Between the Briefs

Latest Episodes:

Innovation Is More Than AI ft. John Koss Sep 25, 2026

Show notes

AI is not a strategy.
Sure, it’s a powerful tool but still, only one piece of the puzzle.
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with John Koss, Chief Innovation and AI Officer at Mintz, for a practical conversation on legal AI, innovation strategy, knowledge management, law firm data, legal education, vendor relationships and what it actually takes to make new technology useful inside a law firm.

What You’ll Learn:

Why John sees innovation as much broader than AI
How people, process, and technology shape real law firm change
How Mintz measures early ROI on AI tools through adoption, usage, and engagement
Why usage is only the baseline, not the full ROI story
How experimentation becomes a repeatable “Mintz way” of doing legal work
Why chasing every new AI tool creates scattered results
Why AI adoption has become easier than earlier legal tech shifts like technology-assisted review
What law schools should and should not be expected to teach about AI
Why mentorship and judgment still need to be taught inside firms
Why a single source of truth for firm data is foundational but deeply unglamorous work
What legal tech vendors need to understand before pitching law firms
Why nobody has the future of legal AI fully figured out yet

The big takeaway: AI strategy is not about panic-buying tools. It is about knowing your problems, choosing your path, building the workflow, and bringing people with you.
Highlights:
00:00 Introduction00:51 John’s Path From Litigation to Legal Tech02:52 What a Chief Innovation and AI Officer Actually Does03:03 Why Innovation Is Bigger Than AI04:24 Moving From Legal Work to Business Strategy06:01 Measuring AI Adoption and ROI06:37 Why Usage Is Only the Starting Point08:34 Turning Experimentation Into Repeatable Workflows09:45 The Biggest Challenge in AI Adoption09:59 Why John Avoids Calling Firm Missteps “Mistakes”12:52 Getting Buy-In From Lawyers13:46 Why AI Adoption Is Easier Than Earlier Legal Tech Shifts17:52 How Law Schools Are Responding to AI18:19 What Law Schools Should Teach About Legal AI22:01 The Risk of Over-Automating Legal Learning23:03 Teaching Judgment in the Age of AI27:49 Building a Single Source of Truth28:09 Why Firm Data Strategy Is Foundational31:14 What Legal Tech Vendors Get Right and Wrong31:53 Why Customer Success Matters After the Sale36:23 John’s Hot Take: Nobody Has This Fully Figured Out38:32 Closing Thoughts
Quotes:

“Innovation to me is much broader than just AI.”
“Technology’s one of those three legs of the stool.”
“How do we take experimentation and turn it into something that’s kind of a repeatable workflow or use case?”
“We’re not a bunch of dummies.”
“We are really all in this together.”

Between The Briefs is handcrafted by our friends over at: fame.so

How AI Is Helping Lawyers Find Cases They’d Never Find Manually ft. Maxwell Weiss Sep 18, 2026

Show notes

Maxwell Weiss has investigated everything from stolen historical artifacts and match fixing to counterfeit medicines, privacy violations and questionable health plans. Now, he is working at the intersection of plaintiff-side litigation and AI-powered case discovery.
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Maxwell Weiss, a partner at Don Bivens and Litigation Counsel at Darrow AI, to unpack how lawyers can find the facts that actually matter, investigate complex wrongdoing and use technology to uncover cases that traditional methods may never reach. Maxwell explains the 80/20 rule he applies to litigation, why brevity matters in legal writing, what federal judges taught him about courtroom advocacy and why the best lawyers often sound more like they are having a conversation than delivering a performance.
The conversation also gets into Darrow AI and how technology can monitor prices, identify potential privacy violations and analyze complicated health-plan structures at a scale that would be nearly impossible for lawyers to handle manually. Maxwell explains how those findings are turned into something lawyers can actually use: a clear case theory, the relevant law, precedent and an evidentiary roadmap.
And then there is Maxwell’s biggest concern about AI: junior lawyers may become so dependent on it that they skip the foundational work that teaches them judgment in the first place.

