Career & Income Center
Career & Income Center

Employee Benefits Checklist

Review workplace benefits beyond salary — health, retirement, protection, leave, and more.

20–30 min Career & Income Center • Downloadable Checklist Last Updated: July 2026
Educational Checklist

Educational PurposeThis checklist helps employees review and compare workplace benefits beyond salary alone.

Use it when:

  • Starting a new job.
  • Reviewing annual enrollment options.
  • Comparing job offers.
  • Preparing for a promotion or transfer.
  • Experiencing a major family change.
  • Planning to leave an employer.
  • Evaluating the full value of compensation.

Benefits vary by employer and plan. Always review official plan documents before making decisions.

Part 1: Employment Information

Employee name
Employer
Job title

Employment status

  • Full-time
  • Part-time
  • Temporary
  • Seasonal
  • Contract
  • Other
Benefits effective date
Annual enrollment period
Human resources or benefits contact
Benefits website or portal

Part 2: Health Insurance

Coverage offered

  • Employee only
  • Employee and spouse
  • Employee and child or children
  • Family coverage
  • No employer health plan offered
Plan name

Plan type

  • HMO
  • PPO
  • EPO
  • High-deductible health plan
  • Other
Employee monthly premium$ __________
Employer monthly contribution$ __________
Annual individual deductible$ __________
Annual family deductible$ __________
Individual out-of-pocket maximum$ __________
Family out-of-pocket maximum$ __________

Review before enrolling

  • Preferred primary-care provider is in network
  • Preferred specialists are in network
  • Preferred hospital is in network
  • Current prescriptions are covered
  • Mental-health services are covered
  • Urgent-care benefits are understood
  • Emergency-care rules are understood
  • Out-of-network coverage is understood
  • Referral requirements are understood
  • Prior-authorization rules are understood
  • Maternity and newborn benefits are reviewed
  • Rehabilitation or therapy benefits are reviewed
  • Durable medical equipment benefits are reviewed
Questions or concerns

Part 3: Prescription Benefits

Prescription-plan provider
Annual prescription deductible$ __________

Copayments or coinsurance

Prescription categoryMy cost
____________________
____________________
____________________
____________________
  • Current medications are on the formulary
  • Mail-order options are available
  • Preferred pharmacies are identified
  • Specialty-pharmacy requirements are understood
  • Prior-authorization requirements are understood
  • Quantity limits are understood

Part 4: Dental Insurance

Monthly employee premium$ __________
Annual deductible$ __________
Annual benefit maximum$ __________

Coverage reviewed

  • Preventive examinations
  • Cleanings
  • X-rays
  • Fillings
  • Crowns
  • Root canals
  • Oral surgery
  • Dentures
  • Orthodontic treatment
  • Pediatric dental care
  • Adult orthodontic coverage
  • Waiting periods
  • Network restrictions

Preferred dentist in network

  • Yes
  • No
  • Unsure

Part 5: Vision Insurance

Monthly employee premium$ __________

Coverage reviewed

  • Routine eye examination
  • Frames
  • Lenses
  • Contact lenses
  • Lens upgrades
  • Frequency limits
  • Network providers
  • Discounts on additional purchases
Allowance for frames or contacts$ __________

Part 6: Health Savings and Spending Accounts

Health Savings Account

  • Eligible for a Health Savings Account
  • Not eligible
  • Unsure
Employee annual contribution$ __________
Employer annual contribution$ __________
  • Contribution limit reviewed
  • Account is portable if employment ends
  • Investment options are available
  • Eligible expenses are understood
  • Beneficiary is named
  • Receipts will be retained

Flexible Spending Account

  • Healthcare Flexible Spending Account available
  • Dependent-care Flexible Spending Account available
  • Limited-purpose Flexible Spending Account available
Planned annual contribution$ __________
  • Use-it-or-lose-it rules reviewed
  • Carryover rules reviewed
  • Grace period reviewed
  • Eligible expenses reviewed
  • Claim-submission deadline recorded

Part 7: Retirement Benefits

Retirement plan offered

  • 401(k)
  • 403(b)
  • 457 plan
  • Pension
  • Profit-sharing plan
  • Employee stock ownership plan
  • Other
  • No employer retirement plan
Employee contribution percentage
Employer contribution or match

