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Ten great reads for family-office advisors

New and classic books recommended by and for FO professionals—some light, some not-so-light

Looking for reading material for the weeks ahead? Whether you’re seeking professional development or just a mental change of pace, here are 10 engaging books that might fill the bill.

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At the top of everyone’s list this year is Wealth 3.0: The Future of Family Wealth Advising by James Grubman, Dennis T. Jaffe and Kristin Keffeler (see our own interview with the lead author.) It covers the evolution of family advising over the past quarter-century and proposes that we’ve entered a new era of professionalism that puts family first.

“I like the positive focus on psychology and the ability to bring the family together and to advance our family capabilities and our value,” says Wendy Sage-Hayward, a senior consultant with the Family Business Consulting Group and academic director for Family Enterprise Canada. She is based in Vancouver.

Patrick O’Connor, founder and CEO of Blackwood Family Enterprise Services in Winnipeg, says this book dispels those historical references that predict wealthy families are bound to fail by the third generation. “It’s providing a lot of hope to families,” he says.

When Our Family Office Inc. in Toronto hires a new person, the book “will be mandatory reading for them because it looks at what the future of family advising will really look like,” says Tim Cestnick, CEO and co-founder.

Rounding out our Top 10 list for this year are the following nine selections:

Richard Leon, partner and portfolio manager, Richter Family Office, Montreal

Manias, Panics, and Crashes: A History of Financial Crises by Robert Z. Aliber, Charles P. Kindleberger and Robert N. McCauley: Now in its eighth edition, this classic is “one of my favourites that I read many years ago. It’s very readable, informative and always relevant,” says Leon. Its latest reissue includes a new section on cryptocurrency and updated material on property bubbles in China, the U.S. and Japan.

Richa Arora technology family office KPMG

Richa Arora, partner and practice leader, Family Enterprise Advisory, KPMG Family Office, Toronto

Family Business on the Couch: A Psychological Perspective by Manfred F.R. Kets de Vries, Randel S. Carlock and Elizabeth Florent-Treacy: This book offers a new perspective on how family firms work together through family dynamics. “It highlights the importance of taking a thoughtful and methodical/psychological perspective in addressing some unique business and relationship dynamics many family businesses face,” says Arora. “It spotlights cases from businesses over the world and offers a deep understanding of various psychodynamic and family systematic frameworks.”

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Kathy Bright, consultant with Trella Advisory Group, Vancouver

Willing Wisdom: 7 Questions Successful Families Ask by Thomas William Deans: Deans’ Willing Wisdom offers a process to help families start the discussion about estate planning. “I saw him at a speaking engagement, speaking about best practices. The idea of having regular conversations to normalize that type of conversation is important,” says Bright.

Tim Cestnick, CEO and co-founder, Our Family Office Inc., Toronto

Freedom From Wealth: The Experience and Strategies to Help Protect and Grow Private Wealth by Charles Lowenhaupt and Don Trone: “It’s a really good book for wealth holders who struggle with finding happiness despite having a lot of money,” Cestnick says. “He gets into things like best practices and finding the purpose for your wealth: It’s a good book for affluent families.”

family business family office

Peter Jaskiewicz, director and founder, Family Enterprise Legacy Institute, Telfer School of Management, University of Ottawa

Surrounded by Idiots: The Four Types of Human Behavior and How to Effectively Communicate With Each in Business (And in Life) by Thomas Erikson: Jaskiewicz (who, with Sabine B. Rau, wrote the bestselling Enabling Next Generation Legacies) says this book “has been around for a while, and advisors really appreciate it. What is really useful is the strategies for dealing with difficult people. Understanding how people might be very different is vital in order to succeed.”

Photo of Wendy Sage-Hayward

Wendy Sage-Hayward, senior consultant, Family Business Consulting Group and academic director, Family Enterprise Canada, Vancouver

Language and the Pursuit of Happiness: A New Foundation for Designing Your Life, Your Relationships and Your Results by Chalmers Brothers: Author Brothers, in his books and an intriguing talk for TEDxBocaRaton, espouses the view that language doesn’t just communicate ideas, it’s also a powerful tool that we use to create our world, and harnessing it is key to success and well-being. “It’s really about understanding human communication at a deeper level,” Sage-Hayward says.

chris reichert family office advisor

Chris Reichert, president, Reichert Family Enterprise Advisors, Winnipeg

Continuity Model Generation: Integrating Wealth, Strategy, Talent, and Governance Plans by Justin B. Craig: This book integrates four types of planning to help family business leaders ensure the continuity of wealth over generations. “The section about the ‘big tent approach’ was eye-opening for me,” Reichert says. “It uses considerate language while demonstrating the multitude of ways in which family members can contribute to the family enterprise—be ‘in the tent’—without joining management. It also offers pathways for family members to contribute in meaningful ways that don’t involve working in the business. An excellent read!”

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Patrick O’Connor, founder and CEO, Blackwood Family Enterprise Services, Winnipeg

The Happy Inheritor: How Successful Families Prepare Heirs and Transition Wealth by Thomas William Deans: This book is “a good Christmassy read in some ways,” O’Connor says. “What it talks about are kind of taboo subjects; it talks about families where personality disorders are at play and how prevalent things like narcissism are out there in society. He’s talking about these challenges that all families face and how sometimes those things can prevent families from having the conversations that are needed around wealth transition.”

Photo of Cindy David

Cindy David, president and estate planning advisor, Cindy David Financial Group Ltd., Vancouver

Estate Planning Through Family Meetings (Without Breaking Up the Family) by Lynne Butler: “If someone is thinking about business succession or estate planning, a great book,” David says. “I have given this book away a lot. It’s such an easy read, and it just really drives the points home: Don’t keep this a secret and don’t wait forever to do your estate planning.”

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