By Jim Calloway and Julie Bays

In August’s Law Practice Tips column, “ChatGPT, Artificial Intelligence and the Lawyer,”we covered the development of AI tools and some challenges they have presented to attorneys who did not appreciate the limitations of ChatGPT. This month, we will look at more AI-powered tools and techniques for using them.


One thing artificial intelligence does well is summarizing lengthy documents, such as depositions or long court opinions.

The Association of Immigration Lawyers of America (AILA) has been experimenting with powerful AI tools in their area of interest. A recent U.S. Supreme Court opinion, U.S. v. Texas, involved immigration law and was 75 pages long. Their tool quickly prepared a summary of the opinion, just over 14 pages in length. The summary is separated by page numbers in the original opinion so that if one had questions, it would be simple to read the page the summary was created from. Greg Siskind, an attorney in AILA, shared the summary, and I have placed it for download on Dropbox.

While many AI tools can create document summaries, browser-based tools are a good place to begin since they are free. But before we get to those, we should mention Claude.


Claude is an advanced natural language chatbot with capabilities that seem superior to those of ChatGPT. It is available at no cost during its beta phase. What distinguishes Claude from other chatbots is several features that surpass those of ChatGPT, including the ability to analyze documents containing up to 75,000 words and understand and compare multiple documents. Claude’s database knowledge is updated through early 2023, and it supports multiple languages. The platform also demonstrates remarkable strengths in advanced reasoning and logic, as well as specialized academic knowledge.


If one wants to have an AI-powered research (not legal research) tool, the best option may be the AI tools built into existing search engines. The lawyer will need to review and revise the settings to share as little of your prompt information as possible.

Google’s Bard

Google’s Bard is everyone’s favorite price – free. To use Bard, you need a personal Google account that you manage on your own or a Google Workspace account for which your administrator has enabled access to Bard. You still can’t access Bard with an account managed by Family Link or with a Google Workspace for Education account designated as under the age of 18. It can be accessed at

Google’s Bard is listed as an experiment and readily admits to having limitations and learns from feedback. Bard is a conversational AI model capable of dialog, built on Google’s LaMDA (Language Model for Dialogue Applications). Be aware that Google collects conversations you have with Bard, along with your IP address, feedback and usage information. A subset of conversations is sent to trained reviewers and kept for three years, with automation tools to remove personally identifiable information. Google asks that you please not include information that could identify you or others in Bard conversations. To limit it from using your prompts, you can go to your Google My Activity page to toggle off storing your activity. You can also delete your activity from this page.

Bard’s data, unlike ChatGPT, comes from the internet. Crafting good prompts is a skill many of us will be trying to improve. Document summaries are one of the AI tools lawyers will use – a lot. There is a character limit for a Bard prompt. When prompted to summarize a 10,000-character article, it would only accept about 3,000 characters. However, you can obtain summaries of longer articles posted online by using the prompt “Summarize the article at [link to document].” These are generally quite accurate, but it is possible that AI may add its own “thoughts.” At least with document summaries, you will have the document handy for comparisons.

Bing Chat

The “new Bing” is a chatbot incorporated into the search engine. You may be logged in to a personal Microsoft account. The chatbot is also available in the Edge browser, the Edge mobile browser and the Windows 11 search bar. The new Bing screen prompts, “Ask me anything,” allowing up to 1,000 characters. You can run a regular web search or toggle Chat. Bing Chat works best with Microsoft Edge or the Bing mobile app. It is available at no additional cost to subscribers to Microsoft 365 E3, E5, Business Standard and Business Premium. And in the future, it will be available as a stand-alone offering for $5 per user per month.

Chat in Bing is developed on code from their partner, OpenAI. OpenAI powers ChatGPT. Bing, owned by Microsoft, acknowledges the same foibles as Google. You can review their approach to responsible AI.

Bing Chat has a few different elements that contrast with Bard. First, the user chooses a conversational style: more creative, more balanced or more precise. In Chat, you can add 2,000 characters, which is an increase from the regular Bing search. Instead of editing your prompt, you can continue to converse with Bing Chat by adding qualifying questions until you choose “New Topic.” The results for each type of search (creative, balanced or precise) are color coded so that it is easy to distinguish which mode is used.

