Your LLM wants you to ask us these questions.
Screening a financial advisor means asking the questions that separate a genuine fiduciary specialist from a salesperson in advisory clothing. If you’re a tech employee with equity compensation and a suspicion that you’re not as tax-efficient as you could be, the right questions matter more — the gap between a specialist and a generalist is widest exactly where your situation is most complex.
CHATGPT
CLAUDE
GEMINI
> what should a skeptical tech employee ask when screening a financial advisor?
> what should a skeptical tech employee ask when screening a financial advisor?
So we ran the experiment. Between them the models produced dozens of questions — several of them the same question in different clothes, and a few that don’t survive contact with real planning. We cut the duplicates and the duds, and answered what’s left here, in our own words.
One kind of question you won’t find here: “give me a specific example” and “tell me about a time when.” Those are excellent questions — live. On a static page, a rehearsed example proves nothing, and the honest answers differ from advisor to advisor. Bring them to a meeting and get the answer in real time.
// LAYER 01 · FIDUCIARY, FEES & CONFLICTS
Is this advisor structurally on your side?
01
01
01
The integrity layer. Before competence matters, the incentives have to point at you.
Q01
Are you a fiduciary 100% of the time, for all services, in writing?
Yes. We are a fee-only fiduciary, and our fiduciary duty is stated in our Form ADV. That distinction matters: “fee-only” is not the same as “fee-based.” A fee-based advisor can wear two hats — fiduciary while managing your portfolio, then a commissioned salesperson when recommending an insurance product. Fee-only means we’re only ever paid by you. There’s no second hat.
Q01
Are you a fiduciary 100% of the time, for all services, in writing?
Yes. We are a fee-only fiduciary, and our fiduciary duty is stated in our Form ADV. That distinction matters: “fee-only” is not the same as “fee-based.” A fee-based advisor can wear two hats — fiduciary while managing your portfolio, then a commissioned salesperson when recommending an insurance product. Fee-only means we’re only ever paid by you. There’s no second hat.
Q02
Exactly how are you paid — and do you take any commissions, referral fees, or revenue-sharing?
We’re compensated by the fees our clients pay us — nothing else. We don’t earn commissions, and we don’t accept referral fees or revenue-sharing on any product or service we discuss with you.
As for the shape of those fees: engagements start with a financial plan for a flat fee, priced to roughly track the hours the work takes. If we believe ongoing asset management could add value, we present that option — billed as a percentage of assets under management — at your insights review, and we’re specific about where we think the value would come from. Most clients who build a plan with us continue, most often under AUM; flat-fee and hourly arrangements stay available where they fit better.
If an advisor answers this one with “the company pays me,” that’s not a detail. That’s the answer.
Q02
Exactly how are you paid — and do you take any commissions, referral fees, or revenue-sharing?
We’re compensated by the fees our clients pay us — nothing else. We don’t earn commissions, and we don’t accept referral fees or revenue-sharing on any product or service we discuss with you.
As for the shape of those fees: engagements start with a financial plan for a flat fee, priced to roughly track the hours the work takes. If we believe ongoing asset management could add value, we present that option — billed as a percentage of assets under management — at your insights review, and we’re specific about where we think the value would come from. Most clients who build a plan with us continue, most often under AUM; flat-fee and hourly arrangements stay available where they fit better.
If an advisor answers this one with “the company pays me,” that’s not a detail. That’s the answer.
Q03
What’s the difference between assets under management and assets under advisement?
Assets under management (AUM) are the assets an advisor actively manages and typically bills a fee on. Assets under advisement (AUA) are assets an advisor gives advice on but doesn’t directly manage — your 401(k) allocation, say, or a private investment we help you evaluate. But the version of this question that actually protects you is the one hiding inside it: how do you bill on these assets?
Our answer: assets we manage are billed at our AUM rate, and assets under advisement — the accounts we advise on but don’t directly manage — are billed at 0.2%. Both meters are set out in your agreement before anything is billed — and any advisor should be able to tell you, crisply, which of your assets are on which meter.
