By Jim Calloway

In the summer of 1997, when I first reported for work at the OBA to develop a program to assist practicing lawyers, I certainly didn’t anticipate I would be retiring from the OBA 28 years later. But here we are. I’ll be retiring at the end of May.

Retirement brings mixed emotions – from the sadness of moving on to the happy anticipation of what’s next. But primarily, I feel gratitude. The relationships I have developed with so many lawyers have been rewarding, and one of the best things was rarely having to argue with other members of the bar. Since this is my last “Law Practice Tips” column, I do promise to end with some tips.

I appreciate that OBA leadership trusted me to try many ideas over the years. After I had shut down my law practice and started in this position, I learned the task force that created the program had some not just unrealistic, but impossible expectations. One was that within a few years, the program would be generating so much consulting revenue that it would largely pay for itself.

I sought an audience with then-OBA Executive Director Marvin Emerson and shared my view that many Oklahoma lawyers didn’t really want the OBA in their offices. Even fewer would be willing to pay for the privilege – at least at that time. Mr. Emerson was a legend with a legendary sternness. But he actually chuckled in response, saying, “You are probably right about that.” So I designed a “mostly free” member benefit program, writing an article in every bar journal, speaking at no charge to any county bar association or Oklahoma lawyer group that invited me, starting a hotline service to answer lawyers’ questions about law office management and technology and many other projects.

I had few objective qualifications for this job. Before the widespread use of the internet, I established a computer bulletin board system named the “Barrister’s Club” as a hobby. Lawyers calling in from other area codes would wait until after 11 p.m. to log in when the long-distance telephone rates were lower. Those on the interviewing committee likely thought that required more technical expertise than it did.

My other “qualification” was that I had been invited to become one of the OBA Family Law Section’s “computer nerds.” The late Doug Loudenback, the late Gary Dean and Charles Hogshead invited me to participate with them in their CLEs. It was at a Family Law Section CLE that I gave one of the first live demonstrations for lawyers, showing how to log in to the internet using a 1,200-baud acoustic modem we dropped a telephone handset into and the Mozilla browser. It was all text and no graphics, with mainly .edu and .gov domains and not much else. Because of the time spent in my youth reading science fiction, I was able to make some accurate predictions on what was ahead for the internet.

Many will remember that Doug Loudenback created the Grande Macros, a collection of interlocking WordPerfect macros that would draft most routine family law pleadings. Doug wasn’t much of a marketer, so we agreed that my department would sell them for him on a commission basis. It is interesting that, while some software tools for lawyers still struggle with perfecting automated document assembly, many Oklahoma family law lawyers had that capability decades ago, even though the macros have now faded into history. 

MANDATORY CLE DOESN’T NEED TO BE BORING

Many lawyers today do not know that the requirements for MCLE and ethics programs arose from a reaction to the Watergate scandal, involving many lawyers behaving questionably or illegally.

As many jurisdictions enacted MCLE requirements, more CLE presentations were given across the nation. The early programs were fairly described as “like law school lectures, but they don’t call on you.” Trial lawyers were often the most entertaining presenters due to their skills.

One of my mentors, the late Ross Kodner of Wisconsin, told me the most important goal of teaching CLE to lawyers is to be energetic and entertaining. For me, bringing energy was relatively easy because I was a true believer. In a time when partners were telling associates that having a computer on their desk would be “unprofessional,” I knew almost every lawyer would have a computer at their workstation soon enough. Having the freedom to try new things was good for me and the OBA members. I got my first Gmail address when you had to be invited to get one. I learned about Facebook at ABA TECHSHOW and created an account within days. I set up a law blog, Jim Calloway’s Law Practice Tips, when it was a cutting-edge thing for lawyers to do. (The blog hasn’t been updated recently, but I may relaunch it in retirement with a new focus.) 

ALTERNATIVE BILLING BOOKS AND SO MANY PODCASTS

My friend, Oklahoma City lawyer Mark Robertson, recruited me to co-author our first Winning Alternatives to the Billable Hour book for the ABA. Mark knew we shared the belief that technology and business process advances would force at least some law firm migration from purely hourly billing.[i] He met me in the hall during an ABA meeting, told me the committee had approved the book proposal and invited me to co-author it with him.

Another good friend, Sharon Nelson, and I launched the Digital Edge: Lawyers and Technology podcast, and we produced 189 monthly episodes. For the first few episodes, Sharon’s husband, John W. Simek, did all the postproduction work. Legal Talk Network later stepped in to do our hosting and production. Our annual “Tech Toys for the Holidays” episode was our most popular and was referenced in the ABA Journal several times. I was also a guest on many podcasts over the years. Even though our podcast has been retired, Legal Talk Network still hosts several great podcasts targeted at lawyers. 

THOUGHTS ON ARTIFICIAL INTELLIGENCE

The impact of AI over the next few years is going to be greater than most readers anticipate. The fact that lawyers first got into trouble using AI to write briefs was a lawyer competency issue, not a technology issue. Just read all the cases you cite. Hallucinations were a known possibility with those AI tools. There were articles and posts documenting this issue, but not necessarily where lawyers normally read. Everyone was talking about ChatGPT. Some research was required to understand the cautionary aspects. The OBA Management Assistance Program received many inquiries about AI tools. We are proud to have presented many CLE programs on the ethics of using AI and possible drawbacks and to have put on an AI conference this past summer.[ii]

AI is not as new in legal circles as some believe. At one time, litigation (with a huge number of documents) involved manual document review. Firms hired young lawyers solely for the uninspiring work of spending day after day manually reading documents to deem them as “relevant” or not. But soon, those lawyers doing document review would be replaced as firms moved to predictive coding, also known as technology-assisted review (TAR).

