Investable assets and account mix

• Roughly how much in investable assets do you expect to bring to this relationship? Options: Under $500,000 (below our typical minimum), $500,000–$999,999, $1,000,000–$2,499,999, $2,500,000–$4,999,999, $5,000,000–$10,000,000, Over $10,000,000 (above our typical range)
• Which types of accounts hold those assets? Options: 401(k) or other employer plan, IRA or Roth IRA, Taxable brokerage account, Pension / defined benefit, Deferred compensation / nonqualified plan, Annuity, Cash or savings, Other
• If helpful, list key custodians or account sources we should know about (optional).

Decision authority and stakeholders

• Who is the primary decision-maker for retirement and financial decisions? Options: You alone, You and your spouse/partner (shared), Spouse/partner alone, Named fiduciary or trustee, Professional decision-maker (e.g., power of attorney), Other
• Are there other advisors or family members who regularly influence these decisions and whom we should include? Options: Financial advisor or planner, Accountant / CPA, Attorney / estate planner, Adult child or family member, No, not typically, Other
• If yes, please name their roles and the preferred point of contact (optional).

Timing and near-term triggers

• What is your expected timeline for completing a retirement income plan or making major income decisions? Options: Within 1 month, 1–3 months, 3–6 months, 6–12 months, No set timeline / exploratory
• Is there a specific trigger driving this timing (for example, planned retirement date, Social Security eligibility, or a health or job change)?

Fee model and budget expectations

• Which fee model do you prefer or expect for planning and advisory services? Options: Percentage of assets under management (AUM), Flat planning fee, Hourly planning fee, Combination (flat + AUM), Unsure / open to recommendations
• Do you have an expected or allocated budget for one-time planning or ongoing advisory? Options: Under $5,000, $5,000–$15,000, $15,000–$30,000, Covered by ongoing AUM fee, No budget allocated / prefer to discuss

Why this moment matters

• Tell me what prompted you to start planning for retirement now.
• How soon do you expect to stop working or change to part-time? Options: Within 12 months, 1-3 years, 4-6 years, 7-10 years, Already retired
• Which people depend on this income decision? Options: Spouse or partner, Adult children, Other family members, No dependents, Charitable commitments
• Roughly how much of your household income comes from wages today? Options: Almost all (>90%), Most (50-90%), About half (25-50%), Little (<25%), None
• How would you describe your biggest concern about entering retirement?

Where your money lives today

• If a market downturn hit tomorrow, which of your accounts would you rely on first and why?
• Which account types make up your investable assets? Options: 401(k) or 403(b), Traditional IRA, Roth IRA, Taxable brokerage account, Defined benefit pension, Income annuity, Deferred compensation, Cash savings, Other
• Do you have any defined benefit pensions or guaranteed income contracts we should model? Options: Yes, a defined benefit pension, Yes, an income annuity, No, Unsure
• Approximately how many custodian accounts will we need to aggregate to build your plan? Options: 1-2, 3-5, 6-10, More than 10, Unsure
• Walk me through the most recent year of contributions or employer matches you received, including amounts and accounts affected.

The real monthly math

• Identify the single unexpected expense or health cost that would force you to change your retirement income plan immediately.
• Please estimate your current average monthly household spending Options: Under $3,000, $3,000–$6,000, $6,000–$9,000, $9,000–$12,000, Over $12,000
• Approximately how many months of expenses do you currently have in liquid cash or short-term accounts? Options: Less than 3 months, 3–6 months, 6–12 months, More than 12 months
• List the recurring healthcare costs you already pay or expect before Medicare Options: Employer plan premiums, COBRA or retiree premiums, High out-of-pocket prescriptions, Long-term care insurance premium, No recurring healthcare premiums, Other
• Rate your comfort with letting portfolio withdrawals vary year to year rather than keeping a fixed income Options: Very comfortable, Somewhat comfortable, Uncomfortable, Not sure
• Provide an example month where your expenses spiked and explain what happened.