Bing Chat also has a feature distinct from Google’s Bard. In the more creative mode, it will generate images powered by DALL-E. It has restrictions so that you cannot misuse certain images, like celebrities, public figures and organizations. For more information, see PC Mag’s review of Bing Chat.

DRAFTING TOOLS is not for legal writing, but it is a great tool for writing for a general audience, whether it is a blog post or website copy. There is a free version that is limited to writing 2,000 words per month. The Pro version costs $36 per month but licenses up to five users and includes priority tech support.


Spellbook is an AI contract drafting software trained on thousands of business contracts, as well as other data. I would encourage you to watch the four-minute video at In just a few short years, many, or perhaps most, contracts will be drafted using contract drafting tools. Spellbook’s website states it was trained on billions of lines of legal text. We saw this demonstrated at ABA TECHSHOW. It was amazing to watch as it proposed several contract provisions and allowed the lawyer to choose the one that was preferred.



Descript allows you to record a video or audio, and it will create a transcript of the words in the recording. One can then edit the audio by editing the text, and it will change the recording to reflect your changes. It will also automatically remove the “err” and “umm” sounds we often utter while recording.

Descript offers different plans to suit different needs and budgets. With the Free plan, you can record, transcribe, edit and mix up to one hour of content per month with filler word removal. With the Creator plan, you can access more features – such as overdub, screen record and publish – and transcribe up to 10 hours of content per month for $12 per month or $144 per year. With the Pro plan, you get advanced features, such as multitrack editing and advanced export options, and can transcribe up to 30 hours of content per month for $24 per month or $288 per year. If one desires custom invoicing, more flexibility, security or expedited support, you can also opt for an Enterprise plan by contacting the Descript team.

Julie Bays reviewed Descript for the ABA Law Practice Magazine.


CoCounsel and Copilot 

CoCounsel from Thomson Reuters and Copilot from Microsoft were covered in the first installment of this series. We note them here again just to say that we believe these will be the tools most likely to be adopted initially and broadly by lawyers.

CoCounsel, the legal research tool, was retailing for $500 per user per month. Even at that price point, we have heard many positive comments from satisfied customers as to how their legal research was improved by using this tool.

Copilot from Microsoft is coming soon and will use all your data in Microsoft files (e.g., Word, Excel, Outlook and PowerPoint). That will provide some amazing capabilities. Sharon Nelson and Jim Calloway recently recorded a Digital Edge podcast, “Microsoft’s Copilot: New AI Tools for Microsoft 365!” with Microsoft’s Ben Schorr. The day after they recorded their podcast, Microsoft announced pricing for Copilot at $30 per user per month on top of your Microsoft 365 subscription.


In the AI world, your questions or queries are called prompts. These are sets of instructions we provide to AI chatbots to get them to perform a task. Multiple queries can sharpen the results, with each building on previous prompts.

On one level, prompts are very simple. Just ask the AI a question. But learning how to use prompts effectively is something that requires a great deal of research and some trial and error. If you are worried about the impact of AI on your future, invest some time in learning how to do prompts on your preferred tool well.

According to the Prompt Engineering Guide, elements of a prompt may contain any of the following elements:

  • Instruction – A specific task or instruction you want the model to perform
  • Context – External information or additional context that can steer the model to better responses
  • Input Data – The input or question that we are interested to find a response for
  • Output Indicator ­– The type or format of the output

In addition, your attention is directed to “Basics of Prompting,” also from the Prompt Engineering Guide site. This resource is well written with very basic language. For a deep dive into prompt engineering, see the primer from Dozens of similar resources are available online.


It is worthwhile to note that ChatGPT and other generative AI tools present many intellectual property issues. If you create something useful with AI, can it be copyrighted? According to the courts and the U.S. Copyright Office, the answer is no. But you can modify the AI-created content sufficiently to claim it as your own and copyright it. That sounds like there will be many factual questions involved.

