What if the financial advisor you choose ends up mattering more than the investments themselves?
It’s a question most people never consider—until it’s too late.
Because over the course of your life, your advisor will be there for more than just quarterly statements and market updates. They’ll guide you through career transitions, market crashes, major purchases, retirement decisions, and the complex work of building a legacy. The right advisor doesn’t just manage your money; they seek to protect your family’s future across generations.
So how do you choose the right one?
A Story Too Many Families Know
When Alex and Dana started looking for a financial advisor, they thought they knew what mattered. They focused on brand recognition, glossy brochures, and promises of market-beating returns. Their first advisor seemed perfect—confident, polished, from a firm everyone recognized.
But over the next few years, reality set in.
When markets dropped 20%, their advisor’s advice was simply “stay the course”—no strategy for generating income, no plan for their daughter’s upcoming tuition bills, no discussion about whether they had enough cash reserves. They weren’t even sure what they were paying in fees, or who was actually managing their investments behind the scenes.
When their advisor retired, they were handed off to someone new who didn’t know their story, their values, or their goals. They had to start over—not just with a new advisor, but with entirely new questions about what they should have asked in the first place.
Alex and Dana aren’t alone. Most investors know they should ask questions when choosing an advisor—but not necessarily which questions reveal what truly matters.
The Questions That Cut Through the Sales Pitch
After working with hundreds of families who’ve been through this process, we’ve identified the questions that reveal the real difference between advisors who sell products and advisors who build legacies.
For each question below, we’ll show you:
- What most firms typically do (the red flags to watch for)
- What a truly exceptional firm should be doing instead
1. “What’s your philosophy on cash—do you invest it all, or preserve it purposefully?”
What most firms say:
“Cash is lazy money. Put it all to work in the market. If you need liquidity, we have margin accounts or credit lines available.”
What exceptional firms do:
They understand that cash isn’t about earning returns—it’s about seeking to protect everything else. They build strategic cash reserves that allow you to avoid selling investments at the worst possible time and seize opportunities when markets create them. They know that keeping 12-24 months of expenses in cash during retirement can mean the difference between running out of money at 85 or leaving a legacy at 95.
2. “How do you prepare portfolios for bear markets—before they happen?”
What most firms say:
“Nobody can time the market. Just ride it out. Markets always come back eventually.”
What exceptional firms do:
They proactively stress-test your plan against historical downturns, systematically raise cash as markets reach extremes, and build “behavioral coaching” into their process to keep you from making emotional decisions. They have a written bear market strategy before the bear arrives.
3. “Do you show investment performance net of all fees—and against relevant benchmarks?”
What most firms do:
They show gross returns, use cherry-picked time periods, or compare your conservative portfolio to the S&P 500 to make performance look worse than it is. Fee disclosure is buried in footnotes.
What exceptional firms do:
Every performance report shows returns after all fees, compared to benchmarks that match your actual allocation. Full transparency, accessible anytime through a client portal. No games, no fine print.
4. “How exactly do you create a retirement paycheck from my portfolio?”
What most firms do:
They withdraw a fixed percentage each year or sell whatever has cash available. No coordination between accounts, no tax strategy, no adjustment for market conditions.
What exceptional firms do:
They engineer a tax-efficient withdrawal strategy across all accounts, coordinate with Social Security and pensions, maintain dedicated cash reserves for down markets, and adjust dynamically based on both market conditions and your spending needs.
5. “What’s your position on securities-backed lines of credit?”
What most firms say:
“SBLOCs (Securities-Backed Line of Credit) are a smart way to access liquidity without selling. Use them instead of keeping cash.”
What exceptional firms do:
They view SBLOCs as short-term bridge tools only—never as a replacement for proper cash reserves. They understand that borrowing against volatile assets in a downturn is a recipe for forced liquidation at the worst possible prices.
6. “What exactly am I paying, and how does that impact my returns?”
What most firms do:
Layer fees upon fees—advisory fees, platform fees, fund expenses, transaction costs—often totaling 2-3% annually without clear disclosure.
