The Questions Every Investor Should Be Asking Their Advisor Right Now

Periods of market instability can test even the most seasoned investors. Headlines become louder. Opinions multiply. And the natural instinct, for many, is to pull out.

But turmoil shouldn’t spur rash decisions. Sometimes, investors just need clarity.

Asking the right questions during volatile stretches can help clarify what’s in your control, confirm if your strategy is still aligned, and spotlight areas that may need closer attention. Conversations can turn unbridled concern into informed decision-making.

And the best advisory teams welcome those conversations. They don’t shy away from questions or scrutiny — they embrace it. Because on top of managing portfolios, their job is to provide perspective, guidance, and, of course, clarity.

In this guide, we’ve outlined the essential questions to ask your financial team across five key areas: 

1. Your investments
2. Your financial plan
3. Your tax strategy
4. Your communication needs
5. And, when necessary, your confidence in the relationship itself. 

Let’s start where most people feel it first: the portfolio.

Portfolio Questions: Is My Investment Strategy Still Built for This?

When markets quake, you’re likely inclined to review (and maybe even question) your holdings. But volatility alone isn’t a reason to overhaul your investments. The real question is whether your investment strategy is still doing what it’s supposed to do based on your goals, risk tolerance, and time horizon.

Here are three key questions to bring to your advisory team:

1. How is my portfolio positioned for the current market and for recovery afterward?

A sound investment strategy accounts for both downturns and rebounds. Ask your advisor whether your allocation is still appropriate based on current market conditions and where we might go next. Be wary of all-defense or all-offense plays — balance and discipline usually win over time.

2. Have there been (or should there be) any tactical changes to my portfolio?

Not every change is reactive. Your advisor may have made small tweaks to reduce risk, add exposure, or take advantage of opportunities. You should understand what (if anything) has changed and why — and whether it’s consistent with your broader strategy.

3. Am I still properly diversified across asset classes, sectors, and geographies?

Strategic diversification is one of the most effective tools for reducing risk. Now is a good time to review your overall allocation and make sure it isn’t overly concentrated in one theme, industry, or region.

A well-constructed portfolio doesn’t need to be reengineered during every bout of volatility, but it should always be comprehensible. Your financial team should explain why you own what you own.

Planning Questions: Is My Broader Financial Plan Still On Track?

Volatility tends to pull focus toward performance. Prudent investors know that portfolio fluctuations matter far less than how those fluctuations impact the broader plan.

Your financial team should help you regain perspective, connecting the dots between short-term noise and long-term goals. 

1. How does this volatility affect my retirement timeline or spending goals?

Market pullbacks can temporarily lower your account balances, but that doesn’t necessarily mean you’re off track. Ask your advisor to revisit your cash flow projections and stress-test your plan under current conditions. 

Sometimes reassurance is warranted. Other times, small tweaks (like adjusting withdrawal timing or spending assumptions) can restore confidence.

2. Should I reconsider any major financial decisions in light of current conditions?

Thinking about buying a vacation home? Helping a child with a large purchase? Selling a business? 

Market volatility shouldn’t dictate your day-to-day decisions, but it should be factored into the timing, tax consequences, and liquidity implications of any big moves.

3. Are there risks I’ve overlooked or opportunities I haven’t considered?

Periods of instability can reveal gaps in cash reserves and downside protection, or even non-portfolio areas like estate planning and insurance. They can also open doors for strategic opportunities, like rebalancing or tax-loss harvesting. 

A strong financial plan isn’t one that avoids disruption — it’s one that’s flexible enough to weather it.

Tax Strategy Questions: Are There Strategic Moves We Should Consider?

While they’re difficult to stomach, volatile markets do have upsides, especially from a tax strategy standpoint. In fact, downturns can be one of the most overlooked windows for tax planning.

Here are three proactive questions to ask your advisory team:

1. Are there tax-loss harvesting opportunities we should capture?

Volatility can depress asset values and enable you to harvest losses. If certain positions are down, you may be able to sell them, realize the loss, and use it to offset capital gains or reduce future taxable income — all while remaining aligned with your long-term strategy.

