High-net-worth planning breaks down when the advisor relationship is built on vague promises instead of auditable process. Your goal in the first 2–4 meetings is not “chemistry.” It’s to confirm three things:
- Claim: what they say they do
- Proof: what they can show (reports, policies, examples)
- Control: what makes it repeatable (governing documents, monitoring cadence, escalation rules)
That framing mirrors how U.S. disclosure is intended to work: Form CRS (Customer Relationship Summary) is designed to spell out services, fees, conflicts, and disciplinary history—and it prompts you to ask follow-ups.
If an advisor can’t answer with (1) a clear policy, (2) an example output, and (3) the document that makes it enforceable, treat the capability as missing.
1) Role clarity, incentives, and regulatory accountability
Before portfolios, establish what the advisor is legally doing for you in each account.
Questions that expose “gray-zone” advice
- “Are you acting as an investment adviser, a broker-dealer, or both for me—and in which accounts?”
- Ask for: Form CRS + engagement letter + account-by-account role summary.
- Red flag: “We do everything” with no capacity-by-account breakdown.
- “What is your legal obligation to me, and how do you operationalize it?”
- Ask for: written conflicts inventory + review/approval workflow.
- “Do you or your firm have any disciplinary history? If yes, what changed after it?”
- Ask for: written incident summary + remediation controls. (This is literally a “conversation starter” in Form CRS.)
Verify independently (live, in the meeting)
- U.S. brokers / firms: FINRA BrokerCheck
- U.K. firms: FCA Firm Checker
- Singapore reps: MAS Financial Institution Representatives Register
- Hong Kong licensees: SFC Register of Licensed Persons and Registered Institutions
Audit move: Ask the advisor to pull up the register themselves and walk you through what you’re seeing.
2) Fees: force “all-in” economics, not a headline rate
HNW clients get hit by layered costs: advisory fees, custody, fund expenses, incentive fees, placement fees, lending spreads, and manager-level costs.
Questions
- “Show me the complete schedule of what I pay—advisory, product, fund expenses, performance fees, custody, and third-party costs.”
- Ask for: a sample all-in fee report with methodology and a real client example (redacted).
- “How do you get paid in each product you recommend (including revenue sharing, distribution/placement economics, or lending spreads)?”
- Ask for: compensation disclosures + product-shelf governance.
Red flag: they talk only about the advisory fee and avoid embedded product economics.
3) Custody, cash controls, and fraud-prevention mechanics
For HNW, operational risk is not theoretical. You want hard controls that reduce theft/misappropriation risk.
Questions
- “Who has custody of my assets, and what is your policy on third-party custody and cash controls?”
- Ask for: custody summary, who can move cash, approvals matrix.
- Why: the SEC custody framework centers on using a qualified custodian and specific safeguards when an adviser has custody.
- “What’s your protocol for wire requests, changes in standing instructions, and ‘urgent’ exceptions?”
- Ask for: written cash-movement policy + client verification steps.
Red flag: advisor-controlled custody, or “we’ll just email you to confirm” with no formal process.
4) Whole-of-wealth planning: balance sheet, liabilities, and liquidity tiers
HNW risk often sits outside the brokerage account: business exposure, guarantees, concentrated equity, real estate leverage, deferred comp, litigation, family obligations.
Questions
- “Show me the balance-sheet view: assets, liabilities, contingent liabilities, and liquidity tiers.”
- Ask for: consolidated household balance sheet template.
- “How do you segment liquidity (immediate, 1-year, 3-year), and prevent capital calls/taxes from forcing selling?”
- “What is your concentration-risk process for a single stock, business, or geography?”
- Ask for: tax-aware unwind plan, hedging policy (if used), timeline and constraints.
Red flag: “We’ll diversify over time” without a schedule, decision rules, or tax plan.
5) Portfolio construction: prove there’s a repeatable system
You’re not buying “market commentary.” You’re buying implementation discipline that survives regime shifts and staff turnover.
Questions
- “How do you build portfolios—strategic allocation, factor exposures, manager selection, and rebalancing triggers?”
- Ask for: rebalancing rules, risk reporting.
- “Do you use leverage or derivatives (directly or through funds), and how do you manage margin/collateral call risk?”
- Ask for: collateral policy + stress tests + limits.
- “What reporting will I get quarterly: performance net of all fees, exposures, and look-through across entities?”
- Ask for: a sample report pack.
Red flag: only brokerage statements, no net-of-fee reporting, no look-through.
6) Alternatives due diligence: force governance, not prestige
Private equity, hedge funds, private credit, and direct real estate can fit HNW portfolios—but they introduce opacity, illiquidity, and fee complexity. Your questions should force a decision trail.
Questions that catch product-push behavior
- “Which goal bucket does this private fund support, and what problem does it solve versus public markets?”
- “Walk me through the full fee stack (management, performance, fund expenses, deal/monitoring fees, placement economics).”
- “What are the liquidity terms—lockups, gates, suspensions—and how do you model liquidity under stress?”
