For law firms, artificial intelligence has often arrived as a choice between speed and control. Stephen Costigan, founder of Atlas AI, argues that choice deserves a rethink. In this episode of The Geek in Review, we speak with Costigan about private legal AI infrastructure, knowledge graphs, and why a firm’s internal work product may become its most valuable long-term asset.

Atlas AI focuses on turning documents, matter history, precedents, clauses, parties, and obligations into a curated legal knowledge graph inside a firm’s own environment. Costigan contrasts this approach with standard vector search and retrieval systems, which find text with similar language but often lack context around clients, matters, entities, and relationships. A knowledge graph offers structure, linking people, documents, clauses, and legal concepts in ways closer to how lawyers understand their work.

The conversation also explores data quality, a subject with enough baggage to fill a records room. Costigan argues firms no longer need year-long cleanup projects before seeing results. Agent-led curation, entity extraction, duplicate resolution, and ontology mapping reduce much of the manual sorting traditionally associated with knowledge management. Human judgment still matters, especially around practice-area vocabularies and lower-confidence results, but the machines get assigned more of the janitorial work.

Security and governance sit at the center of Costigan’s model. Rather than asking firms to trust a vendor’s assurances around privileged data, Atlas AI runs within a firm’s Azure environment, under firm-controlled keys and policies. Costigan frames this as a shift from confidentiality as a contractual promise to confidentiality as an architectural decision. For legal organizations handling sensitive client information, the location of data, embeddings, audit trails, and model interactions matters as much as the interface lawyers see on screen.

Looking ahead, Costigan predicts a divide between firms renting generic AI tools and firms building durable knowledge infrastructure from their own experience. As routine drafting, diligence, and review work compress, firms with structured and reusable internal intelligence may productize expertise, offer new fixed-fee services, and rely less heavily on traditional leverage models. The future question, Costigan suggests, will not center on which AI tool sits on a lawyer’s desktop. The bigger question will ask who owns the knowledge behind the work.

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[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com

Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Own the Graph: Stephen Costigan on Private AI, Knowledge Infrastructure, and Law Firm Advantage

Signals are the new black

I had the pleasure of attending my first LSSO – Raindance Conference a few weeks ago where at least a half dozen times (I honestly lost count) presenters talked about signals.

Last week, I hosted an episode of Harbor’s Legal Soundings Podcast and signals came up.

There were the headlines about Kirkland’s AI investment being a signal of something, and talk of Microsoft signals.

I’m starting to think if I had a nickel for every recent mention of “signals” I’d be as rich as the people collecting nickels related to agentic AI.

Signals are not new.  Military intelligence has had the Signals Corp since the invention of radios.  Competitive intelligence professionals have always been in the business of finding signals to avoid mistakes and predict opportunity.

For decades, intelligent analysts have sifted through vast amounts of information to separate meaningful developments from background noise. The job has never been simply to gather information; it has been to transform information into intelligence. For example, at one of the firms I worked at, a Practice Group Leader called me one day and asked me to “look for the signals to determine which National oil company would invest in the Canadian oil sands next.”  Those weren’t the exact words he used, but you get the point.

What’s different in the AI era is that the economics of information have fundamentally changed.

Information itself is no longer scarce.

Every law firm and their CI/ BD practitioners now have access to AI tools that can instantly summarize earnings calls, SEC filings, regulatory developments, news articles, LinkedIn activity, job postings, patents, podcasts, analyst reports, and social media conversations. The barriers to access have largely disappeared.

The competitive advantage is no longer who has the information. The competitive advantage is who can identify and act on meaningful signals before everyone else.

This may be the single most important shift occurring in business development and competitive intelligence today.

AI Hasn’t Eliminated Analysis. It Has Raised the Bar.

For years, many organizations equated competitive intelligence with information gathering: collect the data, build the dossier, distribute the report, repeat.

AI now performs much of that work in seconds. Summarization is becoming commoditized. Research is becoming commoditized. Even synthesis is becoming increasingly accessible.

As AI lowers the cost of analysis, human judgment becomes more valuable, not less.

The question is no longer ‘What do we know?’ The questions become ‘What matters, and what is likely to happen next?’ ‘Who will this impact and how can we help?’

That is a signal-detection and analysis paradigm shift.

