Legal Malpractice Pitfalls: Retainer Agreements, Cybersecurity, Technology, AI, and Nonlawyer Assistants (2025 Edition) (Including 1 Hour of Ethics)

Michael R. Overly | Foley & Lardner LLP

Michael Overly is a partner in Foley & Lardner’s Information Technology & Outsourcing Group and Privacy, Security and Information Management Groups. He is one of the few practicing lawyers who has satisfied the rigorous requirements necessary to obtain the Certified Information System Auditor (CISA), Certified Information Systems Security Professional (CISSP), Information Systems Security Management Professional (ISSMP), Certified in Risk and Information Systems Controls (CRISC), Certified Outsourcing Professional (COP), and Certified Information Privacy Professional (CIPP) certifications. He writes and speaks frequently regarding negotiating and drafting technology transactions and the legal issues of technology in the workplace, e-mail, and electronic evidence. He has written numerous articles and books on these subjects and is a frequent commentator in the national press (e.g., the New York Times, Chicago Tribune, Los Angeles Times, Wall Street Journal, ABCNEWS.com, CNN, and MSNBC) and has testified before the U.S. Congress regarding online issues.

Ashley M. Kennedy | Foley & Lardner LLP

Ashley Kennedy is a Technology, Transactions, Cybersecurity & Privacy Practice Group member within Foley & Lardner’s Intellectual Property Department. Ashley provides counsel on structuring and negotiating technology agreements to create strategic and advantageous business relationships between companies. She has experience drafting and negotiating commercial agreements, including intellectual property licenses, software-as-a-service agreements, master services agreements, distribution agreements, non-disclosure agreements, and technology transfer agreements. Ashley also has experience structuring and addressing the intellectual property components of mergers and acquisitions and other corporate transactions.

Cari Sheehan | Taft Stettinious and Hollister, LLP

With over 15 years of legal experience in civil litigation, conflicts of interest, and professional responsibility, Cari serves as the firm’s Assistant General Counsel. In this role, she advises firm attorneys with respect to ethics compliance, risk prevention, and conflicts of interest. In addition, she assists in the review and negotiation of outside counsel guidelines, conflict waivers and engagement letters, and other items with ethical implications. In addition, she assists in providing ethical training and education within the firm to its attorneys and staff.

Session I – Cybersecurity, technology risks, and legal malpractice prevention | 1:00pm – 2:00pm

• Cybersecurity risks in legal practice
  • Common cybersecurity threats facing law firms
  • Practical tips for protecting client data
  • Ensuring compliance with data protection regulations
• Emerging technology and legal malpractice
  • Risks associated with adopting new legal technologies
  • Managing compliance with technology competence rules
  • Mitigating risk when using cloud services and new legal tools

Break | 2:00pm – 2:10pm

Session II – Retainer agreements, AI integration, and nonlawyer assistant oversight | 2:10pm – 3:10pm

• Drafting effective retainer agreements
  • Essential clauses to protect against malpractice claims
  • Addressing fee disputes: Best practices
  • Incorporating clear client communication standards to avoid misunderstandings
• Artificial intelligence in legal practice
  • Benefits and risks of using AI for legal research and drafting
  • Ethical obligations under ABA Model Rule 1.6 related to AI use
  • Addressing liability and accountability in AI-driven processes
• Supervising nonlawyer assistants
  • Delegation do’s and don’ts: Maintaining professional responsibility
  • Preventing Unauthorized Practice of Law (UPL)
  • Training and oversight strategies to reduce malpractice risks