Getting Comfortable — Tell Us About You

• What brings you to retirement planning today? In a sentence or two, what's the one thing you want solved?
• Which of these best describes your household right now? Options: Single, Married/partnered (both involved), Married/partnered (one primary decision-maker), Divorced/widowed, Other
• What are you and your partner's ages? (list both if applicable)
• When do you expect or hope to stop working (or have you already retired)? Options: Already retired, Within 1 year, 1–3 years, 4–7 years, 8–10+ years, Unsure
• Who will need to be involved in financial decisions or sign paperwork for your plan? Options: Self, Spouse/partner, Adult child, Power of attorney/trustee, Existing advisor, Other
• Roughly how much investable assets do you expect to use for retirement (excluding primary residence)? Options: <$500k, $500k–$1M, $1M–$2M, $2M–$5M, >$5M, Prefer not to say

What Keeps You Up at Night About Money?

• If you had to bet on one thing that could derail your retirement income, what would it be?
• Which single worry feels most urgent to you right now? Options: Running out of money, Making the wrong Social Security decision, Rising healthcare/long-term care costs, A market crash early in retirement, Unexpected taxes or penalties, Leaving an adequate legacy, Other
• How often does that worry affect your daily life or decisions? Options: Daily, Weekly, Monthly, Rarely, Never
• How long has this been a concern for you? Options: Less than 6 months, 6–24 months, 2–5 years, More than 5 years
• Tell me about a recent moment when this worry surfaced—what happened and how did it make you feel?
• If you could erase one financial worry tomorrow, which would it be? Options: Running out of income, Wrong Social Security choice, Unexpected healthcare costs, Market losses, Tax surprises, Other

How Your Money Actually Shows Up (and Where It Hides Risks)

• What is one account, benefit, or habit you suspect is quietly costing you money or creating risk?
• Which of these account types do you currently hold? (Select all that apply) Options: 401(k)/403(b)/401(a), IRA/Roth IRA, Taxable brokerage, Pension (defined benefit), Deferred compensation/executive plan, Annuity, Health Savings Account (HSA), Cash/savings, Employer stock/significant position, Other
• Do you have a pension with a lump-sum option or only lifetime payouts? Options: Lump-sum option available, Only lifetime annuity option, No pension, Not sure
• Are your accounts consolidated or fragmented across multiple custodians? Options: Mostly consolidated (one or two custodians), Fragmented across many institutions, A few key custodians, Prefer not to say
• Is any single position or asset more than ~20% of your investable assets (e.g., company stock)? Options: Yes — single stock, Yes — sector concentration, No significant concentration, Not sure
• Describe any experience you’ve had managing withdrawals or taking income—what worked and what felt risky?

Decisions That Change Everything — Social Security, Pensions, and Claiming

• Do you realize a single Social Security or pension election could change your household’s lifetime income by tens of thousands—how confident are you in your current choice? Options: Very confident, Somewhat confident, Uncertain — want help, Not confident at all
• At what age are you planning to claim Social Security (or at what age did you claim)? Options: Already claimed, 62, 63–64, 65–66, 67 (Full Retirement Age), 68–70, Unsure
• Do you understand how spousal, survivor, or divorced-spouse benefits may change your household income? Options: Yes — confident, Somewhat — need clarification, No — need explanation, Not applicable
• If you have a pension, were you given options like lump sum vs. lifetime payout, and which direction are you leaning? Options: Lump sum, Lifetime annuity/joint survivor, Undecided — need analysis, No pension, Not sure
• How important is guaranteed lifetime income (pension/annuity) compared with flexibility/liquidity for you? Options: Very important, Somewhat important, Neutral, Prefer liquidity, Unsure
• Share any advice you’ve already received about Social Security or pensions and how you felt about it.

What Would a Comfortable Retirement Actually Feel Like?

