Retirement Questions to Ask Your Employer: Don't Get Caught Off Guard!
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Retirement Questions to Ask Your Employer: Don't Get Caught Off Guard!

Writer: Adam Smith, CFP®Adam Smith, CFP®

Retirement questions to ask your employer.

Are you asking the right retirement questions to your employer?


Many professionals approaching retirement, especially eligible employees, find themselves caught off guard by crucial details about their retirement benefits that they wish they had known years earlier.



At Covenant Wealth Advisors, we’ve seen countless situations where asking the right questions early could have significantly improved our clients’ retirement outcomes.


Here's what you need to know.


Key Takeaways


  • Understanding your employer's retirement benefits can potentially add hundreds of thousands of dollars to your retirement savings

  • Many employees miss out on valuable benefits by not fully understanding their company's retirement match formula

  • Knowing your vesting schedule can prevent leaving money on the table when changing jobs

  • Special retirement benefits like mega backdoor Roth contributions or deferred compensation plans are often overlooked

  • Early retirement options and retiree healthcare benefits can significantly impact your retirement planning strategy


Table of Contents



 

See How Our Firm Can Help You Retire With Confidence


  • Will my money last in retirement? Find when you can retire and if you'll be able to maintain your lifestyle.

  • How should I invest in retirement? Personalized investing to grow and protect your wealth in retirement.

  • How can I reduce taxes in retirement? Identify tax strategies including Roth conversions, RMD management, charitable giving and more...




 

Understanding Your 401(k) Plan Structure


The foundation of most corporate retirement plans is the 401(k), but the details can vary significantly between employers.



Man thinking, holding paper. Text on 401(k) plan structure with points on matching, provisions, vesting, and investing limits. Green-checked background.


Matt Brennan, CFP® at Covenant Wealth Advisors in Richmond, VA, emphasizes,


"The most costly mistake I see is employees not fully understanding their company's matching formula. I've had clients leave tens of thousands of dollars on the table simply because they didn't structure their contributions optimally."

Essential 401(k) Questions


  1. What is the exact matching formula?

  2. Is there a true-up provision for the match?

  3. What is the vesting schedule for employer contributions?

  4. Are after-tax contributions allowed?

  5. What are the investment options and their associated fees?


Here are IRS Contribution Limits to help you understand how much money you can defer in your employer 401 (k).


💡 Pro Tip: Don't assume your employer's matching formula is simple. Some companies have complex tiered matching systems or require specific contribution patterns to maximize the match.


Exploring Additional Retirement Income Benefits


Many employers offer retirement benefits beyond the standard 401(k) plan. Understanding these additional options can significantly enhance your retirement strategy.


Engaging a financial planner can help you navigate these additional benefits and ensure you are making the most of your retirement strategy.


Deferred Compensation Plans


Some employers offer non-qualified deferred compensation plans (NQDC) that allow you to postpone receiving a portion of your income until retirement.



Key considerations for a deferred compensation plan.


While deferred compensation plans can be powerful tax-planning tools, they come with risks that need to be carefully evaluated. Understanding the distribution options and company credit risk is crucial.


Healthcare and Health Insurance Considerations



Your retirement date marks a significant transition from employer-provided health and life insurance to personal responsibility for healthcare coverage.


Understanding your employer’s healthcare benefits into retirement can be worth its weight in gold!


Retirement health benefits. A checklist to review with your employer befire you retire.


Critical Healthcare Questions


  1. Does the company offer retiree health insurance?

  2. What happens to my HSA when I retire?

  3. Is there a transition plan to help bridge the gap until Medicare eligibility?

  4. Are there any wellness program benefits that extend into retirement?


💡 Pro Tip: If your employer offers an HSA-eligible health plan, consider maximizing these contributions even if you're healthy. HSAs offer triple tax advantages and can be an excellent way to save for retirement healthcare costs.


Stock Options and Equity Compensation


Understanding your equity compensation can be like trying to solve a Rubik’s cube blindfolded - there are lots of moving parts!


It is essential to understand the income tax implications of exercising stock options to prevent unexpected tax liabilities.


“One of the biggest mistakes we see is clients exercising stock options without considering the tax implications,” says Scott Hurt, CFP®, CPA at Covenant Wealth Advisors in Richmond, VA. “A strategic exercise plan can potentially save hundreds of thousands in taxes.”



Exercising stock options? Don't forget the taxes, types of equity stock compensation and tax impact, vesting schedules, and more.