What You’ll Learn:

How Maxwell applies the 80/20 rule to litigation strategy and focuses time on the facts that actually drive a case
Why investigative work often requires lawyers to bring in private investigators, technical experts and other specialists
What Maxwell learned from his federal clerkship about brevity, courtroom advocacy and communicating with judges
Why strong advocacy looks more like a conversation than a rehearsed courtroom performance
How class actions can create meaningful relief by stopping harmful conduct, not just recovering money
How AI can surface potential privacy violations, misleading pricing practices and health-plan problems at a scale that would be difficult to investigate manually
Why translating AI findings into clear legal analysis is still a deeply human part of the process
How lawyers identify and recruit strong named plaintiffs for class action cases
Why Maxwell is concerned that AI could leave junior lawyers without the foundational skills needed for good legal judgment

The big takeaway: AI can expand the scale of legal investigation, but lawyers still need the judgment to turn what they find into a real case.
Highlights:

00:00 Introduction
01:25 The Stolen Artifact Investigation
03:52 Maxwell’s Unusual Path Through Big Law and Federal Court
05:05 Investigating Counterfeit HIV Medicines
08:01 The 80/20 Rule for Litigation Strategy
09:10 How Lawyers Actually Investigate Complex Cases
11:19 The Ethics of Representing Clients
14:00 Why Brevity Matters in Legal Writing
15:30 What Federal Court Taught Maxwell About Advocacy
18:04 The Real Purpose of Class Actions
21:31 How Darrow AI Finds Hidden Legal Wrongdoing
24:46 The Problem With Dominated Health Plans
27:34 AI Cases That Would Never Be Found Manually
28:59 Will Lawyers Actually Adopt Legal AI?
30:42 What Happens When Both Sides Have AI?
31:47 Maxwell’s Next Big Litigation Target
35:17 Why Purpose Drives Maxwell’s Practice
36:45 Using Targeted Advertising to Find Plaintiffs
38:42 What Makes a Good Named Plaintiff?
41:27 The Emotional Side of Plaintiff Litigation
42:28 Maxwell’s Biggest Fear About AI and Junior Lawyers
43:47 Closing Thoughts
Quotes:

“The 80/20 rule is just so true.”
“The best advocates are having a conversation with the jury or the judge.”
“You don’t have to be absolutely perfectly polished.”
“I worry that junior lawyers will grow to rely on artificial intelligence so much that they’ll never get the basic skills.”

Between The Briefs is handcrafted by our friends over at: fame.so

The Next Era of Between the Briefs Sep 11, 2026

Show notes

75+ episodes. 1,200+ followers. A new look. A bottle of hot sauce. And a legal industry that is changing faster than most people can keep up with.
In this special episode of Between the Briefs by Steno, hosts Joe Stephens and Adrian Cea record live from ILTACON 2026 to reflect on the conversations, guests, hot takes and recurring themes that have shaped the show so far.
Join them as they revisit standout guests including Elaine Barsom, Colin Levy, Eric Friedman, Andrew Finkelstein, Matthew Pringle, Bob Simon, Katie DeBorde, and others, while also introducing the show’s new Hot Takes hot sauce.
What You’ll Learn:

Why “go slow to go fast” keeps coming up in legal AI conversations
Why AI is better understood as leverage, not a lawyer replacement
How legal tech is changing firm structures, billing models, hiring, training and education
Why law schools are still figuring out which AI skills actually matter
Why empathy, relatability and storytelling remain major legal advantages
How guest conversations have shaped Joe and Adrian’s view of the industry
Why attorney-client privilege and consumer AI use are becoming urgent client-counseling issues
Why judges and clerks keep coming back to the same advice: be brief
How private equity, remote-first firms, and AI-driven models are shifting the business of law
Why the rebrand marks a new chapter for Between the Briefs, not a reset

This episode is a milestone, a reintroduction and a reminder that the future of legal innovation will not be built by technology alone. It will be built by people who know how to use it well.
Quotes:

“We’ve hit over 75 episodes now. We’ve had some amazing guests.”
“It’s not about matching that pace. It’s actually about being methodical and thoughtful about how you adopt, when you adopt, how you change.”
“AI is there to assist, free up space, allow you to do the job that you spent a lot of time preparing to be brilliant at, which is exercise judgment.”
“You can use AI to optimize, change the way things are done, but you’re still working with people.”
“Sometimes you want to say a million things, but the best thing that you can say can live in three paragraphs or three pages instead of 10.”