• If money were no object, describe a typical day in your ideal retirement—and what about your current plan makes that feel far or near?
• Which of these elements are must-haves in your retirement lifestyle? (Select all that apply) Options: Travel regularly, Maintain current lifestyle spending, Downsize or relocate, Support family/legacy gifts, Pursue part-time work or hobbies, High healthcare flexibility/coverage, Other
• What annual pre-tax income do you believe you’ll need to live comfortably? Options: <$50k, $50–$100k, $100–$150k, $150–$250k, $250k+, Unsure
• How willing would you be to adjust lifestyle spending to increase the certainty your plan lasts? Options: Very willing, Somewhat willing, Reluctant, Not willing, Unsure
• What would 'peace of mind' in retirement look like specifically for you (concrete examples welcome)?
• Do you have legacy or family goals that are non-negotiable (gifts, trusts, education funding)? If so, brief description. Options: Yes — specific plans, Yes — general intent, No, Undecided

Where Are You Ready to Trade for Certainty?

• What would you be willing to give up today—lower returns, less liquidity, or delaying benefits—to materially increase the chance your money lasts?
• Which of these trade-offs are you open to discussing? (Select all that apply) Options: Delay Social Security to age 70, Purchase an annuity for partial lifetime income, Shift to lower-volatility investments, Convert assets to Roth over time, Consolidate accounts for simplicity, Pay for fiduciary planning/advice, Sell or diversify concentrated positions, None of the above
• How comfortable are you with paying for planning or advice if it measurably reduces your risk of running out of money? Options: Very comfortable, Somewhat comfortable, Neutral, Reluctant, Not comfortable
• Would you consider delaying retirement or returning to part-time work to strengthen your income plan? Options: Yes — open to delay, Maybe — prefer flexibility, No — plan to retire as scheduled, Already retired
• Have you ever purchased an annuity or other guaranteed-income product? If yes, how well did it meet your needs? Options: Yes — satisfied, Yes — not satisfied, No, Considering
• What is the largest, realistic change you could commit to in the next 12 months to improve certainty (describe briefly)?

Making This Real — Documents, Timeline, and the People Involved

• If we produced a clear, actionable plan tomorrow, what is the real chance you could act on it within 90 days—and what would help or stop you?
• Which documents can you share right away to help us build a full plan? (Select all that apply) Options: Recent 401(k)/IRA statements, Pension benefit statement, Most recent tax return (Form 1040), Social Security statements, Investment/brokerage statements, Insurance policies (life/long-term care), Estate documents (will/trust/POA), None/Prefer not to share
• How soon would you like a first draft of your retirement income plan? Options: Within 2 weeks, 2–4 weeks, 1–2 months, Longer than 2 months, Unsure
• Who else must approve or be involved before implementing recommendations? (Select all that apply) Options: Spouse/partner, Adult child, Existing advisor/CPA, Attorney/executor/trustee, Financial power of attorney, Other, No one else
• Preferred way for us to receive sensitive documents and deliver updates? Options: Secure client portal, Encrypted email, Postal mail, Phone call, In-person meeting
• Are there any legal, health, or cognitive limitations that could affect decisions or signatures? If yes, please describe. Options: Yes — I will describe, No, Prefer to discuss in person
• What's the single most important thing we could do in our first meeting that would make you feel understood and ready to move forward?

• Data Confirmation & Current State Alignment
• Baseline Cash-Flow Scenario Walkthrough
• Optimization Workshop — Social Security, Pension & Withdrawal Sequencing
• Stress Tests, Sensitivity Analysis & Validation

