Managing all of this takes time and brain power. You’re contacting the employee, looking up policy details, doing unconfident math, and trying to figure out payroll work-arounds. The lost productivity cancels out the amount you’re saving by relying on these outside subsidies. Meanwhile, the new parent thinks it’s all your fault and blames you for the terrible experience you’re putting them through.

I get that it’s expensive to pay someone not to work for several months, but there are strong business reasons why you should do it anyway. 

The game begins. You have one calendar year to spend the money. The company has a year to collect it back from you. If you both follow the plan, you’ll both walk away scot-free, with the taxes you didn’t spend still in your pocket.

Maybe you’ve had this experience: You’re in crisis. You can’t work, so you call in. A well-meaning person you hardly know sends you information about the Employee Assistance Program (EAP). You look into what it covers and wonder how this could possibly help. The minimum CYA measure to guard against the wild things that people in crisis do.

A hundred years ago, in the heyday of unions, non-unionized businesses needed a way to make their low wages, long shifts, and poor working conditions look a little more attractive. So they did what lazy corporate wonks have done to increase morale since the beginning of time: They threw a pizza party. 

When someone is paid for a day they didn't work, it MUST be entered into payroll as some kind of Paid Time Off type. Otherwise, there's no way to pay it. Most of the uncommon leave types don't allow negative balances in payroll systems. So if your time off isn't allocated to another bucket, it can't get paid. The discrepancy could even block payroll and prevent everyone from getting paid.

What if, instead of inflating wages with cash, the company offered to pay for something even more valuable than cash? The health of workers and their families. 

Did you know that if your company has more than 50 employees (100 in CA, CO, NY, and VT), the employer sees all the prescriptions people take?  They don’t know who, but if there are fewer than 100 people it’s pretty easy to guess who needed a prescription to control their excessive underarm sweating. Or who's on Lithium.

Hourly workers often accrue time off based on the time actually worked, which may or may not be under their control.

The many layers of humans and technology that go into insurance deductions can make it hard to track down where the problem is. And because of the old school systems insurance companies still use, it can be like traveling back in time. 

Nearly everything that happens in the company goes through payroll. And the person managing it needs to have the skills of an accountant, IT, lawyer, insurance agent, and operations manager, all rolled into one.

For years, health insurance costs have already been increasing at more than double the rate of inflation. But even factoring in that trend, next year’s numbers seem like a prank. 

Both of these tools are available to companies for less than a dollar per employee per month. They can transform someone’s exit from cold paperwork to meaningful support.  If it rips your heart out to see what’s happening in the job market, Callings and Kept are two things you can offer right now that make a real difference.

You’re probably sleeping on the biggest company perk just because you think it isn’t free. You may think you’re maximizing the company perks, but if you aren’t maxing out your 401(k), you’re playing like an amateur. 

Insurance premiums have been increasing at more than double the rate of inflation for the past 3 years. In 2026, employer group plans are expected to increase nearly 8%. 

Short term disability insurance (STD) isn’t sexy. It doesn't attract top talent, but it can keep a company from the kind of tough decisions that can end with lawyers. Many employers don’t even know that the situations that are draining their budget are insurable. 

Is it okay for an hourly employee to work 30 hrs/week (instead of 40) for 3 weeks due to illness without taking intermittent FMLA? Their manager is cool with it and the employee doesn't want to take PTO.

He was quite confident that people always know when their paycheck is wrong. I wish that were always true. Payroll is complex, and you don’t know what you don’t know. I see a ton of these kinds of silent errors with 401(k)s. 

Employers have discretion about what's covered in their HRA plan, which is what makes them so useful. The company decides the annual limit, as well as specifications like whether to cover deductible expenses, post-deductible expenses, and/or over-the-counter expenses and services.

Let's get one thing straight: It's perfectly fine for your company to reimburse people for having a life. But if there's no business purpose or tax-preferred program for it (like an HRA, commuter benefit, or 401k), it has to be taxed as income.