304: 5 Questions Every Tax-Aware Investor Should Ask Before Hiring an Advisor

Choosing the right financial advisor isn’t just about performance — it’s about clarity, tax awareness, and long-term decision-making. Hilary Hendershott, CFP® and founder of Hendershott Wealth Management, walks through five thoughtful questions every tax-aware investor should ask before hiring or continuing with a financial advisor.

This conversation is especially relevant if your financial life is becoming more complex — whether you’re managing equity compensation, concentrated stock, business income, illiquid investments, or significant taxable assets. A single decision can meaningfully impact your after-tax outcomes for years to come.

You’ll learn:

• Why after-tax returns matter more than pre-tax performance
• How real advisor value shows up through coordination with your CPA
• What to ask about tax planning, fees, and fiduciary responsibility
• How great advisors help clients make confident, thoughtful decisions

Key Takeaways

• 01:19 Why Choosing the Right Advisor Matters
• 02:26 Question 1: After-Tax Returns
• 02:54 Question 2: Working With Your CPA
• 03:39 Question 3: Reducing Your Tax Bill
• 04:37 Question 4: Fees and Value
• 05:15 Question 5: How Advisors Help You Decide
• 06:20 What These Questions Really Reveal

Show Notes
To get access to the full show notes, including all the resources mentioned, visit: https://hendershottwealth.com/podcast/5-questions-before-hiring-a-financial-advisor

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Hendershott Wealth Management, LLC and Love, your Money do not make specific investment recommendations on Love, your Money or in any public media. Any specific mentions of funds or investments are strictly for illustrative purposes only and should not be taken as investment advice or acted upon by individual investors. The opinions expressed in this episode are those of Hilary Hendershott, CFP®, MBA.