Have you ever received an email that required your attention, but you didn’t have time to deal with it right away?

Maybe it was a project update, a client request, or a feedback form. You probably thought, “I’ll get back to this later,” and moved on to other tasks. But then, hours or days later, you realized that you forgot to reply to that important email, and now you’re in trouble. You missed a deadline, lost an opportunity, or disappointed someone. How can you avoid this scenario and make sure you always respond to the emails that matter most?

One simple way to do this is to use a pin to place an email at the top of your inbox. A pin is a small icon that you can click on to mark an email as important and keep it at the top of your inbox, regardless of the date or time it was sent. This way, you can easily see which emails need your attention and prioritize them accordingly. You can also unpin an email once you have responded to it or completed the action it required. This will help you clear your inbox and keep track of your progress.

How to pin or unpin an email in Outlook

The pin feature is available in both the New Outlook and the online version of Outlook. To pin an email, you can hover over the pin icon next to the sender’s name and click on it. The email will move to the pinned section at the top of your inbox. To unpin an email, you can hover over the pin icon again and click on it. The email will move back to its original position in your inbox. You can also pin or unpin an email by selecting it and clicking on the pin icon in the toolbar. The pin feature is not available in Classic Outlook at this time. But we have seen some classic features restored to the new Outlook.

Microsoft Help file https://support.microsoft.com/en-us/office/flag-or-pin-a-message-in-outlook-com-8e911e69-30d6-4cc8-8c71-a1163560618a

By Jim Calloway

Lawyers have held and safeguarded client data for generations. Of course, in the past, it wasn’t called data. Our data was in paper client files, forms to “go by” and brief banks.

While it wasn’t planned this way in advance, my most recent Law Practice Tips columns blend as a series. In the January 2024 Oklahoma Bar Journal, the subject was “Automated Document Assembly is Easy, Right?” The February 2024 column was “A Time of Great Change Caused by Artificial Intelligence Developments.” If the connection with these three topics isn’t readily apparent to you, that is understandable. But to adopt automated document assembly, you must have your data in a usable, digital format. Otherwise, the best automation you can accomplish is “fill in the blank” or “copy and paste.”

We are moving to a time when many of us will employ artificial intelligence “assistants” to expedite task management. The primary way that it will operate is by “reading” your documents and emails. This will be relatively simple and largely risk-free, as the AI assistant will access the content stored on your computer – if it can!

I’ve attended several conferences and presentations focusing on AI. A main point that everybody is convinced of is that it is now time to make certain your data is well organized. This not only allows other law firm employees to access it easily, but it will also be more accessible when you want to access it with AI tools.

For solo and small firm lawyers, practice management software systems may be the best way for them to organize their information. As I’ve noted before, OBA Practice Management Advisor Julie Bays will assist Oklahoma lawyers by answering questions or providing brief demonstrations to help in making your practice management software subscribing decision. Some larger law firms may opt for more powerful full-featured document management systems, which can be set up to track different versions of a document.

In some ways, your practice management software is like romance and marriage. In the early stages, it is fun. Exiting the relationship early on is relatively simple. But later, it becomes more like marriage – you can get out of it, but it’s often not easy or cheap. Transferring data from one system to another can sometimes be challenging. Plus, there is the matter of everyone retraining on the new system. So invest some time in this important decision if it has not been made for your firm or if you are considering a change.


Everyone in a law firm needs to understand how to name the new documents they are creating and how the documents should be stored. It is too inefficient for different lawyers to have different systems. If a staff member is absent, it is easier to cover if the documents are named and filed in the same system as the rest of the firm. Generally speaking, a good file name will include the client or matter name, something about what type of document it is (e.g. Decree or Motion for Summary Judgment) and some numbers relating to the date of first creation. Hopefully, combining these three elements will eliminate duplicate file names.

The firm must also have a policy on how documents are stored. Those using practice management software systems will have that dictated for you. But if you are storing everything in Windows file management folders, make certain it is a drive and folder that is secure and frequently backed up. Microsoft OneDrive is a good example and is provided as a part of your Microsoft 365 subscription. There are other options in the marketplace, of course.