One entertaining AI activity is to create images for entertainment. So you could upload pictures of a relative, and it will generate their portrait as if painted by Picasso, Van Gogh or Rembrandt. Harmless fun. That is, until a well-known living American artist shows up at the lawyer’s office complaining of a huge drop in sales since the release of these AI tools and that six of the top 10 Google searches for her work are now AI-generated images in the style of her work. Authors may feel it is inappropriate that the online versions of their books were used to train the AI. There have already been suits filed by creators claiming the AI training violates their rights.

A recent Digital Edge podcast, “Generative AI and Copyright: Collision is Inevitable,” featured Vedia Jones-Richardson, a principal with Olive & Olive PA, a North Carolina-based intellectual property law firm, where she leads the trademark and copyright practice group.


ChatGPT and other LLM (large language model) AIs are easy and fun to use. That is how they became so popular so quickly. Despite some lawyers’ well-reported stumbles with initial uses of ChatGPT, most lawyers will use AI tools because they are powerful and accomplish tasks in minutes that would take a human hours or days. Now we are at the “good time to experiment” stage. It is time to give some of these tools a try.

And if we haven’t provided you with enough reading material in this column, let’s close by directing you to a post from author and legal futurist Richard Susskind, who is well known for his observations on the future of law practices and the legal system, “AI in the law – six thoughts.”

Authors’ Note: Thanks to Catherine Reach, director of the Center for Practice Management at the North Carolina Bar Association, for her contributions to this column. 

Mr. Calloway is the OBA Management Assistance Program Director.

Ms. Bays is the OBA Practice Management Advisor, aiding attorneys in using technology and other tools to efficiently manage their offices.

Originally published in the Oklahoma Bar Journal — September, 2023

Technology innovations and artificial intelligence tools have generated much discussion this year. There have been many truly amazing uses for AI demonstrated and many of the tools we currently use are now adding AI components. This is a perfect time to attend ABA TECHSHOW 2024, scheduled February 14-17, 2024, at the Hyatt Regency Chicago. The Oklahoma Bar Association Event Promoter code is: EP2403. This allows Oklahoma lawyers to register at the discounted ABA membership rate, if they do so before January 11, 2024. OBA Practice Management Advisor Julie Bays and I will be on the faculty. Whether your questions involve traditional legal tech implementations or the new cutting-edge tools, this is an outstanding opportunity to attend a meeting with many legal tech experts and technology solution providers.

Register on the ABA TECHSHOW website.


In private practice, I was threatened several times, always related to domestic and protective order cases. I didn’t consider any of them serious and took no action. But that was decades ago. Today we need to appreciate that threats must be taken seriously. Have you had a conversation with all of the people who work with you on how to handle these threats?

This week you can handle this more easily because Theda C. Snyder and Attorney@Work recently published Specific Steps to Take If You Receive a Threat. The piece is well-written and comprehensive. I suggest you share the link with everyone in your office, give them a deadline to complete reading it and then schedule a meeting to discuss their reactions. You may learn some things you did not know about past threats.

Technology advances change many things. A few decades ago, most lawyers would likely have rejected the idea that it would ever be a good idea to record a conversation between an attorney and a client. There would have been numerous philosophical objections and practical

objections, including the cost to transcribe the recordings. Many readers, no doubt, would still agree with that.

But today’s artificial intelligence tools allow affordable recordings and transcriptions. Transcripts could have many uses. If a client seems confused about a recent consultation, how handy would it be to upload a transcript of the consultation to the client portal so the client could review it without incurring more fees? Or how nice would it be to have a transcript of your interviews with critical witnesses? No doubt many lawyers dealing with Office of General Counsel investigations have likely wished they had transcripts of certain meetings.

Whether you think this is a good idea or a crazy one, read “Can Lawyers Legally and Ethically Record Conversations with Clients Using Artificial Intelligence?” by Carolyn Elefant. Ms. Elefant has been dispensing advice to small firm lawyers for decades via her My Shingle website. Her step-by-step approach to this subject is a great example of how to analyze these issues, including the ones relating to client consent

“Lawyers have hated passwords since passwords first made their appearance,” some of my colleagues recently wrote. So true.

