Start Here — The Short Story About Why You’re Here

• In one sentence, what specific tax or wealth question brought you to seek new advisory help right now?
• Which best describes your primary role or identity for tax planning purposes? Options: Family office principal, Founder / business owner, C-suite executive, High-net-worth investor, Trust beneficiary / trustee, Other
• Which recent event most prompted this conversation (select the single biggest trigger)? Options: Business sale / liquidity event, Inheritance or family transfer, Relocation / state residency change, Concentrated equity vest/exit, Significant investment gain or loss, Succession / estate planning need, Other
• Briefly, what outcome would make you feel this meeting was time well spent?

Are We Ignoring a Bigger Issue?

• What area of your current tax situation have you been treating as 'good enough'—and why might that be risky now?
• How long have you accepted that status quo—weeks, years, or generations? Options: Less than a year, 1–3 years, 3–10 years, 10+ years
• Has there been a time where relying on the status quo produced an unexpected tax bill, missed opportunity, or advisor disagreement? Tell us what happened.
• If we uncovered a single leverage point that could permanently lower your tax burden, how willing would you be to change longstanding practices? Options: Immediately and decisively, After careful review, Only with consensus from other advisors, Unlikely to change

Where Your Taxes Live — A Clear Inventory

• If you had to list every tax-paying entity or filing stream you own or control, which of these apply? Options: Individual returns (Form 1040), Trust tax returns (1041), Partnership / family partnership (1065), S-corp or C-corp returns, Foundations / nonprofit returns, Foreign entities / filings, State nonresident returns
• Which types of income create the most complexity for you? Options: Wages / deferred compensation, Capital gains from sales, Business sale proceeds, Passive rental income, Trust/estate distributions, Foreign-source income, Investment partnership income
• Approximately how many separate tax jurisdictions do you have reporting or filing obligations across (states and countries)? Options: 1, 2–3, 4–6, 7–10, More than 10, Not sure
• Please describe the single most complex or fragile item on that inventory (entity, asset, or filing) and why it worries you.

The Trigger in Detail — Tell Us the Story That Changed Everything

• Walk us through the turning point that made you seek new tax advice—what happened, when, and who was involved?
• Which of these best describes the status of that event now? Options: Completed (closed) in the past 12 months, Completed more than 12 months ago, In progress / pending, Likely but not yet decided, Other
• What quantifiable impact did or will that event have on your taxable position (approximate ranges are fine)? Options: <$250k, $250k–$1M, $1M–$5M, $5M–$20M, >$20M, Unsure
• How satisfied were you with how your prior advisors handled that event (communication, timing, coordination)? Please give a specific example if possible. Options: Very satisfied, Somewhat satisfied, Neutral, Somewhat dissatisfied, Very dissatisfied

Who’s in the Room — Powers, Roles, and Friction

• Who must sign off on major tax or estate decisions (select all that apply)? Options: You (primary), Spouse/partner, Trustee(s), Family governance committee, Outside family office CIO, Personal attorney, Other advisors
• Who is your current primary tax advisor or firm? (name and short description of relationship)
• How well do your tax, legal, and investment advisors coordinate today? Options: Seamless and proactive, Occasional collaboration, Siloed but functional, Rarely communicate, Not sure / no coordination
• Is there anyone not currently involved whose buy-in would be critical to implement new tax strategies? Who and why?
• Do family dynamics, heirs, or beneficiaries influence how aggressive or conservative you are with tax planning? Options: Yes — they push conservatism, Yes — they push aggressiveness, Mixed influence, No significant influence, Prefer not to say

How Much Risk Feels Right For Your Family?

• When it comes to tax positions that could invite scrutiny, where would you draw the line between bold and reckless? Options: Prefer conservative, low audit risk, Balanced — accept some audit risk for material savings, Comfortable with aggressive but defensible positions, Open to litigation if needed
• Have you or any related entities had an audit, notice, or controversy in the past 10 years? If yes, briefly describe outcome and year. Options: No, Yes — IRS audit, Yes — state audit, Yes — foreign tax authority, Yes — other (explain)
• Which of these strategies would you consider accepting if properly documented and supported? Options: Income timing and deferral, Roth conversions and timing, Opportunity zone investments, Estate freeze techniques, Grantor trust planning, International tax restructuring, Prefer not to select now
• What is the maximum percentage of estimated tax savings you would trade for an elevated chance of examination (approximate)? Options: 0–5%, 5–10%, 10–20%, 20–40%, 40%+

