More Than Just Money: Navigating Life’s Big Moments with Expert Advice 

By Sarah Walker

For many, financial advice and investment planning still start with spreadsheets and end with rates of return. But for a growing number of people, it looks entirely different. It’s relational. Long-term. Personal and relationship driven, and often, transformative.

These are the stories of five CIBC Wood Gundy Investment Advisors, who are thoughtfully transforming the advisory experience, one conversation, intervention, and family at a time.

The Power of Preparation

Financial advice and investment planning isn’t just about performance. It’s about foresight and making thoughtful decisions that protect wealth across generations. By anticipating life’s turning points, families can preserve their legacy and act with confidence when the unexpected happens.

When Karen Shea, Senior Wealth Advisor, hosted a cottage succession planning webinar during COVID-19, she invited her clients and their family members who might one day inherit these cherished properties. Among the attendees was a couple whose family had owned their cottage for three generations.

During that webinar, they learned something that would change everything: renovation invoices — new roofs, repairs, and upgrades — could be used to increase the property’s value for tax purposes. This would help significantly reduce future tax burden when transferring ownership to the next generation.

“A lot of people aren’t aware of this,” Karen explains. The couple spent months gathering bills, invoices, and documentation, working with their mother to compile everything their family had invested in the cottage over the years.

Armed with this knowledge, they transferred the cottage to the fourth generation while everyone was still alive to enjoy it together. The family was able to take proactive steps before the parents’ estate was settled, resulting in meaningful tax savings and greater financial flexibility.

“It was an eye-opener,” Karen reflects. “They were ecstatic that they could use all these different renovations they’d done.”

This is the power of thoughtful financial advice and investment planning. It’s about going beyond managing money to create new possibilities for families and their legacies.

Karen has built her 28-year practice around a philosophy of education-first planning. She’s seen too many clients arrive with investment portfolios they don’t understand, some having worked with advisors who never bothered explaining their strategies.

“One client told me their previous advisor said, ‘Don’t worry … I know better than you. This is a good investment,’” Karen recalls. “She had no idea what she was investing in.”

Karen’s approach begins differently. She uses discovery tools to understand her clients’ values, priorities, and dreams, then builds investment plans that work backward from their goals. She’s known for using simple analogies that make complex concepts easier to understand. For example, she compares a TFSA to a house with different rooms for different types of investments. When discussing retirement savings, she compares an RRSP to a greenhouse: “You plant the seeds early and tend to them over time. The goal isn’t just to have a pile of vegetables at the end; it’s to cultivate a sustainable garden that can feed you for the rest of your life.”

This commitment to education led Karen to create a series of learning resources, like workshops covering everything from understanding borrowing costs to building credit and basic budgeting.

“I realize there’s a need for women to learn more about financial literacy,” she says. “It’s never too late. The best time to start investing is always yesterday. But starting is the hardest part.”

Life Happens Beyond Portfolios

Advisors often find their work extends beyond numbers. Sometimes, it’s about helping clients navigate through life’s unexpected turns.

When Leora Sherwood’s phone rang one afternoon, the voice on the other end was barely holding it together. It was one of her clients, and she’d just signed a lease for a new apartment that she no longer wanted to move into.

“I’m frozen,” the woman said. “I can’t do this, and now I don’t know how to get out of it.”

Within hours, Leora — a Senior Wealth Advisor with over 30 years at CIBC — provided timely assistance to her client during a difficult situation, resulting in significant cost savings for the family.

“I didn’t do anything extraordinary,” Leora reflects. “It was just something I could do to help her out.”

This intervention had a profound impact by preserving a family’s financial foundation during a crisis, ensuring resources would benefit the client as well as her children and grandchildren.

“It’s a powerful reminder that for many clients, financial peace of mind isn’t just about their own portfolio,” Leora explains. “It’s about knowing they have the resources and the right team to protect their children when life inevitably happens.”

This holistic philosophy shapes how Leora approaches all planning. During sessions, she regularly uncovers missing buy-sell agreements, outdated wills, and unspoken family fears. She’s worked with clients who struggled to accept inheritances because of guilt, and others who gave away assets too early only to find themselves unprepared later.

“The reality is that money conversations are rarely just about money,” she notes. “They’re about life, family dynamics, fears, and coping with challenges no one sees coming.”

