Shakespeare Blog: View from the Lake

Group 512

By Kevin Reardon, CFP®

Open Enrollment – So Many Questions!

It’s that time of year again, when we either review group benefits at work OR our Medicare options (for those over age 65).  We have written several great articles about these topics in the past and list those links at the bottom of the article for those looking for additional resources.

Year after year we all struggle through the open enrollment process, doing just enough to renew our benefits.  The problem we see most often is people don’t know what benefits they actually have.  This year, I would like to challenge you to ‘conquer’ your benefits by digging in and learning the details.  In that regard, I have challenge questions you can answer that will help you get an ‘A+’ on your next benefits test.

Employer Group Benefits

Retirement Accounts

  • What is your 401k contribution rate?
  • What is your 401k employer matching percentage?
    • Does your employer provide a profit-sharing contribution and what is their historical contribution rate?
  • How is your 401k account invested? Reach out to Shakespeare if you need us to review your investments.
  • Do you have a pension or Cash Balance Plan at work? If so, what is your projected benefit?

Group Health Insurance

  • If you have different plans to choose from, your employer provides a summary of how each plan works. Print it out and review to determine which plan is best for your family.
  • What are the premiums, deductibles, co-pays and other out-of-pocket expenses? What is the out-of-pocket maximum on each plan?
  • Do different plans provide access to different doctors? Make sure your preferred providers are covered in-network.
  • Does your spouse have access to health insurance through their work? Are they allowed on your plan and vice versa? What are the differences between the plans? Is there an additional cost for covering a spouse on your plan if they have their own employer plan?
  • If you select a high deductible plan, are you contributing to an HSA account? Does the employer contribute to the plan?

Group Life Insurance

  • How much group life insurance do you have through your employer? This benefit is either a fixed dollar amount or a multiple of income.
  • Are you able to purchase more life insurance through the group plan? If you need or want additional life insurance, you may be better served (cheaper) buying individual life insurance.
  • Does your employer offer Accidental Death and Dismemberment (AD&D) Insurance? If so what’s the coverage?

Group Disability Insurance

  • Do you have both short- and long-term disability?
  • What percentage of your income will the group disability insurance replace?
  • What is the disability elimination period?
  • Is there a maximum monthly benefit provided by your plan?
  • Will the benefit be taxable or tax-free if you ever go on disability? If you’re paying a small tax on your W2, the benefit is tax-free.
  • How long do you have to be disabled before the policies start?

Individual Health Insurance Plans

  • Spend a few minutes reviewing
  • Based on your health, do you want a high deductible plan (good health) or a plan that provides more immediate coverage and a lower deductible (moderate to poor health)?
  • Do you spend an extended period in a different state and how do the different policies handle an out of state illness?
  • Do you qualify for a Premium Tax Credit that can significantly lower your cost?
  • What level of prescription drug coverage does each plan provide?

Medicare & Medicare Advantage Plans

  • Have you reviewed the various plans available to you?
  • What are the co-pays and deductibles for each plan?
  • Are your doctors included in all of the plans you’re looking at?
  • What level of drug coverage do you have? Are you taking any prescriptions that aren’t covered or are on a specialty tier?
  • Do you spend an extended period in a different state and how do the different policies handle an out of state illness?
  • Based on your income level, what will the various policies cost?


It’s not easy at the beginning.  Doing the research initially can make benefit choices in the future easier.  Plus, knowledge is always a good thing.  If you need help with any of the above, your Shakespeare Team is here to help.

Now, time to login and enroll.  Good luck!

Note:  Keep in mind laws and rules may have changed since these articles have been written.

Medicare Advantage vs. Medicare Supplement policies – What is best for you? 

Medicare Enrollment..What’s so Hard about That?