What Success Really Feels Like — Outcomes, Not Activities

• In three years, what measurable changes would make you say this engagement was a success?
• Which of these outcome types matter most to you (pick up to three)? Options: Lower effective income tax rate, Reduced estate tax exposure, Simpler annual compliance, Better coordination with estate plan, More certainty against audits, Preserving family control / legacy
• What non-tax outcomes are equally important (privacy, liquidity, business succession, family education, philanthropic structure)?
• If you had to prioritize one success metric above all others, which would it be? Options: Dollars saved (taxes), Risk reduction / defensibility, Simplicity of ongoing compliance, Speed of implementation, Advisor responsiveness / relationship

Practical Constraints — What Will Stop a Plan Cold

• What is your rough budget comfort for advisory fees on a meaningful planning engagement this year? Options: <$25k, $25k–$75k, $75k–$200k, $200k–$500k, >$500k, Undisclosed / flexible
• What timing constraint matters most—tax filing deadlines, transaction close dates, or estate timelines? Options: Immediate (30 days), Quarter-term (1–3 months), Near-term (3–6 months), Longer (6–12 months), Flexible
• Are there governance or approval processes (family council, board, trustees) that could slow decision-making? Describe briefly.
• Do confidentiality or privacy concerns limit who we may contact or what level of access we can receive? Options: Yes — strict limits, Some limits, No significant limits, Discuss later

Data & Access — The Documents That Make Planning Real

• How many years of personal and entity tax returns can you provide if requested? Options: 0–2 years, 3–5 years, 6–10 years, 10+ years, Not sure
• Which of the following access/records can you provide within 30 days? (select all that apply) Options: Account statements / custodian access, Entity formation documents and ledgers, Trust instruments and decedent estate papers, Cap table and equity grant schedules, Prior tax opinions or planning memos, Foreign account and filing records
• Do you have a secure portal or family office system we can use for document exchange, or would you need us to set one up? Options: Existing secure portal (preferred), We need you to set up secure exchange, Ad-hoc email secure delivery, Other
• Are there specific custodians, banks, or advisors we must route requests through (name them)?
• What is the realistic timeline for gathering the core materials we’d need to build actionable scenarios? Options: 1–2 weeks, 2–4 weeks, 1–3 months, 3+ months, Uncertain

What Would Make You Say Yes — The Final Gate

• What single deliverable in our first engagement would most convince you to move forward (scenario modeling, fee transparency, reference call, pilot project)? Options: Detailed tax savings model, Clear scope + fixed fee quote, Reference from similar family, High-level roadmap with milestones, Pilot advisory module
• Would you prefer a phased engagement (start with modeling then move to implementation) or a single comprehensive engagement? Options: Phased engagement, Single comprehensive engagement, Undecided / need guidance
• Who besides you would need to be present or consent at the proposal/engagement decision meeting?
• Realistically, when are you prepared to make a decision on engaging a tax advisory partner? Options: Immediately, Within 30 days, 30–90 days, 3–6 months, Longer / exploratory
• Is there anything else we should know that would change how we design the right first step?

• Current State Confirmation
• Exposure Diagnosis & Consequence Quantification
• Scenario Modeling Workshop (Proof of Outcomes)
• Advisor Coordination Workshop — Estate & Investment Alignment
• Decision & Execution Roadmap