No matter how well organized and well trained those who work in a law firm are, there will be some mistakes. And if you are searching for a misfiled document, one easy way to do it is by searching the computer for a unique word or phrase that appears in the misplaced document. To accomplish that, the document must be searchable.


When I receive a PDF from someone that I’m going to use later, I want to make certain it is searchable. As almost every lawyer understands now, a PDF can be made searchable by applying optical character recognition (OCR) to make it searchable. I usually do that at an initial stage so that I can easily find it, but a growing reason now to make certain that these documents are searchable is so your AI assistant can have access to them.

If you have a sophisticated scanner, it may be possible to set the default settings to OCR everything. While that may make the scanning process a bit slower on occasion, it means the scanner will produce searchable documents, which is well worth it, in my opinion.

All documents (except Excel spreadsheets) should be stored in PDF format. These are your digital file copies. Opening documents in Word creates the possibility of accidentally editing the documents. If you want to keep Word documents in the file so they can be used if an amended document is required, that is a fine idea. But I suggest you create a folder titled “Word Documents” in the digital client file to store these to prevent confusion.

Documents have a life cycle, and the firm should decide on a closed file destruction policy. The date of destruction need not be set until the client file is closed. I favor some file destruction policy for most types of documents, but a recent conversation with an intellectual property lawyer who does patents reminded me that there are certain types of law practices that may actually have a good reason to maintain client files for an extended period of time, maybe even permanently.


Frequently, I hear from law firms wanting to scan and then destroy old, closed client files that pack storage rooms. Sadly, I usually advise caution. First, it will cost a lot of money and time to do this. It is also very possible that the result will not be perfect. Automated document feeders work very well today, but there is still the possibility they will skip a page now and then. Those of us in the legal profession will be concerned that the missing page will contain critical information – even though the closed file may not have been opened for years. Finally, you will be paying workers to do much time-consuming work, removing staples and brads and fixing dog-eared pages to prepare for scanning.

The best plan is to make certain you are properly creating and storing documents going forward. There may come a time when you believe you will need some content from closed files to better inform your AI assistant. But that will mainly be completed documents and legal memos that are harvested from the closed file as opposed to scanning the entire file.

If you are going to be using documents from closed files as forms, then it is a wise and ethical decision to remove people and company names and replace them with simple placeholders like a few letters.

You may not be ready to jump on the AI bandwagon today. But making sure your client data is well organized and easily searchable will provide other benefits.

Originally published in the Oklahoma Bar Journal — March, 2024 — Vol. 95, No. 3

Judge Scott Schlegel from Louisiana was a speaker at the 2023 Oklahoma Access to Justice Summit. Last year, I noted his conviction that both courts and law firms should embrace text message reminders to reduce failure-to-appear issues. Lawyers want to make certain their clients, especially potential new clients, do not miss their scheduled appointments as well as any court appearances.

“Embracing AI in the Legal Sphere: A Necessity, Not a Choice,” was the title of Judge Schlegel’s recent post on his Substack account. He explains the inevitability of AI adoption quite well:

If there was any lingering doubt about the pervasive role of AI and generative technologies in our professional lives, Microsoft’s recent move to integrate an AI button into their keyboards should dispel it. This is not just a fleeting trend; it’s a clear signal of a future where generative AI is seamlessly woven into nearly every product we use, especially in the practice of law.

As lawyers and judges, the temptation to view AI as a distant, abstract concept may be strong. However, it’s crucial to acknowledge that AI is not just a passing fad. We must recognize that the genie is out of the bottle and that AI will reshape the landscape of numerous industries, including our own, over the next few years. Microsoft’s addition of an AI button to its keyboard is a testament to the increasing integration of AI in everyday tools, heralding a future where AI’s presence is ubiquitous.

For the legal profession, this evolution brings both challenges and opportunities. The shift towards AI-enhanced tools is not just about adopting new technologies; it’s about fundamentally rethinking how we approach our work. AI has the potential to make the justice system more efficient, effective, and accessible, but it requires us to be proactive learners so we can understand its capabilities and limitations. We cannot bury our heads in the sand.

