Five Questions That Can Lead to a Better Retirement Conversation
The Retirement Protection Checkup is designed to help financial professionals facilitate broader retirement planning discussions—from accumulation alone to the income needs, risks and priorities clients may face as retirement approaches.
Many retirement conversations begin with a familiar question: How much have you saved?
It is an important question. But as clients approach or enter retirement, other questions become increasingly relevant.
How much of their income will be predictable? What happens if markets decline at an inconvenient time? How could changing interest rates affect their plans? How long might retirement last? And what role should different portions of their savings play?

Oceanview’s Retirement Protection Checkup is designed to help financial professionals open those conversations.
The key is how you use it.
The Checkup is a conversation starter—not a score, diagnosis or indication that a particular financial or insurance product is appropriate. A “Partly” or “Not yet” response does not automatically signal a problem. Instead, it may identify an area the client wants to understand more clearly.
That distinction can help turn five simple questions into a more meaningful retirement-planning conversation.
Start with the question. Then listen.
The Checkup focuses on five areas:
- Predictable income
- Market resilience
- Interest-rate uncertainty
- Income that lasts
- A balanced role for every dollar
Rather than immediately connecting an answer to a solution, use each question as an opportunity to learn more about the client’s goals, assumptions and priorities.
A simple approach is:
ASK. Use the Checkup question as written.
LISTEN. Pay attention to questions, assumptions and competing priorities in the client’s response.
CLARIFY. Ask a follow-up question to better understand the client’s circumstances before discussing solutions.
CONNECT. Summarize what you heard and ask permission to explore the client’s current approach and relevant alternatives.
Here is how that can work in practice.
1. Predictable income
Checkup question:
Do you know how much of your expected retirement income is predictable and how much may change from year to year?
The answer may lead to a broader discussion about Social Security, pensions, withdrawals and other anticipated sources of retirement income.
Listen for whether the client understands which sources are predictable and which may vary. It may also be useful to explore how essential expenses relate to those income sources.
A natural follow-up might be:
“Which expenses would you most want covered by predictable income?”
The objective is not to assume an income solution is needed. It is to better understand how the client thinks about income planning and the relationship between essential expenses and more predictable income sources.
2. Market resilience
Checkup question:
Could your plan continue to cover essential expenses during a prolonged market decline without forcing an unwanted change in strategy?
Clients may have thought extensively about long-term market growth without spending as much time considering how withdrawals and spending might work during a downturn.
Listen for questions about how essential expenses would be covered, whether near-term spending depends on assets that fluctuate with the market, or whether a decline could change the timing of planned withdrawals.
Consider asking:
“What would you most want to avoid changing if markets declined early in retirement?”
That can lead to a broader discussion of liquidity, withdrawal sequencing and the possible role of different asset types and risk-management approaches —without assuming that any particular approach is appropriate.
3. Interest-rate uncertainty
Checkup question:
Have you considered how changing interest rates could affect your savings, reinvestment decisions and income plan?
Interest rates create a different kind of uncertainty.
A client may have CDs, bonds or other assets maturing at particular points in time. They may be weighing the value of rate certainty against flexibility and liquidity. Or they may simply be unsure how future rate changes could affect their strategy.
A useful follow-up is:
“How important are rate certainty, liquidity and flexibility within this part of your plan?”
The response can help you better understand the client’s time horizon, liquidity needs and how much certainty they value before evaluating available alternatives.
4. Income that lasts
Checkup question:
Have you considered how long your retirement income may need to last—including the possibility of living longer than expected?
Longevity can affect many elements of a retirement plan.
Listen for whether the client has considered a specific longevity assumption, whether a spouse or other household member could have different future income needs, and whether later-life expenses warrant additional discussion.
One way to move the conversation forward is:
“How would the plan need to work if retirement lasted 25 or 30 years?”
The goal is not to predict lifespan. It is to understand how the client is thinking about longevity, survivor needs and available income options.
5. A balanced role for every dollar
Checkup question:
Have you decided how much of your savings should be available for near-term needs, positioned for growth, allocated to address different levels and types of risk, or used to support income?
This may be one of the most useful questions in the Checkup because it moves the conversation away from treating all retirement assets as if they have the same job.
Listen for whether the client can clearly describe the purpose different portions of savings are intended to serve.
Are emergency reserves and near-term spending needs accounted for separately? How does the client think about liquidity versus growth? What role do different types of risk and income needs play?
You might ask:
“How would you like different portions of your savings to support liquidity, growth, risk management and income needs?”
That can help establish a more intentional framework for discussing asset roles and tradeoffs.
Make the transition without making the leap
The most important part of the process may be what happens after the five questions.
A client expresses uncertainty about an area of the plan. It can be tempting to move immediately from that concern to a potential solution.
Instead, slow the transition down.
Reflect:
“What I am hearing is that [topic] is an area you would like to explore further. Is that accurate?”
Prioritize:
“Of the areas we discussed, which would you most like to understand more clearly?”
Ask permission:
“Would it be helpful to review your current approach and relevant alternatives for that area?”
