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. 

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.

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. 

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. 

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.

What we’re really seeing is misaligned incentives disguised as authority. They have no reason to follow through, just respond. We wouldn’t put up with this in any other business service.

Parental leave combines the most complicated parts of HR into one policy: protected classes, disability, paid time off and sick time, obscure payroll esoterica, employees who are "active" but not "working" (and sometimes don't come back when you expect), insurance (policy details, deductions, and a qualifying event), onboarding and offboarding (maybe more than once per person), a bajillionty federal, state, and local laws, many of which conflict

Even the fancy ben admin tools. Somewhere behind the curtain, someone is downloading a form and forwarding it to a carrier. Often using unsecured email.

"Is this because I said I wasn't pregnant?" He scratched his beard. He was the first non-birth parent to use the policy. And it wasn’t working as planned. And yes, his claim was denied because he wasn't pregnant.

Everywhere I went, I saw the same thing: Employees didn’t understand what they signed up for. Brokers didn’t really understand either. HR didn’t want to touch it. Claims were denied. People thought their plans sucked.

I don't know who needs to hear this, but Qualifying Life Events (QLEs) aren't written in stone.

These problems don’t show up right away. They lie in wait until someone balances the books and notices thousands of dollars missing.