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Charitable planning can be an important part not only of managing income and estate taxes, but of engaging the family and strengthening family values. Adding in a multigenerational component can make it even more meaningful and compelling. Just as every family is unique, so is the philanthropic approach where communication is key and there is more than one way to involve a family in philanthropy.

Few, if any, roles are more significant in ensuring a foundation's success than that of the board chair. This may be why many people find assuming this position a daunting project. And yet the successful businessperson who serves as chair of a family foundation dedicated to a cause that was dear to his or her parents' hearts or the community leader who serves as chair of an independent foundation that provides deserving youth with life-changing opportunities will tell you that few roles are more rewarding.

The field of philanthropy has primarily been built around the more tactical aspects and the how of giving while taking the why for granted.

Just as an individual goes through life cycles, so does a charity. From the start-up phase to adopting a strategic vision to looking at ways to grow the charity, there are many steps to consider at each important phase of the charity’s lifetime. By bringing discipline and focus to your family philanthropy and going beyond just writing checks, your charity has the best chance of making a greater impact.

Travis Roy’s story is well known—in 1995, the rising college hockey star suffered an on-ice injury that left him paralyzed from the neck down after only 11 seconds of his first Boston University game. That tragic accident ended Travis’ hockey career, but it marked the beginning of his decades-long commitment to helping others through the Travis Roy Foundation. As the Foundation grew, Travis faced a critical question: how can a grass roots organization powered by volunteers manage growth and sustain its impact without a sophisticated support structure?

Strategic philanthropy is similar to intentional asset allocation in that it requires as much of the giver’s intellect as it does the bank account. A careful and disciplined approach to philanthropic giving combines purpose, practicality, and passion. In planning for charitable giving, families can review their choices with a planning matrix that outlines the types of gifts and their basic features, control features, term, administrative considerations, income tax benefits, deduction limits, estate and gift tax benefits, costs, and other benefits and considerations.

As high-net-worth investors discuss plans for charitable giving and investing with their financial advisors, it is absolutely crucial for them to be on the same page in terms of the outcomes desired, both financially and philanthropically. For this reason, advisors and their clients need a set vocabulary of terms going into the first meeting. Only then can they discuss goals (and ways of achieving them) without stumbling over communication roadblocks.

Jessica Jackley, cofounder of KIVA, the world’s first microfinance website, shares her unique wisdom on financial inclusion and social justice. Jessica highlights stories and lessons from her book, Clay Water Brick: Finding Inspiration from Entrepreneurs Who Do the Most with the Least, as well as experiences from her own life as an entrepreneur, investor, and philanthropist.

A rising generation of clients in their 20s and 30s turned to Jim Steiner, president of Abbot Downing, and asked him to share his insights, both as a parent and a wealth management leader. Through four memorable stories and thoughtful questions, Mr. Steiner reflected on matters of career, philanthropy, family, and leaving a legacy. He began with a cab ride in Chicago, learning to see with fresh eyes.