Your Clients Aren’t Planning For This. Are You Asking?

Your clients trust you with their taxes—but who is asking them the questions that could protect their family, their business, and their financial future?

In this episode, Eric Green sits down with financial advisors Rick Wells and Doug D’Andrea to discuss the planning conversations every tax professional should be having with clients. From life and disability insurance to retirement planning, buy-sell agreements, long-term care, and estate planning, these are issues clients often overlook until it’s too late.

They also explore why these conversations represent a major opportunity for tax professionals to move beyond compliance and into higher-value advisory services—without necessarily becoming financial advisors themselves.

Plus, Eric shares real-world examples of what happens when clients fail to plan—and how tax professionals can help make sure those conversations happen before there is a crisis.

Download the free “10 Estate Planning Questions Every Tax Professional Should Ask Every Client” resource and learn how to start these conversations in your own practice.

Register for the free webinar series “What Happens When a Client Dies” here: https://taxrepnetwork.com/programs/estate-planning

Download our free Guide “The 10 Estate Planning Questions Every Tax Pro Should Ask Every Client” here: https://taxrepnetwork.com/resources

Contact Rick Wells here: rwells@baystatefinancial.com

Contact Doug D’Andrea here: douglasdandrea@financialguide.com

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Watch the episode here

Listen to the podcast here

Important Links

• Richard Wells on LinkedIn
• Doug D’Andrea at MassMutual
• Baystate Financial
• The 10 Estate Planning Questions Every Tax Pro Should Ask Every Client (free guide)
• When a Client Dies: What Every Tax Professional Needs to Know

About Rick Wells

Rick Wells is a dedicated leader, educator, and advisor with over three decades of service to his community and country. A retired Lieutenant Colonel in the United States Marine Corps Reserve, Dr. Wells spent his military career in both active duty and reserve roles, culminating in his retirement after years of exemplary service.

In addition to his military career, Dr. Wells retired as a highly respected elementary school teacher from the West Hartford Public Schools. Throughout his tenure, he inspired young minds with a commitment to fostering growth, resilience, and achievement. His innovative approach to education emphasized the importance of perseverance, mastery, and the cultivation of self-awareness—skills he believes are foundational to both academic and personal success.

As a financial advisor, Dr. Wells brings his service-oriented ethos to helping families, professionals, and organizations build strong financial futures. His expertise in retirement planning and wealth management reflects his dedication to guiding others through challenges to create sustainable solutions that align with their values and goals.

A staunch advocate of health and wellness, Dr. Wells champions the principles of commitment and consistency as a key to building strength and overcoming challenges. Drawing from his military, educational, and personal wellness journey, he inspires others to embrace challenges as opportunities for mental, physical, and spiritual growth.

Through his work as a mentor, speaker, and advisor, Dr. Wells shares powerful insights on goal setting, leadership, and wellness. With decades of dedicated service to the community and the country, Dr. Wells continues to lead by example, offering practical strategies to elevate individuals and organizations alike.

About Douglas D’Andrea

Douglas D’Andrea has been in the financial services industry for more than 20 years, providing clients with creative planning strategies that integrate all aspects of their financial lives. He delivers strategic solutions in employee benefits, retirement plans, and personal wealth management. By focusing on each client’s unique financial and investment objectives, Doug develops customized strategies designed to help them achieve their goals.

Doug graduated from Western Connecticut State University with a Bachelor of Business Administration in Finance and holds FINRA Series 7, 63, 65, and 24 securities registrations.

He also holds the Accredited Investment Fiduciary (AIF®) designation, reflecting his commitment to fiduciary excellence, ethical standards, and prudent investment guidance. This specialized training reinforces his dedication to helping clients make informed financial decisions while always serving their best interests.

In addition, Doug has earned the Certified Plan Fiduciary Advisor (CPFA®) designation, demonstrating specialized expertise in retirement plan fiduciary responsibilities, ERISA compliance, and plan governance. This credential underscores his commitment to helping plan sponsors navigate the complexities of employer-sponsored retirement plans and fulfill their fiduciary obligations.

Outside of his professional responsibilities, Doug serves as a Trustee of the Watertown Foundation, a 102-year-old nonprofit organization that awards more than $200,000 annually in scholarships and grants to members of the local community. He enjoys spending time with his family, traveling, woodworking, and photography. Doug resides in Watertown, Connecticut, with his wife, Kristi, and their daughter, Brooklyn.