Between The Briefs is handcrafted by our friends over at: fame.so

Why Small Firms Can Move Faster Than Big Law ft. Nicole Brenecki Aug 28, 2026

Show notes

Personal injury law has a lot of big promises, big ads and big firms. Nicole Brenecki is more interested in what actually works.
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Nicole, Founding Partner at Jodré Brenecki LLP, for a candid conversation on personal injury litigation, boutique firm strategy, client service, New York court delays, fraud scrutiny, AI and why efficiency matters more than size.
What You’ll Learn:

Why firm size can become a marketing gimmick when service breaks down
Why Nicole’s firm files suit on most cases immediately after intake
How small firms can use speed and coordination as a competitive advantage
Why New York’s fragmented court system makes client expectation-setting so important
How multilingual advocacy helps clients better understand the legal process
Why hiring for intelligence and instinct can matter more than resume polish
How Nicole uses AI for narrow tasks without giving up the personal touch
Why judges with overloaded dockets need clear, concise arguments
Why legal professionals need to cut through inefficiency instead of building careers around it

The crux of this episode: Building a firm with zero capital into a small but sharp personal injury practice that handles hundreds of cases with speed and intention.
Highlights:
00:00 Introduction
01:05 Nicole’s Media Work and Legal Commentary
01:29 Preparing for Live TV Legal Analysis
03:28 Nicole’s International Legal Background
03:53 Comparing Statutory and Precedent-Based Legal Systems
05:45 Explaining the Legal Process to Multilingual Clients
07:09 How Personal Injury Litigation Has Changed
07:18 Why Nicole Files Suit on Most Cases Right Away
08:45 Keeping Up With New York’s Court Rules
11:03 Small Firm vs. Big Firm Client Service
11:36 Why Bigger Does Not Always Mean Better
14:48 Nicole’s Hiring Philosophy
14:58 Why Intelligence Beats Resume Obsession
16:44 The Skills Nicole Believes Are Hard to Teach
17:34 Developing Litigation Instinct
20:39 How Nicole Uses Technology in Her Firm
20:51 Why AI Is Useful, But Limited
23:31 Nicole’s Intake Process and Fraud Red Flags
23:57 Why Fraud Scrutiny Is Hitting Ethical Firms Too
29:21 Multilingual Advocacy and Client Expectations
29:43 Why Language Is a Tool for Trust
31:40 Underrated Litigation Skills
31:58 Why Brevity Matters in Court
35:58 Nicole’s Work in Music and New York Tracks
38:47 What Event Production Taught Her About Business
40:28 Nicole’s Long-Term Motivation
42:39 Nicole’s Hot Take: Legal Inefficiency Hurts Everyone
43:59 Closing Thoughts
Quotes:

“It’s just a marketing gimmick that you get more with a greater size. Very often you get less with a greater size because there’s just so many people and the work is so compartmentalized.”
“If you’re intelligent, you can learn anything.”
“Use AI as a tool and not as a replacement of you.”
“Stop going in circles for your own benefit. Try cutting through the inefficiency.”

Between The Briefs is handcrafted by our friends over at: fame.so

Every Paralegal Needs The One-Step-Ahead Mindset ft. Christina Carter Aug 21, 2026

Show notes

Paralegals are the people attorneys rely on when deadlines are tight, documents are moving fast and the work needs to get done right.
But they’re often treated as background support.
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Christina Carter, Senior Manager of Firm-Wide Paralegal Management at Venable, for a practical conversation on paralegal leadership, legal operations, team culture, generational dynamics, AI adoption and what law firms often miss about the people who keep the work moving.
What You’ll Learn:

