You've found some potential advisors and scheduled your first meeting. Congratulations—that's a big step! But what should you actually ask? Here are ten questions that will help you evaluate fit and understand exactly what you're signing up for.

Most advisors offer a free initial consultation. Use it to interview them—you're hiring someone to manage your financial life. Meet with multiple advisors before deciding.

Questions About Compensation

  1. "How exactly do you get paid, and by whom?"

    Listen for clarity and completeness. A trustworthy advisor will explain their fee structure without hesitation. Watch for vague answers or reluctance to discuss specific numbers. Follow up with: "Are there any other ways you receive compensation that I should know about?"

  2. "What would I pay in total fees in my first year?"

    Get a specific dollar amount, not just a percentage. If they manage $500,000 at 1%, that's $5,000 per year. Make sure you understand what's included: Does this cover financial planning, or just investment management?

  3. "Are you a fiduciary, and what does that mean in practice?"

    A fiduciary is legally required to act in your best interest. But dig deeper: Are they always a fiduciary, or only in certain situations? Some advisors are fiduciaries for investment advice but not insurance sales.

Questions About Their Practice

  1. "What's your typical client like?"

    You want an advisor who regularly works with people in your situation. If you're retiring with $800,000, an advisor who typically works with $5M+ clients may not be the best fit—and vice versa. Ask about age range, career stage, and financial goals of their typical client.

  2. "How often will we communicate, and in what format?"

    Expectations should match. Some clients want quarterly check-ins; others prefer to be left alone. Clarify: Will you have a dedicated advisor or work with a team? How quickly do they respond to questions?

  3. "What services are included vs. extra?"

    Understand the scope. Does their fee include tax planning? Estate planning referrals? Insurance review? Some advisors offer comprehensive services; others focus strictly on investments.

Questions About Investment Approach

  1. "What's your investment philosophy in plain English?"

    You should be able to understand their approach without a finance degree. Are they active traders or long-term investors? Do they use individual stocks, mutual funds, or ETFs? What role does diversification play? A good advisor can explain their strategy clearly.

  2. "How did your clients' portfolios perform in 2022?"

    2022 was a tough year for markets. This question reveals how they handle downturns and communicate during difficult times. Listen for honesty about losses and how they helped clients stay the course (or not).

Questions About Compatibility

  1. "What would make me a bad fit for your practice?"

    This question reveals self-awareness and honesty. Every advisor has limitations. Maybe they don't work well with clients who want daily updates, or they're not experts in stock options. A thoughtful answer shows they prioritize fit over making a sale.

  2. "Can you provide references from clients similar to me?"

    A confident advisor should be able to connect you with existing clients (with their permission, of course). If they can't or won't, that's worth noting.

Before You Leave: Logistics

Make sure you understand:

  • Minimum investment requirements: Do you qualify?
  • How to get started: What paperwork and process?
  • How to end the relationship: What if you want to leave?
  • Custodian: Where will your money actually be held? (Should be a major institution like Schwab, Fidelity, etc.)

Red Flags to Watch For

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Be cautious if the advisor:

  • Guarantees specific returns (no one can do this honestly)
  • Is evasive about fees or compensation
  • Pressures you to decide immediately
  • Doesn't ask questions about your situation
  • Can't clearly explain their investment strategy
  • Dismisses your concerns or questions
  • Focuses only on past performance (past results don't guarantee future returns)

Green Flags to Look For

Good signs include an advisor who:

  • Asks thoughtful questions about your goals and concerns
  • Explains fees clearly without being asked
  • Acknowledges what they don't know or don't do
  • Discusses both potential gains AND risks
  • Seems genuinely interested in whether they're a good fit
  • Has a clear, understandable investment philosophy
  • Provides written documentation of fees and services

After the Meeting

Take time to reflect:

  • Did you understand everything they explained?
  • Did you feel comfortable asking questions?
  • Did they listen as much as they talked?
  • Can you afford their fees comfortably?
  • Do their services match what you actually need?

It's okay to meet with multiple advisors. In fact, it's encouraged. The right advisor relationship can last decades—take the time to find someone you trust and can work with long-term.

Find advisors to interview