Leora draws from her decade of banking experience to help clients navigate everything from mortgages to credit cards.

“I can leverage that experience to assist my clients,” she says. “My own experience can help them navigate situations because I’ve been through similar challenges myself.”

Comprehensive support requires genuine partnership. Leora’s clients know they can call about anything financial, trusting she’ll either help directly or connect them with someone who can.

“We’re sitting on the same side of the table,” she says. “If it’s beneficial for the client, it will be beneficial to me.”

Building Bridges Between Generations

The call came from a 26-year-old woman whose parents recently sold their business. They’d set aside money for their adult children. But within minutes of the meeting starting, Marie-France Delisle, Portfolio Manager, watched the young woman hand over control of her financial future.

“I don’t understand much [about money], so I’ll have my boyfriend on the line,” the woman said.

The woman’s boyfriend took over — asking questions, making decisions, and speaking on her behalf. The irony was that she had the stronger earning potential.

Marie-France encouraged the woman to take ownership of her own financial future. She offered the same kind of honest, caring guidance she would give her own family member.

Today, that young woman works directly with Marie-France — part of an all-women team that views financial advice as life planning.

“We tend to do as we would do for our own children,” Marie-France explains.

This philosophy has guided her work with families for decades, including another client she’s worked with for over 25 years. One of Marie-France’s longtime clients, a business owner she’s advised for over two decades, came to her when most of his assets were tied up in his company. Over time, she helped him move funds into personal accounts, navigate succession planning, and sell his business. Now, they’re planning how to use his wealth to support the next generation.

This multigenerational lens appears in the subtleties, too. Marie-France’s team regularly helps couples address unequal wealth accumulation when partners have uneven earnings.

“When partners contribute unequal incomes but split expenses evenly, it creates imbalance,” she explains. “Over time, one may accumulate a million in investments while the other has just $100,000. The gap compounds quickly.”

Family Legacy in Practice

Sandra and Rachel Dyck embody the philosophy of family legacy in their own practice. As a mother-daughter advisory team at CIBC Wood Gundy, they offer clients living proof that multigenerational planning works.

“Our clients see how successful working as a team can be,” Sandra explains. “They know we have a succession plan. Our clients know Rachel will one day take over. People want that same security for their own families.”

That same focus and care shape the way Sandra and Rachel support their clients. Their long-term perspective guided one client relationship in particular — a woman who was deeply philanthropic and intentional about the legacy she wanted to leave. Without children of her own, she hoped to balance meaningful gifts to loved ones with significant support for the charities closest to her heart.

Sandra and Rachel listened closely to her priorities and aligned her investment strategy with her estate plan, building the resources to fulfill her wishes reliably and with minimal burden on her family.

When it became clear her chosen executors might struggle to manage the complexity of her estate. Sandra and Rachel worked with her to establish contingency measures and bring in CIBC Trust as a corporate executor. When she passed, the transition was seamless: CIBC Trust administered the estate with precision, so her chosen beneficiaries were cared for exactly as she intended.

“It’s a reminder that no two clients are alike,” Sandra reflects. “Estate planning often involves navigating family dynamics, charitable goals, and long-term financial considerations. By partnering with legal and tax professionals, we make sure our clients’ wishes are carried out and that they — and their families — have lasting peace of mind.”

The Heart of Wealth Management

In an industry that’s often criticized for being transactional, these advisors demonstrate what’s possible when relationships and comprehensive planning come first.

They listen without judgment. They educate without condescension. They ask the right questions — and wait for real answers. They understand that money decisions carry significant psychological weight, shaped by family history, values, responsibilities, and aspirations.

And while markets rise and fall, the trust they build with families stays constant.

Whether it’s helping a young woman reclaim her financial voice, untangling a client from a costly lease, showing a family how to preserve their cottage for the fourth generation, or walking families through complex succession planning, these advisors prove that modern wealth management is about much more than growing portfolios.

As Marie-France puts it: “We feel like we do good for our clients. We help them achieve their dreams, or at least reach their goals. They’re why I love coming into work.”

Connect with a CIBC Private Wealth Advisor to explore your ambitions and financial goals. We’ll help match you with an advisor who can offer personalized guidance to support your unique wealth journey — for you and for the generations who will continue your legacy.