Review the match

  • Match formula is understood
  • Contribution required to receive full match is understood
  • Contribution election has been completed
  • Automatic escalation is available
  • Roth contribution option is available
  • Pretax contribution option is available

Vesting — my own contributions are:

  • Immediately vested
  • Unsure

Employer contributions vest:

  • Immediately
  • Gradually
  • After a stated period
  • Unsure
Vesting schedule

Investment and account review

  • Beneficiary is current
  • Investment choices have been reviewed
  • Fees have been reviewed
  • Target-date fund option reviewed
  • Loan rules reviewed
  • Hardship-withdrawal rules reviewed
  • Rollover options understood
  • Previous employer accounts have been located

Part 8: Life Insurance

Employer-paid life insurance

  • Offered
  • Not offered
  • Unsure
Coverage amount$ __________

Coverage formula

  • Flat amount
  • Multiple of salary
  • Other

Optional employee-paid coverage

  • Additional employee coverage available
  • Spouse coverage available
  • Child coverage available
Additional coverage elected$ __________
  • Beneficiary is current
  • Secondary beneficiary is named
  • Coverage amount is adequate for family needs
  • Portability or conversion options reviewed
  • Coverage end date after employment reviewed
  • Evidence-of-insurability requirements reviewed

Part 9: Disability Insurance

Short-Term Disability

  • Employer-paid
  • Employee-paid
  • Not offered
  • Unsure
Percentage of income replaced
Maximum weekly benefit$ __________
Waiting period
Maximum benefit period

Long-Term Disability

  • Employer-paid
  • Employee-paid
  • Not offered
  • Unsure
Percentage of income replaced
Maximum monthly benefit$ __________
Waiting period
Maximum benefit duration

Important questions

  • Definition of disability reviewed
  • Partial-disability benefits reviewed
  • Base salary versus total compensation reviewed
  • Bonuses and commissions included or excluded
  • Tax treatment of benefits reviewed
  • Preexisting-condition limitations reviewed
  • Portability after employment reviewed

Part 10: Paid Time Off and Leave

Annual vacation days
Annual sick days
Personal days
Paid holidays

Policy review

  • Accrual method understood
  • Maximum carryover understood
  • Use-it-or-lose-it rules understood
  • Approval requirements understood
  • Unused-leave payout policy reviewed
  • Waiting period for new employees reviewed

Additional leave

  • Paid parental leave
  • Unpaid parental leave
  • Family-care leave
  • Bereavement leave
  • Military leave
  • Jury-duty leave
  • Medical leave
  • Caregiver leave
  • Sabbatical
  • Other

Part 11: Family and Caregiving Benefits

  • Childcare assistance
  • Backup childcare
  • Dependent-care account
  • Adoption assistance
  • Fertility benefits
  • Paid parental leave
  • Elder-care resources
  • Caregiver support
  • Employee-assistance program
  • Family counseling
  • Legal-assistance program
  • College-planning support
  • Other
Benefit most valuable to my household

Part 12: Workplace Flexibility

  • Remote work
  • Hybrid work
  • Flexible start and end times
  • Compressed workweek
  • Part-time scheduling
  • Job sharing
  • Shift selection
  • Predictable scheduling
  • Reduced schedule during certain periods
  • Work-from-another-location policy
  • Other

Questions to clarify

Is flexibility permanent or temporary?

  • Permanent
  • Temporary
  • Unsure

Is manager approval required?

  • Yes
  • No

Can the arrangement be changed later?

  • Yes
  • No
  • Unsure

Are specific in-office days required?

