Interviewing a Financial Advisor? Read This Before You Decide

Choosing a financial advisor is an important one, no doubt. It is one that affects your investments, your taxes, your family, and often your legacy. 

Most investors focus on investment returns and market performance first. That is understandable. But performance alone rarely tells you how decisions are made, how risks are managed, or how your broader financial life is coordinated.

If you are exploring advisors, here are the questions you should be asking. These are the conversations that separate a pitch from a partnership.

1. Have you worked with someone in my situation before?

Experience should be relevant, not generic.

If you hold concentrated stock, ask how they approach low-basis diversification. If you are a business owner, ask how they prepare clients for liquidity events. If retirement is approaching, ask how they design sustainable income plans that adapt to changing markets.

The goal is not to hear that they “work with everyone.” The goal is to understand whether they have navigated complexity similar to yours.

2. What would you recommend if you were in my position?

This question reveals how an advisor thinks.

Do they immediately move to a product? Or do they begin by outlining tradeoffs, tax implications, and long-term consequences?

Strong advisors explain reasoning. They articulate a framework. They walk through options and consequences before prescribing action.

You are not hiring a transaction. You are hiring judgment.

3. How do you build and update a financial plan?

Process matters.

Ask how information is gathered. Do they review tax returns? Do they model multiple scenarios? How do they stress test assumptions? How often is the plan revisited?

A disciplined, repeatable process signals professionalism. Vague answers suggest improvisation.

4. How do you incorporate taxes into investment decisions?

This question is often overlooked and deeply important.

Do they actively monitor losses? Do they coordinate Roth conversions, charitable strategies, and liquidity events? Do they evaluate portfolios based on after-tax outcomes?

Performance before taxes is a projection. Performance after taxes is your reality.

5. How are you compensated?

Transparency should be simple.

Ask for a clear explanation of advisory fees, underlying investment expenses, and any other compensation. Ask how their structure aligns with your long-term success.

Alignment builds trust. Complexity without explanation erodes it.

6. What does communication look like?

Understand what the relationship feels like after the onboarding process.

How often will you meet? What happens during periods of volatility? Who is on the team? How proactive are they?

Clarity around cadence and expectations prevents frustration later.

7. What infrastructure supports you?

Wealth management is not just about one individual.

Ask about the broader team, investment committees, operational systems, and succession planning. Your advisor should have depth behind them. Your financial life deserves durability.

8. What makes your firm different?

Listen carefully.

You are evaluating philosophy, structure, and discipline. You are listening for a coherent approach to planning and portfolio construction. You are assessing whether their model feels thoughtful and intentional.

At the end of these conversations, you should feel three things:

Clarity about how decisions are made.

Confidence in the structure supporting those decisions.

Alignment between your goals and their incentives.

Hiring a financial advisor should simplify your financial life, not complicate it. Ask meaningful questions. Expect thoughtful answers.

The right relationship will bring organization to complexity, discipline to investment decisions, and confidence to the path ahead.