Ask Your Advisor These 8 Questions During Your Annual Review

If you’re at the stage where your career is well underway, and you’re beginning to think seriously about retirement, your annual meeting with a financial advisor is a lot more than another calendar tick. It’s one of the most important conversations you’ll have all year. Approaching it with the right questions would ensure your strategy stays aligned, responsive, and optimized for your changing life.

This article presents eight carefully chosen questions to ask your financial advisor during your annual review. Each reflects a vital dimension of your plan: performance, risk, tax, withdrawal, costs, alignment, measurement, and life changes. Use these questions to steer the conversation, and don’t leave the meeting until you’re satisfied with the answers.

Below are the top questions to ask your financial advisor during an annual review:

Question #1: Is our plan still aligned with what I want to achieve and how my life is changing?

Too often, an annual review becomes a mechanical check-off: “Yes, we met. No, we didn’t. Here are the returns.”

But your financial plan is not static. Your life evolves with events such as job promotion, second home, elder-care responsibilities, changes in health, or simply the fact that your retirement horizon is shortening.

A clear sign of a good review is when your advisor asks you first, “What’s changed? What do you imagine next year will bring?” Then they translate those changes into the plan. For example, if you’re now planning to retire at 62 instead of 65, your risk exposure and withdrawal assumptions should shift. Ask the question to ensure the plan is flexible and not built and forgotten.

Question #2: How have my investments performed relative to the plan, and what does that mean for my expectations going forward?

Performance is obvious, but meaningful performance analysis doesn’t stop at “we made x% this year.” It should focus on whether the results still keep you on track for the goal you set. The real question is: what does this performance imply for the future?

So ask your advisor to frame performance in terms of your target. Did you beat, meet, or fall short of the assumptions? Why? More importantly, will the current projection get you where you need to go?

If the answer is, “yes, but only if we assume 8% returns every year,” push further: Is that realistic? What happens if returns are 4% instead?

This kind of discussion moves you from hindsight to foresight.

Question #3: What is the total cost of our working relationship, and is it reasonable given the value I’m getting?

Costs matter more than many clients realize, especially as you near retirement and every dollar has more work to do. One of the best performance-review questions for financial advisors is: “What am I paying in total, and what am I receiving in return?” For example, you may see a portfolio expense ratio, but you may also have transaction fees, advisory fees, custodial fees, or investment-product conflicts buried in the “management” line.

You should ask your advisor for a clear breakdown: advisor fee, fund/ETF expense ratios, transaction or custodial fees, and then ask: what did you deliver for that cost?

A transparent advisor will welcome scrutiny because aligning cost with value is precisely their job.

Question #4: How much risk am I taking versus how much risk I can reasonably tolerate, and is that consistent with where I am in life?

As you approach retirement, your risk tolerance usually declines, and the importance of income stability rises. That means your advisor must check both the technical risk (volatility, drawdown potential) and the behavioural risk (how you’ll respond).

Ask: “If the market falls 20% in the next year, how will my portfolio fare? And how much can I safely withdraw in retirement without endangering the plan?” These make the review real because, as in life, it’s easier to plan for sunshine than for a storm.

Don’t accept “we have a diversified portfolio” as a full answer. Ask for numbers. Ask for potential outcomes so you know what you’re really signing up for.

Question #5: What are we doing about tax efficiency, withdrawal sequencing, and account location as we move into retirement mode?

When you’re further away from retirement, it’s easy to treat tax strategy or withdrawal sequencing as a minor detail. But as you get closer and especially when you start drawing income, these issues become major levers on your long-term outcomes. In your annual review, ask:

• Which account will I draw from first in retirement?
• Are we using tax-advantaged and taxable accounts optimally now?
• Have recent tax law changes (or expected changes) been factored in?

If your advisor glosses over these with “yes, we’re good,” probe further. This is where thoughtful planning before retirement really pays off.

Question #6: What life events, goals, or changes should we anticipate in the next 12 months, so the plan doesn’t get caught flat-footed?

Sometimes the most significant value in an annual review is not what happened, but what could happen. Your advisor should be probing for upcoming changes that may impact your plan, such as planning for a second home, elder care responsibilities, starting or winding down a business, a change in marital status, or health issues.

Think of this as updating the map before you continue the journey: we know where we’ve been, but we also need to know the new terrain ahead. If your advisor doesn’t ask and document these changes, you should ask them to.