A lawyer once told me the idea of AI doing document summaries gave her a negative physical reaction. She would be haunted by the idea that the summary left out something important. But the young lawyers crammed in a warehouse doing document summaries all day were not perfect either, while e-discovery tools allowed you to use multiple queries on the evidence.

For a lawyer in private practice, using AI to review and summarize documents will be an important part of law practice, even if you are not involved in e-discovery. Just imagine asking your AI to draft a motion for summary judgment using a certain fact pattern – but to only reference the forms in your MFSJ file, which contains all the motions you have drafted over the years, plus a few from opposing counsel. The odds of hallucinations are vastly reduced.

Let me note again that I believe a $30 per month subscription for Microsoft Copilot is a great value. One paragraph in this column read a bit awkwardly, and I was having trouble repairing it. I highlighted the paragraph and selected “Auto Rewrite” in Copilot. In seconds, AI gave me a much-improved paragraph with a one-third reduction in length.

Your vLex Fastcase legal research member benefit has a tool called Vincent AI. It is available via a separate subscription of $360 per month, which is discounted from its retail price of $400. OBA members can receive a free three-day trial with Vincent. I would encourage you to wait until you have some big legal research projects and clear your schedule to give Vincent a dedicated three-day try. Vincent provides flexible subscriptions. You can subscribe on a month-to-month basis or just for one month with no annual subscription required. 

A TIP FOR YOUNG LAWYERS

When I co-taught a class at the OU College of Law on setting up a law practice a few years ago, I was surprised that most of the students’ business plans involved transactional practices, and many told me they had a goal of never going to the local courthouse. Since then, I’ve received similar feedback from other law students and young lawyers.

I will break my self-imposed rule about not lecturing lawyers on what they should and should not do to say that young lawyers should appreciate the value of courthouses and courtrooms for society and their careers. Legal deserts exist where there are not enough lawyers, leading to severe consequences for many people that often happen in court, placing their families, their freedom and their finances at risk. Generally, many do not require the most experienced lawyers, just one committed to helping them. Appearing in courthouses regularly also helps your career: You meet other lawyers, receive referrals and connect with experienced mentors. It is also fulfilling to help someone avoid or mitigate a personal disaster. 

TIPS FOR KEEPING UP WITH LEGAL TECH

There are resources online to learn about legal technology. Vendors will, of course, put their product’s best foot forward with their content. But my friend Bob Ambrogi’s blog Law Sites is widely considered the “go-to” source for legal technology news. His journalistic background shines through. His recent feature outlining how most small-firm practice management tools are now consolidated under one of six ownership groups is a great example. Subscribe or visit regularly.

Catherine Sanders Reach, director of the Center for Practice Management for the North Carolina Bar Association, writes great original content on legal tech and practice management. Anyone can subscribe to receive regular summaries and links to her writing, as well as links to other online content she finds useful. 

ONE MILLION THANKS

So many deserve my appreciation. In addition to the ABA TECHSHOW gang, I’ve benefited from my association with my colleagues at the ABA Law Practice Division, the National Association of Bar Executives, my close colleagues who are fellow practice management advisors across the U.S. and Canada and, of course, my co-workers here at the OBA, past and present.

John Morris Williams was the OBA executive director for many years, leading the association through many interesting times. He supported my endeavors and often grilled me with pointed questions. That was far better than hearing difficult questions for the first time in front of a room full of lawyers.

OBA Executive Director Janet Johnson has been a great source of support and good advice. The OBA is lucky to have her leadership. One cannot overstate the joy she brings to the workplace.

My team, MAP Assistant Nickie Day and Practice Management Advisor Julie Bays, is excellent. Nickie is the best and most organized assistant I’ve ever had during my legal career, which was valuable as I kept hatching new ideas. She keeps us all organized with our schedules. Julie received so much positive feedback on her great job as the 2025 ABA TECHSHOW co-chair. Her knowledge of practice management software is particularly important for new lawyers setting up a practice or firms contemplating a change of practice management software tools. I have certainly benefited from her candid counsel.

Thanks to all of you, Oklahoma lawyers. I was always so proud when conference vendors told me after conferences how well-informed our lawyers were about legal technology products and services. Whether you’ve read my column, seen a CLE I taught, attended the Solo & Small Firm Conference or we’ve discussed your questions via phone or email, I hope you benefited. I certainly did. I was able to work at a job I truly loved for a long time.

Mr. Calloway is the OBA Management Assistance Program director. Need a quick answer to a tech problem or help solving a management dilemma? Contact him at 405-416-7008, 800-522-8060 or jimc@okbar.org (until the end of May.) It’s a free member benefit.

[i] I will concede that we all underestimated the tenacity of the legal profession in hanging on to the billable hour far longer than we would have thought. Maybe AI will finally be the tipping point. But maybe it won’t.

[ii] Julie Bays and I will both remember giving an early AI CLE in a courtroom. When Julie showed how she used a tool called Descript to alter a video she had recorded just by editing the transcript of the video, the judges in the audience immediately had a lot of questions.

Originally published in the Oklahoma Bar Journal — May, 2025 — Vol. 96, No. 5