• Investment advisor prepares a liquidity/timing plan and pre-trade checklist for implementation windows.
• Demonstrate, with numbers, which scenario(s) achieve the stated future state and eliminate prioritized consequences.
• Obtain client validation (explicit yes/no or requested modifications) for 1–2 scenarios to advance to implementation planning.
• Agree on documentation and defensibility steps required for chosen scenario(s).
• Client indicates preferred scenario(s) or requests adjustments and provides approval to engage coordinating advisors.
• Advisory team prepares a scenario defensibility memo and a draft implementation checklist tied to each selected scenario.
• Schedule the joint coordination session with estate and investment advisors.
• Recap Selected Scenario & Key Outcomes
• Confirm legal feasibility and any required amendments to estate/trust documents.
• Agree on investment actions and liquidity planning needed to implement the scenario.
• Assign clear owners and deadlines for all implementation deliverables.
• Estate counsel drafts required amendments or opinion letters and provides estimated timing and costs.
• Introductions & Meeting Objective
• Advisory team compiles an audit-defense packet template and assigns document owners.
• Final Confirmation of Chosen Scenario(s)
• Secure explicit client sign-off to proceed with the selected, validated scenario(s).
• Deliver a concrete 90-day roadmap with owners and milestone dates that operationalizes the future state.
• Establish success metrics and the reporting cadence to monitor implementation and defensibility.
• Advisory team issues a detailed implementation plan and assigns the project manager within 48 hours.
• Client provides formal sign-off (email or countersigned summary) to begin execution.
• All advisors confirm availability for the kickoff meeting and commit to first deliverable dates.
• Produce and confirm a one-sentence statement of the current state that all attendees accept.
• Identify and prioritize missing data required for accurate modeling.
• Confirm stakeholder decision rights and required advisors to include in subsequent sessions.
• Client delivers confirmed packet of returns, entity charts, and recent transaction documents within 3 business days.
• Advisory team prepares a concise one-page baseline summary and model input checklist.
• Schedule the Exposure Quantification meeting after required documents are received.
• Recap Confirmed Current State
• Quantify the dollar impact and risk likelihood for the top exposures.
• Create a prioritized list of issues tied to measurable consequences.
• Confirm assumptions to be used in scenario planning and modeling.
• Advisory team refines numeric projections based on client feedback and final assumptions.
• Client confirms any disputed facts or provides missing items that materially change projections.
• Prepare scenario modeling inputs for the Scenario Modeling Workshop.
• Frame the Workshop: Preconditions & Success Criteria
• Estate Plan Impact & Legal Requirements
• Scenario A — 'Conservative / High Defensibility'
• Baseline Tax Projection
• One‑Sentence Current State Readout
• 90‑Day Roadmap & Key Milestones
• Investment & Liquidity Considerations
• Walkthrough of Key Facts & Documents
• Scenario B — 'Value‑Optimized / Moderate Risk'
• Diagnosed Exposures Inventory
• Success Signals & Validation Tests
• Documentation & Audit Defense Strategy
• Immediate Tasks & Quick Wins
• Consequence Quantification
• Comparative Proof Table
• Stakeholder Map & Decision Rights
• Forced Validation & Client Confirmations
• Assumption Validation & Sensitivity
• Roles, Timeline & Immediate Next Steps
• Governance, Reporting & Next Checkpoints
• Data Gaps & Pre-work for Modeling

• Prepare and file individual federal and state tax returns (1040)
• Prepare and file trust income tax returns (Form 1041)
• Prepare and file federal estate tax returns (Form 706)
• Prepare and file partnership and S‑corporation returns (1065, 1120S)
• Prepare and file gift tax returns (Form 709)
• Prepare K‑1s and partner/beneficiary allocation schedules
• Prepare foreign reporting filings (FBAR, Forms 8938, 5471, 3520, 8865)
• Prepare multistate returns with nexus analysis and apportionment
• Prepare and file opportunity zone and QOF investment tax filings
• Prepare qualified business income deduction calculations and forms (Form 8995/8995‑A)
• Execute Roth IRA conversions and prepare related tax reporting
• Prepare and file amended federal and state tax returns (1040X, etc.)
• Handle IRS representation and compile audit defense packages
• Prepare and file Section 83(b) election letters

Prepare and file individual federal and state tax returns (1040)

• What is the primary filing status for the taxpayer(s)? Options: Single, Married Filing Jointly, Married Filing Separately, Head of Household
• How many individual tax returns need preparation this year? Options: 1, 2, 3+
• Which states will require tax returns or part-year filings? (list states)
• Which types of income are relevant this year? (select all that apply) Options: Wages (W-2), Self-employment, S-Corp/Partnership K-1s, Capital gains, Rental income, Foreign income, Deferred compensation, Pensions/IRAs, Other
• Do you expect significant foreign income, foreign tax credits, or foreign withholding? Options: Yes, No
• Are prior-year returns or carryforwards/carrybacks that affect current filings in scope for review? Options: Yes, No

Prepare and file trust income tax returns (Form 1041)

• How many trusts require Form 1041 preparation? Options: 1, 2-3, 4+
• What trust types are involved? (select all that apply) Options: Grantor trust, Simple trust, Complex trust, Charitable trust/CLAT/CRUT, Other
• Will the trusts issue K-1s to beneficiaries that require allocations? Options: Yes, No
• Does the trust have active business income, rental properties, or investment trading activity? Options: Yes, No
• Are there foreign assets, foreign trusts, or foreign beneficiaries involved? Options: Yes, No
• Do you require review of prior trust filings, basis reporting, or trustee accounting reconciliation? Options: Yes, No

Prepare and file federal estate tax returns (Form 706)

