Between the Briefs

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:

1. “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.”
2. “The biggest mistake that I see clients make is that they don’t involve attorneys early enough.”
3. “Most cases are won or lost on papers.”
4. “I can deal with bad facts. I can’t deal with surprise facts.”
5. “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

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:

1. “Everyday people can be everyday leaders.”
2. “You don’t have to have the big title or the fancy position in order to demonstrate leadership.”
3. “The people closest to the issue understood it better than I could.”
4. “We’re not the department of no. We’re the department of “let’s figure it out.”
5. “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

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:

1. “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.”
2. “AI could either make the justice gap smaller or bigger.”
3. “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.”
4. “Legal tech is really weird. You don’t have to trade really good tech for fair pricing.”
5. “Not everyone needs these gigantic end-to-end solutions.”

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

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:

1. “AI is a tool, and I think of it in terms of something like a knife.”
2. “Every layer of AI potentially solves a problem and potentially creates risks.”
3. “Start with literacy with the end goal of being fluent.”
4. “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

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:

1. “Building it yourself isn’t always cheaper. It’s not always easier. It’s almost never faster.”
2. “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.”
3. “Show me your product. I don’t want to just see your PowerPoint.”
4. “I don’t think anybody has cracked change management in law firms, and AI is change management.”
5. “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

Legal AI has no shortage of promises. Now, the real challenge is figuring out which ones are worth adopting. In this episode of Between the Briefs by Steno, Adrian Cea and Joe Stephens sit down with Colin Levy, General Counsel at Malbek, legal tech author, and educator, to discuss how lawyers can adopt AI thoughtfully without sacrificing professional judgment.
What You’ll Learn:

• Why the biggest obstacle to AI adoption is often lawyer mindset, not the technology itself
• How to distinguish meaningful AI capabilities from legal tech marketing hype
• Why testing AI with real legal workflows is more valuable than watching polished product demonstrations
• How to build realistic expectations for AI by treating it as an assistant, not an infallible expert
• Why human judgment remains the defining skill that AI cannot replace
• How junior lawyers can develop confidence in evaluating AI-generated work despite having less practical experience
• Why legal tech vendors should focus on education and partnership instead of overselling AI
• How law schools can prepare future lawyers by embedding AI literacy throughout legal education rather than treating it as a standalone subject

This episode explores how lawyers can make smarter technology decisions, and build a future where legal expertise and artificial intelligence work together, not against each other. 
Highlights:
00:00 Introduction 
02:30 Colin's Journey Into Law and Technology
06:58 Navigating AI Adoption in the Legal Industry
11:30 Why Lawyers Are Embracing AI More Cautiously
17:19 Cutting Through AI Hype With Practical Legal Tech
23:13 Teaching AI and Judgment to the Next Generation of Lawyers
29:06 Writing, Creativity, and AI as a Legal Assistant
35:46 The Human Skills AI Can't Replace
37:07 Hot Takes & Closing Thoughts

Quotes:

1. “Technology, as I've long recognized, and like you both recognize as well, doesn't hold back and doesn't wait for any industry or anyone or anything to keep up with it. It just continues to march on forward and evolve.” 
2. “AI is not self-aware, it is not thinking the way you and I think, it is not reasoning, it doesn't understand context beyond what you provide it with. And so, you can't think about it in human terms.”
3. “There is an incumbent need for AI to be part of the curriculum of legal education. Perhaps from the very first year, but I would argue that it shouldn't be taught in isolation. It should be taught as sort of a cross disciplinary type of thing.” 
4. “I think for law firms, as well as for legal departments, frankly, who are also buyers of legal tech, the most effective way to get through to them is to almost in some ways consult with them, build a relationship with them, understand their needs. Understand where they're coming from and educate them in a non-salesy way with content, with resources, and take things slow rather than foist the things upon them.”
5. “Humans being so fickle, so imperfect, flawed and emotional - these are all things that technology historically and continues to really struggle with, and I don't see that changing anytime soon or ever. So I dare say that, the humanness element is something that technology can never conquer.”