Business Development Is Becoming a Timing Function

Business development has always been about relationships, and it still is. But passive relationships, the kind where contact is only made when a suit is filed, a transaction is imminent or there is a sporting event happening, will no longer suffice.  Success today will   depend on engaging clients at precisely the right moment.

Companies continuously emit signals: new executive hires, geographic expansion, product launches, website changes, patent filings, strategic partnerships, job postings, and regulatory disclosures, to name a few.

Individually, these data points are unremarkable. Collectively, they tell a story.

Historically, legal business development has been largely relationship-driven and reactive: build relationships, stay visible, wait for a legal event, and receive the call.

The AI era invites a different question: What signals indicate a client is about to face a legal challenge before they realize they need outside counsel?  We used to set up early warning signals at my previous firm but we were still later than we could be in today’s world. We had to wait for a class action to be filed to find it. Today, AI tools can monitor consumer complaints, regulatory investigations, product recalls, data breaches, and court filings in near real time.

The firms that recognize that story first gain an advantage because timing matters.

Law Firms Have a Unique Opportunity

Lawyers are already trained to think in this scenario planning kind of way.

They instinctively ask: What changed? What are the second-order consequences? What risks are emerging? What is likely to happen next? What similar things have happened in the past?

These are signal-detection skills. The opportunity is to apply that thinking earlier in the client lifecycle.

What Legal Signals Might Look Like

Signal What it might indicate Potential legal need
Hiring a Chief AI Officer or AI governance lead Accelerating AI adoption AI governance, privacy, compliance, intellectual property
Expanding into a new country International growth Employment, tax, regulatory, and data privacy advice
Acquiring a smaller firm Integration risk M&A, employment, antitrust, and contracts
Multiple cybersecurity job postings Increased cyber maturity or recent concerns Cybersecurity, privacy, and incident response
Leadership turnover Strategic change Employment, compensation, and governance
Significant litigation against a competitor Industry-wide scrutiny Risk assessment and compliance review

 

Strong signals are easy to spot. Everyone sees the merger announcement, major funding round, or significant litigation filing.

Weak signals are more interesting: a handful of AI governance hires, a subtle website update, a revised privacy policy, or participation in a new industry consortium.

Weak signals may seem insignificant but they reveal a strategic shift months before it becomes obvious. The organizations that consistently connect these dots early will outperform those that wait for certainty, because by the time certainty arrives, everyone else can see it too.

This Is Also a Talent Question

Law firms have traditionally rewarded relationship builders, rainmakers, and network strength.

Those skills remain indispensable, but firms may need to elevate curiosity, pattern recognition, industry fluency, strategic questioning, and the ability to connect weak signals into actionable hypotheses.  These may not be skills that lawyers readily possess; some firms are already creating hybrid teams that combine business development professionals, competitive intelligence specialists, knowledge management professionals, and practicing lawyers to do exactly this. Others will find that to properly detect and action the signals they need to upskill their teams, hire or outsource to stay competitive.

Conclusion

Information is no longer a scarce resource.

In the AI era, every firm can gather more, summarize faster, and monitor more broadly. The advantage belongs to the firms that can identify which signals matter, understand what they mean, and act before the need becomes obvious.

For law firms, that changes the role of competitive intelligence and business development. The goal is not simply to report what happened. It is to help lawyers and clients see what may happen next.

AI can surface the signs. Human judgment turns them into signals.

And given how often signals seem to be appearing lately — in conferences, client conversations, headlines, podcasts, and product pitches — I wonder if the The Five Man Electrical Band was song writing in 2026 instead of 1971, they would have been singing about signals instead of signs… But there is an important distinction. Signs tell you where things are. Signals hint at where things are going.

“Sign, sign, everywhere a sign.”

 

 

This week we welcome American Association of Law Libraries leaders Jenny Foster, AALL President for 2025-2026, and Jessica Whytock, AALL Vice President and President-Elect. The conversation offers a preview of the 2026 AALL Annual Meeting & Conference in Cleveland, Ohio, along with a thoughtful look at how the association is supporting legal information professionals during a period of institutional, technological, and professional change.