Why paralegal management should be treated as strategic operations
How Christina supports 80+ professionals across practice groups and career stages
Why law firms need to recognize paralegal work before people burn out or leave
How proactive staffing helps prevent retention problems before they start
How onboarding should be shaped around the person, the practice group and the culture
Why AI should be used as an assistant, not treated as the leader of the work
How paralegals can use the “one step ahead” mindset to become indispensable
Why treating people like humans is still the best management principle out there

Strong legal teams are not built only around attorneys. They are built around the people who anticipate needs, hold the work together and make everyone else look better.
Highlights:
00:00 Introduction
01:27 What Firm-Wide Paralegal Management Actually Means
01:39 Supporting 80+ Paralegal Professionals Across Venable
03:23 Why Christina Is the Gears of the Law Firm
04:26 Christina’s Path From Aspiring Attorney to Paralegal Leadership
04:51 Starting at Skadden and Learning Law Firms From the Inside
07:52 Why Paralegals Do Not Get Enough Credit
08:41 How Venable Recognizes Paralegal Contributions
11:40 When Law Firms Need a Paralegal Manager
11:55 Why Staffing Requires One-Step-Ahead Thinking
14:21 Managing Across Generations
14:51 How Community Bridges Generational Gaps
17:31 How Christina Onboards New Paralegals
17:55 Why Training Has to Be Individualized
20:38 Christina’s Management Principles
21:09 Treating People Like Humans, Not Headcount
24:17 How AI Is Changing Paralegal Work
24:39 Why Technology Should Be Your Assistant
27:38 Coaching Paralegals Through AI Anxiety
28:34 Why Human Judgment Still Matters
32:55 Advice for New Paralegals
33:25 The One-Step-Ahead Mindset
37:56 What Dance Taught Christina About Community
38:27 Why Relationships Matter in Legal Careers
40:54 Christina’s Hot Take: Legal is Having an Evolution Moment
43:35 Closing Thoughts
Quotes:

“My role is very much on a strategic level.”
“Treat every individual as an individual and see them as such.”
“Use that technology to be your assistant versus being the leader of the work that you do.”
“Not knowing about it, not learning about it, not becoming comfortable with it isn’t going to make it go away.”
“You really need to think about things from a one-step-ahead mindset.”

Between The Briefs is handcrafted by our friends over at: fame.so

The Email That Ruined a $10M Lawsuit ft. Kat Mateo Aug 14, 2026

Show notes

Litigation does not begin when a lawsuit is filed. By then, the story has often already been written in contracts, emails, missed deadlines and the very human decision to wait because “maybe it’ll blow over.”
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Kat Mateo, Counsel of Litigation at Olshan Frome Wolosky LLP, for a practical, lively conversation about what clients, founders, business owners and legal teams often misunderstand about litigation.
What You’ll Learn:

Why clients should involve attorneys before disputes escalate
How litigators can spot risks in deals that transactional teams may miss
Why most cases are won or lost on papers, not dramatic courtroom moments
How emotional emails, sarcasm and jokes can become serious evidence
Why discovery now reaches work emails, personal phones, WhatsApp, Signal, Slack and social media
Why attorneys can manage bad facts, but not surprise facts
How storytelling helps juries understand complex commercial disputes

Good litigation strategy is not just about fighting well. It is about preventing problems early, documenting carefully, communicating wisely and knowing when to call the lawyer before things get expensive.
Highlights:
00:00 Introduction
01:09 Kat’s Journey From the Dominican Republic to Litigation
03:44 How Culture and Community Shape Kat’s Advocacy
05:04 The Pressure and Responsibility of Being First-Gen
07:08 Staying Hungry Through a Hard Journey
08:50 Kat’s Advice for First-Gen and Immigrant Law Students
10:52 Why Litigation Starts Before the Lawsuit
11:16 The Biggest Mistake Clients Make Before Litigation
15:01 What People Misunderstand About Litigators
15:36 Why Most Cases Never Go to Trial
16:41 Why Emotional Emails Can Wreck a Case
18:06 The Courtroom Poster Test for Client Communications
21:22 Why Clients Should Never Hide Bad Facts
25:16 Why Storytelling Matters in Litigation
25:47 The Difference Between Truth and What You Can Prove
30:15 How Kat Approaches Storytelling for Juries
34:38 Kat’s Love-Hate Relationship With AI
35:33 The AI Privilege Trap Clients Need to Understand
38:51 What Kat Learned Inside a Judge’s Chambers
39:34 How Judges Really Approach Decisions
43:55 Kat’s Hot Take on Technology and Lawyers
44:48 Closing Thoughts
Quotes:

