in various jurisdictions, including New York. Here's a look at the implications and enforceability of such clauses in the state of New York:


Protection of Business Interests: Employers often use non-compete clauses in New York to protect legitimate business interests, such as safeguarding trade secrets, proprietary information, and customer relationships.

Limiting Employee Mobility: On the flip side, non-compete clauses can limit an employee's ability to find subsequent employment in their field, especially if the non-compete has broad geographical and temporal limits.

Impact on Innovation and Free Trade: Overly restrictive non-compete clauses can potentially stifle innovation and free trade in the state by preventing skilled professionals from freely moving between employers or starting their own ventures.

Enforceability in New York:

Reasonableness Test: Historically, for a non-compete clause to be enforceable in New York, it had to pass a reasonableness test. This means the restriction should:

Be no greater than required to protect the legitimate interests of the employer.
Not impose undue hardship on the employee.
Not harm the public.
Be reasonable in both temporal and geographic scope.
Post-Employment Restrictions: New York courts have been hesitant to enforce non-compete agreements that restrict an employee's ability to work post-employment, especially if it prevents them from earning a livelihood. The courts tend to lean towards the protection of employees in these cases.

Protection of Trade Secrets: If an employer can demonstrate that an employee had access to trade secrets or other highly confidential information, New York courts might be more inclined to uphold a non-compete clause.

Potential Change in Legislation: As of my last update in September 2021, there were discussions and potential legislative actions to limit or ban non-compete clauses, similar to what has been seen in other states. Therefore, it's always a good idea to check the current legal status and any recent legislative changes regarding this issue.

Partial Enforceability: If a court in New York finds a non-compete agreement overly broad or restrictive, it has the "blue-pencil" authority, which means the court can modify the agreement to make it reasonable and enforceable rather than invalidating it entirely.

Profession-Specific Limitations: In some professions, non-compete clauses have been specifically limited or banned. For instance, New York law prohibits non-compete agreements for lawyers.

In conclusion, while non-compete clauses can be part of employment contracts in New York, their enforceability hinges on their reasonableness and the balance between protecting the employer's legitimate business interests and not unduly restricting an employee's right to work. Employers and employees in New York should consult legal counsel when drafting or entering into agreements containing non-compete clauses to ensure they are both compliant with current laws and likely to be enforceable in court.


Mastering prompt engineering is a crucial skill for legal professionals utilizing AI. By refining your prompts, understanding potential pitfalls, and applying the strategies discussed, you’ll optimize ChatGPT’s potential in your legal practice.

In our next lesson, “Directing AI Conversations,” we’ll explore advanced techniques to guide and shape AI dialogues effectively. Ensure you’re well-versed in prompt crafting, as it will lay the foundation for our upcoming topics.

Stay tuned and keep enhancing your AI skills for a competitive edge in the legal domain!

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