• Advisor: Schedule the Plan Scope & Deliverables meeting and deliver the timeline and checklist for onboarding and implementation.
• Client: Confirm priorities among levers (e.g., maximize guaranteed income vs. liquidity for legacy) to guide the optimization session.
• Advisor: Run and save the baseline report with charts and key metrics for distribution after the meeting.
• Re-state Problem, Consequence & Desired Future State
• Select a recommended strategy or narrow to a final choice for Social Security, pension, and withdrawal sequencing.
• Demonstrate how the recommended strategy produces the defined future state (income sustainability and tax control).
• Force client validation of trade-offs and obtain explicit directional consent to proceed to written plan preparation.
• Advisor: Produce a detailed scenario report for the chosen strategy including tax projection and cash-flow charts.
• Client: Sign off on directional decisions (Social Security age, pension election preference, withdrawal sequencing rule) so advisor can finalize recommendations.
• Advisor: Identify any additional paperwork needed for pension elections or account conversions and send checklist.
• One-Sentence Future State Confirmation
• Confirm the recommended strategy is robust or identify exactly what adjustments are required under stress.
• Agree on concrete contingency triggers and a monitoring cadence tied to the plan.
• Obtain final client authorization to proceed to the written retirement income plan and implementation phase.
• Advisor: Finalize the stress-test appendix and contingency trigger framework to include in the written retirement income plan.
• Client: Provide final signatures/authorizations or confirm any outstanding preferences needed to implement pension or Social Security elections.
• Introductions & Objectives
• Produce a crystal-clear, one-sentence current-state diagnosis based on verified client data.
• Surface and quantify at least one concrete financial consequence (shortfall, tax cost, or sequence risk).
• Identify and assign any missing inputs required to run accurate scenarios.
• Agree on scope and timing for the next Scenario Walkthrough meeting.
• Client: Upload missing account statements, pension election docs, and the most recent tax return.
• Advisor: Build and circulate a baseline cash-flow model and a one-sentence current-state summary before the next meeting.
• Advisor: Prepare a list of decision knobs to test (Social Security ages, pension options, withdrawal order, Roth conversion ranges).
• Recap Current State & Goals
• Ensure the client clearly understands expected outcomes under the baseline scenario.
• Identify the highest-impact decision levers (SS timing, pension election, withdrawal order) that materially change outcomes.
• Obtain client confirmation on which levers they want to explore in the optimization workshop.
• Advisor: Prepare at least three alternative scenarios showing the impact of key levers (delaying Social Security, alternate pension elections, different withdrawal sequences).
• Downside Stress Tests
• Present Three Candidate Strategies
• Baseline Cash-Flow Timeline
• Review of Client Inputs
• Sensitivity Analysis
• Social Security Baseline Analysis
• Live Modeling & Client-Directed Tests
• Current-State Diagnosis (one sentence)
• Contingency & Trigger Plan
• Consequence Summary
• Trade-off Discussion Linked to Client Goals
• Pension & Other Income Defaults
• Decision & Next Steps
• Confirm Prep for Scenario Walkthrough
• Initial Tax & Withdrawal Sequencing Notes
• Validation & Next Steps to Written Plan

• Implement income-focused investment portfolio
• Execute Roth IRA conversions
• Initiate and complete Social Security application
• Purchase immediate or deferred annuity contracts
• Set up bond ladder for scheduled income
• Roll over pension or 401(k) to IRA
• Establish automatic withdrawal and cash sweep rules
• Coordinate Medicare and Medigap/Part D enrollments
• Process Required Minimum Distribution transfers
• Execute Qualified Charitable Distributions (QCDs)
• Fund and activate Health Savings Account catch-ups
• Retitle accounts and update beneficiary designations

Implement income-focused investment portfolio

• Which accounts should be considered when building the income-focused portfolio? Options: Taxable brokerage, Traditional IRA/401(k), Roth IRA, Trust accounts, Annuity contracts, Other
• What is the target recurring income need (monthly or annual) you want the portfolio to help provide?
• Which allocation objective should guide construction? Options: Conservative (20-40% equities), Moderate (40-60% equities), Income-first with fixed income and alternatives, Total return with income overlay, Custom — advisor to recommend
• What is your tolerance for sequence-of-returns risk and principal drawdown to secure income? Options: Low (preserve principal), Moderate (accept some drawdown), Higher (prioritize income), Unsure — need advisor guidance
• What liquidity needs should the portfolio accommodate over the next 1-5 years (amounts or months of expenses)? Options: <3 months, 3-6 months, 6-12 months, >12 months, Specify amounts below
• Are there restrictions, screening preferences, or prohibited investments (e.g., ESG, sin stocks, employer securities)? Please list.
• Do you require active rebalancing, tax-loss harvesting, or cash-management overlays for the income portfolio? Options: Active rebalancing, Tax-loss harvesting, Cash sweep & liquidity overlay, Passive/index approach, Combination