Q03
What’s the difference between assets under management and assets under advisement?
Assets under management (AUM) are the assets an advisor actively manages and typically bills a fee on. Assets under advisement (AUA) are assets an advisor gives advice on but doesn’t directly manage — your 401(k) allocation, say, or a private investment we help you evaluate. But the version of this question that actually protects you is the one hiding inside it: how do you bill on these assets?
Our answer: assets we manage are billed at our AUM rate, and assets under advisement — the accounts we advise on but don’t directly manage — are billed at 0.2%. Both meters are set out in your agreement before anything is billed — and any advisor should be able to tell you, crisply, which of your assets are on which meter.
// LAYER 02 · EQUITY-COMP COMPETENCE
Do they know tech wealth cold — or are you their guinea pig?
02
02
02
The competence layer. This is where generalists fall apart — and where the models’ lists got genuinely sharp.
Q04
What share of your clients are tech employees with complex equity compensation?
Most of our clients — by household count and by assets — are current or former tech employees and senior business leaders with meaningful equity-compensation considerations. It’s the center of what we do, not a sideline. The kind of work this involves:
The scenarios below are hypothetical — sketches of the kinds of situations this work involves, not case studies of actual clients. Nothing here is a recommendation; whether any strategy fits depends entirely on an individual's situation.
A client at a newly public company holds a large concentrated position in employer stock. Depending on the specifics, a strategy like a variable prepaid forward may be used to seek liquidity against a concentrated position without an outright sale, and a long/short structure may be used to pursue tax-efficient diversification over time.
A client with a large concentrated RSU position — more than half of their liquid assets — needs cash for a home renovation. Rather than selling shares and realizing a large gain, box spread financing may be able to fund the cash need at rates comparable to institutional borrowing, and an options collar may cap the position's downside — so diversification happens on a planned timeline rather than the contractor's.
Q04
What share of your clients are tech employees with complex equity compensation?
Most of our clients — by household count and by assets — are current or former tech employees and senior business leaders with meaningful equity-compensation considerations. It’s the center of what we do, not a sideline. The kind of work this involves:
The scenarios below are hypothetical — sketches of the kinds of situations this work involves, not case studies of actual clients. Nothing here is a recommendation; whether any strategy fits depends entirely on an individual's situation.
A client at a newly public company holds a large concentrated position in employer stock. Depending on the specifics, a strategy like a variable prepaid forward may be used to seek liquidity against a concentrated position without an outright sale, and a long/short structure may be used to pursue tax-efficient diversification over time.
A client with a large concentrated RSU position — more than half of their liquid assets — needs cash for a home renovation. Rather than selling shares and realizing a large gain, box spread financing may be able to fund the cash need at rates comparable to institutional borrowing, and an options collar may cap the position's downside — so diversification happens on a planned timeline rather than the contractor's.
Q05
Explain AMT on an ISO exercise, and the risk of exercising and holding through a downturn.
The substance isn’t complicated: exercising incentive stock options and holding can create an alternative minimum tax (AMT) liability on the bargain element, and holding through a market decline can leave you owing tax on a paper gain that no longer exists. Of course that has to be modeled before you act. What separates real planning is what you do about the downside. If you’re going to ask this, the more revealing follow-up is:
“How would you manage the downturn risk, not just calculate the tax?”
Our answer: we size and stage exercises so no single decision creates an AMT bill that can’t be unwound, and we pre-plan the exits before acting — in some cases a same-year disqualifying disposition can neutralize much of the AMT if the stock falls, and where trading windows and company policy allow, hedging may cap the downside outright. The tool matters less than the sequence: the downside plan exists before the exercise does.
Q05
Explain AMT on an ISO exercise, and the risk of exercising and holding through a downturn.