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

Everyone wants an AI strategy but far fewer companies are ready to actually use one.In this episode of Between the Briefs, hosts Adrian Cea and Joe Stephens welcome Elaine Barsoom, AI and innovation leader and Venture Partner at Silicon Foundry, for a grounded and practical conversation on what it really takes to turn AI ambition into measurable business outcomes.
What You’ll Learn:

• Why most AI efforts fail because of readiness, not technology
• How to identify where repetitive work, trapped knowledge and overloaded judgment are slowing teams down
• Why “go slow to go fast” means doing the work in the right order, not moving timidly
• How leadership urgency and employee buy-in have to work together
• Why fear often shows up as “we’re too busy” or “the tools aren’t ready”
• How legal teams can act as accelerants instead of gatekeepers in AI transformation
• Why reskilling is really about rewiring how people work with technology
• How proprietary data and tribal knowledge can become a company’s real AI advantage

Tune in to understand what it takes to be truly AI ready. 
Highlights:
00:00 Introduction & Meeting Elaine Barsoom01:04 Elaine’s Background in Innovation, Emerging Tech and Growth02:06 Building a $200M Joint Venture at American Express03:13 What It Means to Architect the Execution Layer04:10 Why Activity Does Not Equal Progress05:38 How Elaine Bridges Legal, Engineering and Business Teams07:09 Aligning Incentives Across Engineering, Legal and Leadership09:02 Why Companies Need Discovery Before Engineers10:06 Why Legal Engineers Can Be Strategic Accelerants11:57 The Problem With AI for AI’s Sake13:27 Balancing Leadership Urgency With Employee Buy-In15:16 How to Prioritize the Right AI Workflows17:03 Why Companies Underestimate Fear19:39 Reskilling, AI Adoption and the Future of Work22:28 Go Slow to Go Fast23:21 The Three Questions Every AI Strategy Should Start With24:45 How Silicon Foundry Supports AI Transformation26:07 What AI Fear Gets Right and What It Gets Wrong28:29 Why AI Can Be a Big Advantage for SMBs30:15 Where to Save Time Without Damaging Trust31:16 The AI Mandate Problem for Small Businesses33:12 Elaine’s Favorite Diagnostic Questions35:42 Build vs. Buy in AI Transformation40:03 What Elaine Finds Most Exciting in Legal AI42:07 Why Tribal Knowledge Is the Real Competitive Edge43:30 Elaine’s Hot Take: It’s a Readiness Problem44:22 Final Thoughts and Closing Remarks
Quotes:

1. "Activity doesn’t actually correlate with progress. We have to understand where the underlying work is."
2. "The leadership can create the urgency, but then it’s really getting the buy-in from the people that are actually doing the work."
3. "When I say go slow to go fast, I don’t mean moving timidly. I just mean doing the work in the right order."
4. "People won’t say, I’m afraid that this is going to make me less relevant. They say I’m too busy, or the tools are not ready, or we need more guidance."
5. "Most companies do not just have an AI technical problem or strategy. They have a readiness problem."

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

Before eDiscovery had a name, George Socha was already asking the questions most of the legal industry had not caught up to yet.
In this episode of Between the Briefs, hosts Adrian Cea and Joe Stephens welcome George Socha, Senior Vice President of Brand Awareness at Reveal and co-founder of the Electronic Discovery Reference Model (EDRM), for a wide-ranging conversation on how legal technology has evolved from floppy disks and early matter management systems to GenAI, agentic tools and AI-powered discovery workflows.
What You’ll Learn:

• Why eDiscovery became an industry standard through collaboration, timing and free access
• Why liberal arts thinking matters in legal tech more than people might expect
• How GenAI and agentic AI are making eDiscovery feel new, open and uncertain again
• Why discovery is not about finding “everything,” but finding just enough to take the next step
• How AI tools like Ask can give lawyers grounded narrative answers with citations
• Why discovery is not a waste of time, but the work that gives lawyers the facts they need
• Why every AI platform may start with similar models, but the difference lies in what gets built on top

Tune in to hear why one of eDiscovery’s most influential voices believes this is the hottest moment legal tech has ever seen.
Highlights:
00:00 Introduction & Meeting George Socha01:16 From Early Programming to Law School03:03 “Real Attorneys Do Not Type”04:07 Refusing to Lose the Computer05:16 Building Litigation Support and eDiscovery Capabilities06:38 How the EDRM Framework Was Created09:04 Why EDRM Stood the Test of Time09:31 Why Free, Collaborative Standards Won12:24 Why Liberal Arts Thinking Matters in Legal Tech14:28 How eDiscovery Has Changed Since the Early Days17:56 Why This AI Moment Rhymes With Early eDiscovery18:11 What Excites George About GenAI and Agentic Tools20:49 The Million-Dollar Data Story Project22:33 What Reveal Is Building with AI23:35 How Ask Gives Lawyers Grounded Answers28:30 The Myth of Finding Everything in Discovery29:11 Why Good-Faith Discovery Matters More Than Perfection33:43 The Biggest Misconceptions About eDiscovery35:52 What Actually Differentiates AI Platforms39:22 Can AI Improve Access to Justice?41:58 George’s Hot Take: Legal Tech Is at a 15 Out of 1043:16 Final Thoughts
Quotes:

