What Questions Should You Ask Before Hiring a Retirement Planner?

A retirement plan involves more than investments alone.
Let's talk about how the different pieces of your retirement plan can work together.

Key Takeaways:

The right questions tell you more than a polished pitch. Before you hand someone your retirement, ask how they work, how they're paid, and whether they're legally required to put you first.
Fee structure and fiduciary status are the two that matter most. How an advisor is paid shapes the advice you get, and whether they're held to a fiduciary duty determines whose interests come first.
A good planner shows you a process. Look for someone who can walk you through how they'll build, test, coordinate, and update your plan, rather than just manage investments.

Choosing who helps you plan your retirement is one of the more important financial decisions you’ll make, and it’s easy to pick based on a good first impression. A confident pitch and a nice office don’t tell you much about how someone actually works, though. The right questions do.

The questions below are the ones we’d want a family member to ask before hiring any retirement planner, us included. They cut through the marketing and get at what matters: what you’ll get, how the advisor is paid, whether they’re obligated to act in your interest, and how they’ll build and manage your plan. Ask these before you commit.

What Retirement Planning Services and Deliverables Will You Actually Provide?

“Financial planning” means very different things at different firms. For some, it’s really just investment management with a plan attached. For others, it’s a full retirement strategy that touches every part of your financial life. You want to know which one you’re getting before you sign on.

Ask what a complete plan includes and what you’ll actually walk away with. A thorough retirement plan should cover your income strategy, investments, taxes, healthcare, and estate or legacy planning, and it should produce something concrete: a written plan you can follow, rather than just a portfolio and a handshake.

At Goldstone, our planning covers all of those areas together, income, investments, taxes, healthcare, and legacy, because in retirement they’re deeply connected, and a plan that handles them in isolation tends to leave gaps.

Will You Act as a Fiduciary Whenever You Give Me Advice?

This may be one of the most important questions on the list. Investment advisers owe their advisory clients a fiduciary duty under federal law, including duties of care and loyalty. Other financial professionals may operate under different standards depending on how they work with their clients. You should ask the professional to explain the standard that applies to your relationship, any conflicts of interest that may affect their recommendations, and whether they will acknowledge their fiduciary status in writing when providing investment advice.

For our part, Goldstone is an independent advisory firm bound by a fiduciary duty to you. That means two things we take seriously: a duty of loyalty, putting your interests above our own and providing full and fair disclosure of material conflicts, and a duty of care, bringing diligence and skill to the advice we give.

How Are You Paid, and What Will I Pay in Total?

How an advisor gets paid potentially shapes the advice they give, so get the full cost picture, well beyond the headline fee. Ask them to walk you through every way they and their firm earn money from you. The pieces to pin down:

Fee-based advisory fees: Many advisors charge a percentage of the assets they manage for you. Ask what the rate is, whether it drops as your balance grows, and what services that fee actually covers.
Hourly or flat planning fees: Some advisors charge by the hour or a flat fee for building a plan, separate from managing investments. This can make sense if you mainly want a plan rather than ongoing management, so ask which model they use.
Insurance or product compensation: If an advisor earns commissions from annuities, insurance, or other products, that's worth knowing, since it can influence what they recommend. Ask directly whether they receive any commissions and, if so, on what.
Investment and account expenses: Beyond the advisor's fee, the funds and products in your portfolio carry their own costs. These expense ratios and account fees come out of your returns, so ask for an estimate of the total, all-in cost.
Exit and liquidity costs: Some products, certain annuities especially, charge steep penalties if you need your money early. Ask whether anything they'd recommend locks up your money or charges a surrender fee, and for how long.
A written total-cost comparison: Ask for the full annual cost, in dollars and percentages, in writing. A good advisor will happily put it on paper. If someone stays vague about what you'll pay in total, treat that as an answer in itself.

What Retirement Planning Experience and Qualifications Do You Bring?

Retirement planning is its own discipline. Someone who’s great at growing wealth for 40-year-olds isn’t automatically the right fit for turning savings into 30 years of income. Ask specifically about their experience with retirees and pre-retirees like you.

Credentials can help, though they aren’t the whole story. Designations like CFP ® (Certified Financial Planner) signal training and a code of conduct. More telling is whether the advisor regularly handles the situations you’ll face: Social Security timing, tax-efficient withdrawals, healthcare and long-term care, and estate planning.

It’s also fair to check their background. You can look up an advisor’s or firm’s registration, experience, and any disciplinary history through public records before you ever meet.² And ask who you’ll actually be working with day to day, since at some firms the person who sells you is not the person who serves you.

Goldstone has focused on retirement planning for families in the Chicago area for over two decades, so the questions retirees bring us are ones we work through every day.

