Use Your Ears First

Jennifer Richard, MaineCF’s new director of gift planning, shares insights from her years as a trusts and estates attorney.  

MaineCF: Working with clients in your former practice, how did the question of charitable giving come up?

Jennifer Richard: As my relationship with clients developed and I earned their trust, I would learn more details about their assets, their businesses, their family values, and lifestyle. I would then feel more comfortable asking more focused questions about whether they supported specific charitable organizations or causes and whether they wanted to support them in a more meaningful way, either now or in the future, through their estate plans.

Not everyone was in a position to support nonprofits; it often depended on their stage in life. Clients without children or other close relatives tended to make charitable giving a high priority. For others, charitable giving became more viable after they helped their children attain a college or graduate degree.

I’ve had several clients who felt their children either already had enough wealth or would have enough wealth if they inherited a portion of their estate. Their focus then shifted from planning for their children to including them in future charitable gift planning.

MaineCF: What do you wish you had known about the Maine Community Foundation when you were practicing trusts and estates?

Jennifer Richard: I mostly wish I had known the depth of charitable giving expertise that exists at the Maine Community Foundation and the willingness of the staff to help donors make charitable gifts in a simple, fun, and effective way—whether those gifts end up with the community foundation or another organization that is improving the quality of life for Maine people.

MaineCF: What advice would you give to your peers related to charitable giving?

Jennifer Richard: Use your ears first and listen to your clients, ask follow-up questions about their interests – and then listen again. This process will help your clients identify the best strategy for their philanthropic goals and for giving in a way that is most meaningful to them.

MaineCF: You’ve been in the trusts and estates field for 20 years. What changes have you seen?

Jennifer Richard: The biggest change I witnessed was volatility in federal and Maine income and estate tax laws. This unpredictability made planning difficult at times. For the most part, my clients’ decisions over the years were based on their desire to help the organizations or communities they supported. However, some of those decisions also were tax-driven.

It was my practice to first discuss personal planning goals without regard to income and estate tax consequences. Next, I would introduce strategies to meet those goals in the most tax-efficient way.

These strategies usually required some compromise by the client or family member and deviated a bit from the original personal goals. After explaining the various strategies, I let the client choose one with which they were the most comfortable and then would implement that strategy in their estate planning documents. I liked to think of this as the “sleep at night factor,” making sure my clients were comfortable with their entire estate plan so they could rest easy.

MaineCF: As you think about your role at the community foundation, how do you hope people might look to you for help?

Jennifer Richard: Donors have a variety of reasons for giving and those reasons may be based on their personal values, may be tax-driven, or a combination of both. As director of gift planning, I will be a resource for donors throughout the state to help them achieve their charitable gift plan in the most significant way possible. At the same time, I intend to reach out to professional advisors to discuss planned giving options available at MaineCF. If anyone has a question or would like to meet, please do not hesitate to reach me at (207) 412-0833 or

Jennifer I. Richard was a trust and estates attorney at Drummond & Drummond, LLP, in Portland for 20 years prior to joining MaineCF as director of gift planning. She is a graduate of the University of New Hampshire Whittemore School of Business and Economics and the Franklin Pierce Law Center. Richard has served on several boards, including Make-A-Wish Maine, the United Way of Greater Portland Foundation, and the Maine Estate Planning Council. She is currently a member of the Maine Estate Planning Council and continues to be an active volunteer at Make-A-Wish Maine. She also serves on the United Way advisory committee for the Kenneth J. Higgins Scholarship. Richard and her husband, Neal, live in Cumberland with their three children, Gina, Sophie, and Alex.