A Technology Lawyer and a Legal Technologist Walk Into a Bar: Musings of AI All Grown Up
Aman Vasavada, Legal Engineer,
If You Run a Small Firm, This One's for You
Here's a question worth your next sixty seconds: if you run a boutique, is the AI conversation something you need to act on now, or something you can safely let the big firms figure out first?
For the last two years, sitting out made sense. The tools were half-built and you'd have been paying to be someone's experiment. That window has closed, and here's the uncomfortable part. Waiting used to be the cautious move. It isn't anymore. The risk has quietly switched sides, and a lot of firms haven't noticed it move.
What follows is what I saw on the ground that convinced me, and what it means for you.
Where I Was Standing
I was a pilgrim at the 2026 International Technology Law Association World Technology Law Conference ("iTechLaw"), held in the genial confines of Chicago's Ritz-Carlton in May. River North was bustling with the annual migration of conference pilgrims: lawyers, businessmen, and consultants, milling about the Magnificent Mile, clutching lanyards and totes, sampling deep-dish pizzas, and convinced they were attending the most important gathering in town. Guilty as charged.
Here’s what I overheard, argued about, and took away across three days in the room and at our booth, and why it's relevant to you.
These are people worth listening to. Technology lawyers have always been the human equivalents of starship rudders, steering business teams, clients, products, and regulators into the great beyond while their peers pore over precedent. They spend their days interpreting emergent systems and bearing early witness to the "next big thing" over and over again. So as legal technology storms into the spotlight, they were exactly the people I wanted to hear from. I was not prepared for how much the conversation had changed.
What I Expected to Hear
I arrived expecting the usual fare of chitchat glazed by Shiny Object Syndrome: AI evangelism, ROI calculations, first "wow" moments, and the perennial question of whether lawyers are about to automate themselves into extinction.
What I Heard Instead
Instead, I was in for a treat. The conversation had grown up. Across sessions on AI governance, litigation workflows, enterprise adoption, and risk management, nobody seemed particularly interested in science fiction. The focus was on the messy, unglamorous realities of implementation: failed pilots, data hygiene, governance policies, interoperability headaches, adoption resistance, and the surprisingly difficult task of persuading highly-paid professionals to change how they work.
One was a candid conversation about a pilot that started with a bang, but died with a whisper. The tool worked, but no one had decided whose job it was to check its output, so the lawyers simply stopped trusting it. Another session turned into a genuine debate over a governance question with no clean answer: when an arbitrator asks whether you used AI on their matter, what exactly do you owe them, and in writing or not?
This was a room of mechanics and builders, not just buyers and users. A cadre of minds that has always handled the emergent, now seeing the emergent play out on its home turf.
The Conversations at Our Booth
At our booth, the conversations were just as honest, if not more so. Firm leaders and general counsel shared how they structured pilots, how they coaxed billables-blinded attorneys into spending time on legal engineering, where their vendors failed to deliver, and how the discovery of just one champion use case converted an entire practice area into AI-enabled superlawyers. Once upon a time, such conversations ended with a musing on whether the ROI justifies an investment. Now, the logical conclusion was an exchange of notes on governance policies, product mix, and cultural change, and how it all fared.
What This Means If You Run a Boutique
Here is where a small-firm owner might reasonably tune out, assuming this is a story about big firms with committees and budgets. It isn't. And the maturing of this market is arguably better news for you than for them.
A bleeding-edge market punishes small players. The tools are half-built, the failure modes are undiscovered, and you pay to be someone's experiment. A maturing one rewards you. The failure modes I heard about all weekend are now known, which means you can sidestep them instead of funding their discovery. The tooling no longer demands a dedicated team to babysit it. And the single biggest adoption obstacle the large firms kept naming, getting highly-paid people to change how they work, is the one problem a boutique doesn't really have. You don't need to win over a committee or convert a practice area. You need to convince a handful of people, possibly just yourself.
So here is the Monday-morning version. Don't buy anything yet, and don't run a "pilot." Pick the work that buries you and hand it to the machine first. Let it compress discovery. Let it crunch the large data sets behind a due diligence exercise that would otherwise eat a junior's month. The point isn't the hours you save, though you'll save plenty. The point is where those hours go. You move from paperwork to strategy, from document review to the judgment your client actually pays you for. The champion use case that converts a whole department at a large firm is, at your scale, simply a Tuesday where you decide to do one thing differently.
The Real Takeaway
The most striking takeaway was that the industry has moved from curiosity into operational reality. The novelty is fading. The hard work is beginning, which is exactly the moment a nimble firm gets to move faster than a slow one.
So return to the question I opened with: act now, or wait for the big firms to figure it out? The honest answer is that it was never really a choice. "Waiting" was always just a slower way of deciding, and the firms congratulating themselves on their caution are the ones taking the bigger risk. As a legal engineer whose very role is a fabrication of these ephemeral times, I walked out onto the Magnificent Mile on Day 3, lanyard and tote in hand, certain of one thing. Phase 1 of the AI experiment is over, the manual for phase 2 is being written, and as a boutique law firm you are light enough to act on it before the careful ones ever finish their committees.
If that's your cue, we should talk.
