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What I Learned About Document Automation at Tech Show 2023

What I Learned About Document Automation at Tech Show 2023

This year I had the pleasure of attending my first ever ABA Tech Show in Chicago. It was an unforgettable experience. It’s hard to pinpoint exactly what it was, but there was magic in the air. After embarking on a red-eye flight from sunny San Francisco, I arrived in the Windy City at 6am, a decision I might rethink in future. I was met with unparalleled hospitality; the Hyatt Regency staff granted me immediate access to my room rather than making me wait until check-in time at 3pm! That allowed me to recover and prepare for my first meeting with Barron Henley of Affinity Consulting Group.


Barron and I had a fascinating discussion about typing and ergonomics. He types on a Logitech Ergo K860. We explored various automations for Microsoft Word. Commonly requested functions, such as "keep with next," "keep lines together," and "page break before" were mentioned alongside innovative ideas, such as automating specific commands without dedicated buttons in Word, those tedious actions that require 5+ mouse clicks. I pondered the thought of creating a “watermark” key. Near the end of our meeting, Bob Ambrogi came by to say hello. I shook his hand for the first time. I was already learning so much about document automation, and Tech Show hadn’t even started yet!

My next meeting was with Mathew Kerbis, the Subscription Attorney. Mathew brought a fresh and innovative perspective to lawyering. According to Kerbis, younger lawyers aged 23 to 40 have an inclination to type themselves, rather than depending on paralegals. Moreover, they demonstrate a preference for Apple's Mac computers over the traditional Windows devices. Kerbis had a new Windows Surface with him. He also expressed enthusiasm for his Logitech Ergo K860 at home. I found Kerbis to be practical and unafraid of using technology differently, not surprising from someone who is disrupting the billable hour. For example, Kerbis prefers Google Docs to Word. He also doesn’t care to remove the page number from the first page of a legal brief: “Page 1 is important!” In terms of automations, Kerbis suggested that a lot of legal professionals, especially paralegals, would get excited about a “bates stamp” key.

Later in the evening I attended a Faculty Happy Hour. We exchanged insights on the mesmerizing world of ChatGPT, AI, and even marveled at the intricacies of keyboards. The evening reached its crescendo as we headed down to the Startup Alley pitch competition.


15 trailblazing startups took to the stage, each presenting a captivating three-minute pitch. The competition was fierce, but Universal Migrator triumphed, seizing the coveted first prize, while Decision Vault and Fidu claimed the second and third spots, respectively. As the contest came to a close, we were treated to a musical and visual tribute to the esteemed Bob Ambrogi — a heartfelt moment that rendered him speechless. The camaraderie carried on as we continued to gather at the Welcome Reception in the Expo Hall. As a first-time attendee and representative of LegalType, a semifinalist in the competition, I was thoroughly captivated by the entire experience and sense of community. We plan to reapply to Startup Alley next year.

Thursday morning began with yoga class at 7am. I’m so glad I went to this. It was the perfect antidote for my weary spine. Yoga was gentle and challenging, and it was a nice way to connect with people. It left me energized and focused.

A riveting inaugural keynote panel "Legaltech Visionaries" incited both thought and motivation. The intimate, dialogue-driven format was expertly steered by Clio's esteemed CEO, Jack Newton, as he led a diverse group of innovative leaders. Among them were Fidu's Kimberly Bennett, TurnSignl's Jazz Hampton, and Erin Levine of Hello Divorce. Collectively, the panelists tackled imperative topics such as accessibility, institutional racism, the billable hour, and the cutting-edge realm of artificial intelligence. Also, Erin Levine wore a hoodie, which I thought was pretty cool.

The first session I attended on “TrialPad, Adobe and Other Technology Solutions in the Courtroom” was guided by Brett Burney and Tara Cheever. The duo meticulously deconstructed the antiquated relics of courtroom technology, such as the cumbersome elmo projector. They highlighted the inadequacies of such devices, citing their tendency to divert attorneys' attention away from jury members.

Burney and Cheever painted a vision of the modern courtroom that blew me away. Imagine a trial attorney, confidently striding into the courtroom, armed with just a compact suitcase containing all the essential equipment for the entire legal proceeding. Gone are the days of unwieldy banker boxes. Within minutes, the setup is complete. An Apple TV screencasts documents from an iPad, sans cables to trip over. A solitary easel showcases one striking image. No Elmo projector. The cutting-edge attorney effortlessly manipulates document displays, calling out and highlighting sentences with the press of a finger, all while roaming the courtroom and forging a compelling connection with the jury. It was fascinating to learn how technology can help lawyers become better presenters, and it got me thinking: “How do lawyers type on their iPads?”

Dan Siegel and Darla Jackson unraveled the wonders of Adobe Acrobat during their presentation: “I didn’t know PDF’s could do that!” They showed us that PDFs are more secure, easy to store in the cloud, and they can be password protected and signed! We were amazed how easy it is with this program to create automations like “confidential watermark”. Even better news – once an automation has been created you can share them across your entire team as long as each person owns a license for Adobe Acrobat. It was fascinating learning from these incredible professionals who made their session both informative and engaging.

Later that evening, after a Happy Hour, fate led me to a Taste of Techshow dinner, despite my initial party disappearing into the urban abyss. Fortune smiled upon me as Brett Burney swooped in and offered sanctuary with his lively entourage. We walked along the river to the restaurant under the shimmering moonlight and shared an incredible meal. I had the best Gin & Tonic of my life, and the king salmon was fabulous. It was the perfect night and a great way to discover a little piece of Chicago.

The next morning at 7am I bravely faced the 6th annual ABA Tech Show 5K marathon. With the vigor of a somnambulist, I tackled the scenic route that took us past a nearby park, the Bean, and the magnificent Lake Michigan. It was tough, but I made it. Hopefully I’ll be a little faster and stronger next year.

Friday, March 3rd was quite the whirlwind! With snow on the horizon and a 5K race under my belt, I dashed through the Expo Hall for a well-deserved breakfast. As I juggled meetings and hotel checkouts, I shared knowing nods with my fellow city-conquering runners.

Later that day, I met with Dan Siegel, an attorney with a small practice in Havertown, Pennsylvania. Dan also types on a Logitech Ergo K860. Siegel was happy to buy ergonomic keyboards for all of his employees, which I found very forward-thinking. In terms of automations, Siegel suggested a “paragraph formatting” key and “numbered list” for citations. Jamie Szal was in the same room gracefully scribing on her iPad. Upon inquiry, she revealed her artfully penned handwritten notes. The screen looked like paper.

Tech Show was amazing. I only wish I’d stayed longer. On the way out of the hotel I was lucky to hitch a ride to the airport with some vendors from the Expo Hall. It started to snow. Chicago's reputation for unpredictable weather definitely kept everyone on their toes — adding yet another memorable layer to such an incredible experience.

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