Hiring a Financial Professional: The Questions to Ask Before You Sign

Hiring an accountant, bookkeeper, fractional CFO, financial planner, or wealth manager is easier when you compare the same things across every conversation. Use this guide as a first-call worksheet: ask the questions that apply to your situation, write down the answers, and compare scope, experience, pricing structure, communication, and fit before you sign.

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Financial advisors and wealth managers

• Are you acting as a fiduciary at all times when working with me? Are there situations where you are not?
• How are you compensated: flat fee, hourly, subscription, assets under management, commissions, or a combination?
• What asset or income minimums apply, and are there separate planning fees?
• How often do you work with clients who have RSUs, stock options, ESPP shares, executive compensation, or a concentrated stock position?
• How do you coordinate investment planning with tax planning, and do you work directly with my CPA or tax attorney when needed?
• How would you describe your investment philosophy and approach to diversification and risk?
• What conflicts of interest should I understand before hiring you?
• Where are client assets custodied, and who has authority to move money?
• Who will actually service my account after I become a client?
• How often will we meet, what happens between meetings, and how quickly should I expect responses?

Accountants and CPAs

• Which services are included in the engagement: tax preparation, tax planning, bookkeeping, payroll, entity work, notices, or advisory?
• Do you primarily prepare returns, or do you also provide proactive tax planning during the year?
• How often do you work with clients in my industry, revenue range, entity structure, or financial situation?
• Who prepares and reviews my work, and who is my day-to-day point of contact?
• How is pricing structured, and what work would create an additional charge?
• What information do you need from me, and what deadlines do you set for clients?
• How do you communicate during the year and during tax season?
• Can you represent clients before the IRS or state tax agencies if a notice or issue arises?
• If relevant to me, how do you handle multi-state filings, equity compensation, K-1s, real estate, or business ownership?

Bookkeepers

• How often will my books be closed and reconciled?
• Which accounts are reconciled each month, and what does the month-end review include?
• Do you handle accounts payable, accounts receivable, payroll coordination, or bill pay, or are those separate?
• Which accounting systems and connected tools do you support?
• Can you take on cleanup or catch-up bookkeeping before recurring work begins?
• What reports will I receive, how often, and who explains unusual items?
• What happens when an issue needs to be escalated to a controller, CFO, or tax professional?
• How is pricing structured, and what causes the fee to change?

Fractional CFOs

• What is included in your scope, and what remains with my bookkeeper, controller, or accountant?
• How much of your work is strategic finance versus transaction-level accounting?
• Do you build and maintain forecasts, cash-flow models, budgets, and KPI reporting?
• What experience do you have with boards, investors, lenders, fundraising, or M&A if those are relevant to us?
• What operating cadence do you recommend for leadership reporting and financial decisions?
• Who is on the team serving us, and how senior is the person in our recurring meetings?
• How do you help management turn financial information into actual decisions?
• How is pricing structured: fixed retainer, project, hourly, or another model, and what is outside scope?

Pricing structures to expect

Pricing varies significantly by professional, scope, complexity, geography, and client size. Rather than comparing one headline number, ask each firm to explain the pricing model and what is included.

• Financial advisors: common structures include assets-under-management fees, flat planning fees, subscriptions, hourly engagements, commissions, or combinations of these.
• Accountants and CPAs: engagements may be fixed-fee, monthly or annual retainers, project-based, hourly, or priced by the specific returns and services included.
• Bookkeepers: recurring monthly fees are common, often based on transaction volume, account complexity, payroll/AP/AR scope, and reporting requirements; cleanup work may be separate.
• Fractional CFOs: recurring retainers and project fees are common, with price changing based on time commitment, team depth, complexity, and strategic scope.

Before signing, confirm the fee, billing cadence, what is included, what is specifically excluded, and what circumstances can increase the price.

What to bring to the first call

• A one-paragraph description of what you need help with and what is not working today
• Your top three outcomes for the next 6–12 months
• For a business: approximate revenue, entity type, industry, current finance team, accounting software, and recent financial statements if available
• For personal planning: approximate income, investable assets, major account types, concentrated positions or equity compensation, and upcoming liquidity or life events
• Your current providers and the responsibilities you expect the new professional to own
• Any hard deadline, notice, transaction, fundraising event, tax filing, or decision driving the search

Side-by-side comparison notes

What to compare	Professional 1	Professional 2	Professional 3
Relevant experience	____________	____________	____________
Scope included	____________	____________	____________
Pricing structure	____________	____________	____________
Minimums	____________	____________	____________
Day-to-day contact	____________	____________	____________
Communication cadence	____________	____________	____________
Important exclusions/conflicts	____________	____________	____________
My follow-up questions	____________	____________	____________

Next step

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Sam's List provides information and comparison tools and does not endorse a particular professional. This guide is educational and is not individualized tax, legal, accounting, or investment advice.