Advanced Claude for Law Practice: Transactional Review and Drafting from Your Own Forms, Automating Repeat Work, and Monitoring Case Law

Michael Showalter, Founder | Showalter PLLC

Michael founded Showalter PLLC to deliver elite appellate and complexlitigation representation at a fraction of the traditional price by building the practice around an AI-augmented workflow. Operating as the AI-savvy senior lawyer at the helm, Michael uses AI as his secretary, librarian, paralegal, and team of associates, replacing the layered staffing model that drives conventional firm costs. Every matter is flat-fee, every citation is verified against primary sources, and client data is always protected. The AI Firm Index, a third-party directory that scores firms on AI integration, describes Showalter PLLC as a credible, early-stage entrant worth watching.

• Education & Credentials

Michael earned his J.D. from Yale Law School, graduating in the top 10% of his class, where he served as a senior editor of the Yale Law Journal. He holds a B.A. in Economics from the University of Michigan, awarded with Highest Honors. Michael clerked for Judge Diane Sykes on the Seventh Circuit and for Judge Dabney Friedrich on the U.S. District Court for the District of Columbia.

• Recognition & Leadership

Michael’s social media writing on law and AI has been viewed by hundreds of thousands of readers, making him a visible voice on how technology is reshaping legal practice. A Gibson Dunn appellate partner described him as among the best legal writers they had worked with at the firm. A D.C. Circuit panel praised his oral argument in its written opinion, and his amicus brief in SEC v. Jarkesy advanced arguments later taken up by Justice Neil Gorsuch in a concurrence.

• Professional Involvement

Michael is an active law-and-AI scholar, with articles on the subject published in the Notre Dame Law Review, the Ohio State Law Journal, and the SMU Law Review. His broader scholarship includes ten published or forthcoming law review articles with journals such as the Harvard Journal of Law & Public Policy and George Mason Law Review, along with writing in Law360 and Bloomberg Law. Michael has taught constitutional law at Catholic University and presented at law schools and legal organizations.

• Experience

Michael has drafted merits and certiorari-stage briefs at the U.S. Supreme Court and dozens of federal appellate briefs spanning constitutional, administrative, and complex commercial litigation, and at Gibson Dunn helped lead a team enforcing an international arbitration award of roughly $500 million, including fraudulent-transfer claims against judgment debtors. He currently serves as lead counsel for a lender in a Virginia state-court action and sits on a trial team before the Delaware Court of Chancery. Two years out of law school, Michael defeated Microsoft pro se before the U.S. Trademark Trial and Appeal Board.

Chandler R. Harris, Partner | Showalter PLLC

Chandler Harris is a partner at Showalter PLLC, where he leads the firm’s corporate and transactional practice. His work centers on the agreements that carry a deal: he advises public and private companies, founders, investors, and boards of directors on mergers and acquisitions, strategic investments, commercial contracts, securities matters, and corporate governance. That contract work runs from negotiating SaaS agreements, nondisclosure agreements, and supply agreements to preparing and revising organizational documents, board and committee policies, resolutions, and minutes, alongside ongoing legal support to businesses and management teams.

• Education & Credentials

Chandler received his J.D. from Yale Law School and his B.A. in history, magna cum laude, from the University of Wyoming. He is admitted to practice in Florida and New York.

• Recognition & Leadership

Chandler leads the corporate and transactional practice at Showalter PLLC, a firm built around an AIaugmented workflow, where he heads the firm’s deal-side work across M&A, securities, and commercial contracting.

• Experience

Chandler’s transactional experience spans the full range of deal sizes and structures, from smaller acquisitions handled end-to-end and founder-owned business transactions through middle-market acquisitions and divestitures, private equity-backed transactions, cross-border investments, and complex public-company M&A, with matters in the healthcare, financial services, transportation, manufacturing, food and beverage, and tourism and hospitality industries. Representative matters handled prior to joining Showalter PLLC include three small asset acquisitions with an aggregate transaction value of approximately $1 million, handled endto-end for the acquiror; the $20 million sale of a healthcare practice to private equity; a $35 million asset acquisition in food and beverage manufacturing; a $56 million acquisition in shipping and transportation; an $80 million cross-border joint venture in tourism and hospitality; a $260 million divestiture of a shipping and transportation business line; the $300 million acquisition of three hospitals; and assistance with a $28 billion public-company merger in the banking sector. On the securities side, Chandler has represented issuers and underwriters in public and private offerings of debt, preferred equity, and common equity, SPAC initial public offerings, convertible securities offerings, and Rule 144A and Regulation S transactions, ranging from growthcompany financings to multibillion-dollar offerings, and he advises public companies on Securities Act and Exchange Act matters, including Forms 10-K, 10-Q, and 8-K, proxy disclosure, and other SEC reporting obligations. Before joining Showalter PLLC, Chandler practiced with Squire Patton Boggs and Carlton Fields in Tampa, and began his legal career with Sullivan & Cromwell in New York, where his practice focused principally on capital markets and other significant corporate transactions.

SESSION 1 – Transactional workflows: contract review, comparison, and diligence | 2:00pm – 3:00pm

This session brings Claude into corporate and transactional practice, working hands-on through contract review, comparison, and diligence. It applies the approach built in “Attorneys Working with Claude” to deal work, with techniques attendees can implement immediately.

BREAK | 3:00pm – 3:10pm

SESSION 2 – Template and skill libraries for deal work: drafting from your own forms at scale | 3:10pm – 3:40pm

Deal documents should start from your own forms, not a blank page. This session shows how to build a template and skill library for deal work, so drafting runs from your firm’s own templates at scale.

SESSION 3 – Skills: turning your repeating work into reusable instructions that run the same way every time | 3:40pm – 4:10pm

Your best work should not be rebuilt from scratch each time. This session shows how to turn repeating work into reusable skills, instructions that run the same way every time, so output stays consistent across matters.

BREAK | 4:10pm – 4:20pm

SESSION 4 – Scheduled tasks: case-law monitors, development tracking, and weekly summaries that run on their own | 4:20pm – 5:20pm

This session shows how to set up scheduled tasks that monitor case law, track developments, and prepare weekly summaries without being asked, running on their own. Attendees will leave with techniques they can implement immediately to capture the staggering productivity gains AI makes available.