1. "When we started EDRM I said no way, how are we going down that path where you have to buy standards. Whatever else we do, the diagram and the content we publish around it comes at no charge to anybody. Everything wrapped around that diagram was the result of 35 people coming from law firms, corporate legal departments, service providers, and software providers, so it wasn't any one person's work or organization's work."
2. "What you can learn through getting a liberal arts undergraduate education that is very hard to learn if you have a technical education focused on a specific area are really powerful critical thinking skills. The ability to stand in the shoes of others and look at things from their perspectives, and to call on foundational elements that come from any number of disciplines like philosophy, sociology, economics and history."
3. "We're seeing more rapid and more extensive change now than we have ever seen. In some ways with generative AI and agentic capabilities, we are back at that same starting point again. History doesn't repeat itself but it definitely can rhyme, and we're on a rhyming stage right now where it's at the same type of open range of possibilities."
4. "The area of eDiscovery that has always been of greatest interest to me is what can you do with this stuff once you've got it. We are now seeing with all of the capabilities emerging with generative AI and agentic possibilities a whole array of opportunities for lawyers to work with content to more effectively prosecute or defend a matter at far lower cost in a much compressed time frame."
5. “The number one preconception is that discovery stuff is just a waste of time and money. What do you do in a lawsuit? There are two things you focus on - the law and the facts. Discovery is what gets you the facts, and if you do discovery well, you're much better placed to combine them together to reach an outcome."

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

Law firms have, historically, struggled with change. In this episode of Between the Briefs, hosts Adrian Cea and Joe Stephens welcome Umair Muhajir, Vice President and Global Head of Managed Review at DISCO, for a sharp, honest conversation about what GenAI is really doing to litigation workflows.
His view is clear: GenAI is not simply making old workflows faster. At its best, it is forcing the industry to ask whether those workflows still make any sense. 
What You’ll Learn:

• Why GenAI replaces first-level document review work, not lawyers themselves
• How AI-powered review can deliver high precision and recall while creating stronger audit trails
• How legal teams can separate case learning from document review using AI-powered Q&A tools
• Why law firms struggle to adopt AI when their billing systems are still built for hourly work
• Why many “AI ethics” horror stories are actually old-fashioned lawyering failures in a shinier outfit
• Why legal education may need more statistics, validation and practical technology literacy

Tune in to hear why the future of legal work will only be won by lawyers who know how to use AI without lowering their standards.
Highlights:
00:00 Introduction & Meeting Umair Muhajir01:07 From Paul Weiss to the Early Days of eDiscovery04:48 What DISCO Does and Umair’s Role in Managed Review06:45 Is AI Replacing Associates or Replacing Document Review?08:52 How DISCO Builds Client Confidence Around GenAI Review09:32 Why Precision and Recall Matter in AI-Powered Discovery13:18 The Biggest Barriers to Law Firm AI Adoption15:48 How Junior Associates Learn Cases When AI Handles Review20:00 Why AI Should Reimagine Workflows, Not Just Speed Them Up21:17 What Comes Next for AI in Discovery and Legal Data24:21 What Big Law Actually Wants From Legal Tech Vendors27:10 Why Legal Has Multiple Historical Periods Inside One Firm29:03 How GenAI Challenges Hourly Billing and Pricing Models32:56 What Law Schools Need to Teach in an AI-Native Legal World38:02 How Global Review Strategy Works Across Jurisdictions40:44 Why Many AI Ethics Failures Are Really Lawyering Failures45:05 Umair’s Hot Take: Legal’s Overinvestment Problem46:47 Closing Thoughts 
Quotes:

