Drafting the Modern Engagement Letter: Scope Limits, AI Clauses, and Clean Withdrawal

Cari L. Sheehan, Assistant General Counsel | Taft Stettinius & Hollister LLP

Cari L. Sheehan serves as Assistant General Counsel at Taft Stettinius & Hollister LLP, drawing on more than 15 years of experience in civil litigation, conflicts of interest, and professional responsibility. She counsels the firm’s attorneys on ethics compliance, risk prevention, and conflicts of interest, and assists in reviewing and negotiating outside counsel guidelines, conflict waivers, engagement letters, and other documents with ethical implications. She also helps deliver ethics training and education to the firm’s attorneys and staff.

• Education & Credentials

Cari graduated from the Indiana University Robert H. McKinney School of Law (2007), magna cum laude, after earning her undergraduate degree from the University of Southern Indiana (2004), cum laude. She is admitted to practice in Indiana and Illinois, before the U.S. Court of Appeals for the Seventh Circuit, and in multiple federal district and bankruptcy courts across Indiana, Illinois, and Michigan.

• Recognition & Leadership

Cari received the Top Live Faculty Award from LexVid (2024–2025).

• Professional Involvement

Cari is a member of the State of Indiana AI Task Force (created by SEA 150), the Sagamore American Inn of Court, the Indiana State Bar Association’s Ethics Committee, and the American Bar Association.

• Experience

Cari is an Adjunct Professor at the IU Robert H. McKinney School of Law, where she teaches Professional Responsibility, and formerly served as an Assistant Clinical Professor of Business Law and Ethics at the Kelley School of Business. A frequent presenter and author on legal ethics and professionalism, she is a recurring contributor to Res Gestae on the Ethics Curbstone and has delivered more than 200 seminars on ethics and professionalism for local and national platforms. Her primary research focus is the ethics of artificial intelligence and its effect on the legal and business communities.

Doug Richmond, Senior Vice President | Lockton Companies

Doug Richmond is a Senior Vice President with the Lockton Companies, where he advises Lockton’s law firm clients on professional responsibility and liability issues. He joined Lockton after retiring as a Managing Director of Aon’s Professional Services Practice, where he led Aon’s loss prevention services across all professions. Before joining Aon, Doug was a partner with Armstrong Teasdale LLP in Kansas City, Missouri (1989–2004), where he had a broad civil trial and appellate practice.

• Education & Credentials

Doug earned his Juris Doctor from the University of Kansas School of Law. His legal education provided the foundation for a career spanning civil litigation, professional liability, legal ethics, and professional responsibility.

• Recognition & Leadership

He tried over 40 major cases to verdict as “first chair.” In 1998, he was named the nation’s top defense lawyer in an insurance industry poll as reported in the publications Inside Litigation and Of Counsel.

• Professional Involvement

He is a Special Advisor to the ABA’s Standing Committee on Ethics and Professional Responsibility, and a former member of the ABA’s Standing Committee on Lawyers’ Professional Liability (2020–2023) and the Standing Committee on Ethics and Professional Responsibility (2016–2019). He chairs the Kansas Bar Association’s Ethics Advisory Opinions Committee.

• Experience

Doug is the lead author of the book Professional Responsibility in Litigation (3d ed. 2021). He has also published over 100 articles in university law reviews and many more articles in other scholarly and industry publications. He teaches Professional Responsibility at the University of Kansas School of Law and the Northwestern University Pritzker School of Law. He formerly taught seminars on legal malpractice at the Texas A&M University School of Law and the University of Florida Levin College of Law.

SESSION 1 – Defensible Engagement Letters: Identity, Scope, and Fees | 12:00pm – 1:00pm ET

This program explains how to draft more defensible engagement letters by focusing on three core pillars: clearly identifying who is—and who is not—the client, defining the scope of the representation with enforceable specificity, and structuring fee provisions so they comply with current ethics and trust‑account rules. The session emphasizes that engagement letters are not merely intake documents, but core risk‑management tools that can reduce malpractice exposure, prevent unintended client relationships, and improve compliance with evolving rules on advance fees and flat‑fee arrangements. The presentation incorporates recent authority, including ABA Formal Opinion 505 on prepaid fees and In re Alexei’s default rule on when flat fees are earned, and provides clause‑level drafting examples that attendees can apply immediately to new and existing templates.

BREAK | 1:00pm – 1:10pm ET

SESSION 2 – Beyond the Signature: AI Disclosures, Client Communication, Conflicts, and Ethical Withdrawal | 1:10pm – 2:10pm ET

An engagement letter should do more than define the representation at the outset—it should establish expectations for how the attorney-client relationship will operate throughout the matter and how it will end when necessary. This session focuses on modern engagement letter provisions addressing artificial intelligence, technology-assisted legal services, client communication protocols, confidentiality, conflicts, file ownership, document retention, and disengagement procedures. Participants will examine emerging ethics guidance on AI-assisted practice and learn how carefully drafted operational and termination provisions can reduce disputes, facilitate clean withdrawals, and minimize post-representation risk.