Ask the questions that reveal whether an advisor is right for you.
Use these questions to understand the advisor's experience, recommendations, fees, conflicts, and approach to working with your CPA or attorney. You do not need to ask every question. Choose the ones that matter most to your situation.
Use the questions to get clear answers.
A strong advisor should welcome direct questions. Pay attention to whether the answer is specific to your situation and consistent with the documents you receive. If an explanation stays vague, ask: “Can you show me where that appears in writing?”
Write down the decision you are trying to make, the deadline that is real, the professionals already involved, and what you do not want to happen. That context makes every answer more useful.
Start with role and fit
Titles can sound similar while legal duties, licenses, and services differ. Begin by making the advisor describe the relationship in plain language.
Ask What role will you be acting in for me, and when are you required to act as a fiduciary?
Why ask it
An advisor may operate under different standards in different parts of a relationship. You want to understand the duty that applies to the specific service you are considering.
Listen for
A direct answer that names the person, firm, service, capacity, and governing agreement, including when another role or standard may apply.
Watch for
A title offered as proof, an absolute promise without context, or reluctance to put the role and scope in writing.
Ask What makes my situation a strong fit for your practice, and what might make it a poor fit?
Why ask it
A precise “not a fit” is often more valuable than a sales-oriented yes. The answer should connect your event, timing, assets, state, and service needs to the practice.
Listen for
Specific client situations the firm handles well, minimums and limitations, and a candid description of cases they refer elsewhere.
Watch for
“We work with everyone,” vague claims of specialization, or a pitch that ignores the financial event you actually need help with.
Ask Who will actually work with me after I become a client?
Why ask it
The person leading the first meeting may not be the person doing the planning, trading, service, or ongoing communication.
Listen for
Names and roles for the lead advisor, planning team, service contacts, specialists, and backup coverage, along with the access you can expect to each.
Watch for
No clear owner, frequent handoffs, or promises of senior attention that are not reflected in the service model.
Test relevant experience
General wealth-management experience is not the same as experience with a business sale, concentrated stock, inheritance, settlement, or tax deadline.
Ask How often have you advised people through situations like mine?
Why ask it
Frequency does not guarantee quality, but it reveals whether your situation is routine for the practice or a one-off learning experience.
Listen for
A useful range, the stages where the advisor typically becomes involved, recurring issues, and what made past cases difficult without exposing client identities.
Watch for
One dramatic success story, guarantees based on past outcomes, or examples that do not actually resemble your timing and decision.
Ask Where should my CPA or attorney be involved before you make a recommendation?
Why ask it
Major financial events cross investment, tax, estate, legal, insurance, and business boundaries. A good process identifies who owns which decision.
Listen for
Clear handoffs, shared assumptions, permission-based communication, and a plan for resolving disagreement among professionals.
Watch for
The advisor dismisses your existing team, gives definitive legal or tax answers outside the engagement, or expects you to coordinate everything alone.
Ask What part of my situation is outside your expertise?
Why ask it
Professional boundaries are a sign of judgment. No one person should claim to cover every technical issue raised by a complex transition.
Listen for
Named limits and a credible process for involving specialists without obscuring who pays them or how they are selected.
Watch for
No acknowledged limits, improvised answers to technical questions, or referrals presented without explaining compensation or relationships.
Get clear answers about fees and conflicts
Do not stop at a label such as “fee-only” or “fee-based.” Ask for the dollars, services, incentives, and changes that would apply to your relationship.
Ask What are all the ways you and your firm could be paid from this relationship?
Why ask it
Advisory fees may sit alongside planning fees, commissions, product compensation, referral payments, cash-sweep economics, or payments to affiliated businesses.
Listen for
A complete list in plain language, tied to written disclosures, including compensation that does not appear as a separate line on your statement.
Watch for
Only quoting a percentage, avoiding indirect compensation, or implying that a disclosed conflict is no longer a conflict.
Ask Using a realistic example, what would I pay during the first year and a normal later year?
Why ask it
Percentages are hard to compare. A dollar example exposes tiers, one-time planning work, product costs, custodian charges, and overlapping fees.
Listen for
A written estimate with assumptions, what is included, what is separate, and how the amount changes if assets or services change.
Watch for
No willingness to estimate, comparisons that omit product or fund expenses, or a first-year discount without clarity about later pricing.
Ask Does anyone receive a referral fee or other benefit if I become a client or use a recommended solution?
Why ask it
Introductions and recommendations can create incentives even when the underlying service may still be useful.
Listen for
Who pays whom, how much or how it is calculated, when it is paid, what alternatives exist, and where the arrangement is disclosed.
