7 Questions Every Investor Should Ask Their Advisor This Spring
Most portfolio reviews go like this: your advisor walks through performance, you nod, you sign something, you leave. An hour gone, nothing changed.
That’s a missed opportunity, especially this year. The S&P 500’s top 10 stocks now make up roughly 41% of the index, more than double their weight a decade ago. Morningstar just lowered its base-case “safe” withdrawal rate to 3.9% for 2026 retirees. And the One Big Beautiful Bill Act, signed last summer, quietly rewrote the rules on catch-up contributions, the SALT cap, the estate exemption, and a new senior deduction.
If you’ve already got an advisor, you don’t need a new one. You need a better meeting. Here are seven questions to bring to your spring review, calibrated to what’s actually happening right now. Each comes with what a good answer sounds like and what should give you pause.
The most important questions to ask your financial advisor in 2026 are: how concentrated your equity exposure really is across all accounts, how your withdrawal plan changes if markets drop sharply, what your international and cash allocations look like given recent shifts, whether you’re in the retirement risk zone, whether you’re tax-loss harvesting, and whether your plan reflects the OBBBA tax changes. Bring them to your spring review and listen for specific numbers, not generalities.
1
What’s my actual exposure to the top 10 S&P 500 stocks across every account I own?
You probably hold an S&P 500 fund. You may also hold a “growth” fund, a tech fund, a managed account, and your former employer’s 401(k). Each of those likely owns the same handful of names.
The top 10 holdings in the S&P 500 represent roughly 40% of the index, the highest concentration since at least 1972, and a single company (Nvidia) recently accounted for around 8% of the index by itself. If you own broad U.S. equities through three different sleeves, you may be three-times exposed to the same five stocks without realizing it. That’s not diversification. That’s a concentrated bet wearing a diversified costume.
Ask your advisor to run a holdings overlap report across every account. A good answer comes back with specific percentages. A red-flag answer is “you’re well diversified across asset classes” without ever showing the underlying single-stock exposure.
If your advisor can’t show you your true single-stock exposure in under five minutes, that’s the issue worth solving before anything else.
Source: RBC Wealth Management, State Street Global Advisors.
2
If the market drops 30% in the next 12 months, exactly how does my withdrawal plan change?
Markets fall. The question isn’t whether, it’s what you do when. And “we’ll cross that bridge” is not a plan.
Morningstar’s 2026 research now puts the safe starting withdrawal rate at 3.9% for a 30-year retirement, down from the famous 4% rule and based on forward-looking return assumptions rather than historical data. More importantly, retirees who use flexible “guardrail” approaches, where you trim spending in down years and increase it in good ones, can support starting withdrawal rates as high as 5.7% without raising the risk of running out of money.
Your advisor should be able to walk you through specific spending adjustments under specific scenarios. Something like: “If your portfolio drops 20% by year-end, we skip the inflation adjustment next year. If it drops 30%, we cut discretionary spending by 10% for two years and lean on cash reserves.” That’s a plan. “We’ll re-evaluate” is a shrug.
Ask for the specific dollar adjustment in a 20%, 30%, and 40% drawdown scenario, written down.
Source: Morningstar State of Retirement Income.
3
Where are we on international, and what’s your current view?
For 15 years, “international diversification” was a tax on returns. U.S. stocks crushed everything. Investors who held meaningful non-U.S. exposure spent a decade explaining themselves at dinner parties.
That story changed. In 2025, non-U.S. stocks returned roughly 30%, outpacing the S&P 500 by double digits. The MSCI EAFE Index trades at about 15.1 times forward earnings versus 22.8 times for the S&P 500, a meaningful discount. Vanguard now projects non-U.S. equities could deliver 7% annualized over the next decade versus 4–5% for U.S. stocks. None of that guarantees the trend continues. But it does mean your advisor should have a current, articulated view.
A good answer includes a specific target allocation (e.g., 25% of equities in non-U.S. developed and emerging markets) and a reason. A red-flag answer is the U.S.-only portfolio that hasn’t been revisited since 2018.
Source: Capital Group, Fidelity.
4
What’s our plan for cash as money-market yields keep falling?
For two years, holding cash felt smart. Money market funds paid more than most retirees needed to live on. That’s now changing.
The Fed’s target rate sits at 3.75% as of early May 2026, and the path of expected cuts means money-market yields will likely keep drifting lower. If you’ve parked a big chunk of your portfolio in cash equivalents because you got comfortable with the yield, that’s a decision worth revisiting.
Your advisor should have a tiered cash plan. Something like: a true emergency layer (six to twelve months of expenses) that stays liquid regardless of yield, a near-term spending bucket (one to three years of withdrawals) that can use short Treasuries or a CD ladder, and longer-term reserves invested for actual return. The number to ask: how many months of withdrawals are sitting in cash today, and what’s the plan if yields drop another full percentage point?
If the answer is “we’ll see what rates do,” you’re paying for a plan you don’t have.
Source: Federal Reserve Open Market Operations.
Only about 1 in 4 American adults has a will. Far fewer have the full set of documents that actually protects a family in a crisis.
5
Are we tax-loss harvesting any of my AI or tech positions?
Even in a strong year for the index, individual stocks zigzag. AI and SaaS names in particular saw real drawdowns in late 2025 and early 2026. If you hold a concentrated position with embedded losses, that’s an asset, not an embarrassment.
