Separation and Release Agreements When the Clause Itself Is the Violation

Amy Moor Gaylord, Partner and Co-Chair, Traditional Labor Law Practice | Akerman LLP

Amy Moor Gaylord is a Partner in the Chicago office of Akerman LLP and Co-Chair of the firm’s Traditional Labor Law Practice. A Fellow of the College of Labor and Employment Lawyers and a former National Labor Relations Board attorney, Amy has spent more than 28 years representing public- and private-sector employers in NLRB proceedings, union organizing campaigns, collective bargaining, arbitration, and employment litigation. Her deep command of the National Labor Relations Act — the statute at the heart of the Board’s McLaren Macomb line of decisions on confidentiality and non-disparagement provisions in severance agreements — makes her one of the most qualified management-side voices in the country on drafting separation agreements that survive regulatory scrutiny.

• Education & Credentials

Amy earned her J.D. with honors from the University of Illinois College of Law (1997) and her B.S. from Cornell University’s School of Industrial and Labor Relations (1994), where she was named a Judge William B. Groat Scholar. She is admitted to practice in Illinois and before the U.S. Courts of Appeals for the Seventh, Eleventh, and D.C. Circuits and the U.S. District Courts for the Northern and Central Districts of Illinois and the Northern District of Indiana.

• Recognition & Leadership

Amy is a Fellow of the College of Labor and Employment Lawyers, the profession’s highest peer-elected honor in the field. She has been listed in The Best Lawyers in America every year from 2022 through 2027, selected to Illinois Super Lawyers (2018–2022, 2025–2027), named to Benchmark Litigation’s Top 50 Labor & Employment Litigators (2025–2026), recognized among Crain’s Chicago Business’s Notable Women in Law (2026), and named one of Attorney Intel’s Top 25 Attorneys of Illinois (2024). She serves as President of the Chicago Chapter of the Labor and Employment Relations Association (LERA), served as Employer Co-Chair of the ABA Section of Labor and Employment Law’s Committee on the Development of the Law Under the NLRA (2020–2022), and sat on the Law360 Employment Authority Labor Editorial Board (2022–2023).

• Professional Involvement

Amy began her career as an attorney with the National Labor Relations Board in Peoria, Illinois (1997–1998), giving her an insider’s understanding of how the agency investigates charges, evaluates employer policies and agreements, and litigates unfair labor practice cases. She has been a member of the ABA Section of Labor and Employment Law since 1999 and is active in the National Public Employer Labor Relations Association and the Illinois Public Employer Labor Relations Association. A contributor to Akerman’s HR Defense Blog, she has presented at more than 40 conferences and webinars since 2015, including programs for LERA, the National Academy of Arbitrators, the American Bar Association, and the National Association of College and University Attorneys, on union organizing, arbitration, NLRA developments, and workplace discrimination.

• Experience

Amy represents employers in healthcare, higher education, hospitality, automotive retail, and the PEO and staffing industries in NLRB proceedings, union organizing drives and Board-conducted elections, labor arbitrations, and discrimination litigation, and has led hundreds of collective bargaining negotiations across multiple industries. She also conducts labor and employment due diligence in corporate transactions and provides compliance training to management. Her daily work advising employers on handbook policies, workplace rules, and separation agreements under the NLRA’s Section 7 and Section 8(a)(1) — precisely the provisions the Board has invoked to find confidentiality, non-disparagement, and non-cooperation clauses independently unlawful — makes her uniquely positioned to guide employers and their counsel through drafting enforceable releases in an environment where the clause itself can be the violation.

Sean H. Sobel, Founding Attorney | Sobel Law Solutions, LLC

Sean H. Sobel is the Founding Attorney of Sobel Law Solutions, LLC in Cleveland, Ohio, where he represents employees and executives in employment matters throughout Ohio and advises parties in Title IX proceedings nationwide. With more than fifteen years devoted to the employee side of the employment relationship, Sean has reviewed, negotiated, and litigated over hundreds of separation and severance agreements — giving him a granular understanding of how confidentiality, non-disparagement, cooperation, and release provisions operate in practice, and where those clauses cross the line from lawful contract term into unlawful restraint of protected rights.