What retirement would actually feel like

• If you had to protect only one retirement goal, which would you choose: preserving legacy, maintaining lifestyle, or minimizing taxes? Options: Preserve legacy for heirs, Maintain current lifestyle, Minimize lifetime taxes, Maximize guaranteed income, Other
• Describe three activities, experiences, or costs that would make your retirement feel successful to you.
• Rate the importance of leaving money to heirs compared with increasing your monthly spending Options: Heirs much more important, Heirs slightly more important, Equal importance, Spending slightly more important, Spending much more important
• Tell me which travel, housing, or healthcare choices could change your yearly spending most Options: Frequent travel, Downsizing or relocating, Second home ownership, Major elective surgery or care, Long-term care needs, Other
• Imagine a sustained 15% portfolio loss, what immediate lifestyle choices would you change?

Decisions you're avoiding

• Name the retirement decision you are postponing because the trade-offs feel too complex: Social Security timing, pension lump versus annuity, or withdrawal sequencing? Options: Social Security timing, Pension lump sum vs annuity, Withdrawal sequencing and tax ordering, Investment allocation change, Other
• Have you run a formal Social Security optimization analysis before? Options: Yes, with an advisor, Yes, with an online tool, No, never, Unsure
• Who currently holds the paperwork and the benefit estimate for any pension you may have? Options: I do, My employer or HR, A previous employer's plan administrator, We do not have it, Unsure
• Choose the factors that most influence your tax-withdrawal preferences Options: Minimize current taxes, Minimize lifetime taxes, Simplicity and predictability, Avoid Medicare IRMAA exposure, Use tax-deferred accounts first, Prefer Roth conversions
• When faced with a trade-off where income security reduces legacy, how do you usually decide?

Where plans break

• What single risk, market, health, caregiving, or tax policy change, would make you stop this plan and look for a different approach?
• Select the risks that concern you most in the next 10 years Options: Sequence of returns risk, Major health event, Unexpected caregiving costs, Significant tax law change, High inflation, Living longer than expected
• Have you experienced a financial shock in the past five years that affected your retirement savings? Options: Yes, job loss or reduced income, Yes, major medical bills, Yes, market loss greater than 20%, No
• Who else would you need buy-in from to change investment or withdrawal strategy? Options: Spouse or partner, Adult children, A family trustee, No one else, Other
• Within what timeframe would a major risk force you to change your retirement timeline? Options: Immediately, Within 6 months, Within a year, Longer than a year, Unsure

Other paths you are weighing

• List who you are actively considering to help with retirement planning right now, and what could make them the winner? Options: Your current advisor, A new independent advisor, An advisor at a large firm, DIY using software, A robo-managed account, A family member handling finances, Other
• What would have to be true about your current approach for you to stick with it rather than change?
• Has anyone internally suggested solving this without an outside advisor? Options: Yes, I would manage it myself, Yes, a family member would help, No, we want external help, Not discussed
• Select the service features from other providers that matter most to you Options: Lower fees, Guaranteed income options, In-person relationship, Fiduciary commitment, Clear written deliverables, Ongoing portfolio management
• Describe the timeline or outcome that would make you switch to a different provider quickly

How ready is your current setup

• Identify the missing permission, account access, or document that would stop us from producing an accurate plan quickly
• Do you have online account access for your major custodians? Options: Yes, for all custodians, Yes, for some custodians, No, Unsure
• Are you willing to share account login or aggregation credentials with a secure aggregation system? Options: Yes, full access, Yes, read-only aggregation, No, Need more information about security
• Please list the documents you can provide within two weeks Options: Most recent 401(k) or plan statement, IRA and brokerage statements, Pension estimate or statement, Tax returns for last 2 years, Insurance policy statements, None of the above
• Are there any legal or compliance approvals, power of attorney, or trustee constraints that could delay implementation? Options: Yes, approvals required, No, Unsure
• Indicate the household primary contact and who has authority to sign agreements Options: I am the primary contact, Spouse or partner, Both jointly, Other authorized person

What would make you say yes

• Imagine we delivered a stress-tested plan showing your income covering your goals for 30 years, what would make you sign within a week?
• Name the three must-have deliverables you expect from a retirement plan Options: Projected cash-flow model with scenarios, Social Security timing analysis, Tax-aware withdrawal sequencing, Healthcare and long-term care forecast, Investment allocation recommendations, Written engagement summary and assumptions
• Indicate your preferred fee model Options: Percentage of assets under management, Flat planning fee, Hourly, Project-based fixed fee, Combination
• Would you be willing to move forward on a single targeted recommendation if it improved your projected 30-year outcome? Options: Yes, Maybe, No
• When would you be ready to begin data collection if terms are agreed? Options: Immediately, Within 1 week, 2-4 weeks, 1-2 months, Unsure
• Is there any non-negotiable condition that would prevent you from engaging with an advisor?

