Retirement & Tax Planning Answers
What Should I Be Discussing With My Financial Advisor?
Quick answer
At least once a year, you should be discussing a written plan for how you will spend and withdraw money, a tax projection for this year and next, how Social Security and Medicare fit together, your investment plan for a down market, what you pay all in, and your estate and insurance paperwork. Performance belongs on the agenda, but measured against your plan rather than only against an index. A good meeting has an agenda sent ahead, notes afterward, and action items with an owner and a date. Retirement is where the stakes rise: withdrawal order, Roth conversions, required minimum distributions, IRMAA thresholds, the ACA subsidy cliff before 65, and survivor benefits all interact, and the decisions are often hard to reverse. Ask what changed in the rules and what changed in your life since the last meeting. Then ask for the answers in writing. A good advisor will welcome these questions, because they are the work. And if you ask them all and decide to stay with the advisor you have, that is a fine outcome. This agenda is useful whether or not you ever change anything.
How to run a better advisor meeting
A repeatable process for preparing for, running, and following up on your annual review with any financial advisor.
- 1
Write a one-page agenda
List four or five topics from the annual agenda where something changed or a deadline is coming, such as taxes, Medicare, required minimum distributions, or estate documents. Add one line per topic stating the question you want answered. A short, specific agenda keeps the meeting on your priorities instead of the advisor's standard presentation.
- 2
Send it a week ahead
Email the agenda at least a week before the meeting and ask what documents the advisor needs. This gives them time to run projections, check account details, and prepare real numbers. If the advisor needs two days' notice to answer a basic question, that tells you something about how the work gets done.
- 3
Gather your documents
Collect the last two years of tax returns, recent statements for every account, your Social Security statement, Medicare and insurance documents, and your estate documents. Include accounts the advisor does not manage. A planning conversation built on partial information produces a partial plan, so share the whole picture.
- 4
Ask each question, then ask for it in writing
Work through the agenda one item at a time. For each answer, listen for specific numbers, named assumptions, and dates. When the answer is vague, ask for the number or the document. Ask which hat the advisor is wearing on any recommendation, and ask for important answers by email.
- 5
Take notes on decisions
Write down what was decided, what was left open, and what assumptions were used. Many people forget the details within a week. Your own notes, plus the advisor's, give you a record you can compare later when the tax return arrives or the plan is updated.
- 6
Confirm action items with owners and dates
Before the meeting ends, restate each action item, who owns it, and the date it is due. Examples include a Roth conversion amount to decide before December 31, a beneficiary form to update, or a call with your CPA. An item without an owner and a date rarely gets done.
- 7
Request meeting notes within a week
Ask the advisor to send a short summary of the discussion and action items within a week. Compare it to your own notes and correct anything that does not match. Written follow-up is the clearest sign of an advisor who treats the meeting as part of an ongoing process.
- 8
Follow up on deadlines
Put each due date on your calendar and check in a week early. If the action item involves your tax preparer or estate attorney, ask whether the advisor will coordinate or whether you need to. Review progress at the next meeting so the same issues do not come up again unresolved.
The Annual Agenda, Topic by Topic
Start with the plan itself. A written spending and withdrawal plan should say how much you expect to spend, which accounts you draw from first, and what happens if the market falls early in retirement. The question to ask is, 'Where is my withdrawal plan in writing, and when did we last update it?' A good answer names the account order (taxable, pre-tax, Roth), the annual amount, and the assumptions behind it. Treat any projection as illustrative, not guaranteed. If the plan lives only in the advisor's head, or was last updated when you retired, that is the first agenda item for the next meeting.
Next is tax. Ask for a projection for this year and next year, not a recap of last year's return. A good answer shows your expected brackets, whether a Roth conversion makes sense and how much, planned capital gains, and where you sit relative to the IRMAA thresholds, which look back two years. In 2026 the first IRMAA tier starts above $218,000 of income for a married couple and $109,000 for a single filer, and crossing it by $1 triggers the full surcharge. If you retire before 65, ask about the ACA subsidy cliff too. Timing matters, because most of these moves must happen before December 31.
Then cover the income sources that arrive on a schedule. For required minimum distributions, ask when they start, how large the first one will be, and whether qualified charitable distributions (QCDs) fit your giving. For Social Security, ask what claiming age the plan assumes, how the survivor benefit changes the answer for the higher earner, and whether the earnings test applies if you are still working before full retirement age. A good answer uses your actual numbers from your Social Security statement. For Medicare, ask about Part B and Part D costs, supplement versus Advantage, and who is watching the October 15 to December 7 annual enrollment window.
Investments come next, but framed around risk rather than returns. Ask, 'If the market falls 30% next year, what do we do, and how many years of spending sit outside stocks?' A good answer describes a cash reserve, a rebalancing rule, and which account you would sell from. Sequence-of-returns risk is the reason this matters: poor returns early in retirement hurt more than the same returns later. Also ask how your portfolio is doing against the plan, not just a benchmark. A year behind an index that carries more risk than you do is not a problem. A portfolio that no longer matches your risk level is.