What exceptional firms do:
Transparent, tiered pricing with all-in costs clearly stated. They show you exactly how fees impact your long-term wealth and work to minimize total costs while maximizing value.
7. “Are you a fiduciary—and what does that actually mean in practice?”
What most firms say:
“Yes, we’re fiduciaries” (but only when providing financial planning, not when selling products or managing investments).
What exceptional firms do:
They go beyond minimum fiduciary requirements. Exceptional firms are process-driven, not product-driven. They focus on clarity, transparency, and helping families make decisions that reflect their values and objectives — not sales quotas or proprietary products.
8. “What professional credentials does your team actually hold?”
What most firms have:
Sales professionals with limited credentials, or a single CFP® supporting dozens of advisors.
What exceptional firms have:
Deep bench strength with CFP® planners, CFA® charter holders for investments, CPAs for tax strategy, JD professionals for estate planning. Real expertise in every discipline that touches your wealth.
9. “What level of ongoing service and proactive communication will I receive?”
What most firms provide:
An annual review if you schedule it. Calls returned within 48 hours. One advisor handling everything.
What exceptional firms provide:
Structured quarterly reviews, proactive outreach when opportunities arise, and a dedicated Client Care Team (Advisor + Planner + Coordinator) ensuring nothing falls through the cracks.
10. “How do you determine which investment strategy fits my situation?”
What most firms do:
Give you a 10-question risk tolerance quiz, slot you into “moderate growth,” and call it personalized.
What exceptional firms do:
Align strategy with your actual capacity for risk, time horizons for specific goals, and purpose for each dollar. They use multiple risk “buckets” (personal, market, aspirational) rather than one-size-fits-all models.
11. “What’s your philosophy on risk—beyond just volatility?“
What most firms focus on:
Standard deviation and downside capture ratios.
What exceptional firms understand:
Real risk isn’t volatility—it’s running out of money, being forced to sell at the wrong time, or not achieving what matters most to you. They manage behavioral risk, sequence risk, and longevity risk—not just market risk.
12. “How is tax strategy integrated into investment and planning decisions?”
What most firms do:
Treat taxes as someone else’s problem. Maybe they’ll mention tax-loss harvesting once a year.
What exceptional firms do:
Build tax efficiency into every decision—asset location, Roth conversions, qualified charitable distributions, bracket management. They use specialized software and coordinate with your CPA rather than working in silos.
13. “Do you work with just me—or my entire family?”
What most firms do:
Focus on the primary breadwinner, with minimal involvement of the spouse and little to no engagement with children. The structure is typically one advisor acting as the relationship manager, supported by staff in transactional roles.
What exceptional firms do:
Operate with a Firm-to-Family model, where every household is supported by a full team of professionals—Advisor, Planner, Coordinator, and Specialists. Planning extends across generations: spouses are fully engaged, children are educated about wealth, and continuity is preserved through leadership transitions on both sides of the relationship.
14. “Is your planning process truly customized—or just software-generated?”
What most firms deliver:
Boilerplate plans from standard software, updated maybe once a year, gathering dust in a binder.
What exceptional firms create:
Living, breathing strategies that evolve with your life, accessible digitally, updated in real-time, and designed around your unique goals—not template assumptions.
15. “Who actually owns your relationship—the advisor or the firm?”
What most firms do:
Individual advisors “own” their client relationships. When that advisor retires, moves firms, or gets sick, you’re handed off to someone new who doesn’t know your story. You’re essentially an asset on someone’s personal balance sheet.
What exceptional firms do:
The firm owns the relationship, supported by integrated teams and documented processes. Your financial life continues seamlessly regardless of individual career changes. Continuity is built into the structure, not left to chance.
16. “Is their technology actually integrated—or just a collection of disconnected tools?”
What most firms have:
Disconnected systems that don’t talk to each other. Your advisor manually moves data between platforms, increasing errors and limiting real-time coordination. Your tax return lives in one system, investments in another, estate plan in a third.
What exceptional firms build:
A unified data architecture where all client information flows seamlessly between planning, tax, investment, and estate systems. One source of truth powering every recommendation. Every specialist sees the complete picture instantly.
