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Where silence isn't golden: Deena Chochinov on holding families together

Therapist and author on the dangers of not communicating, entitlement traps and how wealth can be a blessing and a burden

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When the rest of us were baking sourdough bread, planting vegetable gardens and creating permanent dents on the sofa, Deena Chochinov’s pandemic aspirations were loftier.

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“I wrote a book,” she says of her tome – HomeWork: How to be a Leader in the Boardroom and the Living Room – over the phone from Vancouver. “And I can tell you, it was absolute torture. It was the hardest thing I’ve ever done.”

Luckily, her day job involves more connection and communication than commas and cover mock-ups. For three decades, Chochinov has worked as a therapist, management consultant and Family Enterprise Advisor for people and organizations seeking meaningful change. In 2022, she joined KPMG Canada’s family office practice.

In an interview with Canadian Family Offices, she talks about what she has learned while advising wealthy families, and why familial silence is far from golden.

How did you get your start as a therapist, coach and counsellor to wealthy business families?

“I was raised in a family business. My mom and dad built a small but mighty chain of drugstores in the Prairies, so I spent every single dinner table conversation listening and learning about the ups and downs of running a business, and growing up in the stores. I stocked shelves, ran the cash register and learned customer service skills. So, it feels like full-circle for me.

Back in 2012, I completed the UBC Sauder Family Enterprise Advisor (FEA) program and was certified as a Family Enterprise Advisor, and I worked in this space on my own for a while. Happily, I joined KPMG’s Family Office practice in 2022, and I work with a super-talented multidisciplinary team of advisors who offer an integrated approach to our family clients. My focus area is family dynamics and governance.”

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Other than your family business background, why is this career a good fit for you?

“Well, I listen for a living. Ever since I can remember, I’ve been totally captivated by other people, how they live, what they think, how they feel. In my years of listening practice, as a clinical counsellor, an executive coach and an OD [organizational development] consultant, my job is really the same as my clients’ – and that is to pay 100 per cent attention to them.

Most people just don’t get enough of that, so I chose to do that for my life’s work.

And I’m committed to two foundational principles. The first is the concept of offering ‘therapeutic love’ to my clients, which essentially means having a deep respect and caring for their well-being, and a total acceptance of each person for who they are and what they’re experiencing. The second is seeing the world through a systemic lens or approach – treating every individual, team, organization, corporation or family as a dynamic, living system of interrelated parts that mutually affect one another.

So when I first heard about this relatively new field called ‘family enterprise advising’ I thought, ‘What a perfect umbrella under which I can bring together my skill set and these principles in one role!’ I can support the well-being of families, and address the systemic issues that might get in the way of their business success – by helping them develop good governance.”

What do you enjoy most about the work?

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“Pretty much everything. I enjoy the privilege of being allowed into these very private and intimate systems, and the opportunity to offer family members my full attention and my objective perspective, tools and frameworks to support their harmony and formal governance practices.

Also, I love discovering and amplifying the strengths within each family, uncovering their challenges, and how they can be addressed compassionately and practically. I want to support families to thrive, not just survive. Basically, it’s really all about great communication, the ability to manage differences of opinion, make effective decisions, and, finally, clarify everyone’s roles and responsibilities.

These governance tools can be everything from a code of conduct to policies on succession planning, dividends, education, employment, social media, conflict of interest and conflict management.”

What have you learned over the years working with wealthy families?

“Wealthy families are families first – always unique, endlessly interesting, and they move back and forth on the continuum of high to low functioning. This is normal. Like all families, they are complex and dynamic systems of individuals who have patterns of relating that are interdependent, complementary and necessary for carrying out their lives.

But here are some of the patterns I’ve gleaned from the families of wealth I’ve served over the years: wealth is a blessing and a burden, a responsibility and an entitlement, a secret to be kept and a public privilege to be shared. Wealthy families are trying to manage these polarities on a pretty constant basis.

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So I’ve been witness to amazing expressions of love, pride, unity and loyalty within wealthy families, and a true desire for continuity. They want their family enterprise legacy to endure from one generation to the next.

Deena Chochinov book

I also sometimes see family members having to manage high expectations from their elders, community and the public. That can cause pressure, obligation, even resentment around ‘shoulds’ – their educational paths, career pursuits, who to partner with, where to live, maintaining the family reputation at all costs, getting caught between their love and respect for the generations who founded the business and created the wealth, and their own need for individuation and independence. Rising generations work and live in sometimes very different ways than their parents and grandparents.”

What are some challenges that inter-generational business families are dealing with today and how do you help them work through them?

“Let’s start with entitlement traps. Families who have access to power and wealth can transmit messages to their children that they have the right to money and power by virtue of birth rather than achievement. To counter this, senior generations can raise responsible kids by instilling a respect for wealth and the effort required to earn it. And my colleagues in the family office and I help them do that.

It’s also important to remember that money-related trauma isn’t just reserved for those without resources. Anyone can be adversely affected by a lack of awareness, information and tools of financial literacy and responsibility. To address this challenge, we help family business owners and wealth inheritors develop competencies including resilience and self-regulation, boundary-setting, courage, collaboration, dealing with conflict and emotional intelligence, as well as the financial skills.”

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Before, you mentioned communication between you and your clients. How does communication between family members, or the lack of it, play into all of this?

“Silence in these family systems is not golden. Many high-net-worth business families, both famous and unknown, have been harmed by silence or the lack of clear communication about their wealth. The harm isn’t just in terms of the potential damage to the business’ continuity, but also to the family’s harmony and emotional wellbeing.

This lack of information or clarity can too often lead to depression, shame and just a host of negative coping behaviours. Most of my time is spent creating permission structures and safe containers for families to communicate, name generational differences – about wealth, business decisions, relationships, anything – and have meaningful conversations to reach some kind of understanding, or even to agree to disagree. I help them develop a common vocabulary, a healthy family language, and learn how to make effective decisions together.

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Silence can breed so much distrust. I’ve learned that even if people don’t like what they hear, it’s better for the family system’s overall mental health to be transparent and communicative. It’s the not knowing that can make people feel psychologically unsafe. Our work is to clarify and create enough of a shared family values narrative that everyone from all generations can support and take action on living those values.”

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I understand you have a background in change management. That must help you when working with families.

“Change is hard. The driving force behind every change is the explicit acknowledgement that the status quo will no longer do. Most social systems, families particularly, tend to have a natural resistance to change. They don’t want to abandon the familiar and accept ambiguity. Who does? I mean, I do this for a living and I’m resistant too!

I help families navigate through their natural resistance to change and understand the dimensions of the change they are considering, like the scope, the timing and the different responses they can take. We look at the four stages of committing to a change. So we want to help them go from awareness to acceptance to adoption to advocacy.”

What are some unexpected emotions that wealth can bring up for some families?

“It’s complex. And I think a lot of people in wealthy family situations can have experiences that are contrary to the general view that their wealth is a huge gift that brings fulfillment.

Some of the questions my clients ask are: How do I navigate being a steward of family wealth and find my own individual purpose? What are my kids’ motivations to find and do meaningful work? How can I tell if someone loves me for myself, or is it just for my money? How do I manage relationships without hiding because I feel shame for my privilege? How can I make an impact in my world by using my wealth productively? I hear stories related to each of those questions from family members and their succeeding generations often.

I’m going to use a word that I don’t normally use, but it does feel right in this context. It feels like a ‘sacred’ trust that I have been given to participate in these family members’ lives. And, you know, families are very powerful systems, and I’m really committed to their success.”

Responses have been lightly edited for clarity and length.

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