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

Jorge R. Aviles | Anderson Kill P.C

Jorge Aviles is a shareholder in Anderson Kill’s Washington, D.C. office. His practice concentrates on complex insurance recovery disputes on behalf of policyholders, including coverage matters arising from cross-border risks and international transactions. He also counsels’ clients on risk management and insurance recovery strategy.

Jorge has helped clients secure millions in insurance coverage following high-staking claims involving a wide variety of losses. He represents commercial and governmental policyholders in all types of sophisticated insurance matters throughout all stages of the insurance process, from pre-purchase policy analysis and review through litigation and settlement of contested claims. He has briefed and handled claims involving trade credit, CGL, D&O, E&O, property, and cyber policies, among many others. Through mediations and arbitrations—including in international forums— and trials, Jorge has assisted in the recovery of millions of dollars in insurance proceeds for clients.

Jorge has been recognized as a Best Lawyer for Insurance Law and as a Breakout Award Winner by Business Insurance. He is also a Fellow of the Leadership Council on Legal Diversity and a graduate of the DC Bar John Payton Leadership Academy.

Jorge also regularly publishes on insurance topics and lectures on insurance coverage issues.

Jorge is fluent in Spanish and conversational in Portuguese.

J. Wesley Hisaw | Holland and Hisaw

J. Wesley Hisaw is a partner with Holland & Hisaw in Horn Lake, Mississippi, where his practice focuses on personal injury, insurance litigation, and family law. He has negotiated and tried hundreds of cases across Mississippi and Tennessee and frequently presents CLE programs on negotiation strategy, insurance practice, and trial advocacy. Known for his pragmatic and psychologically grounded approach to negotiation, Wesley teaches attorneys how to anticipate adjuster behavior, frame their cases for value, and close settlements that reflect the true strength of the claim.

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

• Types of insurance adjusters
  • Company/Staff adjuster: Employed in-house by insurers
  • Independent adjuster: Hired contractors working for insurers on a case-by-case basis
  • Public adjuster: Hired by policyholders
  • Key distinctions in authority, incentives, and communication style
• Adjuster objectives and tactics
  • Common strategies adjusters use for claim costs
  • How to identify and respond to negotiation tactics to achieve claim resolution
• Negotiation strategies
  • Principles of effective negotiation: Preparation and documentation
  • Adjuster duties and conduct
  • Tailoring your approach based on adjuster type
• Practical tips and examples
  • Common pitfalls and how to avoid them
  • Knowing when to involve counsel or escalate to litigation

Break | 3:00pm – 3:10pm

Session II – Positioning the Case for Maximum Settlement Value | 3:10pm – 4:10pm

• Positioning the case for maximum valuation
  • How adjusters internally evaluate files: Reserves, documentation, and authority levels
  • Building a “valuation narrative” through medical summaries, visual evidence, and loss charts
  • Timing your demand to align with internal insurer review or reserve meetings
• Psychological leverage and adjuster behavior
  • Recognizing behavioral cues that indicate flexibility or internal constraints
  • Language patterns that trigger defensive vs. cooperative responses
  • Using reciprocity, consistency, and anchoring principles in written and verbal offers
• Timing, follow-up, and offer management
  • Structuring follow-ups to create movement without appearing desperate
  • How and when to escalate to a supervisor or litigation adjuster
  • Turning “lowball” offers into productive counter-anchors that set new negotiation baselines
• Documentation and presentation tactics that move the needle
  • Crafting the perfect demand letter: Narrative, visuals, and valuation metrics
  • Leveraging pre-suit expert input to influence adjuster expectations
  • Using social proof and verdict data to justify your ask without overreaching