Meet With Us
CLIENT LOGIN

Questions Every Woman Should Ask Before Choosing a Financial Advisor

Choosing a financial advisor can feel like standing at a crossroads. The decision isn’t only about finding someone who manages money well; it’s about finding someone who will walk alongside you, respect your story, and honor your values. Money is more than numbers. It touches relationships, choices, and futures.

For women, this decision often carries even greater weight. Some are stepping into financial leadership for the first time after a major life change like divorce, inheritance, or a career pivot. Others already feel confident in their financial knowledge but want an advisor who can match their expertise while offering structure, foresight, and emotional support.

At Somerset, we’ve learned through decades of guiding women and families that clarity comes from asking the right questions early. Knowing what to ask (and listening carefully to how an advisor answers) can reveal much about their style, priorities, and approach. Below, we’ve outlined ten questions every woman should ask before trusting someone with her financial future, along with reflections, examples, and insights on why each matter.

1. Do you truly understand my cash flow?

The foundation of financial planning is understanding what comes in, what goes out, and how money moves through your life. Cash flow tells the story of your day-to-day financial reality: mortgage payments, childcare, tuition, travel, personal hobbies, and even the small joys like dinner with friends or yoga classes.

Too often, advisors skip this step and dive straight into investment strategies or retirement projections. While those are important, they are built on the assumption that your day-to-day financial base is stable and accounted for. Without a clear picture of cash flow, even the most sophisticated investment strategy can falter.

For women, cash flow can be particularly complex. Career interruptions for maternity leave, caregiving for aging parents, or transitions between jobs are common. Advisors who fail to consider these nuances may miss opportunities to optimize spending, savings, and investment timing.

Illustrative example: Consider a woman returning to the workforce after a five-year caregiving pause. An advisor who begins with cash flow can create a realistic plan to rebuild retirement savings, pay down debt, and prepare for future life events, rather than simply suggesting a generic investment allocation.

Ask an advisor how they analyze cash flow and how often they revisit it. Do they consider future changes, such as expected college expenses or healthcare costs? The answers will show if they understand your life or just your account balances.

2. Will you listen before giving advice?

Financial planning should never feel like a monologue. Unfortunately, many women have experienced conversations where their concerns are minimized or overlooked. The best advisors listen first, creating space for clients to share their stories, fears, and aspirations.

A listening-first approach ensures that recommendations are relevant, personalized, and actionable. Advisors who ask probing questions about values, goals, and priorities demonstrate that they view you as a whole person, not just a portfolio.

Real-world reflection: A mid-career professional initially felt frustrated because her previous advisor focused solely on investments. She wanted guidance on managing student loans, planning for her children’s education, and balancing retirement savings. Once she switched to a listening-focused advisor, she gained a plan that aligned with all her priorities: financial, professional, and personal.

When evaluating an advisor, notice whether they ask about your emotional relationship with money, your long-term dreams, and your concerns for family or dependents. Listening is the foundation of trust; without it, even the most robust strategies fall flat.

3. How do you approach asset allocation?

Asset allocation (the distribution of investments across stocks, bonds, cash, and alternatives) is often presented as a technical exercise. In reality, it reflects how your money is positioned to meet your goals, manage risk, and provide stability over time.

Ask how an advisor constructs portfolios, how frequently allocations are reviewed, and how life events might trigger adjustments. Women, in particular, may have unique priorities such as funding college tuition, supporting aging parents, or ensuring retirement security after career interruptions. These needs can shift the balance of risk and liquidity in your portfolio.

Somerset insight: We guide clients to consider both time horizon and life stage when designing allocations. For instance, a single mother nearing retirement may prioritize stable income and low volatility, while a young professional with decades until retirement may emphasize growth opportunities balanced with periodic liquidity.

4. How do you handle retirement… or in some cases, real estate?

Retirement planning isn’t one-size-fits-all. For some women, retirement planning focuses on traditional income streams, Social Security strategies, and employer-sponsored accounts. For others, particularly those with significant wealth or business interests, real estate (such as vacation homes or investment properties) becomes central to long-term planning.

