Strategic Negotiation with Insurance Adjusters: Outsmarting the System with Negotiation Psychology and Proven Settlement Strategy

Jorge R. Aviles, Shareholder | Anderson Kill P.C

Jorge R. Aviles is a nationally recognized insurance recovery attorney and shareholder at Anderson Kill P.C., one of the country’s preeminent policyholder-side law firms. Based in the firm’s Washington, D.C. and New York offices, he concentrates his practice on complex insurance coverage disputes on behalf of commercial and governmental policyholders, with particular depth in cross-border and international coverage matters arising from global transactions, multinational operations, and London-market insurance programs. A trusted counselor and skilled advocate, Jorge guides policyholders through every stage of the insurance process—from pre-purchase policy analysis and risk management strategy through high-stakes litigation and settlement of contested claims—and is widely regarded as a go-to practitioner in the policyholder insurance recovery space.

• Education & Credentials

Jorge earned his Juris Doctor from Fordham University School of Law, where he served as an Associate Editor of the Fordham Journal of Corporate & Financial Law, and his Bachelor of Arts from Harvard University. He is admitted to practice in the District of Columbia and New York, as well as before the U.S. Court of Appeals for the Second Circuit and the U.S. District Court for the Southern District of New York.

• Recognition & Leadership

Jorge has been recognized by The Legal 500 United States for Insurance Law (2025) and has been listed in Best Lawyers: Ones to Watch for Insurance Law since 2024. He is a Business Insurance Break Out Award winner (2022) and a Negocios Now NYC–Tri-State Latinos 40 Under 40 honoree (2025). Additional honors include selection as a Fellow of the Leadership Council on Legal Diversity (2024), a Fellow of the American Bar Foundation, inclusion on the Capital Pro Bono Honor Roll (2021), and graduation from the D.C. Bar’s prestigious John Payton Leadership Academy, Class of 2024.

• Professional Involvement

Jorge is actively engaged in the legal profession and broader business community. He serves as a member of the Law360 Insurance Authority Specialty Lines Editorial Advisory Board (2025) and previously served as Diversity, Equity and Inclusion Director for the ABA Business Law Section’s Directors and Officers Liability Committee (2022–2025). He is a member of the Young Lawyers Network Leadership Council of the D.C. Bar Foundation. A frequent speaker and thought leader, Jorge has presented at conferences and seminars hosted by the International Bar Association, the RIMS Potomac Chapter, the Federal Bar Association, the Academy of Judicial Interchange and Studies (AIJE), and numerous continuing legal education providers, on topics ranging from cross-border supply chain risks and insurance negotiation strategies to D&O coverage and emerging cyber liability issues. He has published articles in leading outlets including Risk Management Magazine, Law360, Supply Chain Brain, the Daily Business Review, and Westlaw Today, among others.

• Experience

Throughout his career, Jorge has helped clients secure millions of dollars in insurance recoveries across a wide spectrum of high-stakes disputes involving trade credit, commercial general liability (CGL), directors and officers (D&O), errors and omissions (E&O), property, cyber, and other specialized policy lines. His representative experience spans Fortune 500 energy companies, publicly traded utilities, international investment firms, major port authorities, global manufacturers, municipalities, and nonprofit organizations. Jorge has handled coverage disputes arising from complex underlying claims including environmental contamination, bodily injury and asbestos-related exposures, shareholder litigation, business interruption, cyber breaches, and multi-million-dollar wrongful death verdicts. He has achieved significant results through federal and state court litigation, mediations, and international arbitrations—including proceedings before the London Court of International Arbitration (LCIA) and the International Dispute Resolution Centre—managing claims involving multi-layered insurance towers with exposures reaching hundreds of millions of dollars, including matters presenting issues of first impression under New York law. Jorge is fluent in English and Spanish and conversational in Portuguese, enabling him to serve a diverse, global client base with cultural fluency and precision.