Anyone interested in how technology can be used in the judicial system should subscribe to Judge Schlegel’s Substack account to receive his posts by email. Despite the well-publicized ethical issues by lawyers who used AI to draft briefs without attempting to read the cases it quoted (which did not exist), AI will reshape many things in society, including the legal profession and the legal system.


Why are so many predicting great change for the legal profession and legal systems because of this particular technological advance? We’ve survived the advent of many new technology tools, from faxing to the internet and email. Simply put, these new AI tools do what lawyers do. They receive input in a conversational format and give output in well-written, persuasive text. Certainly, AI does not just impact lawyers. Do you know how many internal corporate memos are completed and communicated each day? I don’t either. But most of these memos are drafted by humans, and that will not be the case in a relatively short period of time. Knowledgeable employees will not lose their jobs. Someone will be needed to proofread the AI’s work product. I would estimate I could proofread and revise 10 memos in the time it takes to draft one or two. So someone’s employment will be ultimately endangered. But, in many situations, AI usage will just allow workers to shift their focus to more high-level work and reduce time spent on the more mundane.

Memos that are just reports based on information in the company’s system will be the first to be automated with no human review.

The flood of new AI tools over the past year is very impressive. But adopting new technologies is a process that does take some time. Famed legal futurist Richard Susskind has opined that we are probably overestimating the short-term impact of AI while underestimating the long-term impact.

These changes will be stressful and challenging. Change management is challenging, especially for those who have been doing things in a similar manner for years. But there is simply no avoiding the changes caused by AI adoption in the legal profession.


In December 2023, I hosted a video roundtable on the ethical challenges of using generative AI in the legal field for the ABA Legal Technology Resource Center. The panel featured four experts: Damien Riehl, Ivy B. Grey, Jayne Reardon and Kenton Brice. We discussed the evolution and impact of AI on the legal profession, the benefits and limitations of AI tools, the ethical implications and regulations of AI and the integration of AI in law schools. The roundtable was summarized by Zoom’s AI companion, which demonstrates the potential of AI. You can watch the video and read the summary on Law Technology Today, which is outside of the ABA members-only paywall.


If you are ready to subscribe to a powerful AI tool, Microsoft made a mid-January announcement that Copilot was available for the rest of us to subscribe. The 300-seat requirement for firms has now been dropped, and individuals can now subscribe. The Verge broke the story and reminded us there are three versions of Copilot:

Microsoft now has three different versions of Copilot. There’s the regular Copilot that’s available free of charge to both consumers and businesses, which is essentially a chatbot much like ChatGPT. Then, there’s the new Copilot Pro option that’s launching for consumers today for a $20 per month premium, offering AI-powered Copilot features inside Office apps and elsewhere. Microsoft now also offers the same premium subscription with more features to businesses in the form of Copilot for Microsoft 365 at $30 per user per month pricing.

Since this just launched at the deadline for bar journal submission, I don’t have all the details available, but the pricing seems to depend on your Microsoft 365 plan, with home users paying $20 per month for fewer features than the $30 version offered to business package subscribers. Using AI to quickly create PowerPoints from text will be a popular feature. For those of us who don’t have graphic design skills, creating graphics from text will be useful as well, even if you mainly use this for personal projects.


LexisNexis is now offering Lexis+ AI, touting the service as “the fastest legal generative AI with conversational search, drafting, summarization, document analysis and linked hallucination-free legal citations.” Currently, a free trial is available.

Thomson Reuters has announced Westlaw Precision now includes generative AI. The company notes, “Simply ask a question in everyday language and get a relevant answer with links to trusted Westlaw authority in moments.” A free trial is available.

Microsoft Bing now offers a very useful AI-powered tool with Bing Chat. It is free, easy to use and quite powerful. For example, some questions it suggests include “Give me a list of new hobbies I could pursue with limited free time,” and “What should I pack for a 10-day trip in a mountainous region?” If you haven’t tried AI yet, Bing Chat would be a good starting place. It is powered by GPT-4, which is an improved version of ChatGPT. This new Bing chatbot is the only way to access GPT-4 for free, according to the company. For more information see the post, “Access ChatGPT 4 Using Bing AI with Ease.”

