By David L. Dunn, CPA/PFS, CFP®, CPWA®
Why Now Is the Right Time to Pause and Prioritize
The holidays are near, tax deadlines loom, and inboxes fill up with last-minute reminders. For high-income executives, it’s the perfect moment to step back and ask, “Is everything aligned across my financial life?”
This isn’t about scrambling to finish a checklist. It’s about asking the right questions to ensure your planning remains coordinated, intentional, and forward-looking. Wealth doesn’t grow in a vacuum. It grows through thoughtful execution by a team that communicates clearly and moves in the same direction.
Here are 10 questions every executive should ask their financial advisor, CPA, and estate attorney.
- Have We Maximized All Available Deductions for This Year?
This isn’t just about charitable gifts or retirement plan contributions. Think business expenses, education credits, loss harvesting, and potential AMT exposure. Take action before December 31 to make sure no deduction is left on the table.
- Does My Equity Compensation Need Year-End Action?
Equity awards often come with time-sensitive decisions. Unexercised options, RSU vesting, and ESPP sales can all impact your tax bracket. Coordinating with your CPA before year-end helps you avoid costly surprises and possibly shift income into a more favorable year.
- Are There Opportunities to Convert to Roth at a Tax-Efficient Level?
Roth conversions can be powerful, especially when you’re in a lower-than-usual tax year or need to create tax diversification for retirement. Timing is critical. This is a conversation for your CPA and advisor.
- Should I Consider Gifting or Estate Planning Moves Before Year-End?
Annual exclusion gifts, trust funding, and family loans are most effective when planned ahead. Waiting until January may mean losing a full year of exemption or missing timing benefits. Your estate attorney should guide the strategy, but your advisor and CPA need to stay looped in.
- Is My Tax Withholding or Estimated Payment Still Accurate?
Significant changes in income can throw off earlier estimates. RSU sales, bonuses, business profits, or asset sales can push tax liability beyond what was projected. A final review can help avoid penalties and keep cash flow running smooth.
- Are My Charitable Strategies Optimized for This Year?
Have you contributed to a Donor-Advised Fund? Gifted appreciated securities? Used Qualified Charitable Distributions if eligible? December is often the last chance to lock in these benefits. Your advisor can help identify what’s possible, while your CPA can help ensure the tax reporting is handled correctly.
- Have We Reviewed My Beneficiary Designations and Account Titling?
Too often, beneficiary forms are outdated or misaligned with the estate plan. That can lead to unintended consequences. Reviewing titling across taxable and retirement accounts can help avoid probate, reduce delays, and better position your wishes to be honored.
- Do My Investments Still Align With My Goals and Risk Tolerance?
The end of the year is a natural point to evaluate asset allocation. Have market changes pushed you outside your intended ranges? Are there unrealized gains or losses that need to be addressed before December 31? Your advisor should guide this review with sensitivity to tax and cash flow needs.
- Is My Insurance Coverage Still Adequate and Efficient?
Life changes. So should your coverage. Have income, family, or business dynamics shifted? Employer coverage may be ending or changing. This is a good time to evaluate life, disability, umbrella, and long-term care policies for both gaps and redundancies.
- What Can We Learn From This Year to Improve Next Year’s Planning?
This question ties it all together. Were there avoidable tax surprises? Missed opportunities? Communication gaps? This isn’t about blame. It’s about refinement. The best planning happens when your team builds on what worked and fixes what didn’t.
The Power of Proactive Questions
These questions aren’t just technical. They’re relational. They invite dialogue, highlight blind spots, and encourage better decisions. When your financial team collaborates with clarity and intention, the results speak for themselves.
Financial planning isn’t one conversation. It’s many conversations that build on each other.
Tips for Leading the Conversation
- Regular touchpoints with each professional – even brief ones – help ensure your planning stays coordinated and responsive to change.
- Share your goals, concerns, and any updates to income, family, or business matters. Context improves recommendations.
- Ask each advisor how coordination happens and what additional information sharing might help strengthen the planning process.
Your Financial Story Deserves a Single Narrative
When each advisor sees only their piece of the puzzle, critical patterns can go unnoticed. An estate plan created without knowledge of current asset titling might miss a key opportunity.
The most successful executives aren’t just well-advised. They’re well-coordinated. They understand that a good plan becomes a great one when all professionals work from the same strategy.
If it feels like your advisors aren’t talking to each other, now’s the time to ask better questions. Not just, “What do I need to do?” but also, “Who needs to be in the room when it’s done?”
The Long-Term Value of Better Questions
The impact of asking better questions before year-end can extend far beyond tax season. It can help shape the foundation of next year’s planning. It may reduce friction and increase confidence.
And maybe most importantly, it reminds everyone – including you – that this isn’t just about numbers. It’s about your life, your goals, and your peace of mind.
Ready to explore working together? Schedule a complimentary 30-minute consultation at DAVIDDUNN.COM.
Disclosures
David Dunn Wealth LLC (DDW) is a member firm of The Fiduciary Alliance, LLC (TFA), a Securities and Exchange Commission-registered investment adviser. See full disclosure at www.daviddunn.com. Information contained herein is for informational purposes only and should not be construed as a solicitation for investment advice or for the purchase or sale of any securities, insurance, or other investment products. DDW does not provide accounting or public accountancy services. While information contained herein is based on sources deemed reliable, the accuracy and completeness are not guaranteed. DDW is independent and not affiliated with, endorsed by, or sponsored by Boeing, Microsoft, or their affiliates. References to these companies are for illustrative purposes only and do not imply any relationship or endorsement.