Fees and conflicts deserve one direct conversation a year. Ask for your all-in cost in dollars: the advisory fee, fund expenses, and any commissions on products recommended to you. For context, a 1.00% fee costs $10,000 a year for every $1 million of assets, and that compounds over a long retirement. That is not an argument against paying for advice. It is the reason to know what planning, tax work, and coordination you get for it. Ask which hat your advisor is wearing: fiduciary adviser or broker-dealer representative under Regulation Best Interest, and whether the answer is in writing.
Finally, review the paperwork that protects your family. Ask whether beneficiaries are current on every account, whether your powers of attorney and trust still match your wishes, and when you last met with your estate attorney. Review insurance as well: long-term care, an umbrella policy, and life insurance only if someone still depends on your income. Add charitable giving (QCDs, donor-advised funds), gifts to children or 529 plans, any concentrated stock or company equity, and the biggest item of all: what changed in your life since the last meeting. A move, a health event, a death in the family, or an inheritance can change the whole plan.
How to Use This Agenda Before Your Next Meeting
You do not need to cover everything every year. Pick the four or five topics where something changed or where a decision has a deadline, and put them on a one-page agenda. Email it to your advisor a week ahead and ask what documents they need from you. Most of the value comes from the advisor arriving prepared with your numbers, not from the meeting length.
Bring your own paperwork: the last two years of tax returns, recent statements from every account (including the ones your advisor does not manage), your Social Security statement, Medicare and insurance documents, and your estate documents. The advisor can only plan around what they can see. If they cannot see a spouse's 401(k) or a rental property, the plan has a hole.
Expect a clear, specific answer to each question, or a commitment to get one by a stated date. 'We keep an eye on that' is not an answer. 'Here is the projection, here is the assumption, and here is what we will do before December 31' is. For anything that depends on tax law, details that change by year, or your own paperwork, confirm with your advisor, custodian, or tax preparer.
After the meeting, ask for notes and action items with an owner and a date. If you find that the advisor cannot cover most of this agenda, you have learned something useful, and your options include asking for the missing pieces, changing how you work together, or looking elsewhere. Flat-fee fiduciary planning is one option among several, and the page on why flat-fee is worth a read if you want to compare. If the answers are good and the advisor welcomes the questions, staying put is a perfectly good outcome.
Common Mistakes
- Treating the annual review as a performance report and never asking for a tax projection, a withdrawal plan, or an update on Social Security and Medicare.
- Showing up without an agenda or documents, so the meeting covers whatever the advisor prepared and nothing you actually care about.
- Comparing portfolio returns to a benchmark that carries more or less risk than you do, and drawing conclusions from one year.
- Never asking for your all-in cost in dollars, including fund expenses and any commissions on products you were sold.
- Leaving beneficiary designations, powers of attorney, and trust documents untouched for years after a move, a death, a divorce, or a new grandchild.
- Letting Medicare enrollment, IRMAA thresholds, or the ACA subsidy cliff come up only after the deadline has passed.
- Accepting verbal answers and leaving the meeting without notes, action items, owners, or dates.
Annual Review Agenda for a Pre-Retiree or Retiree
A framework for what to cover each year, the question to ask on each topic, and what a good answer includes. Use it with any advisor. Details that depend on tax law or your own accounts should be confirmed with your advisor, custodian, or tax preparer.
| Topic | Question to ask | What a good answer includes |
|---|---|---|
| Spending and withdrawal plan | Where is my withdrawal plan in writing, and when was it last updated? | Annual spending target, account order for withdrawals, stated assumptions, and a date for the next update |
| Tax projection | What is my projected tax picture this year and next? | Expected brackets, Roth conversion room, planned capital gains, and actions to take before December 31 |
| IRMAA and ACA thresholds | How close am I to an IRMAA tier or the ACA subsidy cliff? | Income projected against the thresholds two years out, and which decisions could cross a line |
| RMDs and charitable giving | When do RMDs start, how large will they be, and do QCDs fit? | A projected first-year RMD, how it lands in your bracket, and whether QCDs or a donor-advised fund make sense |
| Social Security | What claiming age does the plan assume, and what happens to the survivor benefit? | Your actual benefit estimates, a claiming recommendation with reasons, and the survivor and earnings-test effects |
| Medicare and health costs | Who is reviewing Part B, Part D, and supplement or Advantage choices each fall? | A named owner for the October 15 to December 7 window, a plan comparison, and HSA coordination if applicable |
| Investments and down-market plan | If the market falls 30%, what do we do? | A cash reserve in years of spending, a rebalancing rule, and a stated source of withdrawals in a downturn |
| Fees and conflicts | What do I pay all in, in dollars, and what do I get for it? | Advisory fee, fund expenses, any commissions, a services list, and a clear statement of which standard applies |
| Estate and beneficiaries | Are beneficiaries, powers of attorney, and my trust current? | A check of every account's beneficiaries, a date for the last attorney review, and any needed updates |
| Insurance and life changes | What changed in my life, and does my coverage still fit? | A review of long-term care, umbrella, and life coverage, plus a discussion of any move, health event, or family change |
Source: Singh PWM planning framework · Verified