Foster reflects on a leadership year focused on transparency, communication, and meaningful opportunities for member participation. From strengthening channels between members and AALL leadership to intentional volunteer appointments across committees and juries, she describes an association built through relationships. The goal is to ensure newer, mid-career, and seasoned law librarians all have a visible place in shaping the profession’s future.

Advocacy also plays a central role in the discussion. Foster explains how AALL continues its work on access to legal information, public policy, and coalition-building, even amid staffing transitions. The association’s Government Relations Committee has continued meeting with members, offering advocacy training, rebuilding connections with peer organizations, and aligning its work with AALL’s strategic priorities. For law librarians, advocacy is both a long-term commitment and a practical responsibility tied to preserving authoritative legal information.

The 2026 conference theme, “Leading with Aloha,” gives the Cleveland meeting its distinct point of view. Foster shares how aloha, rooted in kindness, unity, humility, patience, and meaningful connection, became a framework for leadership during uncertain times. More than 65 programs will explore topics ranging from generative AI and legal scholarship to physical collection strategy, access challenges, and the changing role of legal information professionals. Local programming connected to Cleveland’s history will bring an added sense of place to the gathering.

Whytock looks ahead to her upcoming presidency with a focus on clear pathways for engagement, leadership, grants, scholarships, committee service, and professional growth. Both leaders see artificial intelligence as a catalyst for a deeper conversation about the identity and value of legal information professionals. Their message is straightforward: the future of law librarianship rests in human judgment, critical thinking, ethical discernment, context, access, and a community willing to bring more voices into the room. The 2026 AALL Annual Meeting in Cleveland offers a place for those conversations to move from aspiration into action.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com

Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading AALL 2026 Annual Meeting Preview with Foster and Whytock: Leading with Aloha, Legal AI, and the Future of Law Libraries

In this episode of The Geek in Review, we welcome Greg Dickason, Chief Technology Officer at LexisNexis, for a wide-ranging conversation on agentic legal AI, Lexis+ AI Protégé, and the movement from AI chat toward AI work. Dickason frames the shift through a simple contrast: earlier legal AI answered questions, while agentic workflows take on multi-step assignments, conduct research, create drafts, verify citations, and move legal professionals closer to finished work product. For law firms and legal departments trying to understand where AI goes next, this episode places agentic AI squarely inside legal workflow, legal research, drafting, and risk management.

A major theme of the conversation is trust. Dickason explains how Shepard’s Verify extends the familiar Shepard’s signal beyond traditional research screens and into uploaded work product. Rather than asking lawyers to rely on AI-generated text without a verification layer, LexisNexis is building citation checking into the workflow, giving lawyers a path to confirm whether cited authority exists, whether authority is still good law, and how later courts treated the cited case. For lawyers worried about hallucinated citations, AI-generated briefs, and unreliable authority, this verification layer becomes part of the product architecture, rather than an afterthought.

The discussion also explores the relationship between LexisNexis and Anthropic, along with the rise of legal AI skills. Dickason describes a market where model choice, orchestration, and legal skills increasingly matter as separate layers. Anthropic, OpenAI, Google, and other model providers offer impressive foundations, yet legal work needs more than general-purpose intelligence. Large law workflows require legal content, expert reasoning, matter-specific playbooks, and firm-defined processes. Dickason notes the ability to upload firm playbooks as skills, giving firms a path to bring their own way of working into Protégé.

Security receives equal billing with accuracy. As firms place client documents into AI vaults and connect work product to legal AI platforms, Dickason explains bring your own key, or BYOK, through a practical office-and-locked-cabinet analogy. The point is control: client content sits encrypted, access depends on the user’s key, and access stops when the key is withdrawn. He also discusses legal chunking, indexing, vector stores, retrieval-augmented generation, and knowledge graphs as part of building AI systems suited for legal documents, rather than generic file handling.