• Retirement Strategy Session

• Confirm the current state and its cost
• You confirm the restated current state and accept the quantified cost of not having a coordinated strategy.
• Prepare and deliver a two-strategy comparison report showing cash flows, tax-year projections, and downside probabilities based on today's numbers before the follow-up session.
• You confirm one preferred income strategy that meaningfully reduces shortfall risk and limits near-term tax exposure.
• Run baseline cash-flow and downside stress test
• Provide recent account statements, pension estimate statements, and the most recent tax return to validate assumptions and finalize projections.
• You agree on the remaining analyses required before finalizing Planning Scope and a target decision window.
• Compare two tailored strategies side-by-side
• Confirm acceptable Social Security claiming window and any non-negotiable income needs or health timelines that affect strategy selection.
• Walk through tax and benefits trade-offs
• Schedule the follow-up Planning Scope session to convert the chosen strategy into deliverables and responsibilities.
• Validate the recommended path

• Retirement Strategy Session
• Retirement Strategy Deck
• Retirement Strategy Brief

• meeting
• slides
• document

• Written Retirement Income Plan with Cash-Flow Projections
• Social Security Claiming Strategy and Filing Support
• Pension Lump-Sum vs Annuity Decision Modeling
• Tax-Efficient Withdrawal Sequencing and Implementation
• Investment Portfolio Design and Ongoing Management
• Required Minimum Distribution Coordination and Execution
• Healthcare and Medicare Cost Projection and Enrollment Support
• Estate and Beneficiary Coordination with Counsel
• Tax Projection and Proactive Tax-Reduction Strategies
• Portfolio Stress Testing and Longevity Scenario Modeling
• Account Consolidation and IRA/401(k) Rollover Execution
• Annual Plan Update and Ongoing Advisory Services

Written Retirement Income Plan with Cash-Flow Projections

• Do you want a written plan that models monthly and annual net cash flow through age 95 using your actual account balances? Options: Yes, No, Discuss options
• Which tax years should be included explicitly in cash-flow projections (for example: current tax year, first 10 years of retirement)? Options: Current year only, First 5 years, First 10 years, Lifetime projection
• Which documents will you provide for building the projections (select all that apply)? Options: Last two years of Form 1040, Recent account statements (IRA/401(k)/brokerage), Pension estimate or SPD (Summary Plan Description), Recent paystubs or pension pay advices, Other
• How should we handle assumptions for inflation and nominal return rates: use advisor-recommended defaults, client-provided assumptions, or show a sensitivity range? Options: Advisor-recommended defaults, Client-provided assumptions, Show sensitivity range (low/medium/high)
• What acceptance criteria will confirm you approve the written plan and projections (for example: addresses your top three retirement goals and cash-flow variance below $500/month)?

Social Security Claiming Strategy and Filing Support

• Which Social Security records can you supply: SSA benefit estimate statement, mySSA access permission, or none? Options: SSA benefit estimate statement, Permission to retrieve via mySSA, None available yet
• Do you consent to retrieval of your Social Security earnings record via SSA online tools to validate historical earnings for claiming analysis? Options: Yes, I consent, No, I will provide documents manually
• Which claiming scenarios should we model for each spouse or beneficiary (for example: claim at full retirement age, claim at 70, spousal benefit only, deferred claiming)? Options: Claim at earliest eligible age, Claim at full retirement age, Delay to age 70, Spousal or survivor scenarios, All of the above
• Are any public pension rules applicable to Social Security calculation for you (for example Windfall Elimination Provision or Government Pension Offset noted in your plan documents)? Options: Yes, No, Not sure — need review of pension SPD
• Which evidence will you provide to support filing assistance (for example: SSA statements, recent Form SSA-1099, signed authorization for filing support)? Options: SSA-1099 copy, Benefit estimate statement, Signed authorization for filing support, Other