Ask your advisor how they integrate retirement planning with real estate considerations. Are strategies tailored to your lifestyle, income expectations, and long-term goals? A rigid, cookie-cutter approach may fail to address the unique financial and personal realities you face.

Illustrative Example: A widow navigating inherited properties and retirement income discovered that her previous advisor ignored the tax implications of real estate transfers. A new advisor helped her restructure the estate, optimize cash flow, and plan for future liquidity needs, turning a complex situation into clarity and control.

5. What is your philosophy on insurance?

Insurance exists to protect what matters most: your income, health, and family security. Life, disability, long-term care, and health insurance can each play an important role in financial stability, especially for women, who often live longer and may bear caregiving responsibilities.

Ask how an advisor evaluates your coverage and how frequently it’s reviewed. Beware of advisors who treat insurance solely as a product sale. A female-centered approach integrates insurance into a broader financial plan, balancing protection with efficiency.

6. How do you think about taxes?

Taxes touch nearly every financial decision: spending, investing, retirement, and philanthropy. Women, particularly those balancing multiple roles as earners, caregivers, or stewards of family wealth, benefit from advisors who incorporate tax strategy proactively.

Ask whether your advisor collaborates with CPAs, plans year-round, and accounts for changes in income, filing status, or deductions. Advisors who see taxes as part of the whole picture can reduce stress and create flexibility, allowing you to pursue financial goals without surprises.

Mini example: A client navigating stock option exercises and retirement plan contributions discovered that integrated tax planning saved her tens of thousands of dollars while aligning with her charitable goals.

7. How do you approach investments?

Investments are important, but only one part of a holistic financial plan. Advisors should approach investing with evidence-based strategies, diversification, and clear communication about risk. Equally important is their approach during volatility.

Ask about:

  • Investment philosophy and research methodology
  • Diversification across asset classes and geographies
  • Communication during market downturns
  • Alignment with long-term goals

 

Somerset guidance: We help clients consider both the financial and emotional aspects of investing. We believe that a calm, structured approach helps clients stay the course, even in uncertain markets.

8. How will you support estate planning?

Estate planning protects your legacy and allows for your wishes to be honored. For women, it often carries additional emotional weight: caring for dependents, passing values, and managing blended family dynamics.

Ask your advisor how they coordinate with attorneys and other professionals. Are wills, trusts, and beneficiary designations reviewed regularly? Do strategies account for taxes, liquidity, and future caregiving needs? A thorough advisor integrates estate planning into the broader financial framework.

9. How do you define stewardship?

Stewardship is the intentional use of wealth to support family, community, and causes you care about. Ask how your advisor integrates stewardship into planning. Some see wealth purely as accumulation; others embrace stewardship, aligning investments with purpose and values.

Reflection: Women often serve as financial stewards, balancing current family needs with long-term impact. An advisor who embraces this view helps you create a financial life that transcends numbers, supporting both security and meaningful legacy.

10. Are you serving as a fiduciary?

A fiduciary is legally obligated to act in your best interest. This ensures advice is transparent, free of hidden incentives, and aligned with your goals. Ask how your advisor lives this standard in practice. Hesitation may signal misalignment.

Real-Life Scenarios: Why These Questions Matter

Imagine a woman stepping into finances for the first time after divorce. She faces uncertainty about cash flow, retirement savings, and estate planning. An advisor who listens first and builds from foundational questions offers not just answers, but relief.

Or consider a seasoned entrepreneur preparing to sell a business. She understands investments and taxes but seeks a partner to align wealth with values and plan for the next chapter. In our experience, the right advisor can transform a transactional process into a structured, thoughtful transition.

Household Dynamics

Some women worry about involving a partner in financial planning. Strong advisors integrate both voices, balancing perspectives while maintaining clarity. Somerset’s CLARITIES Process aims to help households navigate differing priorities while striving to maintain cohesion.. It’s not just a framework; it’s a method for harmonizing financial goals with family relationships and life transitions.

