Questions to ask when you meet a financial advisor

Most people will work with a financial advisor at some point in their lives. Yet few approach that decision with the same rigor applied to other important hires. A senior executive might be vetted through multiple rounds of interviews, but the advisor entrusted with managing family wealth is often chosen after only a handful of surface-level questions. 

That approach leaves too much to chance. Selecting an advisor isn’t about friendliness or convenience. It is about uncovering how they think, what they believe, and how they act under pressure. In short, it is about philosophy and process. 

The following questions reveal far more than the standard inquiries about performance or fees. 

Do you take a holistic view?

A common opening question is: “Tell me about your firm.” That may provide background, but it doesn’t illuminate the advisor’s approach. A more effective question is: “How do you connect investment management with tax planning and estate planning, so there are no gaps in the plan?” 

Many investors maintain solid investment portfolios yet lack integration with estate strategies or tax planning. True wealth management requires viewing the parts as a whole. 

What’s your philosophy when markets are volatile? 

Every advisor can recite an investment philosophy. The real measure is behavior when markets decline by 10%, 20%, or more. Do they rebalance? Do they seek opportunities in oversold assets? Do they use downturns for tax-efficient moves such as Roth conversions? Or do they simply advise patience while doing little behind the scenes? 

An advisor without a clear, decisive philosophy in difficult times is akin to a pilot flying without instruments—ill-equipped for turbulence when it matters most. 

Are you truly a fiduciary?

The label “fiduciary” is often used loosely. The more revealing inquiry is: “How do you ensure recommendations prioritize the client’s interests, especially when coordinating across taxes, investments, and estate planning?” 

One clarifying test is to ask: “Would this same strategy be recommended to a family member?” An unequivocal answer indicates alignment; hesitation suggests otherwise. 

How do you address conflicts of interest? 

Large institutions often populate portfolios with proprietary funds. That may benefit the firm more than the client. Independent advisors with access to the full investment universe are better positioned to avoid these conflicts. The ability to articulate how potential conflicts are eliminated or mitigated is essential. 

How do you measure success? 

Asking about “average return” produces little insight. Each client’s portfolio is unique. A more constructive approach is: “How is performance measured and reported, accounting for taxes, fees, and the level of risk taken?” 

Risk-adjusted returns, transparency in reporting, and stress-testing under different market and tax conditions offer a truer measure of success than a single percentage on a statement.

What assumptions drive your planning?

Financial plans are often built on overly generous assumptions: 8% annual returns, 2% inflation, or static healthcare costs. Such inputs can make any portfolio look sustainable on paper. The essential questions are: What assumptions were used? Were they stress-tested? Do they reflect realistic conditions? 

Plans built on optimism alone ignore the reality that markets, taxes, and healthcare costs rarely move in straight lines. 

Who is on your team?

Headcount is less important than capability. A small team that includes Certified Financial Planners (CFPs®) or a Chartered Financial Analyst (CFA) may provide more value than a large roster without specialized expertise. 

The makeup of the team matters: are portfolios overseen by qualified professionals, and does the structure allow multiple advisors to understand a client’s situation? Continuity and competence are the critical factors. 

How do you justify your fees? 

Fees are neither high nor low in isolation; they are meaningful only in relation to the value received. The key question is: “What services are provided for the fee, and how do those services produce outcomes that justify the cost?” 

The goal is not the lowest fee, but the greatest net benefit—after taxes, after fees, and after risks have been considered. 

Why should a client choose you? 

This final question strips away technicalities. The correct answer is not a list of products or features but a demonstration of commitment. An advisor should articulate a philosophy centered on putting client interests first, supported by experience with families in similar circumstances.

Closing Thoughts

Interviewing a financial advisor is less about collecting facts and more about uncovering philosophy, process, and integrity. The answers to these questions reveal whether an advisor has the temperament, discipline, and structure to guide wealth through both calm and turbulent times. 

Advisors who provide thoughtful responses demonstrate not only technical competence but also the alignment and judgment necessary to serve as a trusted partner in the long term. 

For a more detailed discussion of these questions — including examples and context from real conversations with families — watch the full video below.