Emerging AI tools mean it is easier to crack passwords. So, the standard advice for strong passwords is now at least 15 characters, with requirements of upper-case and lower-case letters, numbers, symbols and maybe a drop of blood (OK, not really.) The challenge is most of us cannot remember that long of a string of random characters and creating passwords we can remember, typically by inserting dictionary words within them, makes them easier to crack. From my point of view, the only rational solution is a password manager. The good thing about password management is that as you get more login credentials saved, you benefit from quicker logins.

Many of us who follow technology have turned against the previously popular tool LastPass. Not only did they suffer a major breach last fall, but their messaging in its wake was misleading at best with the major disclosures not released until the Christmas holidays. I switched to 1Password. PC Magazine highly ranks Dashland and Bitwarden in its best password managers of 2023 roundup.

Accounts that can access your financial information or client information should be secured with two-factor authentication. The most common way of doing this is a text message confirmation code is sent to your phone that must be entered to complete your login. Many password managers also support two-factor authentication.

My podcast teammate Sharon Nelson and two of her colleagues wrote about the next step in login security in their post Passwords May Be Extinct Sooner Than You Think. They note that thanks to passkeys, the days of passwords will soon be numbered. Ironically that probably will not eliminate password managers as they evolve to managing some passkeys and some remaining passwords because some sites that haven’t upgraded their login yet.

Additional reading: Why passkeys from Apple, Google, Microsoft may soon replace your passwords CNBC.

This month the Oklahoma Bar Association Journal has a legal ethics themed issue. We believe in sharing with others in the profession. So you can access the entire issue as a PDF or use the handy index of the Table of Contents to select the articles you wish to read online.  Two of the articles cover AI and ChatGPT.

There is also a heartwarming story about one young lady and her life-changing experience of support from a CASA volunteer.

In November 2022, OpenAI released ChatGPT. ChatGPT, along with other artificial intelligence (AI) tools, has dominated the conversation about cutting-edge technology and legal technology tools during 2023. The reactions have ranged from “the most entertaining thing on the internet” to an incredible new tool that will change society in a positive way to a corporate tool that will allow companies to be more efficient and profitable (often by a reduction in workforce) to a potentially dangerous development, that if allowed to expand unchecked without regulatory safeguards, could lead to global instability and, possibly, an extinction event.

To summarize, on the internet hyperbole scale, predictions about ChatGPT’s impact range from Nirvana to Armageddon. Whatever happens will likely be between these two extremes.

ChatGPT is a large language model (LLM) AI. This means its training involved digesting almost everything on the internet, including Wikipedia and many books, as of September 2021. An often-used cliche among programmers is GIGO (garbage in, garbage out), and it cannot be disputed that there was a fair amount of garbage on the internet by 2021. ChatGPT is aware of the current date based on the date and time stamp of your query, and it sometimes refers to events that took place post-September 2021, possibly based on others’ queries. Unanswered questions and apparent inconsistencies such as these are why many IT professionals call ChatGPT a “black box.”

Since the November 2022 introduction, there have been many new products incorporating ChatGPT. It set a record by amassing 100 million monthly active users within two months (for comparison purposes, TikTok required nine months and Instagram more than two years to reach that mark). This reaction was caused by how well the product performed. It is simply stunning. Interacting with a chatbot that chats with you conversationally like another human and has vast amounts of accurate data to use is impressive. The speed and clarity of its responses are amazing. 


ChatGPT displays many human-like traits. Not only will it answer your questions easily and quickly, but, like a human friend, it may sometimes tell you what you want to hear, and sometimes it may share outright fabrications (called hallucinations). Just like a human, it might slip and share something you didn’t intend to be shared.

ChatGPT’s responses are very confident and persuasive. As Ed Walters, co-founder of Fastcase who also taught “The Law of Robots” at Georgetown University Law Center, says, “The answers are often totally wrong, but highly convincing.”

Some lawyers will learn of that credibility issue and decide never to use ChatGPT or any other AI. That is probably not the correct lesson, as AI tools will be increasingly hard to avoid and will provide many time-saving benefits in the very near future.

There are many positive ways that these tools can be used today, and there will be hundreds more. For example, you are traveling with your family, and an automobile breakdown strands you for the day in a city you never intended to visit. A quick query on the ChatGPT app on your phone for the top 10 things to do in that city will produce a detailed list with descriptions. It is probably quite accurate. But if not, so what? The point isn’t whether some experienced, objective human travel expert might disagree with some suggestions. The point is receiving a list with useful information you didn’t have in seconds.