- “How is it valued, who validates marks, and what happens if marks are disputed?”
- “What’s our exit plan—secondaries, wind-down terms, and distribution timing assumptions?”
Red flag: “Everyone wealthy owns this” or “it’s standard 2-and-20” without net-of-fee modeling.
7) Tax and cross-border: separate “ideas” from defensible execution
Cross-border HNW planning fails in the gaps: advisor vs CPA vs attorney vs trustee. You need defined accountability and a reporting calendar.
Questions
- “Who is accountable for final tax positions—advisor, CPA, attorney, or trustee?”
- Ask for: RACI matrix (who’s Responsible, Accountable, Consulted, Informed).
- “How do you coordinate entity classification and reporting across jurisdictions?”
- Ask for: entity map + compliance calendar + who signs what.
- “Show me side-by-side after-tax modeling for competing strategies.”
- Ask for: assumptions + sensitivity analysis.
Red flag: “We collaborate” with no ownership of deliverables and deadlines.
8) Estate, governance, and continuity: documents + liquidity + operating system
HNW estate planning isn’t “get a trust.” It’s: structure + funding + liquidity + governance.
Questions
- “Where does liquidity come from to pay taxes, equalize heirs, or execute buy-sell obligations?”
- Ask for: liquidity-at-death model; insurance/credit plan if relevant.
- “How do you validate ownership, beneficiary designations, and trust funding match plan intent?”
- Ask for: annual reconciliation checklist.
- “What happens if you leave—who takes over, and what service standards apply?”
- Ask for: team coverage plan + escalation policy.
Red flag: no bench, no continuity plan, no annual reconciliation process.
9) Risk management beyond investments: the “protection gap” questions
HNW households can be overbuilt on investments and underbuilt on real-world risk: cyber, liability, property, travel, family security, reputational exposure.
Questions
- “Do we have a household risk register beyond investments, and do you review it annually?”
- “How do you evaluate insurance recommendations given commissions and surrender schedules?”
- “What cyber controls do you recommend beyond insurance, and who do you coordinate with?”
Red flag: insurance sold as a product, not managed as an exposure-mitigation plan.
10) Monitoring, decision speed, and the subtle edge of AI
At HNW scale, the problem isn’t “finding investments.” It’s seeing risk early, coordinating actions across accounts/entities, and documenting why decisions were made.
A useful question is blunt:
- “How do you monitor my holdings for material changes, and what triggers an action—not a meeting?”
- Ask for: monitoring cadence, alert thresholds, and examples of actions taken after new information.
This is where modern tools can matter—not as hype, but as workflow. For example, Michael Flatley describes pairing traditional wealth management work (planning, tax-aware portfolio management, reviews) with always-on monitoring and event categorization tools like LevelFields AI so clients aren’t relying on periodic check-ins alone.
The diligence angle: you’re not buying “AI.” You’re checking whether the advisor has a repeatable system for surfacing risks/opportunities and turning them into documented actions.
FAQs about What Questions to ask Financial Advisors
What questions should I ask my financial advisor?
You should ask questions that clarify strategy, incentives, and accountability, not just performance.
Strong questions include:
- How do you build portfolios, and why?
- How do you manage risk during market downturns?
- How are you compensated, and are there any conflicts?
- What decisions will you actively manage vs. review periodically?
- How will this plan change as my life or markets change?
The goal is to understand how decisions are made, not just what products are used.
How do I prepare for a financial advisor meeting?
Preparation makes the meeting productive.
Before the meeting:
- List your goals (retirement age, income needs, major purchases)
- Gather key documents (accounts, debts, insurance, estate docs)
- Know your approximate net worth and monthly spending
- Write down questions or concerns you want addressed
You don’t need perfect numbers—clarity about priorities matters more.
What are some good financial questions to ask?
Good financial questions focus on trade-offs and outcomes, not predictions.
Examples:
- What risks am I currently exposed to?
- What assumptions does this plan rely on?
- How do taxes affect my long-term results?
- What would cause you to change this strategy?
- How do you measure success beyond returns?
These questions reveal how thoughtful and adaptable the advice really is.
What are good questions to ask your advisor?
The best questions test fit and transparency.
Ask:
- Who is this strategy best suited for?
- What happens if markets perform worse than expected?
- How often will we review and adjust the plan?
- What decisions should I not make emotionally?
A good advisor welcomes these questions and answers them clearly.
What are good 5 questions to ask?
If you only ask five, ask these:
- What is my biggest financial risk right now?
- How are you paid, and what does that cost me annually?
- How do you adjust during market stress?
- What assumptions could break this plan?
- How will you help me stay disciplined?
These questions cut through surface-level advice quickly.
Is $500,000 enough to work with a financial advisor?
Yes—$500,000 is often enough to work with a financial advisor, depending on the firm.
Many advisors:
- Work with clients starting around $250,000–$500,000
- Offer tiered services or flat-fee planning
- Focus on complexity, not just account size
At this level, advice on taxes, asset allocation, and long-term planning can be more valuable than trying to manage everything alone.