The CLARITIES Process (Expanded)

Each question in this article connects back to Somerset’s CLARITIES Process, our cornerstone framework for female-centered planning. Here’s a deeper look:

  • Cash Flow: Understanding day-to-day finances, career interruptions, caregiving responsibilities, and projected expenses.
  • Listening: Prioritizing client goals, values, and emotions to confirm advice is meaningful.
  • Allotment: Analyzing your current assets and building a net worth statement.
  • Retirement & Real Estate: Integrating Social Security, employer plans, and real estate assets to optimize income and legacy planning.
  • Insurance: Evaluating life, disability, long-term care, and health coverage to protect both wealth and family well-being.
  • Taxes: Incorporating tax strategy into every decision, reducing liability, and increasing flexibility.
  • Investments: Building evidence-based, diversified portfolios while helping clients navigate market volatility.
  • Estate Planning: Coordinating with legal professionals to protect legacy and ensure wishes are executed.
  • Stewardship: Aligning wealth with personal values, family impact, and philanthropic goals.

Frequently Asked Questions About Choosing a Financial Advisor

1. What types of clients typically seek female-focused financial advisors?

Families, individuals navigating life transitions, and women stepping into financial leadership for the first time often seek female-focused advisors. Many appreciate a collaborative, listening-first approach that integrates cash flow, investments, taxes, and estate planning.

2. Can male clients benefit from working with female financial advisors?

Absolutely. Male clients can gain from a perspective that emphasizes holistic planning, active listening, and thoughtful stewardship. The clarity and structure provided benefit anyone who values long-term planning over transactional advice.

3. How do female advisors handle challenges unique to women?

Female advisors design strategies around longevity, career interruptions, wage gaps, caregiving responsibilities, and retirement security. These factors are woven into every aspect of planning, from cash flow and investments to estate planning and insurance.

4. Do female advisors work differently with couples?

Yes. Many encourage balanced participation, ensuring both voices are heard. Household priorities are harmonized, not dominated by one perspective. This approach creates alignment without sacrificing individuality or long-term goals.

5. How do I know if an advisor is truly a fiduciary?

Ask directly if they are a fiduciary and how they uphold this standard in daily practice. A fiduciary is legally obligated to act in your best interest, with transparency and no hidden incentives. Hesitation or vague answers may signal a misalignment of priorities.

6. How often will I meet or communicate with my advisor?

Frequency varies, but thoughtful advisors typically offer regular reviews and ongoing communication. Life changes like marriage, children, career shifts require revisiting the plan. The right advisor makes sure you’re never left navigating decisions alone.

7. What should I look for in terms of credentials?

Look for a CERTIFIED FINANCIAL PLANNER® designation or other relevant certifications. Credentials matter, but so does style. Choose someone who listens, explains clearly, and integrates cash flow, taxes, insurance, and estate planning into a cohesive strategy.

8. How do I evaluate if the advisor’s approach aligns with my values?

Observe how they ask questions, respond to your concerns, and incorporate long-term goals. Advisors who focus solely on products or returns may overlook the human side of finance. Alignment comes from both technical skill and relational understanding.

9. What if I want guidance on complex issues like stock options or business sales?

Ask how the advisor integrates specialized strategies into a broader financial plan. Experienced advisors collaborate with CPAs, attorneys, and other professionals to ensure these events support your long-term objectives and personal values.

10. Where can I start if I’m unsure of my financial priorities?

Begin with a structured framework like Somerset’s CLARITIES Process. It organizes planning into nine pillars: Cash Flow, Listening, Allotment, Retirement & Real Estate, Insurance, Taxes, Investments, Estate Planning, and Stewardship. Even if you’re uncertain, this process creates clarity and actionable next steps.

Lauren Pearson, CFP®
Website |  + posts

The most important thing in my life is my family. My husband, Andrew, and our three smart and brave daughters.