The Best Financial Advice Starts With Better Questions

Most of the people I work with have spent decades making good decisions.

They’ve run businesses, climbed the corporate ladder, invested consistently, and lived within their means even as their means expanded. While their paths may be different, they tend to share a common set of qualities: discipline, good instincts, patience, and deliberate decision-making.

Because of that success — because their finances are in such strong shape by the time they sit down with me — they assume working with a financial advisor is largely a technical exercise. Of course, they’re partially right in that assumption; much of my job is technical: reviewing investments, evaluating taxes and insurance, assessing estate planning strategies, building projections, and so on. But that’s only part of the picture (an important part, but a part nonetheless). 

To give genuinely useful advice, I need to understand something that financial statements alone can’t show: the person behind them. Two clients with identical balance sheets can make completely different decisions, because they don’t have the same objectives for or perspective on money.

I think of financial planning as a puzzle. The financial pieces are essential: assets, liabilities, income, expenses, tax exposure, time horizon, and any other personal factors. But they’re incomplete without the experiences that shaped how you think about money, the beliefs you formed early in life, the specific concerns on your mind, and the life you’re ultimately striving to live.

Consider two people with vastly different relationships with money. One grew up watching a parent lose everything and has never shaken the feeling that it could happen again — having more than enough, mathematically, doesn’t quell that fear. Another built everything themself through hard work and self-reliance, and asking them to delegate financial decisions may feel threatening to something deeper than money. Unless I understand what’s driving those responses, the technical recommendations I make, however sound, may never be implemented.

Before I spent my career in wealth management, I worked as a Deputy Sheriff in Contra Costa County. As you can imagine, the work was quite different, but one principle has carried over. The quality of what you learn depends almost entirely on the quality of the questions you ask. The right question, asked at the right moment, tells you what’s actually going on instead of what’s presented on the surface.

That principle applies here more than I expected when I made the transition. The questions I’ve come to rely on in client conversations aren’t complicated, but they tend to surface things that projections don’t:

• What does financial security mean to you?
• What would a successful retirement look like beyond the numbers?
• What financial decisions are causing the most uncertainty today?
• What experiences have molded your relationship with money?
• What are you hoping your wealth makes possible for your family?
• What does “enough” mean in your life?

What surprises me, even now, is how often these questions reveal that the real obstacle isn’t financial. Someone’s definition of security might have nothing to do with a portfolio balance and everything to do with a fear formed decades ago. Someone’s vision of a successful retirement might center on relationships instead of a lifestyle. 

That’s what makes financial planning a combination of technical expertise and a deep understanding of the individual sitting across the table. It recognizes that money decisions are really decisions about family, freedom, opportunity, purpose, security, and legacy.

I became a financial advisor because I wanted to be the person a client thinks of before they make an important decision — not because I have all the answers, but because I know which questions to ask first. 

If any of those questions resonate, I’d be glad to explore them with you. 

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