17. “Can they scale their service—or will quality degrade as they grow?”
What most firms experience:
Service quality declines as they add clients because everything depends on individual advisor bandwidth. Response times slow, meetings get shorter, attention gets divided. Their solution? Serve fewer, wealthier clients.
What exceptional firms design:
Scalable systems with standardized deliverables and team-based service models. Quality actually improves with scale as resources deepen and specialization increases. Growth enhances capability rather than diluting it.
18. “Do they have a real succession plan—for your advisor AND the firm?”
What most firms avoid discussing:
No clear succession plan. When the founder retires, the firm often gets sold to the highest bidder, disrupting relationships and changing the service model. Your advisor’s retirement becomes your problem.
What exceptional firms plan:
Multi-generational leadership with equity structures ensuring continuity. Younger advisors are owners, not just employees, creating natural succession and aligned long-term thinking.
19. “How do they handle the industry’s ‘capacity crisis’?”
What most firms do:
Move “upmarket” to serve fewer, wealthier clients. If you’re not in the top tier, you get relegated to junior advisors or robo-solutions. They call it “right-sizing” but it’s really just abandoning smaller clients.
What exceptional firms innovate:
Separate client acquisition from service delivery. Use segmentation, specialization, and systematic workflows to maintain high-touch service across all client tiers. Every family gets institutional-quality care.
The Advanced Questions Most People Never Think to Ask
The Ownership Question: “What happens when your advisor leaves?”
Here’s what most investors don’t realize: In traditional firms, your advisor likely “owns” your relationship. They can take you with them to another firm, sell you as part of their book, or hand you off to whoever they choose. You’re not a client of the firm—you’re an asset on someone’s personal balance sheet.
Forward-thinking firms structure relationships differently. The firm owns the relationship, supported by integrated teams and documented processes. Your financial life continues seamlessly regardless of individual career changes.
The Scale Question: “How do you serve more clients without degrading service?”
Most firms hit a capacity ceiling. As they grow, response times slow, meetings get rushed, and you feel like a number. Their solution? Move “upmarket”—focusing only on ultra-wealthy clients while everyone else gets relegated to call centers or robo-advisors.
Exceptional firms solve this differently. They separate client acquisition from service delivery, use systematic workflows and specialized teams, and leverage technology to maintain high-touch service at scale. Growth actually improves their capability rather than diluting it.
The Integration Question: “Is your data actually connected?”
Ask your current advisor: “Can you see my tax return while reviewing my investment performance and update my estate plan accordingly—all in real-time?” Most can’t. Their systems don’t talk to each other. Your information lives in silos, manually transferred between platforms, increasing errors and preventing coordinated advice.
The best firms own their data architecture. Everything flows seamlessly between planning, tax, investment, and estate systems. One change updates everywhere. Every specialist sees the complete picture. This isn’t just convenience—it’s the difference between fragmented advice and truly integrated wealth management.
Now, How Does Gatewood Measure Up?