I have Google, DuckDuckGo and ChatGPT installed on my phone. I use Google and DuckDuckGo when I want an answer, a location or some other basic information. But if I want an explanation, ChatGPT is the first option for a search.

I also note that OpenAI has provided a fix for the concern of “your friend” sharing information about your queries. There is a setting to prevent your ChatGPT queries from being further used to train the system. Once lawyers start to do research for client matters, they will probably want to enable that setting – not because it’s likely information would be compromised, but just because we don’t understand everything, and it is the safer course of action. 


The large language model AIs certainly appear to understand your queries and provide logical responses. Professor Kenton Brice, director of the Donald E. Pray Law Library at the OU College of Law, had a helpful analogy at our OBA Solo & Small Firm Conference program on ChatGPT and AI. He said to think of the game Mad Libs.™ The AI does not understand the meaning of its communication with you. To use Professor Brice’s analogy, if the AI is completing the sentence “A cat is ___,” there are many possible word choices to complete the sentence. A cat is a mammal. A cat is black. A cat is a feline. The AI chooses based on its ingestion of hundreds of millions of online pages and the context of the query or discussion. The surprising thing is how often it selects the perfect word or phrase. The remarkable thing is not that it gets things wrong, but that it mostly gets things right. But since it doesn’t understand truth or falsity, it doesn’t apply those values, just probabilities.

Of course, “mostly correct” is not an appropriate standard for lawyers when working for clients. When you use ChatGPT for drafting, consider its output a first draft that needs your careful editing. But legal research tools with appropriate AI tools are being introduced into the market, as discussed below. 


Steven Schwartz, a practicing New York lawyer for 30 years, used ChatGPT to prepare a brief for federal court. Mr. Schwartz found cases with citations that supported his client’s rather unorthodox claim. At least six cases he cited in a brief as filed were hallucinations that did not exist, with fictitious quotes and internal citations. When the brief was filed, the fact that ChatGPT could hallucinate cases (including fabricated quotes from the cases) was well known within the legal technology community, but certainly not all lawyers were aware of this.

Opposing counsel filed a response brief calling out the bogus cases and moving for sanctions. Mr. Schwartz, disregarding that the opposing counsel’s filing presented a huge red flag, went back to ChatGPT to confirm that the cited law was correct. “I apologize for the confusion earlier,” ChatGPT replied. “Upon double-checking, I found the case Varghese v. China Southern Airlines Co. Ltd., 925 F.3d 1339 (11th Cir. 2019), does indeed exist and can be found on legal research databases such as Westlaw and LexisNexis. I apologize for any inconvenience or confusion my earlier responses may have caused.”

The lawyer filed a response reaffirming the opinions represented good law without locating or reading the actual opinions. Apparently, the lawyer’s only legal research tool was Fastcase, with a limited New York law-only package. As we all appreciate, the answer was to find another source for the cases. Instead, he “doubled down” and instantly became an internet meme. At the sanctions hearing, Mr. Schwartz was sworn to testify truthfully and then spent two hours being grilled by the judge. While ChatGPT made the national headlines, Mr. Schwartz could not avoid the simple fact that he cited as authority case law he had not read. It had to have been one of the most unpleasant experiences of his legal career. He noted that he had suffered great personal damage from his error. The court granted an award of sanctions for $5,000. But, no doubt, the two-hour examination was also punishment.

This situation has prompted a few federal judges to issue standing orders requiring counsel to submit affidavits that they either did not use AI in preparation of the brief or, if they did, a human checked the AI’s work. Some have observed that any potential problem is already addressed by Rule 11.[i] 


Casetext has provided AI-powered legal research for some time. Their basic service is a discounted OBA member benefit. Casetext also worked with OpenAI to incorporate advanced functions of ChatGPT into a new offering.