• Is the decedent's gross estate expected to be near or above the federal exemption threshold? Options: Below threshold, Near threshold, Above threshold, Unsure
• Which complex asset types are in the estate? (select all that apply) Options: Closely-held business, Real estate (domestic), Foreign real estate or assets, Securities concentrated position, Personal goodwill, Other
• Do you anticipate portability elections, disclaimers, or special estate planning elections? Options: Yes, No
• Do you require valuation coordination (appraisals), expert reports, or executor representation? Options: Yes, No
• Were prior taxable gifts made that need reconciliation on Form 706? Options: Yes, No
• Is a preliminary estate tax projection or cash-flow analysis required to determine liquidity needs? Options: Yes, No

Prepare and file partnership and S‑corporation returns (1065, 1120S)

• How many partnership and S-corporation returns must be prepared? Options: 1, 2-5, 6+
• Do the entities issue K-1s to owners that must be prepared and distributed? Options: Yes, No
• Are there multi-tier or tiered partnership structures (partnerships owning partnerships)? Options: Yes, No
• Do entities have multi-state activities, nexus considerations, or apportionment complexity? Options: Yes, No
• Do any entities have special elections or adjustments (Section 754, tax basis adjustments, QSub, etc.)? Options: Yes, No
• Are there material book-tax differences, owner distributions, or corrective/amended entity filings needed? Options: Yes, No

Prepare and file gift tax returns (Form 709)

• Are there taxable gifts this year or gift-splitting elections to consider? Options: Yes, No
• How many donors will require Form 709 preparation? Options: 1, 2, More than 2
• Were gifts made to trusts or family entities (e.g., GRAT, family LP) that require reporting or valuation? Options: Yes, No
• Do gifts include non-cash property that will require appraisals or third-party valuations? Options: Yes, No
• Do you need assistance reconciling prior gift returns or applying gift credit/adjusted taxable gifts? Options: Yes, No

Prepare K‑1s and partner/beneficiary allocation schedules

• Approximately how many K-1s across all entities/trusts are expected? Options: 1-5, 6-20, 20+
• Are allocations complex (special allocations, guaranteed payments, tiered ownership, capital account adjustments)? Options: Yes, No
• Do you require reconciliations of allocations to tax basis, capital accounts, and financial statements? Options: Yes, No
• Will K-1 recipients require state apportionment or consolidated reporting support? Options: Yes, No
• Do any recipients have foreign filing obligations or nonresident status that affect K-1 reporting? Options: Yes, No
• Do you prefer electronic distribution of K-1s and secure recipient access? Options: Yes, No

Prepare foreign reporting filings (FBAR, Forms 8938, 5471, 3520, 8865)

• Which foreign reporting forms may be required? (select all that apply) Options: FBAR (FinCEN 114), Form 8938, Form 5471, Form 3520/3520-A, Form 8865, Other
• Do you or any entities hold foreign bank accounts or assets exceeding reporting thresholds? Options: Yes, No
• Are there ownership interests in foreign corporations, partnerships, or trusts? Options: Yes, No
• Were there foreign gifts, inheritances, or transfers during the year? Options: Yes, No
• Do you need voluntary disclosure support, penalty mitigation analysis, or prior-year catch-up filings? Options: Yes, No
• Do you expect foreign tax credits, withholding issues, or coordination with foreign advisors? Options: Yes, No

Prepare multistate returns with nexus analysis and apportionment

• How many states are potentially involved for personal and entity filings? Options: 1, 2-3, 4-10, 10+
• Do you have income sources across states (wages, rentals, business operations) that may create nexus? Options: Yes, No
• Do you require a nexus study or residency analysis for individuals, trusts, or entities? Options: Yes, No
• Should we prepare apportionment calculations, state credits, and withholding reconciliations? Options: Yes, No
• Are there open state notices, audits, or voluntary disclosure needs in any jurisdictions? Options: Yes, No
• Do you expect part-year residency, dual residency, or domicile change impacting state filings? Options: Yes, No

Prepare and file opportunity zone and QOF investment tax filings

• Do you have investments in Qualified Opportunity Funds (QOF) or Opportunity Zone projects? Options: Yes, No
• Is there capital gain deferral or recognition timing that requires elections or tracking? Options: Yes, No
• Do you expect to require Form 8997 or other OZ-specific disclosures? Options: Yes, No
• Are investments held through partnerships or pass-through entities that will require entity-level reporting? Options: Yes, No
• Do you need analysis of basis step-up, holding period tracking, and exit event planning? Options: Yes, No
• Have third-party fund documents, capital call schedules, or investor K-1s been provided for review? Options: Yes, No

Prepare qualified business income deduction calculations and forms (Form 8995/8995‑A)

