7 Questions You Should Ask When Interviewing a Retirement Planner
Introduction
Choosing a retirement planner is one of the most important financial decisions you’ll ever make.
But not all planners offer the same services, philosophy, or level of commitment.
The best way to separate a good fit from the rest? Interview 3-5 different advisors, and ask the right questions.
Below you’ll find 7 questions you should ask any retirement or financial planner before hiring them, along with what to listen for, and how Sanders Retirement Planning approaches each area.
We’ve also included links below to both a digital and printable guide you can download for free to help make your interviewing and note-taking experience as convenient as possible, because we know it can feel overwhelming at times.
(Note: Not all these questions will apply to everyone, but they should help you uncover what matters most to you.)
1. How do you incorporate taxes into retirement planning?
Why this matters:
Taxes will likely be one of your largest lifetime expenses. They don’t disappear in retirement—if anything, they get more complicated. Income taxes, capital gains, Medicare premiums (IRMAA), and even how much of your Social Security is taxable all hinge on the amount and type of income you recognize each year.
And beyond federal income tax, there are also state taxes, property taxes, sales taxes, and itemized deduction limits (like the SALT cap) to consider. Many of these aren’t “taxes” in the traditional sense, but they still directly impact your financial picture.
Poor tax decisions, like withdrawing too much from a pre-tax account in a high-income year or missing a Roth conversion window, can be costly.
What to Listen For:
· Does the planner proactively incorporate tax planning into their recommendations?
· Can they give specific, real-world examples (e.g., Roth conversions, withdrawal sequencing, capital gains/loss harvesting)?
· Do they seem knowledgeable and engaged on the topic, or are they just checking a box?
Sanders Retirement Planning’s Approach:
Tax planning is at the heart of every retirement plan we build.
We design strategies focused on minimizing your lifetime tax burden, not just this year’s return. That means we project years (and often decades) into the future to evaluate how today’s decisions will impact tomorrow’s tax brackets, Medicare premiums, and required distributions.
Our goal is to help you withdraw the right money, from the right place, at the right time so your savings go further and last longer. That includes considering strategies like Roth conversions, asset location optimization, tax-efficient withdrawal sequencing, and more.
Key takeaway:
Tax planning should be at the forefront of any financial or retirement plan.
2. What Is Your Investment Approach?
Why This Matters:
Your investment strategy plays a major role in determining not just when you can retire, but how your retirement unfolds.
One of the biggest threats near or early in retirement is sequence of return risk, where poor market performance early on can significantly reduce how long your portfolio lasts. Having a thoughtful, well-structured investment plan can help mitigate that risk and provide stability when you need it most.
What to Listen For:
· A disciplined, evidence-based philosophy, rather than promises of high or guaranteed returns
· Tax-aware portfolio construction, including asset location strategies and efficient withdrawal planning
· Customization based on your personal goals, not just a “set it and forget it” model
· A clear focus on risk management and cost control
Sanders Retirement Planning’s Approach:
We use an evidence-based approach built on:
· Broad diversification across asset classes
· Risk alignment based on your time horizon and comfort level
· Tax-aware strategies to enhance after-tax returns
· Cost-efficiency, using low-cost funds where appropriate
Every portfolio we build is tailored to your specific goals, preferences, and circumstances. We regularly stress-test our strategies using historical downturns and simulated market conditions to help keep your plan on track through a variety of market conditions.
Key takeaway:
Investments should be built around your goals, taxes, and risks, — not a one-size-fits-all model.
3. What other services do you provide beyond investments?
Why this matters:
Retirement planning is about more than just growing a portfolio. It’s about integrating:
· Retirement income strategies
· Taxes
· Insurance (life, long-term care, Medicare)
· Estate planning
It also means helping with real-life decisions like buying a new home or car, helping kids financially, or planning major trips.
What to listen for:
· Do they offer comprehensive planning or just investment management?
· Do they coordinate with experts where they lack in-house specialties?
· Are they honest about what they do well (and what’s outside their scope)?
Sanders Retirement Planning’s Approach:
We go far beyond investments. Sanders Retirement Planning integrates taxes, income strategies, insurance reviews, and estate planning considerations into a cohesive plan. We also help clients navigate big life decisions, from major purchases to supporting family, ensuring each choice fits into their bigger retirement picture.