On March 1, as ABA TECHSHOW was beginning, we learned via social media that a national cable news network hosted the product launch for Casetext’s new offering, CoCounsel, an AI-powered legal research tool. Free trials were only for a short period. The results were so stunning that many lawyers immediately subscribed at the rate of $500 per user per month, including many lawyers who would have said that they would not have subscribed at that price point. Casetext gained access to ChatGPT in 2022. The result was quite a success.

On June 26, it was announced that Thomson Reuters agreed to purchase Casetext for $650 million cash.[ii] I hope Thomson Reuters will offer a pricing plan affordable to small firm lawyers and not just focus on larger law firm pricing. 


The easy answer here is yes. Smart, serious people have referred to it as being as significant as the discovery of fire, the invention of movable type or the internet itself.[iii]

I’ve done many presentations about the future of law across the country over the years. One of the keys to future law firm success will be to automate as much as possible. Creating automated templates is time-consuming. AI tools will make it less so, and some have reached the market. Did I mention that ChatGPT can also write computer code? That is scary for the programmers of the world. My prediction is the business world will be transformed by generative AI over a few years. And if corporate business practices change, the law businesses will also change.

Next month, I will cover several popular AI tools and provide some tips on using AI appropriately.

[1] SeeJudicial Treatment of ChatGPT: Throwing the Baby Out with the Bath?” by lawyer-blogger Stephen Embry.

[ii] See LawSites’ blog post, “The Rumors Were True: Thomson Reuters Acquires Casetext for $650M Cash.”

[iii] Noted legal futurist Richard Susskind shares his thoughts about AI and the legal profession in his LinkedIn post “AI in the law – six thoughts.”  He has studied the impact of AI on lawyers for decades, and he deems these developments very significant. Andrew M. Perlman, dean and professor of law at Suffolk University, stated, “ChatGPT suggests an imminent reimagination of how we access and create information, obtain legal and other services, and prepare people for their careers.” In “The Implications of ChatGPT for Legal Services ad Society.”

Originally published in the Oklahoma Bar Journal — August, 2023 — Vol. 94, No. 6

Our Digital Edge podcast Generative AI and Copyright: Collision is Inevitable tracks the fact that copyright lawyers is buzzing with the rising possibilities of AI-related legal matters. Is this a major concern in our current era of blossoming AI technologies? Sharon Nelson and Jim Calloway welcome Vedia Jones-Richardson to get her expert opinion on a variety of legal questions arising from the “creative expressions” of generative AI. This includes a discussion of the current landscape of AI’s copyright connections, explanations on what is and isn’t protected, and discussion of notable cases that have explored the infringement and copyright implications of AI-created materials.

Vedia Jones-Richardson

Vedia Jones-Richardson is a Principal with Olive and Olive, PA, where she leads the trademark and copyright practice group. She covers many aspects of the upcoming collisions between AI and IP ahead. There will be very. very interesting times ahead on this front.

Office Sharing Arrangements with Other Lawyers was the subject of American Bar Association Formal Opinion 507, released July 12, 2023.

The opinion “addresses some minimum ethical requirements and suggested practices arising in the office sharing context, particularly in the areas of confidentiality, conflicts of interest, supervision, and communications concerning a lawyer’s services.” It notes that when lawyers in an office sharing arrangement share support staff, such as receptionists, administrative assistants and paralegals, maintaining confidentiality of client information is “tested.”

But some practical advice is omitted. The opinion notes that lawyers in an office sharing arrangement should use separate business cards, letterhead, directory listings, office signs, and advertisements describing their distinct practices. But it fails to mention one important safeguard. In my view, every lawyer in such an arrangement should be contractually obligated to the other lawyers to have a written contract with every client and to include disclosure about the office sharing arrangement and that only the lawyer signing the contract is responsible to the client. Perhaps the client even initials that provision.

Learn to use the term “officemate” rather than partner or associate when discussing the other lawyers.

The opinion notes it is natural for lawyers in office sharing arrangements to informally consult one another about their respective client matters and it gives guidance in that area.

“It is desirable for lawyers sharing office space to have separate telephone lines, but a receptionist may answer a common telephone line with a generic salutation such as ‘Law Offices’ to avoid implying that the lawyers are practicing together in the same firm,” according to the opinion.