• Do you have pass-through business income that may qualify for the QBI deduction? Options: Yes, No
• Are multiple pass-through entities producing QBI across the owners? Options: Yes, No
• Is W-2 wage data and UBIA (unadjusted basis in qualified property) available for each entity? Options: Yes, No
• Are you near threshold amounts or in a specified service trade that may limit QBI? Options: Yes, No
• Would you like pro forma scenarios comparing Form 8995 (simplified) vs Form 8995-A (detailed) outcomes? Options: Yes, No
• Should QBI calculations be coordinated with estimated tax planning and withholding adjustments? Options: Yes, No

Execute Roth IRA conversions and prepare related tax reporting

• Are you considering Roth conversions for one or more retirement accounts this year? Options: Yes, No

• Non-Disclosure Agreement (NDA)
• Engagement Agreement
• Statement of Work (SOW)
• Fee Schedule & Payment Terms
• Retainer / Trust Account Authorization
• Service Level Agreement (SLA) & Response Times
• Confidentiality & Data Security Addendum (DPA)
• Advisor Coordination Authorization
• Tax Representation & Power of Attorney
• Data Access & Third-Party Consent
• Change Order & Scope Amendment
• Termination, Renewal & Transition Plan

• Success Outcomes Review
• Tax Position Validation & Audit Readiness
• Savings Realization & Performance Analysis
• Issues, Exceptions & Continuous Planning Channel Setup
• Stakeholder Coordination & Future-State Planning

• Agree on the ongoing cadence and who will produce which deliverables between meetings.
• Baseline & Outcome Reconciliation
• Validate the monetary reconciliation from baseline to realized tax outcomes and obtain client confirmation.
• Agree on attribution of savings by strategy and a KPI set for ongoing tracking.
• Establish a recurring reporting cadence and responsible parties for producing the reports.
• Deliver the detailed savings workbook with strategy-level attribution and sensitivity tabs to the client.
• Publish an agreed KPI dashboard and schedule quarterly distribution and review meetings.
• Update internal forecasting models with realized outcomes to improve future projections.
• Current Open Issues Inventory
• Establish a secure, governed shared channel for issues and ongoing planning with defined access and SLAs.
• Triage and prioritize open exceptions that materially affect success signals and assign owners.
• Opening & Objectives
• Create the shared secure channel, invite agreed participants, and publish channel governance and SLA document.
• Load the open issues backlog into the channel with owners, priorities, and due dates.
• Schedule the recurring planning cadence (quarterly reviews, pre-season check) and invite stakeholders.
• One-sentence Current State from Each Advisor
• Achieve cross-advisor alignment on the validated outcomes and a single, operational future-state description.
• Secure explicit commitments, decision authorities, and a timeline for integrated actions.
• Schedule any required joint workshops and confirm points of contact for coordination.
• Draft and distribute an integrated action plan documenting decisions, owners, and timeline for reaching the future state.
• Schedule the first cross-advisor workshop to execute on time-sensitive items (e.g., gifting timetable, entity elections).
• Assign a single client-facing liaison and confirm escalation contacts for each advisory firm.
• Confirm and sign off on realized tax savings and how they compare to the forecasted model.
• Identify and agree remediation for material variances or unmet success signals.
• Establish owners and timeline for all follow-up items and communications to other advisors.
• Deliver a client-facing outcomes summary that reconciles forecast vs. realized savings and obtain client sign-off.
• Create an issues/variance log with owners, root causes, and proposed remediation timelines.
• Share outcomes summary with estate and investment advisors and schedule any required alignment meetings.
• State Current Positions
• Confirm each material tax position has a defensible technical memo and supporting documents.
• Classify positions by audit risk and assign owners for any remediation or amendment work.
• Create an audit defense package template and finalize storage/access procedures.
• Prepare or finalize technical memoranda for all high- and medium-risk positions and route for partner review.
• Assemble an audit defense packet (calculations, client authorizations, contemporaneous memos) and place it in the shared secure channel.
• If required, draft and calendar any amended returns or disclosures with owners and deadlines.
• Explicit Consequences of Non-Coordination
• Define Shared Channel & Access Governance
• Confirm Current State (Baseline vs. Today)
• Technical Support Review (Diagnosis → Proof)
• Attribution by Strategy
• Quantify Realized Outcomes
• Define the Integrated Future State
• Sensitivity & What-If Scenarios
• Issue Triage & Escalation Process
• Risk Assessment & Consequence
• Surface Consequences & Variances
• Documentation Gaps & Remediation
• Map Decisions, Timelines & Ownership
• Ongoing Planning Cadence & Deliverables
• KPI Review & Reporting Cadence
• Commitments & Next Steps
• Validate Future State
• Client Q&A and Validation
• Filing/Amendment Decisions
• Access & Onboarding Tasks
• Sign-offs, Next Steps & Communications