“Usually cases are not hard because the law is hard. They’re hard because of the decisions the clients have made before litigation even commenced.”
“The biggest mistake that I see clients make is that they don’t involve attorneys early enough.”
“Most cases are won or lost on papers.”
“I can deal with bad facts. I can’t deal with surprise facts.”
“Technology is changing what things look like, but it doesn’t mean that lawyers go away.”

Between The Briefs is handcrafted by our friends over at: fame.so

Where Are the Legal Leaders We Need? ft. Nicole Lester Arrindell Aug 07, 2026

Show notes

Leadership in law is often treated like something that comes after the promotion, after the title or after someone hands you a team and assumes you magically know what to do with them.
Nicole Lester Arrindell sees it differently. In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Nicole, Head of State Regulatory and Legislative Affairs and Associate General Counsel at Equitable, for a wide-ranging conversation on servant leadership, legal education, public service, in-house counsel, mentorship, and what it actually means to lead in the legal profession.
What You’ll Learn:

Why leadership is not about a title, but about how you show up in any role
How Nicole’s South Side Chicago upbringing shaped her commitment to service
Why the people closest to the issue often understand it better than anyone else
How in-house lawyers can become business partners instead of the “department of no”
Why “soft skills” should be treated as core legal skills
What law schools should teach about client relationships, team management, and communication
Why students need to practice presenting ideas, even if they never plan to litigate

This episode is a reminder that legal excellence is more about judgment, empathy, communication, influence and the ability to help people get where they are trying to go, than about sheer knowledge.
Highlights:

00:59 Welcome to Between the Briefs
01:36 Meeting Nicole Lester Arrindell
03:04 Nicole’s Career & The Through-Line of Service
04:45 Community Service on Chicago’s South Side
07:37 Teaching the Next Generation of Lawyers
10:19 Everyday People Can Be Everyday Leaders
12:12 The Kind of Leadership That’s Actually Valuable
12:36 Nicole’s Career GPS: Goals, Purpose and Skills
13:57 Why Self-Reflection Matters in Leadership Development
16:24 Lessons From Legal Aid and Chief of Staff Roles
16:54 Why the People Closest to the Issue Know It Best
18:45 Legal Leadership Means Figuring It Out Together
19:21 Nicole’s Role in State Regulatory and Legislative Affairs
21:48 Why “Soft Skills” Are Really Core Skills
24:29 Nicole’s Work as an Adjunct Professor
24:38 Bringing Practical Lawyering Into the Classroom
28:18 What Nicole Hopes Her Students Take With Them
30:42 Being a Partner to the Client, Not the Department of No
33:04 Leading the Metropolitan Black Bar Association
36:01 Nicole’s Journey With the MBBA
39:24 Protecting the Rule of Law
40:42 Leadership as Practice, Not Position
41:35 Nicole’s Hot Take: AI Fluency
42:32 Closing Thoughts
Quotes:

“Everyday people can be everyday leaders.”
“You don’t have to have the big title or the fancy position in order to demonstrate leadership.”
“The people closest to the issue understood it better than I could.”
“We’re not the department of no. We’re the department of “let’s figure it out.”
“The fact that you were a great litigator does not now mean you can manage 20 of them.”