How Will You Build and Test My Retirement Plan?

A good planner has a process and can explain it. Vague reassurance, the “don’t worry, we’ll take care of it” kind, is a red flag. You want to hear the actual steps: how they’ll turn your savings into income, how they’ll pressure-test the plan, and how the pieces fit together.

Ask them to walk you through how they’d build your plan and, just as important, how they’d stress-test it against things like a market downturn, higher inflation, or a longer-than-expected retirement. The two questions below get at the heart of it.

Our own process, the Goldstone Retirement Roadmap, works in three stages: discover, evaluate, and plan, so you can see how we move from understanding your situation to building and testing a strategy around it.

How Will You Turn My Resources Into a Retirement Income Strategy?

This is the core of retirement planning: turning what you’ve saved into income that lasts. A strong answer covers how they’ll handle each of these:

Define the spending need: They should start with what your retirement actually costs, then work out how much your portfolio needs to provide after your other income. Everything else builds on this number.
Map the income timeline: A good plan lays out when each income source starts – Social Security, pensions, withdrawals – so you can see how the pieces come online over time and where any gaps appear.
Plan portfolio withdrawals: Ask how they'll decide which accounts to draw from and in what order, since a thoughtful withdrawal strategy can stretch your money and lower your lifetime taxes.
Test retirement risks: The plan should be stressed against the big threats, a rough market early on, inflation, and a long life, to confirm it holds up when conditions aren't ideal.
Prepare for survivor changes: A solid plan considers what happens when one spouse passes away, as income and taxes can shift significantly for the survivor. Ask how they build that into the strategy.

How Will You Coordinate the Rest of My Financial Life With That Income Strategy?

Income is the center, but a retirement plan that ignores everything around it leaves value on the table. Ask how they’ll connect the other pieces:

Align investments with retirement spending: Your portfolio should be built around your income needs and timeline, with stability for near-term spending and growth for the long haul, rather than a one-size-fits-all allocation.
Evaluate taxes across several years: Good planning looks beyond this year's tax bill to your lifetime tax picture, using tools like Roth conversions and smart withdrawal timing. Ask whether they plan taxes proactively or just react at filing time.
Connect healthcare with the financial plan: Medicare decisions, healthcare costs, and the risk of long-term care all belong in the plan. Ask how they account for these, since they're among the biggest wild cards in retirement.
Address major household risks: Insurance, liability, and protecting against a large unexpected loss should be part of the picture, so a single setback doesn't derail everything you've built.
Coordinate estate and legacy decisions: If leaving something behind matters to you, the plan should address how your assets transfer, beneficiary designations, and basic estate documents, ideally alongside your attorney.

How Will You Implement, Monitor, and Update My Plan?

A plan isn’t a one-time document; it has to be put into action and maintained. Ask what actually happens after you sign on: who implements the recommendations, and how quickly.

Then ask how often you’ll meet, who you can call with questions, and how the plan gets updated as things change – markets, tax laws, your health, your goals. Retirement can last 30 years, and a plan that’s never revisited slowly drifts out of date. You want an advisor who stays engaged rather than one who disappears after the sale.

We treat the plan as an ongoing relationship, revisiting it as your life and the rules around you change, because the plan that’s right at 62 usually needs adjusting by 72.

Get Retirement Planning Answers You Can Trust From Goldstone

The right retirement planner should welcome every one of these questions, and answer them clearly. How they respond tells you a lot: whether they’re transparent about costs, obligated to act in your interest, and able to show you a genuine process rather than a sales pitch.

At Goldstone, these are the standards we hold ourselves to. We’re an independent firm bound by a fiduciary duty to put your interests first; we’re transparent about how we’re paid, and our Retirement Roadmap process covers the full picture: your income, investments, taxes, healthcare, and legacy, coordinated together.

If you’re weighing whether an advisor is the right fit, or you’d like to see how we’d answer these questions for your situation, we’d be glad to talk. Schedule a complimentary retirement review with our team, and bring every question on this list.

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Disclosure:

Goldstone Financial Group, LLC (“GFG”) is an investment adviser registered with the U.S. Securities and Exchange Commission. Registration does not imply a certain level of skill or training. This material is provided for informational and educational purposes only. The opinions expressed herein are those of GFG as of the date of publication and are subject to change without notice.

Nothing contained in this material is intended to constitute personalized investment, tax, legal, or insurance advice, or an offer to sell or a solicitation of an offer to buy any security or insurance product. The information presented should not be relied upon as the sole basis for any financial decision and is not intended to address the particular needs, circumstances, or objectives of any individual. Individuals should consult with appropriate financial, tax, legal, or other professionals regarding their specific circumstances.