Every firm claims they’re different. Here’s how Gatewood actually answers these critical questions:
| THE QUESTION | GATEWOOD’S ANSWER |
| Cash Philosophy | Cash is foundational: 24 months of net expenses in retirement, emergency funds while working—protecting you from forced selling in down markets. It’s not what you earn on cash that matters, but what cash allows you to earn on everything else. |
| Bear Market Preparation | Bear Market Ready, Bull Market Positioned. Your stage, your strategy: In retirement, we buffer with bonds (5-8 years) after cash reserves. While working, we keep emergency funds but stay equity-focused—downturns are discounts, not disasters. |
| Performance Reporting | Complete transparency: net-of-fee performance, proper benchmarks, accessible 24/7 through your Gatewood Portal. |
| Retirement Income | Sophisticated “retirement paycheck” engineering across all accounts, tax-optimized and dynamically adjusted. |
| SBLOCs | Used sparingly as bridge financing only—never as a substitute for proper cash management. |
| Fee Structure | Transparent, tiered pricing. No hidden layers. Performance reported after all costs. |
| Fiduciary Standard | Upholding the philosophy of a fiduciary (acting in your best interests) even when it’s not required. Putting your plan first. |
| Team Credentials | CFP®, CFA®, CPA, JD, CLU®, ChFC®, CEPA®, MBA, MFS, MAcc—deep expertise across every discipline. |
| Service Model | Dedicated Client Care Team of professionals — Wealth Advisor, Wealth Planner, Wealth Coordinator, and Specialists — with regular reviews and proactive outreach. You’re never just a number. |
| Investment Strategy | Goals-based alignment using the CFA® standard, “three-bucket risk framework” for portfolio management — not generic questionnaires. |
| Risk Management | Comprehensive approach addressing longevity risk, sequence of return risk, and behavioral risk—not just volatility. |
| Tax Integration | Holistiplan software, bracket management, Roth optimization, QCDs—fully integrated with your investment strategy. |
| Family Approach | With our Firm-to-Family™ approach, Gatewood as a firm serves as your advisor—not just one person—providing multi-generational continuity through structured succession planning. |
| Planning Process | Real-time planning through eMoney, regular benchmarking against goals, continuous refinement—never a dusty binder, always a living strategy. |
| Relationship Ownership | Firm-owned relationships with systematic continuity—you’re never dependent on one advisor’s career. |
| Data Architecture | Unified, integrated systems where all information flows seamlessly—one source of truth. |
| Scalability | Systems-driven growth model that improves with scale rather than degrading service quality. |
| Succession Planning | Multi-generational ownership structure with younger advisors as equity partners. |
| Capacity Model | Separated new client acquisition from service delivery, allowing us to serve more families without compromise. |
The Three Questions That Matter Most
After all these details, it really comes down to three fundamental questions:
- Do you want a relationship with one advisor—or the backing of an entire firm? When your advisor retires, gets sick, or changes firms, what happens to you? Firms with true team models and firm-owned relationships ensure you’re never dependent on a single person.
- Do you want someone who reacts to your life—or proactively guides you through it? Most firms wait for you to call. Gatewood anticipates your needs, identifies opportunities, and reaches out before issues become problems.
- Do you want an advisor for your money—or a partner for your family’s future? If you’re just looking for someone to manage investments, plenty of firms can do that. If you want someone who understands that wealth is personal, that your “why” matters more than your rate of return, and that the true value of planning is the confidence it creates—that’s different.
The Bottom Line
Choosing a financial advisor isn’t about finding the biggest firm or the smoothest salesperson. It’s about finding professionals who understand that wealth with purpose requires more than investment management—it requires a comprehensive, integrated approach that puts your family’s unique goals at the center of every decision.
The questions above aren’t just conversation starters. They’re the difference between having an advisor and having a true wealth partner. Between managing money and building legacies. Between financial products and financial confidence.
If your current advisor—or the one you’re considering—can’t answer these questions in ways that give you complete confidence, maybe it’s time to expect more.
Because when it comes to your family’s financial future, “good enough” isn’t good enough.
Looking for an exceptional firm? You’ve come to the right place.
If these questions resonated with you—if you want an advisor relationship built on expertise, transparency, and genuine care for your family’s future—we invite you to start a conversation.
No sales pitch. No pressure. Just an honest discussion about what matters most to you and whether we’re the right fit to help you pursue it.
Important Disclosures:
The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results. All indices are unmanaged and may not be invested into directly.
Investing involves risk including loss of principal. No strategy assures success or protects against loss.
This is a hypothetical example and is not representative of any specific situation. Your results will vary. The hypothetical rates of return used do not reflect the deduction of fees and charges inherent to investing.
Bonds are subject to market and interest rate risk if sold prior to maturity. Bond values will decline as interest rates rise. Bonds are subject to availability, change in price, call features and credit risk
This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor.
Standard deviation is a historical measure of the variability of returns relative to the average annual return. If a portfolio has a high standard deviation, its returns have been volatile. A low standard deviation indicates returns have been less volatile