Execute Roth IRA conversions

• Do you have tax-deferred accounts eligible for conversion (Traditional IRA, 401(k), etc.)? Options: Yes, No, Not sure — need review
• What is your expected taxable income (MAGI) this calendar year? Options: Less than $100,000, $100,000–$199,999, $200,000–$299,999, $300,000+, Prefer not to say
• What conversion timeline do you prefer? Options: Single-year full conversion, Multi-year plan (3 years), Multi-year plan (5+ years), Opportunistic/when tax-efficient
• What is the maximum incremental tax you are willing to pay in a single year to perform conversions?
• Do you have carryforward losses, business deductions, or unusually low-income years that could offset conversion taxes? Options: Yes, No, Not sure — need review
• Which accounts would you like to source conversion funds from or convert into (select all that apply)? Options: Traditional IRA, 401(k)/403(b), Taxable brokerage (to pay tax), Rollover IRA, Other
• Do you want advisor assistance to model long-term tax outcomes and the impact on RMDs and Medicare premiums? Options: Yes, No

Initiate and complete Social Security application

• Have you or your spouse already filed for Social Security benefits? Options: Neither filed, Primary applicant filed, Both filed, Other / partial
• What are the birth years (or ages) for you and your spouse to confirm earliest eligibility and FRA?
• What is your primary objective for claiming? Options: Maximize lifetime benefit, Maximize spousal/survivor benefit, Immediate income due to need, Defer for higher benefit, Undecided — want advisor analysis
• Are there potential offsets (pension, government service subject to WEP/GPO) that could reduce or complicate benefits? Options: Yes — government pension, Yes — non-covered earnings, No, Not sure — need review
• Do you want the advisor to prepare claiming illustrations, survivor scenarios, and breakeven analyses before applying? Options: Yes, No
• Do you need direct assistance completing the SSA application (online submission / representative payee / POA)? Options: Yes — full assistance, Partial assistance (documents only), No — will self-submit
• Are there health, employment, or longevity considerations that should alter the recommended claiming strategy? Please describe.

Purchase immediate or deferred annuity contracts

• Are you considering an annuity? If yes, which type(s)? Options: Immediate income annuity, Deferred income annuity (DIA), Fixed indexed annuity, Variable annuity with income rider, Not considering / undecided
• When would you want income to begin from an annuity? Options: Immediate (within 12 months), 1–5 years, 5+ years, TBD — model options
• Which annuity features are important to you? Options: Guaranteed lifetime income, Inflation protection / COLA, Period certain, Return of premium / death benefit, Liquidity / withdrawal rider
• What percentage of investable assets are you willing to allocate to annuities? Options: <5%, 5–15%, 15–30%, 30%+
• What surrender period or liquidity constraints are acceptable? Options: Need liquidity (no long surrender), Short surrender (1–3 yrs), Moderate (4–8 yrs), Long surrender acceptable (9+ yrs)
• Do you have carrier preferences or companies to avoid (list names)?
• Do you want advisor assistance with carrier comparison, illustrations, and underwriting coordination? Options: Yes — full support, Yes — illustrations only, No — self-manage

Set up bond ladder for scheduled income

• Do you want a bond ladder to match scheduled income needs? Options: Yes, No, Unsure — want advisor recommendation
• What ladder horizon do you prefer? Options: 1–3 years, 3–5 years, 5–10 years, 10+ years
• Which credit-quality / yield trade-off do you prefer? Options: High quality (Treasury/AAA/AA), Intermediate credit (A/BBB), Municipal bonds for tax-efficiency, Yield-focused (including lower credit)
• What percent of your portfolio should the ladder represent? Options: <10%, 10–25%, 25–50%, 50%+
• Which custodial or account types should hold the ladder? Options: Taxable brokerage, Traditional IRA, Roth IRA, Trust account, Other
• List the known future cash needs (amounts and approximate dates) you want matched to the ladder.
• Do you prefer ladder rebalancing/rollover automation when bonds mature? Options: Yes, No, Manual review each maturity