• Education & Credentials

Sean earned his J.D. from Case Western Reserve University School of Law (2010) and his B.A. in Political Science from the University of Wisconsin–Madison. He is admitted to practice in Ohio and before the U.S. Court of Appeals for the Sixth Circuit and the U.S. District Courts for the Northern and Southern Districts of Ohio.

• Recognition & Leadership

Sean has been recognized by Super Lawyers for fourteen consecutive years — selected to Ohio Rising Stars every year from 2014 through 2025 and elevated to Super Lawyers in 2026 and 2027 — a distinction reserved for the top five percent of attorneys in the state. He holds a 10.0 “Superb” rating from Avvo and has been named one of the Top 3 Employment Lawyers in Cleveland by Three Best Rated®. He is the co-author of “When Severance Agreements Bar ERISA Long-Term Disability Claims,” published in the Cleveland Metropolitan Bar Journal (January/February 2026), an analysis of the frequently overlooked consequences of overbroad release language.

• Professional Involvement

Before founding Sobel Law Solutions in March 2026, Sean was a founding partner of Sobel, Wade & Mapley, LLC, a Cleveland employment and civil rights litigation boutique, where he built a plaintiff-side practice spanning discrimination, harassment, retaliation, whistleblower, wage and hour, and wrongful termination claims. He is an active member of the Cleveland Metropolitan Bar Association and a regular contributor to bar programming and publications on employment law developments, including the enforceability of post-employment restrictions and the evolving regulatory scrutiny of severance terms.

• Experience

Sean’s practice concentrates on employment discrimination, workplace sexual harassment, FMLA and pregnancy-related leave rights, whistleblower and retaliation claims, wrongful termination, executive employment and compensation disputes, sales commission and wage claims, non-compete counseling, public employee rights, and Title IX matters for both complainants and respondents. A core component of his work is the review and negotiation of separation and release agreements on behalf of departing employees — the vantage point from which he sees firsthand how confidentiality, non-disparagement, no-rehire, cooperation, and general release provisions are drafted, how they are enforced, and how they collide with the NLRA, Title VII, the ADEA and OWBPA, whistleblower statutes, and state speak-out laws. That experience makes him uniquely positioned to explain, from the employee’s side of the table, when the clause itself becomes the violation.

SESSION 1 – What a Separation Release Can Lawfully Waive and What It Cannot | 12:00pm – 1:00pm

This session examines the federal and state law boundaries on what a separation and release agreement can and cannot waive, covering OWBPA requirements for employees 40 and older, the expanding universe of unwaivable statutory rights under the FLSA, ADEA, and NLRA, and the SEC and DOJ whistleblower protection rules that have generated active enforcement against overbroad release language. Attorneys will leave with a working understanding of the specific clauses that render agreements void or expose employers to regulatory penalty, and the drafting fixes required to achieve an enforceable release. The session draws on enforcement actions through May 2026, including the Foot Locker SEC penalty and the NLRB’s Valley Radiology decision, and addresses the current legal uncertainty created by the 2025 NLRB General Counsel memo rescission.

BREAK | 1:00pm – 1:10pm

SESSION 2 – Structuring Severance Pay and Avoiding the Clauses That Void the Agreement | 1:10pm – 2:10pm

This session examines the specific drafting vulnerabilities that render severance and release agreements void or unenforceable, covering the current NLRB posture on non-disparagement and confidentiality clauses post-McLaren Macomb, SEC Rule 21F-17(a) whistleblower pitfalls, federal and state NDA restrictions under the Speak Out Act and state Silenced No More laws, and the structural requirements of OWBPA waivers in RIF contexts. Attorneys will leave with a working framework for threading five simultaneous compliance needles — NLRA, SEC, federal statute, state law, and OWBPA — in a single severance agreement. The session is designed for practitioners who draft, review, or negotiate separation agreements and need to identify which specific clauses create liability exposure.