The substance isn’t complicated: exercising incentive stock options and holding can create an alternative minimum tax (AMT) liability on the bargain element, and holding through a market decline can leave you owing tax on a paper gain that no longer exists. Of course that has to be modeled before you act. What separates real planning is what you do about the downside. If you’re going to ask this, the more revealing follow-up is:
“How would you manage the downturn risk, not just calculate the tax?”
Our answer: we size and stage exercises so no single decision creates an AMT bill that can’t be unwound, and we pre-plan the exits before acting — in some cases a same-year disqualifying disposition can neutralize much of the AMT if the stock falls, and where trading windows and company policy allow, hedging may cap the downside outright. The tool matters less than the sequence: the downside plan exists before the exercise does.
Q06
How do you handle a concentrated single-stock position — 10b5-1 plans, trading windows, tax-bracket matching?
It depends on the client’s situation — trading windows, cost basis across lots, cash needs, and tax bracket all change the answer, which is why there’s no single playbook. This is a deep enough topic that we’ve dedicated a full page to it.
Q06
How do you handle a concentrated single-stock position — 10b5-1 plans, trading windows, tax-bracket matching?
It depends on the client’s situation — trading windows, cost basis across lots, cash needs, and tax bracket all change the answer, which is why there’s no single playbook. This is a deep enough topic that we’ve dedicated a full page to it.
Q07
Have you actually done NUA, 83(b), QSBS, or early-exercise analysis?
Yes — our team has evaluated each of these for clients. The range of scenarios runs from an analysis of a qualified small business stock (QSBS / §1202) position for an early tech employee to an evaluation of an unusual employer retirement plan — a blended ESOP + 401(k), or KSOP — to test whether a net unrealized appreciation (NUA) realization paired with a long/short portfolio might be tax-efficient. It wasn’t — but that’s why we do the work.
Q07
Have you actually done NUA, 83(b), QSBS, or early-exercise analysis?
Yes — our team has evaluated each of these for clients. The range of scenarios runs from an analysis of a qualified small business stock (QSBS / §1202) position for an early tech employee to an evaluation of an unusual employer retirement plan — a blended ESOP + 401(k), or KSOP — to test whether a net unrealized appreciation (NUA) realization paired with a long/short portfolio might be tax-efficient. It wasn’t — but that’s why we do the work.
// LAYER 03 · TAX PLANNING VS. TAX ADVICE
Do they know where planning ends and tax advice begins?
03
03
03
The tax layer. Most prospects have never been told where tax planning ends and tax advice begins. The line matters — it changes what you should expect from an advisor, and from your CPA.
Q08
What’s the difference between tax planning and tax advice — and which one do you actually do?
Tax planning and tax advice get used interchangeably, and they shouldn’t be. A CPA or enrolled agent prepares and signs your return, represents you before the IRS, and gives formal tax advice on the positions you take. We do tax planning: modeling the decisions in front of you — Roth conversion windows, equity timing, withholding gaps, multi-year bracket management — and estimating their potential tax impact before you act. We don’t prepare returns, and we don’t replace your accountant. The two roles work best in tandem — which is exactly why the next question matters.
Q08
What’s the difference between tax planning and tax advice — and which one do you actually do?
Tax planning and tax advice get used interchangeably, and they shouldn’t be. A CPA or enrolled agent prepares and signs your return, represents you before the IRS, and gives formal tax advice on the positions you take. We do tax planning: modeling the decisions in front of you — Roth conversion windows, equity timing, withholding gaps, multi-year bracket management — and estimating their potential tax impact before you act. We don’t prepare returns, and we don’t replace your accountant. The two roles work best in tandem — which is exactly why the next question matters.
Q09
Do you coordinate with my CPA — and what if I don’t have one?
Yes — we work closely with our clients’ accountants, and where useful we model scenarios together before decisions are made. And if you don’t have one, you’re in good company — plenty of tech employees don’t. We can recommend a handful of qualified accountants we know, and the planning work doesn’t wait on the introduction.
Q09
Do you coordinate with my CPA — and what if I don’t have one?