Key Questions About Equity Compensation


  • What types of equity compensation do I receive (RSUs, ISOs, NSOs)?

  • What are the vesting schedules and expiration dates?

  • How does retirement impact unvested equity?

  • Are there any special retirement provisions for equity compensation?


Special Retirement Programs


Here's where things get interesting!


Many companies offer special retirement programs that can be absolute game-changers for your retirement planning. Think of these as the secret sauce in your retirement recipe!


5 retirement program types listed, with an elderly person looking thoughtful. Green grid background, blue and green text highlights.


Programs to Ask About


  1. Phased retirement options

  2. Retirement transition consulting

  3. Financial planning services

  4. Volunteer or consulting opportunities

  5. Alumni networks and benefits


💡 Pro Tip: Some companies offer "retirement transition" programs that let you gradually reduce your hours while maintaining full benefits. This can be a fantastic way to test-drive retirement while still earning income.


Pension Plan Questions


If you’re one of the lucky ones with a pension plan, you’ll want to dig deep into the details.


Man in suit pondering with hand on chin. Background text: Mission-Critical Pension Plan Questions. Topics include payments and benefits.


Here are the mission-critical questions to ask:


According to the Employee Benefit Research Institute, understanding these details can significantly impact your retirement planning.


Essential Pension Questions


  • What are my payment options (lump sum vs. monthly payments)?

  • How is my benefit calculated?

  • Are there early retirement reduction factors?

  • What survivor benefits are available?

  • How are cost-of-living adjustments handled?


Understanding Your Retirement Benefits


Navigating the landscape of retirement benefits can feel overwhelming, but understanding what you’re entitled to is crucial for a secure and comfortable post-work life.


Here’s some additional insights to help you decode your retirement benefits.


What Retirement Benefits Am I Eligible For?


Understanding your retirement benefits is crucial for planning a secure and comfortable post-work life. Retirement benefits can vary greatly depending on your employer, location, and individual circumstances. Here are some key points to consider when evaluating your retirement benefits:


  • Retirement Plan Options: Your employer may offer various retirement plan options, such as a 401(k), 403(b), or pension plan. It’s essential to understand the details of each plan, including contribution limits, investment options, and vesting schedules. Knowing these details can help you maximize your retirement savings and ensure you’re making the most of your employer-sponsored plan.

  • Retirement Savings: Your retirement savings are a critical component of your overall retirement benefits. Consider contributing to a retirement account, such as an IRA or Roth IRA, to supplement your employer-sponsored plan. Diversifying your retirement accounts can provide additional financial security and flexibility.

  • Retirement Income: Your retirement income will depend on your retirement savings, Social Security benefits, and any other sources of income you may have. A financial advisor can help you create a sustainable income strategy for your retirement years, ensuring you have enough funds to cover your expenses and enjoy your retirement.

  • Retirement Benefits Eligibility: Check with your HR department to determine which retirement benefits you are eligible for. This may include health coverage, life insurance, or other perks. Understanding your eligibility can help you plan more effectively and take advantage of all available benefits.

  • Early Retirement: If you’re considering retiring early, understand the implications on your retirement benefits. You may be eligible for early retirement packages or phased retirement options, but these can impact your benefits and income. It’s important to weigh the pros and cons of retiring early and how it will affect your financial situation.

  • Full Retirement Age: Your full retirement age, as determined by the Social Security Administration, will impact your retirement benefits. Understand how your retirement age affects your Social Security benefits and other retirement income sources. Delaying retirement can increase your benefits, so it’s worth considering if you can afford to wait.

  • Health Insurance: Health insurance is a critical component of your retirement benefits. Understand your options for health coverage in retirement, including Medicare, employer-sponsored plans, and individual insurance policies. Ensuring you have adequate health coverage can protect you from high medical costs and provide peace of mind.

  • Financial Advisor: A financial advisor can help you navigate your retirement benefits and create a comprehensive retirement plan. They can assist with investment strategies, income planning, and benefit optimization. Working with a financial advisor can help you make informed decisions and maximize your retirement benefits.


By understanding your retirement benefits and options, you can make informed decisions about your retirement planning and ensure a secure and comfortable post-work life.


 

See How Our Firm Can Help You Retire With Confidence


  • Will my money last in retirement? Find when you can retire and if you'll be able to maintain your lifestyle.

  • How should I invest in retirement? Personalized investing to grow and protect your wealth in retirement.

  • How can I reduce taxes in retirement? Identify tax strategies including Roth conversions, RMD management, charitable giving and more...