Pension Lump-Sum vs Annuity Decision Modeling

• Which pension plan documents can you provide: Summary Plan Description, recent pension estimate showing lump-sum and annuity values, or contact for plan administrator? Options: SPD (Summary Plan Description), Recent pension estimate or estimate letter, Plan administrator contact, None available
• Name the survivor benefit election options shown in your pension materials (for example: single-life, 50% spouse survivor, 100% survivor).
• Which mortality table or discount rate would you prefer us to use when converting annuity to lump-sum present value, or should we provide a sensitivity range? Options: Use advisor-recommended discount rates, Client-specified rate, Provide sensitivity range
• Who is the pension plan administrator or benefits contact for required election forms and processing?
• Are there rollover restrictions, spousal consent requirements, or taxable withholding rules noted in your pension SPD we must model? Options: Yes, No, Unsure — need SPD review

Tax-Efficient Withdrawal Sequencing and Implementation

• Which account types should be included in withdrawal sequencing (for example: Traditional IRA, Roth IRA, 401(k), taxable brokerage)? Options: Traditional IRA/401(k), Roth IRA/Roth 401(k), Taxable brokerage, Pension distributions, All of the above
• Specify any preferred annual Roth conversion target or maximum dollar amount you would allow for modeling purposes. Options: No conversions, Up to a specific dollar amount (specify below), No limit — model optimal conversions
• Which tax documents will you upload to model withdrawal impacts (for example: Form 1099-R for prior distributions, last two Form 1040s, state tax returns)? Options: Form 1099-R, Last two Form 1040s, State tax returns, K-1s or other pass-throughs
• Identify any planned residency or state tax changes in retirement that we should include in state tax modeling. Options: No residency change planned, Planned move — specify state, Undecided
• Who will execute withdrawal transactions with custodians when the sequence is agreed (you via portal, custodian paperwork, or advisor-assisted transfer)? Options: I will execute online, Paper forms I will sign, Advisor-assisted execution

Investment Portfolio Design and Ongoing Management

• Select the portfolio objective you prefer for retirement assets (for example: income-focused, total-return to support withdrawals, liability-driven matching RMDs). Options: Income-focused, Total-return with withdrawals, Liability-driven / cash-flow matching, Hybrid
• How will you provide current asset allocation: upload recent consolidated statements, list percentage allocation, or request assistance aggregating across custodians? Options: Upload consolidated statements, Provide allocation summary, Request help aggregating accounts
• Are there illiquid holdings or concentrated positions (for example employer stock, private equity, restricted shares) that require special handling? Options: Yes — list below, No
• Select your preferred rebalancing approach for taxable and tax-advantaged buckets. Options: Calendar quarterly, Threshold-based (e.g., 5% drift), Semi-annual, Annual
• Do you want ongoing discretionary portfolio management or advice-only recommendations for implementing trades? Options: Discretionary management, Advice-only (you implement), Hybrid
• Which fee or cost documents should be reviewed when designing the portfolio (custodial fee schedule, mutual fund expense ratios, manager fees)? Options: Custodian fee schedule, Fund expense reports, Manager/advisor fee schedule, All of the above

Required Minimum Distribution Coordination and Execution

• List the retirement accounts with RMD exposure and the custodians holding them.
• Indicate the year RMDs are scheduled to begin for you or your beneficiaries based on current birthdates. Options: RMDs already started, Starting this year, Starting within 1-3 years, Starting after 3 years
• Select the level of service you want for RMDs: calculation only, calculation plus initiation of distributions, or calculation plus tax withholding setup and execution. Options: Calculation only, Calculation + initiation, Full execution with withholding
• Choose distribution delivery method for RMDs: cash to checking, in-kind transfer to brokerage, or direct rollover to another account type. Options: Cash to checking, In-kind transfer, Direct rollover
• What documentation will you retain to confirm RMD completion (for example: Form 1099-R, custodian final statement, confirmation email)? Options: Form 1099-R, Custodian final statement, Transaction confirmation

