Family Philanthropy Playbook for Community Foundations

Unit 2: Basic Know-How

This unit provides resources for learning and practicing fundamental skills in advising families, asking good questions, and understanding generational styles.


READ: The Culture of Advising Families 

Participants in the Chartered Advisor in Philanthropy® courses learn about four styles of conversations with generous individuals and families. Based on work by noted consultants Kathryn Miree, Jay Steenhuysen, Scott and Todd Fithian, and others, the styles are:

  1. Fundraising – selling the donors on a particular idea, project, or fund and then soliciting a current or multi-year contribution. The conversation often fulfills the community foundation’s goals of increasing assets and/or finding co-investments in leadership initiatives. However, the conversations are transactional in nature and don’t necessarily build trust and loyalty in the donors.
  2. Gift/Grant Planning – articulating a course of action based on the staff member’s expertise and knowledge. Staff usually develops the course of action through a small number of interactions with the donor and hopefully the donor’s advisor(s). On the gifting side, the solutions – CLTs, CRTs, DAFs, etc. – are technical in nature and sometimes jargon-filled. On the grantmaking side, the solutions are typically funding specific types of grantees or implementing strategic grantmaking approaches favored by the program team.
  3. Consultative – beginning with open questions about the donor’s values, overall philanthropic goals, and community connections without having a pre-ordained or specific solution. Multiple conversations over time advance a shared vision of legacy and impact, resulting in a negotiated solution (gifts, funds, grants, etc.) that both benefits the donor’s goals and the community foundation’s goals.
  4. Discernment – asking open questions to help the donor achieve his or her own conclusions, helping to define purpose, legacy, passion, life story and more. Staff are seen as a coach, strategy advisor, collaborative learner, and facilitator as the donor and their family define, live out, and re-evaluate their philanthropic journeys over time. This style forms deep, trusting, long-term relationships, and the results of the donor’s philanthropic journey can include gifts to, through, and outside of the foundation.

The most successful family philanthropy services are based on the third and fourth styles – discernment and sometimes consultative relationships. Those relationships should be backed by an organizational culture that allows for smaller portfolios of clients per staff member and that focuses on longer-term success metrics for the client work.


READ: Effective Advising and Discernment

Effective philanthropic services staff build skills in asking open-ended questions, active listening, and probing for clarity. Helpful resources include:

  • Philanthropic planning tools [link to Module 3: Unit 3] – this Family Philanthropy Playbook unit has links to fundamental tools for helping families discern and refine their values, principles, vision, interest areas, goals, and more.
  • Charitable Gifts of Noncash Assets (Clontz, Raffin, et al, 2017) – in the first chapter of this guide, Jay Steenhuysen provides terrific lists of questions to learn a donor’s charitable history, family philanthropy and volunteer activities, political activities, definition of good grantees and gifts, charitable philosophy, and goals, and more. (Free PDF)
  • Client Advisor Skills (Sobel, 2006) – Andrew Sobel is a well-known speaker and blogger on helping individuals build long-term relationships with clients. This collection of posts covers the advisor mindset, effective questioning and listening, effective relationship-building, and more. He’s also distilled his thinking into a Power Questions App ($3.99).
  • Core Techniques for Effective Client Interviewing and Communication (Grubman and Jaffe, 2010) – two respected trainers of financial planners share their insights into interviewing clients effectively, communicating clearly about your process, speaking the client’s language, listening well, and managing yourself in the process. (Free)
  • American College of Financial Services GS 839 – the first course of the three-course Chartered Advisor in Philanthropy® certification provides “the knowledge needed to elicit client or donor goals for self, family and society and to convene a team to achieve those goals now, later, at death or beyond death.” ($1,250+)

READ: Generational Styles

There are dozens of articles and books on navigating the differences between generations. Here are key starting points for discussion with your staff and board members:

  • BridgeWorks Generations 101 – this short series of blog posts covers the cultural basics of each of five generations and how each generation shows up in the workplace. (Free)
  • The Next Generation of American Giving – in 2017, Blackbaud updated its 2013 report on giving preferences and habits of five generations. (Free)
  • 21/64 101 Course – dozens of community foundation staff have taken the firm’s 101 Multigenerational Training course to understand generational differences and generational assumptions about wealth, family, and philanthropy. ($2,500+) You can purchase the Generational Personalities guide and 21/64 Toolbox without attending the course.

DO (90 minutes): Family Philanthropy Case Study: Initial Meeting with Couple [members only]

This case study gives you practice in navigating a couple’s differing philanthropic goals in your first meeting with them. The Philanthropic Initiative (TPI) developed it for community foundations in 2007.

The role play exercise requires at least four people —a facilitator, two people to play the couple, and one person to play the foundation staff member. It also requires the staff member’s familiarity with TPI’s Giving Together: A Workbook for Family Philanthropy or similar tools and processes.


DISCUSS (45-60 minutes): Family Philanthropy Case Study: Engaging Adult Children [members only]

This case study, for facilitated group discussion with your staff, describes the challenge a community foundation faced when attempting to authentically involve the adult children. The Philanthropic Initiative (TPI) developed it for community foundations in 2007.


DO (90–120 minutes): Family Grantmaking Case Studies

GMA Foundations contributed two case studies for community foundation staff to consider. The Angell Foundation Case Study and the Casalli Family Foundation Case Study both look at how a family is managing changing its grantmaking priorities. After you’ve discussed the case studies internally, tune-in to this 60 minute topical call recording in which Mary Phillips from GMA Foundations facilitates a discussion of the case studies.

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