Workplace Benefits

8 Retirement Questions to Ask Your Employer 

2 min read
Dec 12, 2023

Retirement can mark the start of a new chapter in your life, where you may finally have the time for things you’ve been putting off, like traveling or pursuing hobbies. As exciting as retirement can be, ensuring that it’s financially possible begins far in advance, often shortly after you start a new job or career. 

Understanding the retirement options offered by your employer is crucial to maximizing the benefits. Whether you’re beginning a new job, you’re planning for the future, or you're trying to get your ducks in a row before you officially retire, here are 8 important questions to ask your employer. 

Retirement planning questions

Your benefits package should include important information about your retirement benefits as well as your health care options, and it’s a great place to start. Your human resource (HR) specialist can also help you find the answers to these important questions: 

1. What retirement benefits am I eligible for?

Retirement benefits can include 401(k) plans, 403(b) plans, employee stock ownership plans, and pension plans. 

Keep in mind that your employer isn’t required to offer retirement benefits, particularly if they operate in the private sector. However, if employers do choose to offer such benefits, there are government enforced policies that companies must follow.  

According to the MetLife 21st annual Employee Benefit Trends Study, in 2023, 75% of employees felt that a 401(k) or other defined contribution retirement plan was a “must-have” benefit.  Knowing which retirement benefits your employer offers can help you make wise financial decisions for your future.

2. Where can I learn more about the retirement benefits provided?

You can find retirement benefits details in a summary plan description (SPD), which is typically sent out within the first 90 days of the job. The plan outlines the benefit you’ll receive upon joining a workplace employee benefits plan. If you can’t find yours, contact your HR specialist.

Carefully review your SPD for details about “retiree health benefits” and information on how your plan works with Medicare and retirement.1 You may want to confirm with HR that you fully understand the SPD and see which of your employee benefits, if any, extend into retirement. 

3. Do you contribute to my 401(k) or other retirement plan?

Employer contributions can boost your retirement savings and help maximize your benefits. If your employer offers a matching contribution, determine what percentage they’ll match based on your own contributions. Typically, the match will max out at a certain percentage. 

If feasible, contribute enough from your paycheck to take advantage of that match. For example, if your employer matches your 401(k) contributions up to 4%, you may want try to contribute at least 4% of your paycheck to your 401(k). It’s also important to find out if there are any limits or restrictions on contributions. Some employer contributions might be subject to a vesting timeline, which means you're required to work for a specific period of time before you have complete ownership of any contributions. 

Starting to contribute to your 401(k) as early in your career as possible is crucial, as it allows your retirement savings to benefit from compounding over time. 

4. Are my retirement benefits portable?

Many retirees use government-funded benefits like Medicare and Social Security for their retirement income. While these benefits are valuable, they might need to be supplemented with additional funding to cover your retirement needs.  

Before planning to fund your own benefits in your retirement, find out if your workplace offers portable benefits. Retirement savings and plans that can be transferred and continued when you change jobs or employers are considered portable. For example, a portable benefits plan could be a 401(k) that can be entirely transferred into an individual retirement account (IRA) or from one employer to another when switching jobs or rolling into an IRA. 

Portable benefits provide greater flexibility to employees, especially to those who may experience multiple career shifts or job changes throughout their working life. 

5. Can benefits be eliminated during my retirement?

Even if your employer provides portable benefits, keep in mind that some employers aren’t legally required to maintain coverage during your retirement. Employers can modify or discontinue benefits at discretion unless they've explicitly promised otherwise. 

Take a close look at your plan’s terms and conditions and stay informed about any potential changes in the future.  

6. Do I have to cash in my 401(k) right away when I retire?

You don’t need to immediately cash in your 401(k) upon retirement. When it comes to managing your 401(k) plan, you have a few options outlined in your summary plan description (SPD). You can typically leave the funds in your 401(k) account, roll them over into an individual retirement account (IRA), buy a fixed income annuity with a portion of your 401(k), or some plans may allow you to initiate withdrawals following the rules set by the Internal Revenue Service (IRS).   

In general, IRS rules state that if your 401(k) holds more than $5,000, the plan administrator will continue to manage it. This means you're not obligated to make withdrawals or receive required minimum distributions until April 1 of the year after you reach age 73 or 75, depending on the year of your birth.2 While this allows your investment to grow and protect it from market volatility, you won’t be able to make additional contributions. To determine your best options, consult with a financial advisor. 

7. How does my HSA work after I retire? 

Even after you retire, you can continue to use the funds in your health savings account (HSA) to help pay for qualified medical expenses. However, you’ll no longer be able to make contributions once you enroll in Medicare, which typically happens at age 65. Any withdrawals used for non-qualified medical expenses after age 65 will be subject to income tax. 

Make sure you fully understand how an HSA works after you retire. Consult with your employer to discuss any restrictions or limitations that may exist. 

8. How does open enrollment change when I retire?

As your healthcare and benefit needs change, the open enrollment process might be slightly different after you retire. You may have access to different benefit options post-retirement. For instance, you may switch from an employer-sponsored plan to a Medicare plan. In this case the timing for open enrollment will also differ. 

Additionally, if your employer offers retiree health benefits, they might have a separate enrollment period for these plans. Make sure you know the dates of enrollment and review your retiree health plan options, including costs, coverage, and plan details. 

Retirement Questions: The bottom line

Asking your employer these retirement questions can help establish a solid foundation for your retirement readiness. Ultimately, the best way to prepare for retirement is to stay informed, evaluate your needs and options, and always ask questions.  

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1 “Retiree insurance,” 

2 “401(k) Resource Guide - Plan Participants - General Distribution Rules,” IRS, 2023