Healthcare and Medicare Cost Projection and Enrollment Support

• Describe your current health insurance prior to Medicare (for example: employer retiree plan, COBRA, individual market plan). Options: Employer retiree plan, COBRA, Individual market, None
• Would you like Medicare premium, Part B and Part D prescription, and Medigap or Medicare Advantage premium projections included through age 95? Options: Yes, include premium projections, No, exclude premiums, Include premiums and sensitivity for income-related monthly adjustment
• Which health-related documents can you provide: recent Explanation of Benefits (EOB), Summary of Benefits and Coverage, HSA statements, or long-term care policy declarations? Options: EOBs, Summary of Benefits, HSA statements, Long-term care policy
• Who will handle Medicare enrollment tasks when eligible: you, a family member, or with enrollment assistance from our support team? Options: I will enroll myself, Family will enroll, I want enrollment assistance
• Are employer retiree health subsidies or retiree-only networks documented in a benefits notice that we should include in cost modeling? Options: Yes — will upload notice, No subsidies, Unsure — need review
• Which out-of-pocket medical expense thresholds should trigger an alternate withdrawal plan in cash-flow modeling (for example: annual unreimbursed medical > $5,000)? Options: $0-$2,500, $2,500-$5,000, Above $5,000, Specify custom threshold

Estate and Beneficiary Coordination with Counsel

• Do you have existing estate documents to share: last will, revocable trust, durable power of attorney, or advance healthcare directive? Options: Will, Revocable trust, Durable POA, Advance directive, None
• Which account beneficiary designations require review and possible update (IRAs, 401(k)s, life insurance, annuities)? Options: IRAs, 401(k)s, Life insurance, Annuities, All of the above
• Do you have estate counsel we should coordinate with or do you need a referral for document updates? Options: I have counsel — provide contact, I need a referral, I will handle on my own
• Who is authorized to sign or file beneficiary change forms at each custodian (for example: account owner, power of attorney, trustee)? Options: Account owner, Power of attorney, Trustee
• Which custodian forms or affidavit types are required by your accounts to change beneficiaries (for example: beneficiary designation form, medallion signature guarantee)? Options: Beneficiary designation form, Medallion signature guarantee, Notarized affidavit, Varies by custodian

Tax Projection and Proactive Tax-Reduction Strategies

• Select the projection horizon for tax modeling: next 5 years, next 10 years, or lifetime. Options: 5 years, 10 years, Lifetime
• List any large expected taxable events during the projection period (for example: sale of rental property, exercise of stock options, large IRA distributions).
• Which tax-reduction strategies should be modeled if feasible: Roth conversions, tax-loss harvesting, donor-advised fund gifts, or charitable remainder trust? Options: Roth conversions, Tax-loss harvesting, Donor-advised fund, Charitable trust, All of the above
• Which state tax jurisdictions should be included for state-level projection (current state of residence and any planned future state)?
• Do you want proactive coordination and direct file exchange with your tax preparer for execution of tax strategies and year-end tax planning? Options: Yes — we can share with tax preparer, No — I will coordinate separately
• Which supporting tax documents will you upload to support accurate projections (for example: last three Form 1040s, K-1s, Form 5498s)? Options: Last three Form 1040s, K-1s, Form 5498s, Other tax docs

Portfolio Stress Testing and Longevity Scenario Modeling

• Select the stress scenarios to include: sequence-of-returns risk, prolonged low returns, high inflation, or early retirement shock. Options: Sequence-of-returns risk, Prolonged low returns, High inflation, Early retirement shock
• Would you like Monte Carlo simulation run with 10,000 iterations to estimate probability of portfolio success? Options: Yes — run 10,000 iterations, No — use deterministic scenarios
• Choose the success probability threshold you would consider acceptable for plan sustainability (for example: 70%, 80%, 90%). Options: 70%, 75%, 80%, 90%
• Which longevity endpoints should scenarios extend to (select all that apply): age 95, age 100, age 105? Options: Age 95, Age 100, Age 105
• Indicate any historical drawdown periods you want used in stress tests (for example: 2008 global financial crisis, dot-com era, 1970s stagflation). Options: 2008 financial crisis, Dot-com era, 1970s inflation period, All of the above, Custom period

Account Consolidation and IRA/401(k) Rollover Execution

• List the custodians and account numbers you propose to consolidate or roll over (provide custodian names and account types).
• Specify any employer plan restrictions or in-service withdrawal limitations noted in plan documents that could block a rollover. Options: No restrictions, Plan has restrictions — will upload SPD, Unsure — need plan review
• What will define successful completion of consolidation and rollover execution (for example: receiving final statements from origin custodians showing $0 balance and combined balances at receiving custodian)?
• Who will provide transfer authorization: online custodian access, signed rollover paperwork you return, or signed trustee-to-trustee transfer forms? Options: Online custodian access, Signed paperwork I return, Trustee-to-trustee transfer
• Are there expected taxable distributions or withholding events during any rollover that we should model (for example: mandatory 20% withholding on an indirect rollover)? Options: Yes — expect taxable withholding, No — direct trustee-to-trustee planned, Unsure — need custodian rules review