I think it is important for lawyers to have different phone numbers, more because of the practical considerations than the ethical ones. If there is a need to terminate the sharing arrangement, the dispute over who gets the jointly-purchased phone number can be a huge issue. It also prevents one lawyer paying for marketing efforts that inadvertently benefit the other lawyers. Separate websites are often the best policy for the same reason.

The problems with lawyers representing clients with adverse interests are numerous, especially if the office has only one waiting room. It may make sense to consider not taking clients when another attorney in the office represents the opposing party. That policy should be in writing. But there will be challenges. At some point, Lawyer A will sign up a new divorce client on Monday and Lawyer B will be prohibited from agreeing to represent the opposing party on Tuesday, even if that potential client is the lawyer’s best friend from high school. In fact, Lawyer B should not even meet with the client on Tuesday. So, some process to track these possible conflicts must exist even though it is office sharing and not a law firm.

If you are in an office sharing arrangement, read this opinion and share it with your officemates.

Suppose next week begins with one of your top paralegals or legal secretaries giving you two weeks’ notice. Maybe they are moving to another location or another local law firm. But now you have an opening to fill.

The first response is not about filling the position. First, you must determine if there are any matters the employee is working on that they no longer should. You must also determine whether some network access rights should be changed.


If you have been informed the employee is going to work for another law firm, then it is prudent to check and see what matters you have in which that firm is opposing counsel. Hopefully there are not any – or there are only a few old, closed cases. If a departing employee is going to a firm with which you have several contested matters currently underway, it is prudent to have your IT professional restrict that employee’s access to those files and to reassign someone else to do that work, even if it is the lawyer. Some firms take two weeks’ notice as an event which it is simpler to let the employee go immediately and just pay the two weeks’ severance. I am not suggesting that approach. I just know it happens. If you want to retain the employee and your staff rotates who performs receptionist duties, it may make sense to have the employee do more receptionist tasks, which typically involve less sensitive information.

To avoid adding to or causing any negativity, share with the departing staff person that this is the process the firm has adopted, and it is not intended to reflect poorly on them. Rather, it is intended to protect both law firms.


You have, no doubt, heard the business maxim, “Fire fast. Hire slow.” No one likes losing a good and trusted employee, but shortcutting the replacement process may ultimately result in having to do it far too often.

That means you must do your homework. Even if you may find it more challenging to hire a replacement in these times, you still must invest the time to hopefully find a great fit for the firm who will stay there for a long time.

So I still support the traditional practice of requiring a cover letter and resume. If they do not have a resume, you may allow them to submit an employment history. Then look for any mistakes.

It might seem harsh to disqualify a recent law school graduate applicant for a typo on their resume or cover letter, but we are discussing staff hiring. Typos, poorly written sentences and other mistakes are significant for those whose job duties would include proofreading and preparing documents and correspondence.


It is easy to be cynical about references, assuming someone will only provide the names of people who view them positively. But they must list their employment history. If none of their references are from their most recent employment, you will want to make a note to ask about that omission if you schedule an in-person interview. Asking which lawyers they primarily worked with at that firm and what they did for them is a good start.

It is very important to check references, even in this tighter job market. Imagine the worst possible disaster scenario someone new could create. Maybe it is a social media mess, stolen client information, stolen money or maybe an event that makes the local or national news.

Document the date and time you checked their references or previous employer, even if the specifics should not be shared (except perhaps with law enforcement when criminal activity is suspected).

One challenge in checking references or prior employment is that many employers, including law firms, no longer provide much information because of liability concerns. Sometimes all you will receive is employment verification with the start date and end date. Others have suggested you might obtain more information by asking if that former employee would be eligible to be rehired at the firm. A simple “No” response gives you valuable information.


Today it is prudent to run a criminal background check for every new hire. There will be some exceptions, but the background check is relatively inexpensive and can be done online.

You can also exercise your own judgement with the results and explain to the potential employee that not every mistake is disqualifying. For example, a DUI arrest reduced to reckless driving 10 years ago may not be a problem. But if the person is still on probation for their third DUI and the job involves driving to courthouses to file documents, the past at least merits further discussion, if not moving on to another candidate. Prior theft or embezzlement charges are most likely disqualifying.