Microsoft Copilot chatbot is accessed via the Microsoft Edge browser.

Bard is Google’s entry into the browser-based AI category. It is free. I asked Bard which features distinguished it from other AI tools. The response included: “Focus on factuality and grounding in the real world, emphasis on safety and responsible AI, multilingual capabilities and the ability to generate texts in many creative formats such as poems, code, scripts, musical pieces, email and letters.”

We first saw ClearBrief at ABA TECHSHOW 2022. ClearBrief is a Word add-on for checking your brief (or opposing counsel’s) for misstating the facts or law. It also is used to easily assemble a table of authorities. But it has since been improved and can now integrate facts from discovery or other documents right into the first draft of your brief. Subscriptions start at $125 per month per user.

Spellbook is an AI contract drafting software that has been trained on thousands of business contracts as well as other data. I would encourage you to watch the four-minute video at www.spellbook.legal. I believe that in a few short years, it is possible most contracts will be drafted using AI contract drafting tools.

Copy.ai is not for legal writing. But it is a great tool for writing for an audience, whether it is a blog post or website copy. The free version is limited to writing 2,000 words per month. The pro version is $36 per month for up to five users and has priority tech support.

The above list is far from comprehensive, and new AI developments seem to be announced almost daily.

Other types of AI tools will have wide-ranging impacts.

Volkswagen is adding ChatGPT into their new cars to allow drivers to have conversations with their cars. The second quarter of 2024 is when they are expected to be available. “Sorry, officer, I was distracted by an in-depth discussion with my car.”

Augmental is developing tongue-controlled mouse pads that users wear inside their mouths. This will likely be a major development for those with disabilities.


I have shared several AI tools that a lawyer may use. Readers likely will not have time to preview all of these tools, so pick one or two to give a test drive. More variations will continue to appear.

If you haven’t settled on an AI tool yet, you are encouraged to consider Microsoft Copilot. While an additional $360 per year is not a small investment, the number of ways it can be used is impressive. Having a database of all the documents the firm or lawyer has created for the AI to use is powerful. But the PowerPoint and graphics creation tools are also something that many lawyers may use as well.

Originally published in the Oklahoma Bar Journal — February, 2024 — Vol. 95, No. 2

Decades ago, I assumed that technology would soon advance to the point where automated document assembly would be fully incorporated in most law offices across the country. While great strides have been made in law office technology tools, and tools for automatically generating documents are much improved over what was available decades previously, many law firms still have not fully embraced automated document assembly.

Why is that? I can speculate.

  • Using a standard form as a starting point and using copy/paste plus some custom editing to create the final isn’t terribly inefficient or error-prone. It is a major improvement from the typewriter age.
  • Automated document assembly involves investing time to set up systems that generate documents (or first drafts of documents) in minutes. The hourly billing model applied to minutes does not properly charge clients for the value of the document and is inadequate for the law firm to recover the time and money invested in creating and maintaining the system – not to mention the responsibility and potential liability associated with any open client file. Flat fees for producing those documents are therefore strongly indicated, but converting to that system involves planning, time and money.
  • Creating the tools for automated document assembly for lawyers is more challenging than it might appear. I draw this conclusion from watching practice management solutions incrementally release tools to improve their document assembly processes. Legal documents are typically much more complex than other documents. The only automated doc assembly many types of businesses need is contact information for emailing offers and invoices. Businesses that sell primarily online have their e-commerce tool doing the sales and accounting records.
  • Investing in new technology is often a hard sell in law firms because of concerns it may impact revenue.

But AI tools have now changed the expectations. The name ChatGPT is perhaps not as well-known as the name Taylor Swift, but most people have heard of it and other AI tools. More potential clients will come to expect that lawyers will use appropriate tools to deliver services for less.

I also note that Comment 5 to Oklahoma Rules of Professional Conduct Rule 1.5 on fees ends with the admonition, “A lawyer should not exploit a fee arrangement based primarily on hourly charges by using wasteful procedures.” Certainly that rule was not drafted with artificial intelligence tools in mind. But the rationale may apply.