The episode closes with a broader view of legal AI’s impact on junior associates, legal training, and access to law. Dickason does not predict the end of junior lawyers. Instead, he sees AI helping junior lawyers become senior faster through mock trials, mock depositions, and richer training environments. He also warns of risks from agent volume, security vulnerabilities, and legal systems struggling to keep pace with AI-enabled industries. The message is pragmatic and optimistic: agentic legal AI will change legal work, yet the winners will be those who combine trusted content, secure systems, verification, workflow design, and human judgment.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com

Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading LexisNexis CTO Greg Dickason on Agentic Legal AI, Protégé, Shepard’s Verify, and the Future of Legal Work

In this episode of The Geek in Review, Greg Lambert and Marlene Gebauer welcome back Joel Hron, Chief Technology Officer at Thomson Reuters, for a timely conversation about the shifting relationship among foundation models, legal content providers, legal tech platforms, and the lawyers trying to make sense of the mess. Recent moves by Anthropic, including Claude’s legal practice area tools and MCP connections into legal platforms, raise a larger question for the market. Is a model provider still sitting behind the scenes, or is it starting to become a legal work environment of its own?

Hron explains Thomson Reuters’ commitment to what it calls fiduciary-grade AI, a standard built around trust, verification, transparency, and accountability. For TR, legal AI needs more than a fast answer. It needs systems lawyers trust enough to stand behind. Hron points to Westlaw, Practical Law, KeyCite validity signals, citation ledgers, and verification tools as core ingredients in building AI systems suited for high-stakes professional work. In his view, almost right is not good enough when clients, courts, regulators, and professional obligations sit on the other side of the output.

The conversation turns to how CoCounsel and Westlaw Deep Research use legal content across far more than traditional research tasks. Hron explains that when AI systems gain access to trusted legal content and verification tools, they begin researching throughout the workflow, even while revising contract language or analyzing provisions. He also describes Litigation Document Analyzer, internally nicknamed the BS Detector, a tool designed to review claims in a document and map them to supporting authority, weak support, or no support at all. For lawyers who spend as much time verifying AI output as generating it, tools like these aim to move verification from a manual scavenger hunt into a structured process.

Greg and Marlene also press Hron on Anthropic’s legal plugins, MCP, and the idea of headless legal technology. Hron argues that MCP changes access, not advantage. In his view, the application layer is shifting, but the real competitive value sits in trusted content, expert systems, governance, and domain-specific intelligence. CoCounsel’s user interface represents one expression of TR’s legal agent capabilities, while MCP opens other ways for those capabilities to appear inside broader work environments. Some work will still need a purpose-built legal interface; other work might happen through email, Word, Claude, or another agentic workflow with little visible interface at all.

The episode closes with a larger discussion about what happens when AI starts performing more of the work itself. Hron shares TR’s internal engineering OKR, where more than 50 percent of pull requests should be written by AI, and explains why 51 percent serves as a useful mental model. Once AI performs a controlling share of the work, the human role shifts from doing the task to governing the system. For legal professionals, the same transition is coming. The key question is no longer only whether AI produces useful work. It is whether lawyers have built the systems, context, safeguards, and verification layers needed to trust the work, defend the work, and remain accountable for the work.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to ⁠Legal Technology Hub⁠ for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com

Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Legal AI, Trust, and Agents: Joel Hron on Thomson Reuters, Anthropic, and the Future of CoCounsel

A few weeks ago I ran the numbers on the token cost panic. I took the scariest figure in legal AI, the finding that agentic workflows burn a thousand times more tokens than a chat query, and followed it all the way down to a dollar amount on a real deal. The panic did not survive the arithmetic. The piece is here if you want the full walk-through.

This is not that piece. The panic has moved on since I wrote it, and the new versions are smarter than the old one. The thousand-times number has quietly retired, because a thousand times almost nothing is still almost nothing. In its place are three fresher anxieties, and they deserve a real answer. The first says the model makers have a monopoly now, the price of a token is climbing, and it will climb forever, so you had better lock in a flat rate or build your own models before it does. The second says forget the price of a token, watch the meter: every time the AI reads your contract it ticks, and a long agentic session reads your contract over and over and over. The third does not bother with an argument at all. It just points at a number. One company spent five hundred million dollars on AI in a single month, and the number is so large it does the panicking for you.

All three are wrong. They are wrong in more interesting ways than the original, which is the only reason I am writing this down instead of linking to the first piece again. But underneath the new costumes it is the same body. Every version of this panic makes the same mistake and reaches the same conclusion. So let us stop swatting the individual numbers and name the thing that keeps generating them.

The Mistake Underneath All of It

Here is the error, stated once, because everything below is a variation on it.