Between The Briefs is handcrafted by our friends over at: fame.so

Legal Tech Doesn’t Need More “Lamborghinis” ft. Kara Peterson and Richard DiBona Jul 31, 2026

Show notes

Everyone claims AI will revolutionize legal, but Kara Peterson and Richard DiBona want to fix the systemic bottlenecks that have broken the system for decades.
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Kara and Richard, cofounders of Descrybe, an AI company focused on making the law easier to find, understand, and verify. Their story began during the pandemic, when a personal legal issue pushed them into the frustrating reality of trying to understand and access the law as nonlawyers. That experience became the starting point for a platform designed to make legal information more accessible, accurate and affordable.
What You’ll Learn:

Why the justice gap is fundamentally an operational supply-and-demand mismatch.
How inaccurate AI outputs could trigger harsh judicial regulations.
Why Descrybe moved from D2C pro se tools to empowering legal aid providers.
How issue-level citation analysis outperforms traditional "good law/bad law" tools.
Why high-quality legal tech does not require enterprise pricing tags.

This episode is a grounded look at what responsible legal AI can actually do: not replace lawyers, not magically fix the system overnight, but give under-resourced legal professionals better tools to serve more people.
Highlights:
00:00 Introduction
01:09 Kara and Richard’s Unusual Founder Story
02:21 Why Access to Justice Matters in Legal AI
02:51 AI, Legal Demand, and the Justice Gap
04:29 How AI Could Make the Gap Smaller or Bigger
05:10 Richard’s Software Engineering Background
06:58 Building From Harvard’s Case Law Access Project
07:33 Why Access to Justice Is Like a Public Health Issue
08:41 The Hallucination Problem in Legal AI
09:46 Why Descrybe Builds for Attorneys and Legal Aid Providers
13:02 Why Legal Research Is More Complex Than It Looks
13:27 The Moment They Learned About Shepardizing
14:36 Why Legal Librarians Matter So Much
16:29 Issue-Level Citation Analysis
19:03 The Four Levels of AI Accuracy in Legal Research
21:40 Why Foundation Models Will Not Eat Everything
23:47 How Descrybe’s Anthropic Collaboration Happened
25:36 What the Claude for Legal Launch Changed
27:49 Why Courts Need Better Hallucination-Checking Tools
29:31 How Descrybe’s Brief Checker Works
31:23 Scaling After the Anthropic Collaboration
33:22 Why Fair Pricing Matters in Legal Tech
36:10 Advice for AI Founders
39:03 Why the Legal AI Ecosystem Matters
40:03 Why Kara Does Not Believe in Declaring War on Incumbents
42:19 Kara and Richard’s Hot Takes on Legal AI
45:49 Final Thoughts
Quotes:

“We can’t “human” our way out of this problem. It’s just too labor intensive, there’s too much need, the cost structures don’t work. People can’t afford lawyers.”
“AI could either make the justice gap smaller or bigger.”
“We realized the better we could serve people serving the people who need to be served is where we could actually have the most impact.”
“Legal tech is really weird. You don’t have to trade really good tech for fair pricing.”
“Not everyone needs these gigantic end-to-end solutions.”

Between The Briefs is handcrafted by our friends over at: fame.so

Is Not Using AI a Malpractice Risk? ft. Shannon Boettjer Jul 24, 2026

Show notes

A few months ago, people were asking whether not using AI could ever be malpractice. Now, that question feels a lot less theoretical.
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Shannon Boettjer, partner at Jaspan Schlesinger Narendran LLP, for a sharp, practical conversation on AI governance, legal risk, and what it means to build defensible systems before technology decisions turn into lawsuits.
What You’ll Learn:

Why the AI conversation shifted from “should we use it?” to “how do we use it responsibly?”
How the knife vs. kitchen analogy helps firms understand different levels of AI complexity
Why AI governance should start with a risk-benefit analysis, not a checkbox list
Why hallucinations are better understood as common side effects, not random surprises
How “parallel from the start” can help firms avoid bad habits that compound at scale
Why AI literacy is only the starting point, and AI fluency is the real goal
Why lawyers need to understand the tools their teams, co-counsel, and vendors are using
Why machines require a zero-trust approach, while humans require trust but verify