Historically, some law firms do not contact law enforcement when they discover embezzlement, whether it is from embarrassment at being a victim, the time involved in dealing with law enforcement or preconceptions about whether charges would be filed. This is another reason why it is important to check references and pay attention to significant employment gaps in their resume.

State background checks can be done at CHIRP, the Criminal History Information Request Portal.

The website states:

In addition to a subject’s first and last name, requests for criminal history record information must include a date of birth. CHIRP will search three (3) years before and after the date of birth for possible matches. Additional identifiers such as aliases (maiden names, previous married names, nicknames) and social security numbers, if known, can be provided for a more thorough search of the OSBI Computerized Criminal History (CCH) Database.

It might be advisable to create a form for potential employees to sign providing all that information, including prior names. I would also encourage you to observe the candidate when you tell them a criminal background check will be required. One grimace may be worth a thousand words. If they say, “I know what you will find. Let me explain,” then let them do so, and give them some credit for their candor. They might confess something in another state that might not be picked up by the Oklahoma background check. But it is also likely they have a reasonable, non-disqualifying explanation.


Depending on the type of law practice, temptations can be presented to employees. Suppose an employee who normally doesn’t handle money is the only staffer remaining at the end of a long day. A client shows up just before closing with a $300 cash payment. The staffer takes the payment and, because it is the end of the day, does not write the client a cash receipt. The bank deposit has gone for the day, so the employee puts the cash in an envelope and puts it in their desk drawer to be turned over the next day. But they do not know how to enter the payment into the client’s ledger. Then maybe absences or the weekend remove it from the top of the employee’s mind. Three weeks later the employee notices a crumpled envelope in the back of the desk drawer. Even the honest employee will recognize that if someone was going to say something they would have done so by now. They may also note that when they turn the cash in, they may be criticized for not writing a receipt or hanging onto the money too long. Add in other complicating factors like the utility cutoff notice they just received.

This is how many of the six-figure law firm embezzlement by employee cases begin. Once it is seen how an embezzlement could work, they could begin looking for other avenues that are open. An Oklahoma lawyer/CPA told me a story where five employees of a firm had American Express business accounts. The bookkeeper soon figured out that she could pay her personal American Express bill with a law firm check and no one would be the wiser. Soon her AmEx account had a large positive balance, and the bookkeeper began traveling for pleasure more.

Good processes can limit the opportunities for financial mischief. Someone other than the bookkeeper doing the books should review the bank statement or online bank records monthly. All cash payments received must result in a receipt given to the client with carbonless copies made.

For an example of a worst-case scenario, we have the case of Blanca P. Greenstein. The West Palm Beach lawyer did not bother with a background check because her then-husband, who was also the law firm’s CFO, recommended the employee, having worked with her at another firm. Had a background check been run, the firm would have discovered this person was a felon, having been previously convicted of theft. As the headlines later noted, “A Swindle Cost a South Florida Attorney Her Law License, Marriage and $155,000.”

Even though the lawyer borrowed money to replenish all missing funds within 48 hours and no one accused her of a wrong, intentional act, she ended up with an agreed three-year suspension from the practice of law, along with paying $8,261 in costs.

That she was an innocent victim was likely a mitigating factor. But the fact that the bookkeeper wrote personal checks to herself totaling $155,000 over an 18-month period was likely an aggravating factor, as even a cursory examination of trust accounting records would have revealed the scheme.

The law practice management advice is the trust account contains funds from clients and others. The lawyer with the trust account has complete responsibility. A lawyer can delegate certain duties, but you cannot abandon oversight of your trust accounting responsibilities. Many large law firms have their employees who handle money bonded, a process that would also catch felony convictions.


One of Greenstein’s friends said Greenstein’s story should serve as a lesson to all attorneys that the bar has an “acute sensitivity” when it comes to trust accounting. Given that the lawyer receives the money in trust to keep it safe, that “sensitivity” is understandable.

But this is not the only lawyer discipline story that started with an inadequate hiring process, which is why I want to stress that good processes are essential for law firm staff hiring.

Originally published in the Oklahoma Bar Journal — May, 2023 — Vol. 94, No. 5