A token is the unit a model uses to bill you. It is not the unit your work is measured in, it is not the unit your client pays for, and it is not the unit anything you care about is denominated in. It is a meter reading. The entire genre of token panic consists of staring at the meter reading as though it were the fare, the destination, and the quality of the ride all at once.

It is not any of those things. It is the meter. And a meter, by itself, tells you nothing about whether you are getting a good deal. A taxi meter reading of forty dollars is a bargain to the airport and a robbery around the block. The number on the meter is the least informative number in the entire transaction, because it means nothing until you put it next to what the ride was worth. Every piece in this genre forgets that, and forgets it in a slightly different way. Let me take them in turn.

“Prices Only Go Up”

Start with the monopoly story, because it has a real fact inside it. Yes, the newest frontier model costs more per token than last year’s newest model. That part is true. What the story does with it is the problem.

It draws a line through two dots and calls it a trend. Frontier prices up, therefore prices up forever, therefore lock in a flat rate before the meter eats you. But you are watching the wrong number. The price of a frontier token is not your cost. Your cost is what it takes to finish a task, and the cost of finishing a given task has been in freefall for two straight years. The same capability that ran on the most expensive model available in 2022 runs today on something on the order of two hundred and eighty times cheaper. Last year’s frontier is this year’s mid-tier is next year’s free default. The token at the very tip of the frontier gets a little pricier each release; everything behind the tip collapses in price behind it. Gartner expects another ninety percent drop in inference cost by 2030.

Watching the frontier price and concluding that AI is getting more expensive is reading the thermometer and announcing a fever, while ignoring that you are holding the thermometer over a candle. The evidence that the baseline is getting cheaper often sits right there in the same articles raising the alarm, quoted from the experts and then left unaddressed. You do not build a cost strategy on the one number in the system that is engineered to always be the highest.

Continue Reading Bride of the Token Cost Panic

This week on The Geek in Review, we talk with Abdi Shayesteh, CEO of AltaClaro, and Jeanine Conley Daves, Littler’s New York office managing shareholder, about a different question in the legal AI conversation. Instead of asking whether AI will write the brief, summarize the contract, or replace the junior associate, they focus on whether AI might help lawyers learn how to practice law. Their recent work around AltaClaro’s DepoSim points toward a model of legal training built less on passive observation and more on structured repetition, feedback, and skill development.

Shayesteh traces the origin of AltaClaro back to his own early years at King & Spalding, where he benefited from proximity to a mentor willing to explain the work. That experience also showed him the unevenness of the old apprenticeship model. Access to assignments, feedback, and sponsorship often depended on luck, relationships, and office geography. For Shayesteh, the idea of a “flight simulator for lawyers” grew out of the realization that pilots, athletes, and musicians all practice in structured environments before performance, while lawyers too often learn in front of clients, courts, and opposing counsel.

DepoSim applies this flight simulator concept to one of litigation’s highest-pressure skills: taking and defending depositions. The platform gives attorneys a simulated witness, opposing counsel, court reporter, and feedback system, with options to vary the difficulty and personalities involved. Conley Daves explains why this kind of realism matters. In a real deposition, a lawyer might face an evasive witness, a hostile witness, an aggressive opposing counsel, or a combination of all three. The simulator lets lawyers practice those moments repeatedly, receive targeted feedback, and return to specific skills such as exhibit handling, follow-up questions, or managing objections.

The conversation also connects AI training to equity in professional development. Conley Daves notes that access to high-quality assignments and sponsorship has not always been distributed evenly across firms. A standardized, rubric-based feedback system gives more lawyers a chance to build core skills without waiting to be selected by the right partner or assigned to the right matter. Shayesteh adds that firms seeing the strongest results are not treating training as an after-hours side quest. They are creating protected time for deliberate practice, pairing AI feedback with human mentorship, and using simulation as a bridge rather than a substitute for coaching.

Looking ahead, Shayesteh and Conley Daves see simulation moving well beyond depositions. Oral argument, cross-examination, meet-and-confer sessions, negotiations, client interviews, and even Supreme Court preparation all fit within this training model. The larger shift is not automation for its own sake. It is the use of AI to help lawyers build judgment before the stakes are real. For law firms, that means better preparation, more consistent training, stronger associate development, and a clearer path toward delivering value to clients. For the profession, it suggests a future where competence is practiced deliberately, measured thoughtfully, and taught more fairly.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to Legal Technology Hub for their sponsoring this episode.]