Question #7: How will you measure and report my progress between now and next year, and what benchmarks or metrics will you use?

A strong annual review doesn’t end at “Okay, everything looks fine.” It sets measurable goals and a schedule for checking in. Without this, you risk the plan going dormant for another year. Ask:

• What performance metrics will we use (return, risk, cash-flow, outcome vs goal)?
• How often will we meet or communicate (quarterly or semi-annually)?
• What documents or dashboards will I receive?
• If something deviates meaningfully from the plan, how will you let me know?

Treat this as a means of establishing accountability for both you and your advisor.

Question #8: If this relationship were to end, what happens to my assets, my plan, and the ongoing commitments?

This might feel like a heavy-handed question, but it’s a critical one. It addresses service continuity, transparency, and readiness for unexpected events. Ask:

• Who holds my assets (as a custodian)?
• How is my plan documented (investment policy statement, engagement letter)?
• If you are unavailable (retiring, changing firms, etc.), who will cover for me?

Think of it like checking the spare tire and the roadside assistance ahead of a long journey. You hope you won’t need it, but you want to know it’s ready.

To conclude: Forcing the conversation off autopilot

When you walk into your annual review with your advisor and cover these eight questions, you’re not just looking backward, but steering your financial future. You’re making sure you’re aligned with your goals, that your money is working for you in a cost- and tax-efficient way, and that you’re ready for whatever next year brings.

Your role in this meeting is active, not passive. Bring your life changes, your concerns, your hopes. Ask for clarity. Demand transparency. Your advisor is there to partner with you, but you’re ultimately in the driver’s seat.

As you near retirement, the stakes are higher. Every assumption about returns, inflation, risk, tax, longevity, and withdrawal rate becomes more critical. A small misalignment now can amplify over the next decade and eat into your lifestyle, not just your portfolio. So, you need a review that asks deep questions, triggers actions, and refreshes your roadmap.

How to prepare ahead

• Bring a summary of what changed in your life this past year (income, expenses, family, health, goals).
• Gather your current portfolio statements and your prior plan assumptions.
• Send your advisor these eight questions in advance so the meeting stays focused.
• Consider drafting your own brief “key assumptions dashboard” (target retirement age, target annual income in retirement, assumed return, safe withdrawal rate, Social Security start date). Then ask: “If one of these numbers changes by 10%, what happens to the plan?”
• Leave the meeting with clear next steps, responsibilities, and a documented summary.

Your annual review with your financial advisor is far more than a polite catch-up. It is a strategic inflection point. Especially as you head into the later phases of your career and approach retirement, you’re managing your future freedom.

By asking the eight questions above, you force the conversation off autopilot and onto the terrain where real value lies. You make sure your plan stays living, breathing, and responsive rather than a static document tucked away in your advisor’s archive.

If you don’t have an advisor you feel comfortable interviewing or your current advisor doesn’t welcome this kind of dialogue, it may be time to explore new advisory services. A professional who encourages these questions is someone worth keeping by your side. Explore our financial advisor directory to find vetted professionals who can help you review your plan, answer these questions in depth, and keep you on track for the retirement you want.

Frequently Asked Questions (FAQs)

1. What questions should I ask my financial advisor during my annual review?

During your annual review with your financial advisor, you should ask questions that address alignment with your goals, investment performance, risk exposure, tax and withdrawal strategies, upcoming life changes, reporting and measurement, advisor compensation, and contingency planning.

2. How often should I conduct an annual review with my financial advisor?

You should meet with your financial advisor at least once a year to review your financial position. For many nearing retirement or undergoing significant change, semi-annual or quarterly check-ins may be advisable to ensure timely adjustments.

3. Why is an annual review of financial planning so crucial as I near retirement?

Annual review of financial planning is important as you near retirement because your time horizon shortens, risk tolerance shifts, tax exposure may increase, and withdrawal sequencing becomes critical. An annual review ensures your plan reflects those evolving dynamics, rather than relying on outdated assumptions.

4. How should I prepare for my annual review with a financial advisor?

Gather a brief overview of what changed this year, including your income, expenses, health, family, or job, along with your latest portfolio statements and key planning assumptions (retirement age, income needs, expected returns). Also, send your advisor the questions ahead of the meeting so the conversation is focused and efficient.