Courageous Conversations…Topics to Avoid at the Dinner Table, but Bring to the Conference Table
As we make our way through the holiday season, we are reminded of the old adage about avoiding certain subjects such as religion, sex, and politics at the dinner table. Many of us know from experience how difficult it can be to discuss these topics in mixed company, even with our own families. The impulse to avoid these subjects for fear of hurting or offending others is a good one, and may be a smart way to navigate polite conversation. However, some sensitive or politically-charged subjects can be vitally important to a client or the client’s family, and failure to discuss them with the client could have a substantial detrimental effect on the client’s estate plan. In some cases, the client will raise the topic, but in others, it may make sense for the attorney to drive the discussion. What is the best way to navigate these conversations? What are some key points estate planning attorneys should know about certain subjects in order to address them with respect and understanding?

Vanessa Kanaga currently serves as InterActive Legal’s Special Advisor on Estate Planning and Legal Strategy. She is the former CEO of InterActive Legal. Vanessa received her J.D. from Cornell Law School and holds a B.A. in Philosophy from Wichita State University, as well as an Advanced Professional Certificate from New York University School of Law. She is licensed in New York, Kansas, and Arizona, and currently lives in Arizona.
Prior to joining InterActive Legal in 2013, Vanessa practiced in New York, at Milbank LLP and Moses & Singer LLP, and in Kansas, at Hinkle Law Firm, LLC. She has experience in a range of estate planning matters, including high net worth tax planning and asset protection planning.
In 2024, Vanessa returned to the practice of law. She is an Associate Attorney at Greengard Law Firm, PLC in Phoenix, Arizona.

Lori Anne Douglass, of Douglass Rademacher LLP in New York, New York, focuses her practice on estate planning and business succession planning, as well as estate administration and estate litigation. Lori handles both contested and uncontested estate matters, representing heirs, beneficiaries, disinherited family members, executors, administrators and trustees in contested probate proceedings, and advising clients in the preparation of family agreements and resolving family disputes. She is frequently interviewed for articles on estate and business planning and is a well-known lecturer at national conferences and continuing legal education seminars. Lori has written extensively in her practice areas and has been named to the New York Metro Super Lawyers list in recognition of her work in estate litigation for 2012-2018.

Elizabeth F. Schwartzhas been practicing law since 1997 and is a nationally recognized advocate for the legal rights of the lesbian, gay, bisexual, and transgender (LGBT) community. She is the author of the book "Before I Do: A Legal Guide to Marriage, Gay and Otherwise" (The New Press, 2015). While her Miami-based firm works with all clients in matters of family formation (insemination, adoption, and surrogacy, as well as nuptial agreements) and dissolution, estate planning and probate, she has been on the forefront of providing crucial legal protections for LGBT+ families before and since the arrival of marriage equality, including name and gender marker changes for trans and nonbinary individuals. She lectures locally, nationally, and internationally about critical topics including the impact of nationwide marriage equality and the continued importance of LGBT couples protecting their loved ones through estate planning, stepparent and second parent adoption. She focuses her practice in family formation (adoption, insemination, and surrogacy) and dissolution, and handled the first divorce for a same-sex couple in Florida.
Elizabeth is board certified by the Florida Bar in Adoption Law, is a fellow of the Academy of Adoption & Assisted Reproduction Attorneys and the Florida Adoption Council, and serves as an adoption intermediary helping make forever families of all kids. Elizabeth has handled surrogacy for almost 20 years, assisting intended parents, gestational carriers and egg and sperm donors with their legal needs. She is the author of "LGBT Issues in Surrogacy" in the Handbook of Gestational Surrogacy, ed. E.Scott Sills (Cambridge University Press, 2016).

Martin M. Shenkman is an attorney in private practice in Fort Lee, NJ, and New York City. His practice concentrates on estate and tax planning, planning for closely held business, and estate administration. Mr. Shenkman is an author of over 42 books and more than 1,000 articles. He is an editorial board member of Trusts & Estates Magazine and the Matrimonial Strategist, and an advisor for InterActive Legal. He is the recipient of many awards including being a 2013 recipient of the prestigious Accredited Estate Planners (Distinguished) award from the National Association of Estate Planning Counsels. Mr. Shenkman was named Financial Planning Magazine 2012 Pro-Bono Financial Planner of the Year for his efforts on behalf of those living with chronic illness and disability. Investment Adviser Magazine featured him on the cover of its April 2013 issue naming as the lead of their “all-star lineup of tax experts.”
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