Annual Plan Update and Ongoing Advisory Services

• Select your preferred review cadence for ongoing plan updates. Options: Annual review, Semi-annual review, On major life events only
• Specify the KPI thresholds that should trigger an out-of-cycle review (for example: portfolio drawdown greater than 10% or spending increases over 15%). Options: Portfolio drawdown >10%, Spending increase >15%, Change in tax law, Other

• Master Services Agreement (MSA)
• Statement of Work (SOW)
• Fee Schedule & Consent
• Fiduciary Commitment & Investment Advisory Agreement
• Data Access & Account Aggregation Consent
• Implementation Authorization (Trading & Transfer)
• Payment Authorization (ACH/Credit Card)
• Delivery & Review Timeline Agreement
• Privacy & Data Processing Addendum (DPA)
• Termination & Refund Policy

• Go-live Health Check (weeks 1-4)
• First Measurement Review (weeks 4-10)
• Acceptance Gate — 90-Day Outcome Review
• Ongoing Quarterly Plan Review

• Owner to close or change the status of each open issue in the tracker and report progress at the next quarterly review.
• Restate Planning Scope acceptance criteria
• Produce a documented acceptance decision against every numeric criterion recorded in Planning Scope, with any failed items accompanied by a remediation plan.
• If accepted, confirm the plan version that is accepted and the buyer signatory who documents acceptance.
• For any failed criteria, assign owners and deadlines that will close the loop before the next quarterly review.
• Buyer to sign and return the acceptance record or conditional-acceptance document within 5 business days.
• Seller to produce a remediation timetable for any failed criteria and schedule a re-test date.
• Record the accepted plan version in the plan repository and note the acceptance date and signatory.
• Review actual cash flows versus plan
• Confirm whether actual withdrawals and portfolio performance keep the plan on track relative to Planning Scope targets, or document required adjustments.
• Ensure all RMDs and tax actions due in the next 90 days have assigned owners and execution dates.
• Maintain a specific backlog with prioritized enhancement requests and clear owners and timelines.
• Seller to update the tax projection and withholding recommendations for the upcoming distribution cycle.
• Buyer to confirm any discretionary withdrawals planned in the next quarter so cash-flow forecasts can be updated.
• Reconfirm Planning Scope acceptance criteria
• All accounts and income sources required by Planning Scope are either confirmed aggregated or a remediation path is assigned.
• Open issues list created with owners and target resolution dates.
• Communication and access channels verified so future data updates will flow without manual intervention.
• Seller to supply a remediation checklist for any failed aggregations with required documents and deadlines.
• Buyer to provide any missing custodian credentials, recent statements, or beneficiary confirmations within the agreed timeline.
• Create an issues tracker entry for each blocker and circulate to both teams within 24 hours.
• Present first measurement results vs Planning Scope targets
• Determine whether the probability of income sufficiency and projected first-year withdrawal rate are on track relative to Planning Scope targets.
• Document the root cause for any metric shortfall and agree concrete corrective actions with dates.
• Confirm next re-run of stress tests with updated assumptions and who will deliver it.
• Seller to re-run the retirement stress test with agreed assumption updates and deliver results within 10 business days.
• Buyer to confirm Social Security claim timing preferences and any pension election decisions needed to finalize tax modeling.
• Update the plan's assumption log (inflation, expected returns, longevity) and circulate to the buyer for sign-off.
• Present 90-day outcome data per criterion
• Review tax projection and Social Security claiming impact
• Validate account aggregation and data accuracy
• Update plan probability and portfolio performance
• RMD and tax coordination
• Confirm access and communication channels
• Document pass/fail for each criterion and decision
• Diagnose root causes for any gaps
• Open issues and enhancement backlog review
• Review early adoption signals and usage
• Agree corrective actions and timeline
• Agree remediation items and resolution timeline
• Agree adjustments and next quarter actions
• Surface blockers and assign remediation