 

FAQ Section


Q: How do I find out about benefits I might have missed? 

A: Schedule a meeting with your HR department specifically focused on retirement benefits. Request a complete benefits guide and ask about any special programs for long-term employees. Consider bringing a financial advisor to this meeting to ensure you're asking all the right questions.


Q: Can I continue working while collecting retirement benefits? 

A: The answer varies by employer and benefit type. Some companies allow you to collect certain retirement benefits while working part-time, while others require a complete separation of service. It's crucial to understand these rules before making retirement decisions.


Q: What happens to my benefits if the company is acquired? 

A: Benefits can change significantly during acquisitions. Stay informed about any transition periods or grandfathered benefits. Keep all documentation about your current benefits, and don't be afraid to ask questions during transition periods.


Q: Should I take a lump sum or monthly pension payments? 

A: This decision depends on various factors including your other income sources, life expectancy, and overall financial plan. Consider working with a financial advisor to analyze your specific situation and make an informed choice.


Conclusion


Taking charge of your retirement future starts with asking the right questions. Think of it as building your retirement puzzle - each benefit is a crucial piece that needs to fit perfectly into your overall picture.


By understanding and maximizing your employer-provided retirement benefits, you can create a more secure and comfortable retirement.


Remember, these questions are just the starting point. Your specific situation might require additional considerations, and that's where professional guidance can be invaluable.


At Covenant Wealth Advisors, we specialize in helping professionals like you navigate these complex decisions to optimize your retirement strategy.


Would you like our team to just do your retirement planning for you? Contact us today for a free retirement roadmap experience.




 

Adam Smith financial advisor in Reston VA

About the author:

Senior Financial Advisor


Adam is a Senior Financial Advisor with Covenant Wealth Advisors and a CERTIFIED FINANCIAL PLANNER™ practitioner. He has over 17 years of experience in the financial services industry in the areas of financial planning for retirement, tax planning, and investment management.


 

Disclosures: Covenant Wealth Advisors is a registered investment advisor with offices in Richmond, Reston, and Williamsburg, VA. Registration of an investment advisor does not imply a certain level of skill or training. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. The views and opinions expressed in this content are as of the date of the posting, are subject to change based on market and other conditions. This content contains certain statements that may be deemed forward-looking statements. Please note that any such statements are not guarantees of any future performance and actual results or developments may differ materially from those projected. Please note that nothing in this content should be construed as an offer to sell or the solicitation of an offer to purchase an interest in any security or separate account. Nothing is intended to be, and you should not consider anything to be, investment, accounting, tax, or legal advice. If you would like accounting, tax, or legal advice, you should consult with your own accountants or attorneys regarding your individual circumstances and needs. This article was written and edited by a CERTIFIED FINANCIAL PLANNER™ professional with the assistance of AI. No advice may be rendered by Covenant Wealth Advisors unless a client service agreement is in place. Hypothetical examples are fictitious and are only used to illustrate a specific point of view. Diversification does not guarantee against risk of loss. While this guide attempts to be as comprehensive as possible but no article can cover all aspects of retirement planning. Be sure to consult an advisor for comprehensive advice.

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Awards and Recognition

 

Covenant Wealth Advisors was nominated by Newsweek/Plant-A-Insights Group in November of 2024 as one of America's Top Financial Advisory Firms for 2025. You may access the nomination methodology disclosure here and a list of financial advisory firms selected.

 

CWA was awarded the #1 fastest growing company by RichmondBizSense on October 8th, 2020 based on three year annual revenue growth ending December 31st, 2019. To qualify for the annual RVA 25, companies must be privately-held, headquartered in the Richmond region and able to submit financials for the last three full calendar years. Submissions were vetted by Henrico-based accounting firm Keiter. 

 

Expertise.com voted Covenant Wealth Advisors as one of the best financial advisors in Williamsburg, VA  and best financial advisors in Richmond, VA for 2025 last updated as of this disclosure on February 12th, 2025 based on their proprietary selection process. 

 

CWA was nominated for the Forbes Best-In-State Wealth Advisor 2022 ranking for Virginia on April 7th, 2022. Forbes Best-In-State Wealth Advisor full ranking disclosure. Read more about Forbes ranking and methodology here.

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CWA did not compensate any of the entities above for the awards or nominations. These award nominations were granted by organizations that are not CWA clients. However, CWA has compensated Newsweek/Plant-A Insights Group for licensing and advertising of the nomination and compensated Expertise.com to advertise on their platform.

 

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