AUTHOR:
James E. Ryan
REVIEWER:
Jillian Wagenheim, Founder & Principal, Sertus Consulting
Farrah Azizi, Private Philanthropy Advisor, Give Great Group
BOOK LINK:
REVIEW:
Wait, What? And Life’s Other Essential Questions is an adaptation of a viral commencement speech by James E. Ryan that encourages readers to adopt what the author calls 5 essential questions for richer, more meaningful experiences. They are: ‘Wait, What?’, ‘I wonder…?’, ‘Couldn’t we at least…?’, ‘How can I help?’, and ‘What truly matters?’.
While an initially simple concept, this book is rich with complexities in each concept. One of which is the idea of asking the ‘right’ questions – an idea which can hold many meanings for family advisors. A ‘right’ question can refer to the timing or to asking clumsy or leading questions. It can also refer to asking questions that keep everyone on task; or as the 21/64 team often says, ‘don’t unpack more than what you can put back together’. Similarly, a ‘right’ question for working with families can include ensuring that the facilitator is fully present, not questioning out of our own fears, and asking questions that are in service of our purpose. One colleague referred to this, while discussing the book, as ‘probing the edges, not poking the beast’.
The author also brings up the idea of being both the provocateur and the peacemaker – roles that family philanthropy advisors must adeptly navigate within each client engagement. Utilizing the ‘couldn’t we at least…” prompt can serve both purposes and it is this dance of pushing and calming that often best demonstrates the value of outside advisors. Often philanthropy advisors must fulfill a role that a family member can’t or chooses not to because of various family dynamics and patterns. We do this by reading the room – interpreting which individual is engaging, where everyone is standing, and what micro aggressions are appearing. In contrast to the idea above, this doesn’t necessarily have to be about asking a bold, or a ‘right’ question. Often times, it is simply tolerating the discomfort and giving everyone a moment to breathe.
This book is a very quick read and can serve as a pre-read to send to families, particularly when there are multiple or conflicting voices or generations. Alternatively, the briefer six-minute video can be shared in service of inviting families to think objectively and perhaps differently about their own families. The book serves as an open invitation to a family member to join you as a thought partner and provides family philanthropy advisors with a refreshed tool belt of questions that challenge our own ‘wash, rinse, repeat’ cycles.