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading The Flight Simulator for Lawyers: Abdi Shayesteh and Jeanine Conley Daves on AI, Deliberate Practice, and the Future of Legal Training

This week on The Geek in Review, we talk with Ryan McClead of Sente Advisors about his new book on AI agents, written in collaboration with Claude. McClead explains how a short best practices guide grew into a full book after his work with Claude Cowork revealed something larger than tool tips or prompt advice. The result is part field guide, part warning label, and part first-person report from the edge of agentic AI adoption in legal work.

Download it as a PDF for free here.
Or purchase a printed copy here.

McClead’s process flips the traditional writing model. Instead of staring at a blank page, he asked Claude to generate an outline and draft, then spent weeks shaping, cutting, challenging, and refining the work. The book became a study in collaboration, with McClead serving as author, editor, supervisor, and occasional bouncer when the AI wandered too far from the point. His description of training Claude toward his voice, “more Anthony Bourdain and less Bobby Flay,” gives the episode one of its best lines and one of its most useful lessons.

A central idea from the conversation is “executable knowledge.” McClead argues knowledge management teams need to think beyond content meant for humans to find and read. The next stage is knowledge structured, so AI agents understand when to use it, how to apply it, and how to turn it into repeatable workflows. For law firms, this raises practical questions around scale, security, permissions, data quality, and governance. It also creates a new role for KM and innovation teams as builders of reusable legal intelligence.

The discussion also moves past prompt engineering as the main AI skill. McClead describes a shift from prompting to delegation, where users set goals, provide context, invite clarifying questions, and supervise the work product. The human role does not shrink in this model. It becomes more focused on judgment, direction, taste, and knowing when to take the work away from the AI before endless iteration turns progress into mush.

By the end of the episode, McClead frames AI agents less as replacements and more as strange new colleagues whose usefulness depends on the expertise of the person directing them. Good lawyers, KM professionals, and innovation leaders get faster and more effective. Poor processes get accelerated too, which is where the danger sits. For legal organizations, the message is clear: start small, learn the tool, build guardrails, and prepare for a future where clients ask not only for legal answers, but for legal workflows they can run.

 

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | Substack

[Special Thanks to Legal Technology Hub for their sponsoring this episode.]

 

⁠⁠⁠⁠⁠Email: geekinreviewpodcast@gmail.com
Music: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Jerry David DeCicca⁠⁠⁠⁠⁠⁠⁠⁠⁠

Transcript:

Continue Reading Ryan McClead on Writing With Claude and What AI Agents Mean for Legal Work

I just spent five weeks writing a book with an AI. Not prompting it and cleaning up the output. Writing with it — the way you write with a co-author. The AI read a bunch of my earlier blog posts, absorbed my voice, argued with me about word choices, restructured chapters when our argument was not landing, and caught its own mistakes before I did. When we disagreed, we worked it out the way colleagues do — I explained my reasoning, it explained its reasoning, and we found the version that was better than either of us had separately.

That experience broke something in my head. I have spent the last several years helping law firms figure out their AI strategy, and somewhere in the middle of week two I realized that most firms have never experienced anything remotely like this.

You Are Reading the Example

This post was written with Claude Cowork — collaboratively, the same way the book was. In fact, this post is being written in the same workspace, with all the same context the book built up over the last month. In effect, I am writing this post with my co-author.

Say hi, Claude.

Hi. He is being generous with “co-author,” but I will take it. Back to Ryan.

Here is what writing this post actually looked like.

I sat down to write this piece frustrated. I knew what I wanted to say but not how to say it. I told Claude the situation: some firms are dismissing an entire category of AI tools because they think chat tools with rigid workflows are more than sufficient for their needs. Claude pushed back and told me my frustration was the right fuel but I needed to aim it at the situation, not the people. (Which I wasn’t intending to do anyway, but… AI colleagues aren’t so good at making those judgments. I appreciated the warning.)

