Our Attorneys
Olivia Bennett
Senior Counsel
Biography
Olivia Bennett leads the firm's estate planning and private client practice. She advises individuals and families on wills, trusts, powers of attorney, and the succession of family businesses and property.
Her planning philosophy is that good documents fail families when the plan around them is unclear. She invests the time to understand family dynamics and long-term objectives before recommending structures, and she keeps plans current as lives change.
- Education
- J.D., New York University School of Law; B.A., Smith College
- Bar Admissions
- New York
- Memberships
- New York State Bar Association, Trusts and Estates Law Section; New York City Bar Association, Trusts, Estates & Surrogate's Courts Committee
Professional Background
A considered practice.
Ms. Bennett practiced trusts and estates at a private client firm in Manhattan before joining Williams Cummings, where she brought a second practice area to the firm and a coordinator's view to clients with both business and family affairs.
She is a frequent drafter of plans that sit at the intersection of business and family: succession arrangements, fiduciaries who are also advisors, and trusts designed to be administered long after the conversations that created them.
Representative Experience
Work with a purpose.
- Designed a complete estate plan for the owner of a manufacturing company, including a successor trustee and a funded irrevocable trust.
- Planned the intergenerational transfer of a commercial real estate portfolio while coordinating ownership, leasing, and estate documents.
- Advised a family on gifts and trusts to reduce the taxable estate while preserving control during the grantor's lifetime.
- Restructured the trusteeship of a substantial trust after family circumstances made the original arrangement untenable.
Approach
How Olivia works.
Ms. Bennett treats estate planning as a conversation about what matters most, family, values, and the future of what a client has built. She asks the questions others skip and writes documents that the people who must read them can actually understand.
She reviews plans on a regular cadence and insists that beneficiaries, ownership, and advisors be checked against the documents. Coordination, not accumulation, is what makes an estate plan work.