1. "The issue isn't associates learning the case, it's how they are learning the case. Technological developments have meant that you can actually bifurcate learning about the case from document review. We have a Q and A chatbot that works with lawyers and associates on the case team to learn the case, and it'll give you a supporting citation and highlights."
2. "The technology ought not to be an invitation to recreate the exact same workflows we've always done, but maybe should also be an invitation to reimagine what those workflows can be in the future."
3. "The reality is not that AI is replacing people. It's that people who use AI are going to replace people who don't. Law students will need to expect certain different things from their legal education, including introductions to statistical thinking, which might not be natural to us in law school."
4. "A lot of the cases and horror stories that get press are really examples of legal malpractice, not a Gen AI problem. If you don't think it's a great idea to discuss your case with someone at the bar, it's probably not a good idea to feed confidential stuff into a public instance of Gemini."
5. "An hourly model will never adequately capture what needs to be done at either the provider or the client side. Law firms have billing systems that might only be set up to process hourly rates, and it is very difficult for them to fit a tech-driven solution into their existing internal billing systems."

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

Paralegals have long been boxed into the role of “document reviewers” but their true value goes far beyond that. And with AI in the mix, their place in law firms is being rewritten entirely. In this episode of Between the Briefs, hosts Adrian Cea and Joe Stephens welcome Michelle Pendleton, Certified Paralegal and eDiscovery specialist at Allen Matkins and President of the San Diego Paralegal Association, to explore how paralegals are quietly becoming the most valuable players in law firms.

What You’ll Learn:

• How to navigate the paralegal profession's shifting identity
• How to structure case management from intake to trial
• Why paralegals must reframe AI prompts for machines, not lawyers
• The art of managing attorney expectations through timeline transparency
• How to treat paralegals as strategic professionals, not administrative assistants
• The paralegal's untouchable value: strategic case orchestration that AI cannot replicate
• Why the next frontier for paralegals is technical infrastructure literacy

Tune in to understand how the role of the paralegal is undergoing a major transformation and what technology has to do with it. 
Highlights:
00:00 Introduction & Meeting Michelle Pendleton 00:01 How Michelle Went from Receptionist to Paralegal00:50 All It Takes is One More Question in Litigation02:53 How eDiscovery Evolved and Why Paralegals Led the Charge04:02 Why Paralegals are the Unsung Architects of Complex Legal Cases06:33 Learning New Legal Technology: Then vs. Now08:28 Why You Need to Prompt AI Like You're Speaking to a Beginner10:04 Managing Attorney Expectations Through Transparent Timelines11:42 How to Treat Paralegals as Strategic Professionals13:34 Why Communication Matters Now More Than Ever13:57 Real-World Applications of AI in Daily Paralegal Work16:16 A Paralegal’s POV on AI Adoption and Job Security18:26 The Evolution of the Paralegal Role from Back Office to Courtroom20:57 Paralegals as Gatekeepers: Evaluating Legal Tech Vendors22:20 Making the Right Sales Pitch to Paralegals 23:54 Career Advice for Aspiring Paralegals and New Professionals25:34 San Diego Paralegal Association: Current Conversations and Concerns28:01 Michelle’s Case for Paralegal-Specific Education29:48 Designing the Courses Paralegals Actually Need32:33 What the Future of Paralegals Looks Like 34:22 Mastering the Nuts and Bolts of eDiscovery Tools35:55 The One Thing Technology Cannot Replace37:29 Emotional Intelligence and Soft Skills in Paralegal Work38:35 How Digital Communication Is Changing Professional Interactions39:34 Michelle's Hot Take: You Can't Avoid It, So Learn It41:17 Key Takeaways and Final Thoughts
Quotes:

1. "The biggest thing for me was to always ask one more question. I think in litigation, that's a big, big thing to think about because even if you get something that looks pretty simple and obvious on its face, it's not always that way when you start to dig in and look at the actual information and the documentation, especially, the evidence."
2. "We are kind of a jack of all trades. I do something different almost every day, at least a little bit that I haven't done before. You know, whether it's today I'm using Google Earth to map a demonstrative for a hearing, but I think just being willing to make those adjustments because it's a constant movement in terms of what the case requires, what the judge requires, what a witness might require to take their deposition properly."
3. "I learned that even though people say use common language, use natural language, you also have to be cognizant that you're talking to a machine or someone who may not know anything about the legal profession. I learned that I have to take a few steps backwards when I'm starting those prompts because I tend to just jump in and I'm used to using the jargon and legal tools that know exactly what those parameters are."
4. "I think it's the case management - that's the key. Because I find when I see a case that hasn't had a paralegal on it, it's not structured. There's no management and no tracking of all of those things that we've been talking about. The ability to know where you're going and what you're gonna need to get there - it's invaluable."

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