This past weekend, I was at a friend’s birthday party. While in a conversation with some new friends, the topic of money came up. As we talked, I realized that most of them didn’t really understand their own benefits packages from their full time employers. I’ve had this experience several times and seen that there is very little information about what employees should be asking their new employers in terms of benefits. I’ve been lucky in the sense that since I work for a large corporation, they have their benefits packages spelled out for every new employee. However, many employers do not provide this information unless it is specifically requested.

This has put many of my friends in the difficult position of not knowing enough and not knowing what questions to ask in order to learn. So, where to start? I’ve put together a list of essential benefits questions to discuss with your supervisor and HR when first starting (or before) a position with a new company.

On Salary/Paycheck

  • Will I get paid on a weekly, biweekly or bimonthly basis?
  • Should I expect an annual review and raise?
  • Is there any kind of incentive (bonus) program that I can qualify for?

On 401Ks/ Retirement Plans

  • Is there a 401K or 403B plan offered?
  • How long will I need to be with the company to get fully vested in the plan?
  • Is there any employer match for this plan?
  • What company do we have these accounts set up with?
  • What kinds of investments are offered within this plan?
  • Are there free or discounted wealth management services offered along with the plan?

On Insurance

  • What kinds of health insurance plans are offered?
  • If they are high deductible health plans, what compaby do we have our FSA or HSA with?
  • Is there any match in the FSA or HSA based on a health/wellness program?
  • Do we have Short term and/or Long term disability insurance plans (add link) offered?
  • Is there a life insurance policy that is offered?
  • If so, what are the possible payout amounts for this plan?
  • Are these costs automatically taken out of my paycheck each pay period?

On Vacation and Leave

  • How many vacation days will I receive upon starting?
  • Does this amount increase and if so, how many years into my employment will that occur?
  • How many personal/sick days do I get each year?
  • Do my vacation or personal/sick days roll over from year to year?
  • What is your maternity leave policy?
  • Do you have parental leave for fathers or same sex spouses?

On Other Services/Discounts

  • Do we get any discounts with local phone companies, cable companies, or other? (This is more common with larger companies, but not exclusive to them.)

I expect to update this list regularly based on input and experience from other resources. So, let me know in the comments below if you’ve found this list helpful or if you have ideas for other essential new employee questions that I can add.