Roll over pension or 401(k) to IRA

• Do you have a pension or 401(k) you are considering rolling over? Options: Yes — 401(k), Yes — defined benefit pension, No, Not sure — need plan documents reviewed
• What is the primary reason to consider rollover? Options: Consolidation, Greater investment choices, Lower fees, Access Roth conversion strategies, Maintain employer plan benefits
• Does the plan offer in-plan guarantees, employer stock, or special tax treatments (e.g., Net Unrealized Appreciation)? Options: Yes, No, Not sure — need review
• Are there penalty-free distribution windows or age-based exceptions to consider? Options: Yes, No, Not sure — need review
• Please provide plan details: provider, approximate balance, plan rules, and any lump-sum options (free response).
• Desired timing for rollover execution? Options: Immediate, Within 30 days, Within 3 months, Coordinate with other actions (e.g., Roth conversion)
• Do you want advisor to prepare comparison (keep vs roll vs annuitize) with projected outcomes? Options: Yes, No

Establish automatic withdrawal and cash sweep rules

• Do you want recurring automatic withdrawals established for retirement income? Options: Yes — recurring withdrawals, No — ad hoc withdrawals, Partially — some recurring, some ad hoc
• Preferred withdrawal frequency? Options: Monthly, Quarterly, Annually, As-needed
• Which source priority should the sweep follow (taxable first, tax-deferred first, Roth first, custom sequence)? Options: Taxable first, Tax-deferred first, Roth first, Custom sequence — specify below
• Specify the dollar amount or percent of portfolio for each recurring withdrawal (e.g., $X/month or Y% annually).
• What cash buffer should be maintained (months of expenses) in sweep account? Options: 0–3 months, 3–6 months, 6–12 months, 12+ months
• Which bank or account should swept cash be deposited into (account details or institution)?
• Do you require tax withholding, estimated tax payments, or coordination with payroll for withdrawals? Options: Yes — set withholding, Yes — coordinate estimated payments, No

Coordinate Medicare and Medigap/Part D enrollments

• What is your Medicare eligibility/timeline status? Options: Not yet within 6 months, Within 6 months, Already enrolled, On employer coverage
• Which current coverage do you have or expect to keep (Original Medicare, Medicare Advantage, employer retiree plan, Medigap + Part D)? Options: Original Medicare only, Medigap + Part D, Medicare Advantage, Employer retiree plan, None / undecided
• Do you want advisor support to compare Medigap plans, Part D formularies, and Medicare Advantage networks? Options: Yes — full comparison, Yes — high level advice only, No — self-manage
• What are your primary concerns when choosing a plan? (select all that apply) Options: Provider network access, Prescription drug coverage, Premium cost, Out-of-pocket maximum, Travel coverage, Other — specify
• Please list current prescription medications and approximate annual cost to assess Part D needs.
• Do you have employer or retiree benefits that coordinate with Medicare and require special enrollment timing? Options: Yes, No, Not sure — need review
• What timeline do you want for enrollment assistance (immediate, 30 days, 90 days)? Options: Immediate, Within 30 days, Within 90 days, TBD

Process Required Minimum Distribution transfers

• Are you currently subject to RMDs or approaching your first RMD year? Options: Already subject to RMDs, First RMD upcoming, Not yet subject, Unsure — need calculation
• What is the estimated RMD amount and the account(s) it applies to?
• How would you like RMDs handled? Options: Distribute to checking/savings, Reinvest into taxable account, Use as QCDs to charity, Consolidate/rebalance before distribution
• Do you want automated RMD calculations and transfers set up annually? Options: Yes — auto schedule, No — manual each year, Review first year then automate