Then establish what the next conversation will consider: the client’s goals, needs, financial circumstances, liquidity needs, time horizon, benefits, limitations, guarantees, costs and relevant alternatives.
That additional discovery is important because a Checkup response alone does not indicate a problem, a recommendation, or the appropriateness of any product or strategy.
When the conversation turns to annuities
An annuity may be one option to consider as part of a broader retirement strategy, depending on the client’s individual circumstances.
Depending on the contract, an annuity may provide features such as certain forms of protection from market losses, interest-crediting guarantees, tax-deferred accumulation and income options, subject to the terms of the contract.
But the features are only part of the discussion.
The Retirement Protection Checkup and the discussion it prompts are educational and exploratory in nature. They are not a substitute for, and should not be used to satisfy, any suitability, best-interest or other review required in connection with an annuity recommendation or sale.
If the conversation progresses to consideration of an annuity, the financial professional must separately complete the applicable fact-finding and suitability or best-interest review required by law, regulation and company procedures. That review may include, among other required information, the client’s:
- Goals and income needs
- Financial circumstances
- Liquidity needs
- Time horizon
- Existing retirement strategy
- Relevant alternatives
A response to the Checkup—or information gathered during the Checkup conversation—should not, by itself, be treated as establishing that an annuity is suitable, in the client’s best interest or otherwise appropriate.
It is equally important to discuss limitations and tradeoffs, including applicable surrender charges, possible market value adjustments, restrictions on access to funds, costs and contract-specific considerations.
Better questions can lead to better conversations
The purpose of the Retirement Protection Checkup is not to lead every client to the same conclusion.
It is to give financial professionals a straightforward way to move beyond an accumulation-only conversation and better understand how clients are thinking about the risks, needs and priorities that can accompany retirement.
Five questions can uncover assumptions.
Follow-up questions can clarify priorities.
And a thoughtful conversation can help financial professionals evaluate the client’s current strategy and relevant alternatives based on their individual circumstances.
Put the Checkup to work
Use the Retirement Protection Checkup with clients, and keep the Retirement Protection Conversation Guide nearby for follow-up questions, listening cues and transition language.
For financial professional use only. Not for use with the general public as a standalone product recommendation.This material is intended as a general educational and conversation-planning resource and does not replace a complete fact-finding, suitability or best-interest review. Responses to the Retirement Protection Checkup alone do not indicate whether any particular financial or insurance product is appropriate.
The Harbourview MYGA (Generic Policy Form ICC19 OLA SPDA) and Harbourview FIA (Generic Policy Form ICC19 OLA FIA) are single premium deferred annuities. May not be available in all states.
OCEANVIEW ANNUITIES ARE PRODUCTS OF THE INSURANCE INDUSTRY AND NOT GUARANTEED BY ANY BANK NOR INSURED BY THE FDIC OR NCUA/NCUSIF OR ANY OTHER FEDERAL GOVERNMENTAL AGENCY. MAY LOSE VALUE. NO BANK/CREDIT UNION GUARANTEE. NOT A DEPOSIT. MAY ONLY BE OFFERED BY A LICENSED INSURANCE AGENT. GUARANTEES ARE SUBJECT TO THE CLAIM PAYING ABILITY OF THE ISSUING INSURANCE COMPANY.
Annuities issued by Oceanview Life and Annuity Company, 1331 17th Street, Suite 1050, Denver, CO 80202. In California, doing business as Oceanview Life and Annuity Insurance Company www.oceanviewlife.com.
Annuities are generally designed as long-term retirement solutions and have certain limitations. They are generally not intended to replace emergency funds, serve as income for day-to-day expenses, or support short-term savings goals. Please refer to the contract for complete details, including features, limitations, and charges.
A.M. Best Rating as of February, 11, 2026, is subject to change. A (Excellent) rating is third highest of fifteen possible rating classes for financial strength. The outlook assigned to these Credit Ratings is stable.
As each client and prospective client’s financial needs differ, care should be taken in making any recommendation to purchase an annuity. Therefore, nothing in this document should be read as investment advice.
Neither Oceanview Life and Annuity Company nor any of its representatives may provide tax or legal advice. Clients should consult their own qualified tax or legal advisors.
Withdrawals in excess of any Free Partial Withdrawal amounts are subject to a Surrender Charge and Market Value Adjustment (MVA). The MVA may have the effect of increasing or decreasing the Surrender Value of the withdrawal depending on the market interest rate changes.
The IRS may impose a penalty for withdrawals prior to age 59 ½. Withdrawals may also be subject to ordinary income tax.
Contracts purchased in an IRA or other tax-qualified plan provide no additional tax-deferral benefit, since they are already afforded tax-deferred status. All annuity features, risks, limitations, and costs should be considered prior to purchasing an annuity within a tax-qualified retirement plan. For non-qualified annuities, tax deferral is not available to corporations and certain other entities.
Rates, renewal caps, and declared interest rates, will always follow contract provisions relative to minimums and maximums stated. Oceanview determines, at its discretion, the rates, renewal caps and, declared interest rates above the contractual minimums that are guaranteed.