J. Wesley Hisaw, Attorney at Law | Stroud, Flechas & Dalton

Wesley Hisaw is a seasoned litigation attorney whose practice spans family law, personal injury, estate planning, and appellate advocacy across Mississippi and Tennessee. Known for his analytical rigor and client-centered approach, he brings over two decades of legal experience to every case he handles. Whether guiding families through complex custody disputes, pursuing full compensation for injured clients, or advising fellow attorneys on intricate legal questions, Wesley combines deep subject-matter expertise with a genuine commitment to achieving meaningful results. He currently serves as an attorney with Stroud, Flechas & Dalton, where he continues to build on a career defined by professional excellence, peer respect, and dedicated public service.

• Education & Credentials

Wesley earned his Juris Doctor from the University of Mississippi School of Law in 2004, following a Bachelor of Arts degree from the University of Mississippi in 2002. He is admitted to practice in the State of Mississippi and the State of Tennessee, and holds admissions before the United States Court of Appeals for the Fifth Circuit, the United States Court of Appeals for the Sixth Circuit, the United States District Court for the Northern District of Mississippi, the United States District Court for the Southern District of Mississippi, and the United States District Court for the Western District of Tennessee.

• Recognition & Leadership

Wesley’s dedication to the legal profession has been recognized through numerous honors. In 2012, the Mississippi Bar awarded him the Curtis E. Coker Access to Justice Award in recognition of his outstanding pro bono contributions. In both 2014 and 2015, he was named one of the Top 40 Under 40 Litigation Lawyers for the State of Mississippi by the American Society of Legal Advocates and the National Trial Lawyers Association. He has also been designated a Top Ten Attorney for the State of Mississippi in personal injury by the National Association of Personal Injury Attorneys, named a Premier 100 Attorney by the American Academy of Trial Attorneys, and selected as a Rising Star by Super Lawyers from 2015 through 2020. He maintains a perfect 10.0 rating on Avvo in the areas of family law and personal injury.

• Professional Involvement

Wesley is an active participant in the legal community at both the state and national levels. He is a member of the Mississippi Bar, the Tennessee Bar, the Mississippi Association for Justice, and the Tennessee Trial Lawyers Association, among other professional organizations. He has served as Chair-Elect of the Mississippi Association for Justice Young Lawyer Division and has represented the Association at the American Association for Justice Board of Governors in Washington, D.C. A published author, Wesley wrote “Post Divorce Contempt in Tough Economic Times,” which appeared in The Mississippi Lawyer. He is also an active CLE presenter, having delivered programs on topics including negotiation strategies in personal injury claims, the internal workings of insurance companies, and the authentication of social media and email evidence. He has served as a faculty member for the Institute for Paralegal Education and as a presenter for National Business Institute programs.

• Experience

Wesley’s career reflects a broad and versatile practice. He began his legal career at Fearnley, Callif, Martin, McDonald, Tate & Kimbrow before becoming a founding partner of Holland & Hisaw Attorneys at Law in Horn Lake, Mississippi, where he helped build a diverse general practice serving clients across a wide range of legal needs. He has since joined Stroud, Flechas & Dalton, expanding the firm’s capabilities in family law, estate planning, probate, and real estate. His core practice areas include divorce, child custody, child support, estate planning, trusts, guardianship, conservatorship, probate, personal injury, wrongful death, appellate law, professional negligence, real estate and title defects, construction defect, and breach of contract. Wesley is routinely consulted by both attorneys and prospective clients on matters involving family law, personal injury, estate planning, appellate procedure, and employment litigation.

SESSION 1 – Types of Insurance Adjusters and How to Negotiate with Them | 2:00pm – 3:00pm

Learn about the different types of insurance adjusters, their objectives, and negotiation tactics. This session covers effective negotiation strategies, practical tips for claim resolution, and guidance on when to escalate matters to counsel or litigation.

BREAK | 3:00pm – 3:10pm

SESSION 2 – Positioning the Case for Maximum Settlement Value | 3:10pm – 4:10pm

Discover how to position cases for maximum settlement value by mastering adjuster evaluation methods, psychological leverage techniques, strategic timing of demands, and crafting compelling demand letters supported by documentation, visuals, and verdict data.