2. Should we explore a Roth conversion?

Lower portfolio values may present an opportunity to convert traditional IRAs into Roth accounts with reduced tax implications. While this approach incurs taxes upfront, it can pave the way to tax-free withdrawals down the road. 

3. Could current market conditions help us execute gifting or estate planning moves more efficiently?

If you’re planning to transfer assets to heirs or make charitable gifts, lower valuations could mean lower gift tax exposure and greater long-term appreciation outside your estate. Now may be the time to accelerate strategies like grantor retained annuity trusts or contributions to donor-advised funds.

Communication Questions: How Will You Help Me Stay Grounded and Informed?

Silence can be just as unsettling as the markets themselves. A strong advisory relationship is rooted in presence, responsiveness, and clarity, especially when things feel uncertain.

These questions help you evaluate whether your financial team is communicating adequately:

1. What’s your process for communicating market updates or recommendations during volatile periods?

Do they reach out proactively or only respond when you call? You should know what to expect in terms of updates and guidance.

2. How often will we revisit my financial plan going forward?

Your plan isn’t static, and neither are your concerns. Volatility is a natural trigger for a rational plan review. Ask your advisor how often you’ll revisit assumptions, stress-test scenarios, or adjust based on what’s happening in your life.

3. What resources are available to help me stay informed?

Do you receive relevant commentary? Educational webinars? Access to planning sessions or investment reviews? 

Your advisor should provide resources that keep you grounded when emotion runs high.

Uncertainty is inevitable, but you shouldn’t have to face it alone (or in the dark).

Red Flags: Signs It May Be Time for a Second Opinion

Market instability tends to reveal the strength — or strain — of an advisory relationship. And while volatility isn’t always a reason to make a change, it can expose patterns that shouldn’t be ignored.

Here are a few signs it may be time to reassess the fit:

1. You’re met with vagueness or avoidance.

If your questions are answered with jargon, vague reassurances, or deflections (or even radio silence), that’s a problem. You deserve transparency, not tap-dancing.

2. The relationship feels overly portfolio-centric.

A great advisor doesn’t simply flex their financial acumen — they help you connect the dots across investments, tax strategy, estate planning, and life transitions. If the conversation never goes beyond returns, you may be missing out on meaningful guidance.

3. There’s a mismatch between your risk tolerance and your strategy.

If your portfolio is keeping you up at night or if it’s overly cautious relative to your goals, it’s worth asking whether the approach is still appropriate. Your strategy should be designed around your comfort level and long-term needs.

Trust and clarity are never more important than during heightened volatility. If you’re not getting either, it’s okay to seek a second perspective.

Your Questions Deserve Thoughtful Answers

It’s easy to become overwhelmed by uncontrollable factors and lose perspective. But asking the right questions brings the focus back to what you can control.

• It clarifies whether your portfolio is doing its job.
• It tests the strength of your plan and your planning team.
• And most importantly, it helps ensure that decisions are logical, not emotional.

A trusted advisor should never shy away from those conversations. They should welcome them.

If your current financial team isn’t helping you feel clear-headed and well-supported, it may be time to explore a second opinion.

We believe clarity is the antidote to uncertainty. If you’re ready for a more grounded perspective on your strategy, we’re here to help. Schedule a free consultation today to discuss your biggest financial concerns and how we can help you build a tailored plan focused on your long-term goals.

About Simon Quick Advisors

At Simon Quick Advisors, we understand the unwieldy challenges that wealth can create — because our founders faced them too. 

In 2004, Leslie Quick was frustrated with financial firms that prioritized sales over service, so he established a multi-family office to provide independent, fiduciary management for his family and others. Similarly, J. Peter Simon, his brother William E. Simon Jr., and their father, former Secretary of the Treasury William E. Simon, opened a family office to protect and grow their family’s legacy.

In 2017, these two firms united to form Simon Quick Advisors, combining their shared values and deep expertise to better serve clients. Today, we continue their mission to deliver wealth management that’s built on trust, not transactions.

One conversation can change your life. Let’s meet, on your terms.

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