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The Questions Your Advisor Should Answer Before You Retire

8 By Martin Cloutier, CFP®, CIM® – July 8, 2026

 

If you are five years or less away from retirement, your financial plan should be doing more than showing you a projection.

A projection may tell you where you are headed. But real planning asks a better question: is there a better route?

At this stage of life, the conversations with your advisor should become more detailed, more coordinated, and more personal. Retirement planning is not just about investments. It is about income, taxes, government benefits, estate planning, portfolio risk, and the lifestyle you want your money to support.

Here are 10 important areas to review with your advisor before retirement.

1. Government Income Timing

Many retirees ask whether they should take CPP and OAS early or delay them. That is an important question, but it should not be answered in isolation.

CPP and OAS need to be coordinated with your other income sources, your tax situation, portfolio withdrawals, OAS clawback, and estate goals.

A better question is: how does this decision affect the rest of my plan?

2. Portfolio Risk

A portfolio may sound conservative based on its name, but that does not always mean the actual risk is conservative.

Before retirement, it is important to understand how your portfolio may behave during difficult markets. What is the potential drawdown? How much volatility should you expect? Are you receiving reasonable returns for the level of risk and cost involved?

The best portfolio is not the one that looks perfect on paper. It is the one you can actually stick with when markets become uncomfortable.

3. Cash Wedge Planning

A cash wedge can help create flexibility during retirement.

If markets are down, you may not want to be forced to sell investments at the wrong time just to create your monthly retirement income. A cash wedge can provide access to cash or lower-volatility investments during difficult market periods.

The key is balance. It should be large enough to provide protection, but not so large that it limits the long-term growth potential of your portfolio.

4. Withdrawal Strategy

Where will your retirement paycheque actually come from?

Will it come from your RRIF, TFSA, non-registered investments, pension, CPP, OAS, or a combination of all of them?

The order of withdrawal can have a major impact on taxes, estate value, and how long your money lasts. Some retirees want to spend more. Others want to preserve capital. Some want to leave more behind to family or charity.

Your withdrawal strategy should reflect your actual priorities.

5. Lifetime Tax Planning

Traditional tax planning often focuses on paying less tax today. But deferring tax and minimizing tax are not always the same thing.

Sometimes, deferring too much tax can create larger RRIF withdrawals later, more OAS clawback, and a bigger tax bill at death.

Instead of only asking, “How do I pay the least tax this year?” the better question may be: “How do I reduce my total tax bill over my lifetime?”

6. Estate Shrinkage

Estate shrinkage refers to the portion of your wealth that does not end up going to the people or causes you care about.

Some may go to tax. Some may go to fees. Some may be lost because of poor planning.

Your advisor should be able to show what your estate is projected to look like, how much may be lost to tax, and whether there are planning opportunities around taxes and estate outcomes.

7. Return Analysis

It is important to know whether your portfolio is producing reasonable returns for the level of risk you are taking.

But your portfolio should not be judged in isolation. Has it been compared against reasonable alternatives? Are there lower-cost options? Are there more tax-efficient options? Are there better risk-adjusted options?

The goal is not simply to own investments. The goal is to understand whether the investments are appropriate for your plan.

8. Fees and Value

Nobody wants to overpay. But the lowest-cost option is not always the best option if it comes at the expense of planning, tax strategy, estate coordination, behavioural coaching, and ongoing advice.

The real question is not only, “How much am I paying?”

The better question is: “What am I receiving for what I am paying?”

If the advice helps improve retirement income, reduce lifetime taxes, preserve more of your estate, and give you more confidence, then the value may be greater than the cost.

9. Plan Improvement Analysis

This may be one of the most important questions to ask your advisor:

Can you show me how this plan improves my outcome?

A retirement projection shows where you may be headed. A real plan should compare your current path with possible alternatives.

Does the plan reduce lifetime taxes? Improve after-tax retirement income? Reduce OAS clawback? Improve estate value? Create more flexibility?

Your advisor should be able to show the difference between your baseline plan and the recommended strategy.

10. Lifestyle Scoreboard

Retirement planning is not only about the financial scoreboard.

It is also about the happiness scoreboard.

Can you travel? Can you help family? Can you enjoy the early years of retirement while you have the health and energy to do it? Can your money support the life you actually want to live?

The goal is not simply to have the highest net worth. The goal is to make sure your financial resources support what matters most to you.

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Disclaimer: Any view or opinion expressed in this article are solely those of the Representative and do not necessarily represent those of Harbourfront Wealth Management Inc. The information contained herein was obtained from sources believed to be reliable, however accuracy is not guaranteed. The information transmitted is intended to provide general guidance on matters of interest for the personal use of the viewer, who accepts full responsibility for its use, and is not to be considered a definitive analysis of the law or factual situations of any individual or entity. Any asset classes featured in this presentation are for illustration purposes only and should not be viewed as a solicitation to buy or sell. Past performance does not necessarily predict future performance, and each asset class has its own risks. As such, this content should not be used as a substitute for consultation with a professional tax or legal expert, or professional advisors. Prior to making any decision or taking any action, you should consult with a licensed professional advisor.

Harbourfront Wealth Management Inc is a member of the Canadian Investor Protection Fund and the Canadian Investment Regulatory Organization .

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