Given the tools available today, here’s how document creation should occur within law firms. You need your clients’ data set in a digital form that can be exported, as well as document templates to receive the data to create the new document.

The law firm has a collection of client data in digital format.

When documents need to be created, that data set is matched with the template that results in a document with all the client’s information correctly inserted. Sometimes, this document is final and only needs to be reviewed by the responsible attorney; sometimes, this document is a starting point with more editing and drafting needed.

Lawyers who use WordPerfect are sometimes referenced as being behind the times. But in terms of the ability to automatically create documents and save and reuse data for those documents, it was light years ahead of Microsoft Word back in the day. For years after Microsoft Word won the market-share war, Word trainers were doing training on how to use mail merge to automate your documents. Sophisticated automation back then required purchasing a third-party add-on. As Microsoft Word evolved and left behind its “Clippy” phase, it became a much more powerful document assembly tool. But, as always, with power comes complexity.


Practice management software tools can assist you in managing all your clients’ information. It is certainly the most logical place to store client data that will be reused. If you don’t subscribe to a practice management solution and are shopping for one, pay attention to its features that can export the data to generate documents.

There is a concept in utilities delivery called “the last mile.” Whether it is electrical service or internet service, if the final link in the data transfer process is weak, then the entire process is weak. For many law firms, the last mile is taking the client data that law firms now hold in digital form and seamlessly utilizing it to create documents – or at least the first draft of documents. Every law firm has a system to create documents. Some use forms and edit these with this client’s information. Some have a digital system where client information is stored and use copy/paste to put it into the form. Some have Word templates rather than Word documents as a starting point.

Many law firms make good use of Word templates. Others only use the standard template. The data is one part of the equation. Creating the templates that the data will be exported to is also a critical step in the automation process. Luckily, creating basic templates is a fairly simple process in Microsoft Word.

Most readers have a document creation process already in place. But some of the steps are copy/paste, which does allow room for error, although not as much as retyping the data. And copy/paste will require a bit more time.

Creating a Custom Template in Word

If your law practice hasn’t created any templates, I suggest you begin with a simple one that will be immediately useful – your stationery or letterhead. While your firm may or may not still purchase printed letterhead for correspondence, much correspondence is created on the computer and is sometimes never printed. Since most people will be looking at copies of the correspondence anyway, more firms are opting to cease or limit purchasing letterhead.

  • Open the Word document you wish to use to create the template. In this case, the soft letterhead you use.
  • Select File – Save As (with some versions, select Save a copy).
  • Type a name for the new template in the File Name box. (It is okay to include the word “template” in the file name.)
  • Click on Word Template in the Save as type If your document contains macros, you will instead click on Word Macro-Enabled Template.


  • Click Save

When you open your new template, you will have a new “Document 1,” including all the information included in the template. This eliminates the possibility someone will accidentally edit the form document because you are not using a form.

Microsoft provides good instructions on creating templates. Editing a simple template is easy. The instructions are at the same link as the above.

These simple templates will speed up starting a new document. But before you can use them in automated document assembly, each item of your data needs to be tagged (e.g., <ClientFirstName>, <ClientLastName>), and a field for each type of data needs to be created in your template. Keeping track of all these labels is important. It is poor practice to use a simple term like Name because there will be many different types of names in the system. Somewhere, the firm must maintain a list of every one of these names. Otherwise, two people will use the same variable for different items, and no one will know until a generated document has incorrect information.

I wouldn’t want to mislead anyone. Creating powerful templates to be used in automated document assembly can be challenging. It is more like coding than word processing. You need to know about using styles, auto paragraph numbering and spacing, and using paragraph glue coding like “keep with next” and “keep lines together.” It requires good planning and a fair amount of time investment.


Because template design can be challenging, many firms opt to invest in third-party software to assist them. These programs combine the powerful tools in Word that are sometimes challenging to access with some more friendly menus and other assistance.