• Engagement Agreement
• Statement of Work (SOW)
• Fee Schedule & Authorization
• Investment Management Agreement (IMA)
• Trading Authorization / Limited Power of Attorney
• Custody & Account Transfer Authorization
• Billing & Payment Authorization
• Service Cadence & Communication Plan
• Privacy Notice & Form ADV Acknowledgement
• Conflict of Interest & Third-Party Disclosure
• Consent to Electronic Delivery & E-Signature
• Client Data & Document Authorization
• Authorized Decision-Makers & Signatories

• Annual Retirement Income Plan Review (Solution Experience)
• RMD Calculation & Tax Coordination Session
• Quarterly Check-in (Performance & Cashflow Variance)
• Shared Channel Triage & Enhancements Review
• Annual Account Health & Estate Documentation Check

• Establish a transparent update cadence within the shared channel for all in-flight items.
• Advisor to notify CPA and send modeling assumptions and scenarios used in recommendations.
• Opening & Key Changes
• Ensure no material deviations from plan that require immediate remediation.
• Assign and track owners for short-term items and operational tasks.
• Maintain client confidence through transparent performance and spending communication.
• Advisor to rebalance or implement tactical changes agreed in meeting and send trade confirmations.
• Client to confirm any one-time withdrawals or transfers and provide authorization.
• Advisor to update cashflow dashboard and circulate a brief variance report.
• Review Open Items from Shared Channel
• Resolve or schedule all items in the shared channel with clear owners and deadlines.
• Ensure clients understand the consequence of outstanding items so prioritization matches their needs.
• Pre-work Confirmation
• Advisor to convert prioritized items into tracked tasks in CRM/project tracker and notify client of assignments.
• Client to provide any clarifying information or approvals required to complete assigned tasks.
• Advisor to post status updates in the shared channel at agreed intervals until closure.
• Document Inventory
• Ensure estate and account documentation supports the retirement income plan and client wishes.
• Identify and prioritize any legal or insurance actions to reduce future distribution friction or tax surprises.
• Assign responsibilities for obtaining missing documents or completing updates.
• Advisor to provide a checklist of required documentation and recommended referrals to estate attorney or insurance specialist.
• Client to execute beneficiary or titling changes and return confirmations to advisor.
• Advisor to update client file with final documents and note secure access protocols.
• Confirm the client's current financial state with documented inputs and acknowledge any material changes.
• Make explicit the financial consequence of taking no action or following alternate choices.
• Demonstrate, with client-specific scenarios, that recommended plan adjustments achieve the defined future state.
• Obtain clear client decisions on any recommended elections or implementations.
• Schedule and assign implementation tasks with dates and owners.
• Advisor to update cash-flow model with any agreed changes and circulate a one-page summary within 5 business days.
• Client to provide missing documents (updated statement(s), pension paperwork, recent tax return) within 7 days if not already provided.
• If benefit election chosen, advisor to prepare execution steps and timeline and confirm with client and custodian/trustee.
• Schedule the following quarterly check-in on the client's calendar.
• Pre-meeting Tax Packet Review
• Ensure accurate RMD calculations and timing that minimize tax impact while meeting regulatory requirements.
• Identify and approve any Roth conversions, QCDs, or other tax strategies for the year.
• Confirm coordination and communication protocol with the client's CPA for filings and projections.
• Advisor to generate and share RMD worksheet and recommended execution plan within 3 business days.
• Client to authorize distributions/conversions via custodian forms and copy advisor on confirmations.
• Current State Snapshot
• Account Titling & Beneficiary Consistency
• Impact & Consequence Assessment
• Portfolio Performance vs Assumptions
• RMD Calculation & Timing
• Tax-Efficient Alternatives
• Consequence Analysis
• Cashflow Actuals vs Plan
• Insurance & Long-Term Care Review
• Decision & Prioritization
• Updated Future-State Projection
• Action Plan for Gaps
• Coordinate with CPA / Tax Advisor
• Assign Owners & Close Criteria
• Immediate Action Items
• Confirm Next Touchpoint
• Communications Protocol
• Signoffs & Execution Plan
• Confirm Storage & Access Protocols
• Walkthrough of Updated Cash-Flow Scenarios
• Validation & Decision Points
• Next Steps & Timeline