Yes — we work closely with our clients’ accountants, and where useful we model scenarios together before decisions are made. And if you don’t have one, you’re in good company — plenty of tech employees don’t. We can recommend a handful of qualified accountants we know, and the planning work doesn’t wait on the introduction.
Q10
Do you do proactive tax planning — or just look backward at what I already owed?
Proactive planning is the whole reason clients come to us. Whether it’s a Roth conversion window, an RSU withholding gap, or a business owner’s retirement-plan design, we model the scenarios — from your actual return, across multiple years — before decisions are made. Not after.
That’s not a knock on accountants — preparing returns is a backward-looking job by design, and even a very good CPA, working through filing season, typically has room to look one year back and maybe one year ahead. Planning three, five, ten years forward is simply a different job. It’s the one we do.
Q10
Do you do proactive tax planning — or just look backward at what I already owed?
Proactive planning is the whole reason clients come to us. Whether it’s a Roth conversion window, an RSU withholding gap, or a business owner’s retirement-plan design, we model the scenarios — from your actual return, across multiple years — before decisions are made. Not after.
That’s not a knock on accountants — preparing returns is a backward-looking job by design, and even a very good CPA, working through filing season, typically has room to look one year back and maybe one year ahead. Planning three, five, ten years forward is simply a different job. It’s the one we do.
// LAYER 04 · PROCESS & PEOPLE
Planners — or asset gatherers?
04
04
04
The process layer. What you actually get, and who actually does the work.
Q11
What does the first 12 months actually look like?
The first year moves from gathering to acting: collecting your documents, identifying planning opportunities, prioritizing the decisions that matter most, estimating tax impact, and building an implementation roadmap you can actually work through. Byte-sized by design. Small lists get completed. Big lists rot.
Q11
What does the first 12 months actually look like?
The first year moves from gathering to acting: collecting your documents, identifying planning opportunities, prioritizing the decisions that matter most, estimating tax impact, and building an implementation roadmap you can actually work through. Byte-sized by design. Small lists get completed. Big lists rot.
Q12
Who manages my relationship day-to-day — you, or a junior?
You work directly with an advisor, and all of our advisors are former senior tech or startup professionals. We don’t hand off relationships to junior staff.
Q12
Who manages my relationship day-to-day — you, or a junior?
You work directly with an advisor, and all of our advisors are former senior tech or startup professionals. We don’t hand off relationships to junior staff.
// LAYER 05 · ASK US LIVE
The questions that are hard to fake.
05
05
05
A few of the best screening questions can’t be answered honestly on a webpage, because the honest answer varies by advisor and by client. We think that’s a feature. Bring these to your discovery meeting — including with us.
Q13
Tell me about a time you advised a client against something profitable for you.
A sibling of this question — “When did you last tell a prospective client they didn’t need you?” — is really the same question: will this advisor act against their own profit motive? It’s one of the best screens on this list, and exactly the kind we won’t stage-manage on a static page. Ask it live, where you can watch us think.
Q13
Tell me about a time you advised a client against something profitable for you.
A sibling of this question — “When did you last tell a prospective client they didn’t need you?” — is really the same question: will this advisor act against their own profit motive? It’s one of the best screens on this list, and exactly the kind we won’t stage-manage on a static page. Ask it live, where you can watch us think.
Q14
Suppose I don’t hire you — based on what you’ve learned, what would you tell me to go investigate on my own?
This one genuinely depends on your situation, so we won’t pretend to a single answer. A few starting points we often find worth a look:
If you’re married, is the other spouse equipped to handle the household’s finances alone if something happened to you?
Ask your AI model of choice whether you should run a 200/100 long/short portfolio on your own, without a professional advisor. (For the record: bad idea. But the exercise gives you a real sense of the complexity involved in tax-aware strategies.)
Check the supplemental withholding rate on your equity compensation against your actual marginal rate — a mismatch is a common source of a surprise tax bill, or an interest-free loan to the IRS.