  • Yes
  • No
Details

Part 13: Education and Career Development

  • Tuition reimbursement
  • Tuition assistance
  • Student-loan assistance
  • Certification reimbursement
  • License-renewal reimbursement
  • Continuing-education support
  • Professional membership reimbursement
  • Conference attendance
  • Leadership-development program
  • Mentorship
  • Coaching
  • Internal training
  • Career-path planning
  • Other
Annual education allowance$ __________
  • Grade requirements reviewed
  • Eligible programs reviewed
  • Repayment requirements reviewed
  • Employment commitment reviewed
  • Approval process understood
  • Tax treatment reviewed where applicable

Part 14: Compensation Beyond Salary

  • Annual bonus
  • Performance bonus
  • Commission
  • Profit sharing
  • Stock options
  • Restricted stock
  • Employee stock-purchase plan
  • Signing bonus
  • Retention bonus
  • Referral bonus
  • Shift differential
  • Overtime
  • On-call pay
  • Travel reimbursement
  • Vehicle allowance
  • Mobile-phone allowance
  • Home-office allowance
  • Other

Compensation details

BenefitAmount or formulaPayment dateConditions
________________________________________
________________________________________
________________________________________
________________________________________

Part 15: Additional Workplace Benefits

  • Employee-assistance program
  • Wellness program
  • Gym membership or discount
  • Mental-health support
  • Financial counseling
  • Legal services
  • Identity-theft protection
  • Pet insurance
  • Critical-illness coverage
  • Accident insurance
  • Hospital-indemnity coverage
  • Long-term care coverage
  • Commuter benefits
  • Parking assistance
  • Public-transit assistance
  • Meal benefits
  • Employee discounts
  • Relocation assistance
  • Other
Optional benefits I should evaluate carefully

Part 16: Benefit Costs

BenefitEmployee monthly costEmployer contributionKeep, change, or decline
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
Total monthly employee cost$ __________
Total estimated annual employee cost$ __________

Part 17: Benefits Comparison Between Job Offers

BenefitCurrent jobOffer AOffer B
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
________________________________________
Which offer provides the strongest overall value?
Which offer best supports my household?
Which benefit difference matters most?

Part 18: Major Life-Change Review

Review benefits after:

  • Marriage
  • Divorce
  • Birth or adoption
  • Death of a beneficiary
  • Child becomes ineligible for coverage
  • New medical diagnosis
  • Spouse changes employment
  • Move to another state
  • Promotion
  • Reduction in hours
  • Leave of absence
  • Retirement planning
  • Other
Changes I need to make

Part 19: Leaving the Employer

Before resigning, retiring, or changing jobs, confirm:

  • Final day of health coverage
  • Health-coverage continuation options
  • Retirement-account options
  • Vesting status
  • Outstanding retirement-plan loan
  • Final paycheck date
  • Bonus or commission eligibility
  • Unused-leave payment
  • Life-insurance conversion or portability
  • Disability-insurance end date
  • Health savings account remains mine
  • Flexible-spending account deadlines
  • Tuition or signing-bonus repayment requirements
  • Stock-option deadlines
  • Employee-assistance access end date
  • Required return of company property
Deadline requiring immediate attention

Part 20: My Benefits Action List

Action 1

What I need to do
Who I need to contact
Deadline

Action 2

What I need to do
Who I need to contact
Deadline

Action 3

What I need to do
Who I need to contact
Deadline
Final Benefits Review
  • I reviewed the complete benefits package.
  • I compared total compensation — not salary alone.
  • I understand my monthly payroll deductions.
  • I reviewed deductibles and out-of-pocket exposure.
  • I understand the retirement match.
  • I reviewed life and disability protection.
  • I updated beneficiaries.
  • I reviewed paid leave.
  • I considered family and caregiving needs.
  • I reviewed education and career benefits.
  • I recorded important enrollment deadlines.
  • I know who to contact with questions.
  • I saved copies of official plan documents.
The TrueWealth Takeaway™
A paycheck tells only part of the compensation story. Health coverage, retirement contributions, disability protection, paid leave, flexibility, education assistance, and family benefits may significantly affect the true value of a job. Review each benefit carefully — understand what the employer pays, what you pay, what is protected, and what may disappear when employment changes.
— The TrueWealth Perspective™

© 2026 TrueWealth Leadership Development Agency. All Rights Reserved.

Educational Disclaimer: This material is provided for educational purposes only and should not be interpreted as financial, insurance, legal, tax, or investment advice. Individual circumstances vary. Consult qualified professionals before making financial or insurance decisions.