At the 2023 Solo & Small Firm Conference, Kenton Brice, director of the Law Library at the OU College of Law, did a very impressive demonstration of Doxserá from TheFormTool. It builds a table at the bottom of each document with two columns, one for that name of the variables and the other column blank for your data. And once you use it to prepare one document for a client, you can save that data so you can reuse it the next time you need to prepare a document for that client. TheFormTool is affordable with a free limited license or a 30-day trial of Doxserá for $1. A lifetime license for TheFormTool PRO is $89, and Doxserá is $149 per user for an annual subscription.

TheFormTool’s CEO spoke at the 2023 Access to Justice Summit and has been consulting with the Oklahoma Access to Justice Foundation on some automation ideas.

Other well-regarded document automation programs include Woodpecker, which was acquired by MyCase in 2021, and Lawyaw, which was acquired by Clio in 2021. While these services will be designed to work well with the parent company’s service, they are also available for subscription for those who do not use the PMS. Woodpecker’s starter subscription is $39 per month, and it offers a free trial. Lawyaw is $67 per month for its Word automation packages and also offers various state court forms to be auto-completed in an additional package. They also offer template design services at $150 per hour.


If the idea of doing the above seems to be something you do not want to commence today, some limited automation can be done using Outlook Quick Parts. Highlight an entire document or just some paragraphs from a document. From the Insert menu, select Quick Parts and then Autotext and give your quick part a name and save it to the Quick Part Gallery. Then, to insert the text into a document, go to Quick Parts, then Autotext and select the desired quick part from the drop-down menu. Quick Parts also works in Outlook. More information is provided by Microsoft.


  • If you have never created a template before, start with the letterhead (aka stationery) on every computer in the office. Make sure everyone knows how it works.
  • Appreciate that the change to automated document assembly begins with saving all of your client information in digital format. Your practice management software package is the most logical place for that to be organized. If you have a cloud-based project management software, you likely do not pay extra for tech support. Contact the company for their aid on this automation.
  • For those who have not yet taken these steps, it is important to think about organizing your client data digitally to be reused in the future.

Originally published in the Oklahoma Bar Journal — January, 2024 — Vol. 95, No. 1

Years ago, I put together a presentation called “The Client-Centered Law Practice.” It focused on the irony that while law firms focused on serving clients and appropriately addressing their legal needs, clients sometimes had an impression that differed from that. To those (hopefully few) clients, it seemed that the law firm was busily engaged doing important work for other, very important people, while their matter was not a priority.

In fairness to lawyers, that was often the perception rather than reality. But in the legal world, your client’s perception often is your reality. Certainly, it is your reality where concerns such as client retention and clients referring others to the firm are involved. So client service improvement is important – even though lawyers understandably focus more on the legal work.

Designing a law practice that provides exceptional client service should be the goal of every lawyer. But this goal requires an understanding that accomplishing great results for the client’s legal problem differs from providing good client service.

Suppose the lawyer settles a claim for $10,000.00 more than anticipated. The lawyer is thrilled by the accomplishment. The client, however, may have their assessment of the lawyer’s performance clouded by the number of times they waited several days for the lawyer to return a telephone call or the in-person office appointment that started 15 minutes late and was then cut short because the lawyer had a court appearance.

What about receiving a better-than-predicted settlement? Once a client is critical of a lawyer’s performance, it is easy for the client to assume the lawyer was just “low-balling” that initial estimate. Weak customer service practices impact every aspect of a lawyer’s representation of a client, including weakening the client’s confidence and trust in the lawyer.


In 1967, businesses constituted 39% of U.S. legal services, and individuals made up 55%. By 1992, it was 51% businesses and 40% individuals. By 2012, the percentages were businesses 72.5%, individuals 23.9% and government 3.6%.

That means that 75% of legal work now involves a client representative who is a general counsel, a government lawyer or a business owner who is knowledgeable about their legal needs. It is understandable that law-firm-to-client communications developed into more like lawyer-to-lawyer communications. Larger law firms may handle more than 90% corporate work, while rural or small-town lawyers may have the opposite ratio, which requires different strategies.

If you haven’t read my thoughts about the practice of people law, I’d encourage you to do so. “The Practice of People Law” was published in the May 2022 Oklahoma Bar Journal. The ABA published my piece, “The Changing Dynamics of a People Law Practice,” in its July/August 2023 Law Practice Magazine “Big Ideas” issue. This is now behind the ABA member’s only paywall, but an earlier piece, The Practice of People Law, was published in the Oklahoma Bar Journal.


