Making a Will and Checking It Twice: Advice For Donors and Others

Preparing a will—making your wishes known for how your worldly possessions will be distributed when you die—is not for the faint-hearted. There’s the necessity of confronting your own mortality, your finances as they really are, the legacy you hope to leave, and quite possibly, family secrets. No wonder so many people, even the rich and famous, die without one.

To help people plan their estates—including how to leave assets to charity—fundraising and governance consultant Carol Weisman has written a thought-provoking book about the many ways donors and the experts who help them plan their estates can structure a person’s final plans. 

Becoming One of the Grateful Dead: Where There’s a Will There’s a Way describes how 13 individuals and families, including Weisman’s own, have handled their wills and related plans for charitable giving. With each example citing lessons for donors, the book could be a good gift for an organization’s most loyal supporters.

With refreshing humor, Weisman offers advice to individuals who put off doing their will. “Think of a will like a colonoscopy,” she writes. “The prep may be awful, but the procedure is a piece of cake. In both cases, you need a professional to take a periodic look to ensure that everything is in order… Take care of yourself, your loved ones, and the organizations that espouse your values, and you will make a difference.”

Becoming One of the Grateful Dead is not only for the wealthy—many people have substantial financial worth—cars, homes, collections, savings accounts, retirement savings—and their assets have to go somewhere when they die. Actively choosing where those resources ultimately go can be a gratifying achievement for such people, especially when money is directed to charitable causes.

For those who want to encourage giving in the next generation, there is Sam’s story of the “Seventh Child.”  A colorful Texan, Sam had grown up in an orphanage but managed to create an affluent life for himself and his large family. He created a will leaving money to each of his six children and a surprise “seventh child”—“a child or children who do not have someone to care about them or love them”—a situation Sam knew all too well. 

Sam’s kids had never gotten along, a fact he attributed to his shortcomings as a father. “I gave my children so much, and yet I failed to teach them the basic concept of taking care of one another,” he told Weisman. “I’m afraid I pitted them against one another, and we are all suffering from my approach to parenting.”

Sam’s solution: He included a proviso in his will that none of his children would receive their inheritances until all six of them agreed on which needy individual or charitable cause would receive the hefty so-called “seventh child” portion. As he told Weisman, getting along with one another through a shared endeavor “is an important lesson, no matter when they learn it.”

The “lessons learned” at the end of this chapter for nonprofits include tuning into the emotions behind a bequest and the effects those emotions may have on the family. After Sam told a nonprofit director about the lesson he was trying to teach his kids in his will, she encouraged him to talk to his children beforehand to get them on board with the idea, avoid hard feelings, and prevent the constant bickering he was trying to stop in his last wishes.

While Weisman’s book is focused on wills, she explores a range of related issues about family dynamics and charitable giving. For example, Weisman includes the story of Lois, who, after years of making small annual donations to a history building project on a beloved island off the coast of Maine, decided to make a big contribution in her lifetime so that she could enjoy seeing her vision take shape and enlist others in the endeavor.

The venture was a ringing success—“one of the most gratifying experiences of my life,” she told Weisman, with the exception of dismay from one of her six children. Lessons from this example include the necessity of careful stewardship among modest donors who might one day become people who give big. And donors should carefully consider how their actions might cause family friction and look to trusted friends for advice before plunging ahead.

There are stories about couples who have different philosophies and approaches to giving, families dealing with sudden wealth, a woman who became dear friends with her cleaning lady and helped her friend decide which nonprofits would benefit from her estate (her house, her car). Without a will, the estate would go to the state, and a court-appointed lawyer would decide where the funds go.  

Each story brings up a new consideration for donors—do you want to leave everything to your children? Or do you feel, like Bill and Melinda Gates, that your children would do better with a meaningful life of work than a vast amount of wealth? Do you want to fund family trips and enjoy your wealth now? How are your decisions now going to affect your family later? Do you want to give during your lifetime so that you can enjoy seeing your vision come alive? Are local causes your passion? How can you plan your gift to get the most bang for your buck and make sure it’s used as you desire? Do you want to involve your family in your decisions, or keep your wishes private? What is your giving philosophy? Do you want to raise charitable children? How do you find a good estate lawyer?

With regard to that last question, Weisman advises against using online will-writing services. “I have heard from too many estate-planning attorneys who claim that they owed much of their business to Legal Zoom, because folks didn’t understand the implications of the legalese and the result was a mess,” she writes.

One busy young man under 30 with a wife and child, a friend and colleague of Weisman’s, dreaded the work involved in creating a will, broaching the subject of death with his wife, finding a suitable attorney, and so on. But with encouragement from Weisman (he calls her “our self-appointed legal dominatrix”), he got an estate attorney, found guardians for his young children, and identified nonprofits that matter to the couple. 

Weisman even has advice for the individuals who people rely on to carry out their final wishes, including which organizations receive their final charitable gesture.

“If you are asked to be an executor or to care for minor children, or, heaven forbid, an animal that you can’t abide, you can negotiate before a death if you are specifically asked to be responsible,” Weisman writes. “You might live in a no-pet building. You might have a specific religious affiliation that would conflict with the requests of parents… if you go to Mass every Sunday, and your friend or family member wants their children to go to a Methodist service, you might have to do some negotiating.”

Lessons in the book for fundraisers include the example of a much-younger wife who was furious when her aging husband made a seven-figure gift to a local hospital without her knowledge or approval. She demanded that her husband cancel the gift. Weisman was called in to try and smooth things over.

When the wife agreed to meet, Weisman jumped on a plane the next day. At their meeting, Weisman asked her how she wanted to be seen in the community, and she said she wanted to be respected. But the hospital’s approach in excluding her from its solicitation, the wife added, was disrespectful.

“Do you want to be known as the woman who prevented a hospital wing to be built or one who takes a leadership role?” Weisman, a talented fundraiser, asked. An hours-long conversation ensued. The outcome? The wife told her husband to double the gift and to tell everyone she thought the initial request was too small.

Another fundraising lesson from Weisman’s career: She once got a call from a furious executive director who had been asked to an event honoring his board chair for making a large gift to another charity. The problem? The executive director’s charity was getting $5,000 annually from the board chair, who was being feted for giving $5 million to the other charity.  

The executive director fumed. “Do I have to go?” he said. No, Weisman replied, but attending the event would be a good opportunity to ask the board chair why he gave $5,000 annually to the executive’s charity and why he made a $5 million gift to the other organization. The executive director followed her advice and asked the question. If he could come up with a $5 million idea, the board chair replied, he’d be willing to give that much to the executive’s charity.

At the end of her book, Weisman includes a “Giving Questionnaire” to help individuals (along with their estate planners) define the type of philanthropists they want to be as they create their wills to shape their legacies. This book will help people seeking to imagine the ways in which their wishes for the world can live on—a potentially gratifying and inspiring jaunt into the future.