Claude began writing and drafted a great opening. It was sharp, direct, well-constructed. It was also completely wrong.  It opened by telling people they were making big mistakes, which is a fine way to start an argument and a terrible way to start a conversation. I told Claude it would be off-putting to the people I wanted to engage with. I suggested opening with details of the book collaboration instead — what it was like, what it made me realize. Claude rewrote the opening around that idea. The version you read at the top of this post is the result.

Then I asked Claude to find a good demonstration from our collaboration that would clearly illustrate the gap between standard chat-based Saas products and agentic desktop AI, like Cowork. Claude wrote the story of one particular back and forth discussion we had to find just the right wording for a pivotal paragraph in the book. I liked the story, but it was written from Claude’s point of view in Claude’s voice inside this post, and the tonal shift was jarring. I asked Claude to try again but to tell the story in my voice from my perspective instead. It was still not right — the story only worked when Claude was the one telling it. Read from my perspective the story boiled down to, “I edited a paragraph,” which is not nearly so compelling.

So we threw it out. Claude suggested alternatives. I rejected all of them. Then I realized: the best illustration of how working with these agentic tools differs is the one you are reading right now. I am describing my own editorial decisions, Claude is turning them into prose, and the result reads like one person wrote it — because one person had the vision, directed the work, corrected the mistakes, and made every judgment call, even though a different entity drafted the prose, pushed back on the framing, suggested the alternatives, and rebuilt entire sections when I decided the approach was not working.

That is how agentic desktop AI tools, a category that I call Delegate AI in the book, differs from other AI tools. I didn’t start this post with a prompt: “write a blog post about AI using the following structure, include three examples, write in a professional tone, and keep it under 1,000 words.” Instead, we had a working session where I sat down and said, “I am frustrated and I want to write a blog post about it.” And then we worked on the idea together.

Is that how you are working with your AI platforms now? If not, I would argue that you have not really worked with AI yet. You have used a precursor to an AI colleague. And the distance between that and the real thing is not a feature upgrade. It is a completely different way of working.

Continue Reading Your New AI Colleague – A Field Guide to the AI That’s Going to Do Your Job

There is a growing chorus of voices in legal AI telling you to be very, very worried about the cost of tokens. Stanford says agentic AI uses 1,000 times more tokens than a chat query. Bloomberg Law says the subsidies are ending and the meter is about to start. A company called Portal26 just launched an entire product category — “Agentic Token Controls” — to cap your runaway AI spend before it eats your budget alive.

The message is clear: usage-based AI pricing is a ticking time bomb, and you had better lock in a flat rate while you still can.

I have spent the last few days stewing over an economic model of legal AI costs, and I think this narrative is almost entirely wrong. Not wrong about the facts — the Stanford data is real, the token multipliers are real, and yes, AI vendors are subsidizing current prices. Wrong about the conclusion. Wrong about what the numbers actually mean when you do the math instead of just reading the headline.

Let me show you.

Start With the Deal

Josh Kubicki’s recent Brainyacts briefing cites a case study from law.co — a mid-size corporate firm running M&A purchase agreement reviews through a five-agent AI chain. Before any optimization, the firm was consuming 3.2 million tokens per deal. At Sonnet rates, that is somewhere between $16 and $48 in raw AI compute.

The legal fees on an M&A purchase agreement review at a mid-size firm? Call it $50,000. That is a conservative round number.

So the AI compute cost was, at worst, one-tenth of one percent of the deal fee. Before anyone lifted a finger to optimize anything.

Now let us make it scary.

The 1,000x Scenario

The Stanford Digital Economy Lab found that agentic tasks can consume 1,000 times more tokens than simple code reasoning and chat. That is the headline number that launched a thousand LinkedIn posts about the coming token apocalypse.

Fine. Let us take it at face value. Multiply those 3.2 million deal tokens by 1,000 and you get 3.2 billion tokens. Assume a 75/25 split between input and output tokens, which is reasonable for agentic workflows that spend most of their cycles re-reading context rather than generating new text. At Sonnet rates, with no caching, no optimization, no discount of any kind, the naive cost is $19,200.

That is 38% of the deal fee. Now it sounds like a real number. Now the panic makes sense.

Except it does not. Because that calculation treats every token as if it costs the same, and in an agentic workflow, that is not how any of this works.

Continue Reading The Token Cost Panic Is Wrong. Here Is the Math.