We are all consumers of goods and services. We can all empathize with poor consumer service, whether it is being stuck in a waiting room for too long after a scheduled appointment or providers not doing things as they said they would when they said they would.

Empathy is an important lawyer skill. Having others in control of very important and personal aspects of our lives is inevitably personal. Being forced to discuss your marital problems or an arrest with a stranger is hard. Clients may be embarrassed to discuss some things and will be more likely to be more forthcoming when they sense an empathic listener.


The design challenge for the law firm is delivering legal services effectively and affordably in a way that assures the client that their matter is being handled diligently and professionally while they are kept informed.

Invite everyone who works in the law firm to participate in brainstorming creative solutions that might improve law office operations. The lawyer’s view of what is most frustrating to clients during the representation process may differ from the law firm receptionist, who may have great input on what they hear.

Post-representation surveys, exit interviews and other techniques can solicit input from your past clients to improve future clients’ representation. One wants to encourage clients to pass along any criticism or frustration they experienced. One good way to solicit these responses is to ask questions like “What is the best thing that our law firm did during your representation?” and “What is an area where we can improve?”

Now let’s discuss some of the major areas that are often ripe for improvement.


It is important to appreciate that different types of clients have different expectations. Using your initial interview with the client to set expectations for the representation is important, especially regarding how long it may take to resolve the matter.

A key to representing someone unfamiliar with the legal process is to provide them with understandable and clear explanations of exactly what the situation is and the possibilities for the future. It may become more common to have clients watch a brief video before meeting with the lawyer to gain familiarity without billing them the lawyer’s hourly rate.

Many clients have no appreciation for how much time certain legal processes involving courts and government agencies can take. This is particularly true if their main exposure to the law is watching television dramas where the crime, investigation, arrest and trial all occur within the same episode.

Law firms appreciate the dockets in their jurisdiction, and it should be an important part of the client intake process to help establish the client’s expectations as to how rapidly their legal matter may take to be resolved.


No matter how much energy is devoted to planning law firm improvements, it is likely that many improvements will be related to attempting to improve the law firm’s client communication. Some challenges in the attorney-client relationship are caused by poor communication practices. Even if they are not caused by poor communication, the primary way to address the challenges is often through improved communication practices.

Clients are entitled to receive communication in a method that is appropriate and useful to them. But it can also be important to explain how many digital methods of communication are insecure and the consequences of confidential information being exposed to help the client appreciate why the law firm insists on using secure communications tools. Online client portals are a primary tool for accomplishing this. Once you explain the challenges, clients may feel better about logging in and posting queries to the portal as opposed to using email or phone.

The client intake process should cover lawyer client communications and create expectations on how quickly responses to inquiries will occur. Client input is required when important decisions affecting the matter are made. Retaining records of those important communications protects the law firm.


Automation wouldn’t have ranked high on lists of law firm needs a few years ago. But today, a law firm should incorporate current automation tools to facilitate client services without needing as much law firm staff time. Your client portal should be configured so that when new documents are uploaded, a notice of the new document availability is automatically sent out to the client. Templates should be created for important client communications that happen regularly just as templates should be created for legal documents frequently used.


The need for greater transparency is often associated with governmental entities.

It is unnecessary to sketch out every aspect of how representation might proceed during the initial interview. But once the client has retained the firm, it is important to provide a clear road map to understand the steps involved. Many legal matters will deviate from standard process as unanticipated developments occur. If a client is upset about “delays,” it may help to review the original road map initially provided where this type of delay was suggested as a possibility. It is also appropriate to note in a nonjudgmental way when the client’s actions or inactions have contributed to a delay. Transparency should apply in both directions.


No one likes waiting in the waiting room 20 or 30 minutes after their scheduled appointment. Once, clients were more tolerant of this. But today, the law firm must exert great effort to make sure that clients are seen at their scheduled appointment time or within a few minutes afterward.