Watch for
“It costs you nothing” used to avoid explaining the incentive, or a disclosure delivered only after you are asked to sign.
Ask Which recommendations would pay your firm more than reasonable alternatives?
Why ask it
This converts an abstract conflict discussion into the actual choices you may face.
Listen for
Specific examples, the firm’s controls, and how the advisor documents why a higher-paying option is still appropriate.
Watch for
Claims that no conflicts exist or that firm approval automatically makes every option equally favorable to you.
Understand how the advisor makes recommendations
A good recommendation is a process, not a product. Learn what the advisor needs to know, which alternatives are considered, and how uncertainty is handled.
Ask What would the first 30, 60, and 90 days look like?
Why ask it
The answer reveals whether the firm begins with discovery and planning or rushes toward asset transfer and implementation.
Listen for
A sequence for data gathering, goal and risk clarification, tax and cash-flow review, team coordination, recommendations, and your approval before action.
Watch for
A transfer-first process, urgency without a real deadline, or a recommendation before the advisor understands taxes, liquidity, liabilities, and existing holdings.
Ask How do you compare keeping my current approach, waiting, or making only a partial change?
Why ask it
The best decision may be incremental or may be to do nothing yet. An advisor should be able to evaluate those paths without treating them as objections.
Listen for
Explicit alternatives, tradeoffs, decision deadlines, reversible steps, and conditions that would change the recommendation.
Watch for
Only one path, false urgency, or treating every uninvested dollar as a problem that must be solved immediately.
Ask How will taxes, cash needs, concentration risk, and downside scenarios be reflected in the plan?
Why ask it
A portfolio proposal can look efficient while missing the reason the money exists, near-term obligations, or the cost of a poorly timed decision.
Listen for
Assumptions documented in dollars and dates, scenario ranges, stress tests, tax coordination, and a reserve policy before long-term allocation.
Watch for
Return projections without planning assumptions, tax claims without CPA coordination, or risk described only through a questionnaire score.
Clarify service, custody, and control
The ongoing experience matters as much as the initial plan. Make sure you understand access, decision authority, asset custody, privacy, and how to leave.
Ask What service should I expect during a normal year and during a major decision?
Why ask it
“Ongoing advice” can mean anything from an annual review to a coordinated planning relationship.
Listen for
Meeting cadence, planning deliverables, response times, proactive topics, who initiates contact, and what triggers an extra review.
Watch for
Service described only as availability, no defined deliverables, or an experience dependent on one person always being present.
Ask Where would my assets be held, and what authority would you have over them?
Why ask it
You should know the qualified custodian, how statements arrive, what discretion the advisor receives, and which actions require your authorization.
Listen for
A recognizable independent custodian, direct statements, clear discretionary limits, multi-factor security, and a process for verifying money-movement requests.
Watch for
Pressure to send funds to an individual or unfamiliar account, shared credentials, or instructions that bypass the custodian’s normal safeguards.
Ask What happens if I decide to leave?
Why ask it
Exit terms expose lockups, termination fees, surrender charges, tax consequences, portability issues, and the practical ownership of your records.
Listen for
A clear termination process, fees and timing, how assets and documents transfer, and which products or services may not move cleanly.
Watch for
Penalties or illiquidity minimized as technicalities, unclear ownership of records, or resistance to discussing a future transition.
A focused 45-minute first meeting
Share this agenda at the beginning so the conversation does not become a generic presentation.
- 5 minYour decision
Explain what changed, the real deadline, and what a useful first conversation should accomplish.
- 10 minFit and relevant experience
Ask how your situation fits the practice and where the advisor would involve other professionals.
- 10 minRole, fees, and conflicts
Clarify capacity, fiduciary duty, every source of compensation, and referral relationships.
- 10 minProcess and alternatives
Learn what the first 90 days would include and how waiting or partial action would be evaluated.
- 10 minService and next step
Confirm who serves you, where assets would be held, what documents to review, and whether another meeting makes sense.
Compare what you learned from each advisor
Do not choose based on personality alone. After each meeting, write one sentence about each topic while the discussion is fresh.
Before you make the final choice
Should I interview more than one advisor?
Often, yes. Two or three conversations can make differences in scope, communication, fees, and process much easier to see. Use the same core questions so you are comparing the same issues.
Is saying “I am a fiduciary” enough?
No single phrase replaces understanding the person, firm, service, legal capacity, agreement, compensation, and conflicts that apply to your relationship. Ask when the duty applies and where it is documented.
What documents should I request before signing?
Depending on the relationship, relevant documents may include Form ADV brochures, Form CRS, fee schedules, the client agreement, privacy notice, product or offering documents, referral disclosures, and a written scope of services. Read the documents that actually govern your engagement.