Tax-loss harvesting works like this: you sell a position at a loss, immediately buy a similar (but not “substantially identical”) security to maintain your market exposure, and bank the realized loss. You can use up to $3,000 of net capital losses against ordinary income each year, with the remainder carrying forward indefinitely against future gains. For a high-bracket investor, that’s worth real money. The pitfall is the wash-sale rule: if you buy back the identical security within 30 days, the IRS disallows the loss.
A good advisor proactively flags loss-harvesting opportunities every quarter, not just in December. A red-flag answer is “we don’t really do that.”
December-only “tax planning.” If your only loss-harvesting conversation happens in late Q4, real opportunities are getting missed all year.
Source: IRS Publication 550, IRS Topic 409.
6
Am I in the retirement risk zone, and how is my plan accounting for it?
This is where the conversation gets specific. The “retirement risk zone” is the roughly 10-year window straddling your retirement date, the five years before and five years after. It’s the period when your portfolio is at its largest, withdrawals are starting (or about to), and a deep market drawdown can do permanent damage.
The math is unforgiving: a 30% market decline in your first year of retirement, while you’re also pulling out 4%, can take a decade of normal returns to recover from. That’s sequence-of-returns risk, and it’s the single biggest reason retirees run out of money.
Your advisor should be able to tell you, plainly: “Yes, you’re in the risk zone. Here are the three things we’re doing about it.” Common defenses include holding two-to-three years of expenses in a cash bucket so you’re never a forced seller, glide-pathing your equity allocation down through the zone, and using flexible withdrawal rules. A red-flag answer: “We’re long-term investors, we don’t worry about that.” That’s true at 35. It’s a problem at 65.
Source: Morningstar, HFFinancial.
7
Has the One Big Beautiful Bill Act changed anything in my plan?
The OBBBA, signed in July 2025, made the 2017 tax cuts permanent and rewrote several rules that probably affect you. If your advisor hasn’t proactively flagged how it shifts your plan, that’s a problem worth raising.
A few specifics worth knowing about. Beginning in 2026, if you earned more than $150,000 in FICA wages in 2025, your 401(k) catch-up contributions must go into a Roth account rather than pre-tax. The standard age-50-plus 401(k) catch-up is $8,000 for 2026, with a “super catch-up” of $11,250 for those aged 60 to 63. The SALT deduction cap rose to $40,000 for 2025 through 2029, but it phases down sharply once income passes $500,000. The federal estate and gift tax exemption is now $15 million per person ($30 million per couple), permanent rather than scheduled to drop in half. And taxpayers age 65 and older get a new $6,000 annual deduction through 2028, phased out above $75,000 of income for singles.
Each of those is a planning lever. A good advisor maps which apply to you and adjusts: maybe Roth conversions look different now, maybe the estate plan can be simpler, maybe you should keep income under $500,000 to preserve the SALT benefit. A red-flag answer is “the tax laws don’t really change much.”
Source: J.P. Morgan Asset Management, IRS Notice 2025-67, IRS.
Common Questions
How often should I meet with my financial advisor in 2026?
Twice a year is a reasonable baseline for most clients, with one of those meetings ideally in the first or second quarter so you can act on tax moves while the year is young. If you’re inside the retirement risk zone, going through a major life event, or saw a meaningful change to your plan from the OBBBA, quarterly check-ins make sense.
What is the safe withdrawal rate for retirement in 2026?
Morningstar’s base-case safe starting withdrawal rate for a 30-year retirement is 3.9% for 2026, up from 3.7% in 2025, assuming a portfolio with 30% to 50% in stocks. Retirees willing to use flexible “guardrail” strategies that trim spending in down years can start as high as 5.7%. The original “4% rule” from 1994 used historical data; Morningstar’s number uses forward-looking return assumptions.
What are the 2026 401(k) and IRA contribution limits?
For 2026, the IRS set the 401(k) employee contribution limit at $24,500. The age-50-plus catch-up is $8,000, and the “super catch-up” for those aged 60 to 63 is $11,250 (a total possible employee contribution of $35,750 in that age band). The IRA contribution limit is $7,500, with a $1,100 catch-up for age 50 and over.
Should I be worried about S&P 500 concentration in 2026?
You don’t need to panic, but you should know your exposure. With the top 10 stocks at roughly 40% of the index and the largest single name near 8%, an S&P 500 fund is meaningfully more concentrated than it was a decade ago. The right response usually isn’t to sell, it’s to make sure you’re not unintentionally tripling-up on the same names through multiple funds, and to consider whether your international and equal-weight exposure should grow.
How do I know if my financial advisor is actually doing the work?
Two tests. First, can they answer specific questions with specific numbers, not generalities? “Your top-10-stock exposure across all accounts is 38%” is real. “You’re well diversified” isn’t. Second, are they bringing you ideas, or only responding when you bring them? A good advisor calls you when something in the law or markets shifts your plan, not the other way around.
Bring This to Your Next Review
Rules of thumb only get you so far. The questions above are general; the right answers depend on your accounts, your timeline, your tax bracket, and what you actually want the next 20 years to look like. If you’d like to talk through how any of this fits your situation, the team at Madison Partners is happy to have that conversation.
This content is for educational purposes only and should not be considered financial, tax, legal, or investment advice. Individual circumstances vary, and readers should consult with a qualified financial advisor, tax professional, or attorney before making decisions based on this information. Madison Partners does not guarantee the accuracy of third-party data cited herein.