This episode is a clear-eyed look at legal AI adoption and the actual governance work required when lawyers start putting powerful tools into everyday practice.
Highlights:
00:00 Introduction
01:19 Is It Malpractice Not to Use AI?
02:56 AI as a Tool: The Knife vs. Kitchen Analogy
05:04 Why Basic AI Skills Are Becoming Expected
07:17 Today’s Design Decisions Become Tomorrow’s Liability Theories
07:36 The Pharmaceutical Lens for AI Governance
09:40 Why EDRM Is an Underused AI Governance Framework
10:18 Choosing the Right Tool for the Right Pain Point
13:10 Why Human Review Still Matters
14:50 AI Literacy vs. AI Fluency
16:21 Lessons From Legal Week
16:43 Common Side Effects and Rare but Serious Risks
18:36 The “Parallel From the Start” Framework
20:16 Why “Grab It and Go” AI Adoption Creates Risk
20:47 The First Question Every AI Strategy Should Ask
23:51 Why End Users Need to Be in the AI Conversation
26:02 Data Governance, Privacy and Cybersecurity in AI Use
29:48 How Firms Should Assess Their AI Maturity
33:17 Why Old Technology Problems Keep Reappearing
37:17 Applying Existing Legal Duties to AI
38:03 Trust Humans, Zero Trust Machines
41:05 Where Legal AI Is Heading Next
47:18 The Cognitive Cost of Working With Machines
49:31 Shannon’s Hot Take: Personal Knowledge Management
52:02 The Swiss Cheese Problem in AI Governance
54:03 Closing Thoughts
Quotes:

“AI is a tool, and I think of it in terms of something like a knife.”
“Every layer of AI potentially solves a problem and potentially creates risks.”
“Start with literacy with the end goal of being fluent.”
“Trust but verify your human colleagues. I would hold a different standard for working with machines: zero trust.”

Between The Briefs is handcrafted by our friends over at: fame.so

Will AI Lower Legal Costs? Tim Fox Explains the Twist Jul 16, 2026

Show notes

Everyone wants AI to make legal cheaper. But what if that’s the wrong promise?
In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Tim Fox, Chief Data and AI Officer at Ogletree Deakins, for a sharp, practical conversation on what AI adoption really looks like when you are trying to scale it across a large law firm.
What You’ll Learn:

Why build vs. buy is rarely as simple as “building is cheaper”
How internal tools create long-term support, maintenance and upgrade costs
Why legal is not a rational economic actor when it comes to technology adoption
How firms can measure adoption through actual use and attorney feedback
Why shadow AI, hallucinations and privilege risks make governance non-negotiable
How peer-to-peer learning moves lawyers faster than another mandatory webinar
Why law schools need to teach AI literacy before students arrive at firms
Why AI may increase quality, capacity and profits without reducing legal costs

This episode gets into the messy middle of legal AI: not the hype, not the doomsday predictions, but the actual work of making attorneys use tools responsibly, strategically and well.
Highlights:
00:00 Introduction
01:17 Tim’s Journey From Technology to Law
04:01 How Legal Tech Led to “Legalmation”
06:21 The Build vs. Buy Question in Legal AI
09:46 Why Legal Tech Vendors Struggle to Sell to Law Firms
10:30 Legal Is Not a Rational Economic Decision-Maker
14:41 How Vendors Should Actually Pitch Lawyers
18:50 What a Chief Data and AI Officer Really Do
19:02 Scaling AI Strategy Across Ogletree Deakins
23:36 Why Product Demos Beat Pitch Decks
26:59 How Tim Measures AI Adoption
29:00 Balancing Leadership With Hands-On Innovation
31:28 What Law Schools Are Getting Wrong About AI
36:03 Building AI Governance at Scale
39:12 The Hallucination Risk That Keeps Firms Awake
42:52 Why Peer-to-Peer AI Education Works
46:39 Tim’s Hot Take: The Truth About Legal AI Costs
48:25 Closing Thoughts
Quotes:

“Building it yourself isn’t always cheaper. It’s not always easier. It’s almost never faster.”
“Legal is not a rational economic actor. You can have the best tool, the best solution out there, and attorneys can still say, no, we don’t want it.”
“Show me your product. I don’t want to just see your PowerPoint.”
“I don’t think anybody has cracked change management in law firms, and AI is change management.”
“AI doesn’t always save time. It makes the work better and it allows you to do more.”

Between The Briefs is handcrafted by our friends over at: fame.so

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