Q14
Suppose I don’t hire you — based on what you’ve learned, what would you tell me to go investigate on my own?
This one genuinely depends on your situation, so we won’t pretend to a single answer. A few starting points we often find worth a look:
If you’re married, is the other spouse equipped to handle the household’s finances alone if something happened to you?
Ask your AI model of choice whether you should run a 200/100 long/short portfolio on your own, without a professional advisor. (For the record: bad idea. But the exercise gives you a real sense of the complexity involved in tax-aware strategies.)
Check the supplemental withholding rate on your equity compensation against your actual marginal rate — a mismatch is a common source of a surprise tax bill, or an interest-free loan to the IRS.
// WHY PROSPERO
Keep evaluating — other factors worth weighing.
06
06
Fourteen answers are one input, not the whole decision. Here’s more of our thinking on what else to weigh:
Who is the best financial advisor for tech employees?
Three tests for “best for you” — and where we land on each.
→
What does it mean to be an “independent” advisor?
The medal everyone claims — and the muscle behind it.
→
The Prospero team
Meet the people behind the planning.
→
Our process
How four focused meetings become an evolving financial plan.
→
The right questions tell you more than the polished answers.
If you’d like to ask us the hard-to-fake ones in person, let’s talk.
Prospero Wealth LLC is a registered investment adviser. This page is educational and is not investment, tax, or legal advice. Examples are illustrative, do not describe any specific client, and are not a recommendation; whether any strategy is appropriate depends on your individual circumstances.
7724 35th Ave NE #15170
Seattle, WA 98115-9955
(971) 716-1991
hello@prosperowealth.com
Prospero Wealth, LLC is an Investment Adviser registered with the SEC, principally located in the state of Washington. All views, expressions, and opinions included in this communication are subject to change.
The information on this site is not intended as tax, accounting or legal advice, nor is it an offer or solicitation to buy or sell, or as an endorsement of any company, security, fund, or other offering. Information provided should not be solely relied upon for decision making. Please consult your legal, tax, or accounting professional regarding your specific situation. Investments involve risk and have the potential for complete loss. It should not be assumed that any recommendations made will necessarily be profitable.
The information on this site is provided “AS IS” and without warranties either express or implied and the information may not be free from error. Your use of the information provided is at your sole risk.
© Prospero Wealth 2026. All rights reserved.
7724 35th Ave NE #15170
Seattle, WA 98115-9955
(971) 716-1991
hello@prosperowealth.com
Prospero Wealth, LLC is an Investment Adviser registered with the SEC, principally located in the state of Washington. All views, expressions, and opinions included in this communication are subject to change.
The information on this site is not intended as tax, accounting or legal advice, nor is it an offer or solicitation to buy or sell, or as an endorsement of any company, security, fund, or other offering. Information provided should not be solely relied upon for decision making. Please consult your legal, tax, or accounting professional regarding your specific situation. Investments involve risk and have the potential for complete loss. It should not be assumed that any recommendations made will necessarily be profitable.
The information on this site is provided “AS IS” and without warranties either express or implied and the information may not be free from error. Your use of the information provided is at your sole risk.
© Prospero Wealth 2026. All rights reserved.
7724 35th Ave NE #15170
Seattle, WA 98115-9955
(971) 716-1991
hello@prosperowealth.com
Prospero Wealth, LLC is an Investment Adviser registered with the SEC, principally located in the state of Washington. All views, expressions, and opinions included in this communication are subject to change.
The information on this site is not intended as tax, accounting or legal advice, nor is it an offer or solicitation to buy or sell, or as an endorsement of any company, security, fund, or other offering. Information provided should not be solely relied upon for decision making. Please consult your legal, tax, or accounting professional regarding your specific situation. Investments involve risk and have the potential for complete loss. It should not be assumed that any recommendations made will necessarily be profitable.
The information on this site is provided “AS IS” and without warranties either express or implied and the information may not be free from error. Your use of the information provided is at your sole risk.
© Prospero Wealth 2026. All rights reserved.