People today have a more limited attention span for reading lengthy material. If it is necessary to provide the client with a lengthy document or memo explaining a legal position or theory, perhaps the firm should consider beginning these documents with a short executive summary.


Lawyers need to appreciate that meeting a client’s preference for receiving information today may require flexibility.

Recently, a colleague talked to a person who was upset about how her 80-year-old father was being treated by his law firm. He was frustrated with his lawyer due to all the emailing, printing, scanning and getting documents notarized he had to do for himself relating to a real estate transaction. When the person tried to discuss her concerns with the lawyer, he became defensive. The father believed he had signed up for full legal representation and was receiving a do-it-yourself experience. Here, expectations were not in line between attorney and client. When we go to a convenience store, we expect to pay a higher price for the convenience. Those with a legal problem have options ranging from online legal information websites to limited-scope services to full-service legal representation. Even though lawyers believe our services are the high-quality option, we must appreciate some clients are hiring us as the easiest, most convenient option.


Every law firm is different. A law firm that serves mainly consumers differs from a firm that serves mainly businesses and corporate clients. A firm in a particular geographical region will reflect the values and culture of that region. Some things that might work for other law firms may not work for yours. Therefore, every law firm must seek its own path forward.

Jack Newton, CEO and co-founder of Clio spoke via video at the 2020 OBA Annual Meeting about this subject. His book, The Client Centered Law Firm, identified five major values of a client-centered law firm approach:

  • Developing deep client empathy
  • Practicing attentiveness
  • Providing ease of communications between lawyer and client
  • Demanding effortless experiences
  • Creating clients for life

What are the values you want your client-centered law firm to prioritize? Improving customer service should be a continuing project for the law firm. But don’t let the scope of this nonbillable task prevent your law firm from taking action. Your clients deserve your best, and less anxious clients make things better both for the clients and those working in your firm.

Originally published in the Oklahoma Bar Journal, October 2023

2023 cast a huge spotlight on Artificial Intelligence tools. That means it is a great year to attend ABA TECHSHOW, which will be held in Chicago February 14 – 17, 2024. But it is time to decide now! The Early Bird registration ends on Friday, January 11 Update: The ABA TECHSHOW website now says the Early Bird Deadline has been extended to January 19. There is a price increase after that deadline.


Those who have previously attended an ABA TECHSHOW know what a great event this is. If you have been thinking about attending TECHSHOW previously, then this year provides a great opportunity to learn from technology experts on subjects ranging from AI to Automated Document Assembly to using Microsoft Word more effectively. I encourage you to spend a few moments looking at the schedule of programs. I’m certain you will find something of interest.

The Oklahoma Bar Association Event Promoter code is: EP2403. This code will allow Oklahoma lawyers who are not ABA members to receive a significant registration discount.

It’s that special time of year. By that I mean it is time for the Tech Toys for the Holiday episode from the Digital Edge podcast. Sharon Nelson and I both agree that it is our favorite podcast of the year and many of our listeners tell us the same thing.

This year we have a wide range of tech toys to add to your shopping list, even if you are just shopping for yourself. Our show notes has links to all of the items featured. So even if you don’t want to listen to the entire podcast you can still see the list of items featured for your online shopping. From dash cams to web cams, from a digital microscope to a personal bug and hidden camera detector, you will learn about a lot of devices that you perhaps cannot live without.

This edition of The Digital Edge will be Sharon and Jim’s final podcast. We close with 189 episodes of the Digital Edge completed. So that is a very long run for a podcast, particularly a podcast hosted by two busy lawyers. Thanks to all of our friends at the Legal Talk Network for supporting us and hosting our podcast. And a special thank you from me to my long-standing friend and ever-patient co-host, Sharon Nelson. I’m absolutely sure I would have never persisted this long without her. One thing I will miss about ending the podcast is I won’t have an excuse to talk to Sharon every month.

Listen the podcast: https://legaltalknetwork.com/podcasts/digital-edge/2023/11/tis-the-season-tech-toys-for-the-holidays-2023/


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 https://bard.google.com.

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.



Copy.ai 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 www.spellbook.legal. 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 aman.ai. 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.