Ready For Retirement with James Conole, CFP®

Episode: 5 Signs You Should Fire Your Financial Advisor
Date: September 30, 2025

Episode Overview

In this episode, James Conole tackles the often-difficult question of when to part ways with your financial advisor. Drawing on his experience as a practicing CFP® and CEO of Root Financial, James lays out five clear red flags that signal it's time to consider a change. He emphasizes that these aren’t about “advisor-bashing” but about ensuring your financial future is in the right hands. James encourages listeners to reflect on their advisor relationships objectively, shares compelling examples, and ends with practical steps for making a transition if it’s time to move on.

Key Discussion Points & Insights

1. Red Flag #1: Advisor Avoids Tax Questions (00:37)

• Issue: An advisor routinely tells you to “ask your CPA” for any tax-related question.
• Why it matters: Good retirement and investment planning cannot be separated from tax strategy. Without this, you're likely missing key opportunities.
  • “The right tax strategy could add tens or hundreds of thousands of dollars, if not more, to the value of your plan over the course of your retirement.” — James Conole (02:18)
• Possible underlying issues:
  • Firm-level compliance handcuffs advisors from discussing taxes.
  • The advisor simply doesn’t know enough about taxes to provide insight, which means their advice can’t be holistic.
• Advice: If your advisor dodges every tax question, it’s time to consider a change.

2. Red Flag #2: Advisor Only Focuses on Investments (03:54)

• Issue: The advisor does nothing beyond picking investments.
• Context: Decades ago, this may have been sufficient, but not today—investment management is now accessible and inexpensive.
• Comprehensive Planning: True value lies in integration: investments, taxes, withdrawal strategies, insurance, and estate planning must work together.
  • “If all your advisor is doing is that, they're still operating in a way that things were done 30-plus years ago.” — James Conole (04:38)
• Consequence: Focusing on only one area creates blind spots and can leave money on the table elsewhere.

3. Red Flag #3: You Don’t Understand What They’re Saying (07:48)

• Issue: Advisor uses jargon or complex language, leaving you confused after meetings.
• Key Insight: If you don’t understand, it’s not your fault; it’s because your advisor can’t (or won’t) explain it simply.
  • “Albert Einstein once said, ‘If you can’t explain it simply, you don’t really know what you’re talking about.’ That is especially true... with advisors.” — James Conole (08:43)
• Two Possible Reasons:
  • Lack of mastery: Hiding limited knowledge behind jargon.
  • Nefarious intent: Using complexity to keep clients dependent and justify higher fees.
• Advice: If you or your spouse regularly walk away confused, it’s time for a new advisor.

4. Red Flag #4: Advisor Ignores Your Spouse (13:18)

• Issue: Advisor only talks to one spouse (often the husband), ignores the other, and doesn’t foster joint engagement.
• Importance: Both spouses have a stake in the future; money is a tool for shared goals.
  • “You absolutely need both spouses to be involved... the money you have is going to fund both of your visions for what you want life to look like.” — James Conole (15:40)
• Practical Concern: If a spouse is excluded, they may be unprepared to work with the advisor if something happens to the other.
• Advice: If one spouse is disregarded in meetings, find an advisor who values both equally.

5. Red Flag #5: You Wouldn’t Rehire Your Advisor Today (18:36)

• Issue: The only reason you’re still with your advisor is inertia, not value.
• Reflection Technique: Ask yourself, “If I were making the choice today, would I hire this person again?”
  • “One of the best things you can do... is look at the things you are doing in your life and say, if I wasn’t already doing that, is that how I would choose to start doing things today?” — James Conole (19:15)
• Remove Emotion: Think about what advice your future self would give you regarding this relationship, to gain objective perspective.
• Advice: If you wouldn’t proactively choose your advisor today, it’s a sign to consider other options.

Memorable Quotes

• On the importance of tax planning:
  “You cannot separate tax planning from your investment strategy, your retirement strategy, especially in your retirement years.” — James Conole (01:17)

• On holistic advising:
  “A good advisor is going to have a very well-rounded knowledge across all these disciplines and apply that to you in a very unique way... that helps you get the most out of life with your money.” — James Conole (05:02)

• On clarity and communication:
  “If you walk away from a meeting with your advisor and you say, ‘I’m really confused; I have no idea what just happened,’ that’s not on you, that’s on your advisor.” — James Conole (07:53)

• On inclusion of both spouses:
  "The future that you want to live into together is very much something that both of you share." — James Conole (15:15)

• On challenging inertia:
  “What would yourself in 10 years from now... recommend you do about your current advisory relationship?” — James Conole (20:18)

Timestamps for Key Segments

• 00:37 – Warning sign #1: Avoidance of tax questions
• 03:54 – Warning sign #2: Over-focus on investments
• 07:48 – Warning sign #3: Lack of clarity and understandable communication
• 13:18 – Warning sign #4: Failing to include both spouses
• 18:36 – Warning sign #5: Wouldn’t rehire your advisor today
• 22:10 – How to “break up” with your advisor: practical steps
• 25:52 – Final thoughts and importance of finding the right advisor

How to Break Up with Your Advisor (22:10)

• It’s usually easier than you think: You own your accounts; transferring to a new advisor does not require confronting your old one if you don’t want to.
• Simple communication: A respectful, straightforward email is all that's needed ("Thank you for your time, I’ve decided to move to XYZ advisor...").
• Deep relationships: If the relationship is personal, schedule a call after sending an email to provide context or closure as you see fit.

Tone & Closing Message

James maintains a practical yet empathetic tone, emphasizing empowerment and reasonable self-assessment rather than fear or rash action. His message is about taking ownership, seeking clarity, and not staying stuck out of habit or guilt.

Final Word:
“The right advisor can be worth an incredible amount, not just to their financial benefit, but to the long term benefit and peace of mind that a good advisor can provide. But it’s really important you find the right advisor, and a part of that is looking at your current advisory relationship, seeing if any of these potential red flags exist and if so, moving on to one that is better for you and your situation.” (26:27)

For more from James Conole and to continue learning about building your dream retirement, subscribe to Ready For Retirement.