Key takeaway:
True retirement planning covers every part of your financial life, not just investments.
4. How do you coordinate with other professionals?
Why this matters:
Your financial life intersects with multiple areas of expertise, including tax, legal, and insurance, and that means it often involves working with professionals like:
· CPAs or tax preparers
· Estate planning attorneys
· Insurance agents (Medicare, long-term care, life, etc.)
If these experts aren’t aligned, it can lead to conflicting advice, missed opportunities, or gaps in your overall strategy.
What to Listen For:
· Will the planner proactively collaborate with your CPA, attorney, or other advisors?
· Do they help bridge the gaps between tax, legal, insurance, and investment strategies?
· Are they comfortable acting as a central point of coordination?
Sanders Retirement Planning’s Approach:
We work directly with your existing professionals, or bring in trusted partners, to help each part of your plan work together seamlessly.
Key takeaway:
A great planner acts as the quarterback of your financial team.
5. How do you get paid?
Why this matters:
Compensation influences incentives. You deserve transparency about the fees you’re paying and what you’re receiving in return.
What to listen for:
· A clear and straightforward explanation of their compensation model (e.g., fee-only, fee-based, commission, AUM, Fixed/Flat Fee)
· Honest acknowledgment of potential conflicts of interest
· Alignment of incentives with your goals
Sanders Retirement Planning’s Approach:
We are a Fee-Only firm, meaning we only receive compensation from our clients, not product commissions.
That doesn’t mean other models are inherently “bad,” but we believe this approach helps us minimize many common conflicts of interest in the financial industry. Still, every advisor (including us) has some form of conflict, regardless of how they’re paid. We believe in addressing those transparently.
We also understand that no single fee structure fits everyone. That’s why we offer two options:
· AUM (Assets Under Management): A percentage-based fee based on the assets we manage and consult on
· Fixed Fee: A predictable flat fee, tailored to your specific situation and planning complexity
Some clients value the stability of a flat fee, while others prefer a percentage-based approach. We’re happy to talk through both options and help determine which works best for you.
Key takeaway:
You should always understand what you’re paying for — and how it benefits you.
6. What makes your planning process effective?
Why this matters:
Many advisors claim to “do planning,” but may not have a defined, repeatable process that delivers ongoing value. You need to know what makes their process effective.
What to listen for:
· A process that is clear, adaptable, and client-focused
· Integration of income, taxes, investments, insurance, and estate planning.
· Ongoing adjustments, not a “one-and-done” plan
Sanders Retirement Planning’s Approach:
Our planning process combines comprehensive analysis with continuous refinement. We start by getting to know you, then build a retirement income plan integrating investments, tax strategies, insurance, and estate planning. We revisit and adjust the plan as your life, and the world, changes.
Key takeaway:
A great process is not just a document — it’s a roadmap that evolves with you.
7. What is your communication cadence and style?
Why this matters:
Retirement is a decades-long journey. You need to know how often you’ll hear from your advisor, and how accessible they are when questions arise.
What to listen for:
· Proactive outreach (not just reactive)
· Regular reviews of your plan
· A communication style that matches your needs
Sanders Retirement Planning’s Approach:
We tailor communication to each client. You can expect proactive updates (at least quarterly), regular reviews & check-ins (at your desired interval), and direct access to our team whenever you need us.
Key takeaway:
Consistent communication allows you to know what to expect, and keeps your plan on track.
Final Thought
The right retirement planner doesn’t just manage investments — they help you navigate every aspect of your retirement with confidence.
At Sanders Retirement Planning, we believe retirement should feel empowering, not complicated.
👉 Schedule your free consultation today →
All content is for informational and educational purposes only and should not be construed as personalized investment, tax, or legal advice. Sanders Retirement Planning LLC does not provide legal or tax advice. Please consult your financial advisor, tax professional, or attorney regarding your specific situation. The information provided is believed to be from reliable sources, but its accuracy and completeness cannot be guaranteed. Links to third-party sites are for informational use only and do not constitute an endorsement. Past performance is not indicative of future results. All investments carry risk, including the potential loss of principal. Advisory services offered through Sanders Retirement Planning LLC, a Registered Investment Adviser. Services may not be available in all jurisdictions.