Employee Benefits Management

We've offered unlimited PTO at my firm from the beginning. But we just changed the policy— So that people will take more PTO.  I decided not to limit PTO thinking it would be great for my team. I want people to have autonomy and freedom in their jobs. And I don't want (or need) to babysit. People are adults. But what actually happened was that people weren’t taking the time off. We've seen that removing the limits on PTO created a lack of clarity around the expectations. Because unlimited PTO isn’t literally unlimited. There is a limit. You can’t just leave for 2 months. So instead of a great benefit, it was almost like I’d accidentally set a trap for my team. Nobody wanted to be the person to find out where the real line was. People took less time off, the exact opposite of what we intended. So last month, we sent out an email about the new policy:  PTO is still unlimited. But we have a mandatory minimum of 10 working days off each year.  Employees just need to request the days two weeks in advance so we can manage workflow.  The response has been surprising, one of the biggest morale boosts I’ve seen in my firm.  If you’ve run into this problem with your PTO policy, consider adding a mandatory minimum. And if you have any insights on unlimited PTO, I'm interested to hear them.

'Your PTO request was denied due to business needs.' Those words cost my client her father's last Christmas. Here's what HR won't tell you about unlimited PTO - their favorite 'perk' (and how to protect yourself): The unlimited PTO trap is the perfect example of HR doublespeak. They sell you freedom while secretly removing your rights. What they don't mention: • No PTO payout when you leave • No guaranteed minimum days off • Zero protection against denial of requests • No way to prove discriminatory enforcement Real story from last week: A tech employee's manager "encouraged" unlimited time off during her hiring. But when she requested 2 weeks for her father's hospice care, suddenly there were "staffing concerns." She came to me too late. The truth? Unlimited PTO lets companies: 1. Erase thousands in PTO payouts from their books 2. Avoid tracking or guaranteeing time off 3. Use peer pressure to prevent usage 4. Deny requests without accountability Don't let this happen to you. Protect yourself: 1. Get EVERY request and approval in writing 2. Track all your time off meticulously 3. Document any pattern of selective denials 4. Save emails showing others' approved time off Watch for my next post: The exact email template to use when HR denies your PTO request. #EmploymentLaw #WorkplaceRights #CorporateCulture Disclaimer: This information is for educational purposes only and does not replace professional legal advice. It does not establish an attorney-client relationship. Please consult a qualified attorney in your state for advice on your specific legal situation.

“Is unlimited PTO a green flag? Does it mean the company is great?” A CareerWareer client asked me this recently. A few years ago, I would have said yes. I worked at a company with unlimited PTO and took more time off than most companies in Asia typically offer (usually 14-21 days). You may have also seen people share stories of extended globetrotting holidays during off-peak seasons, made possible by unlimited PTO - and thought, “That must be a great place to work.” But after some time of seeing (and hearing) dynamics in various organizations, I’m now more nuanced. Here’s why unlimited PTO isn’t always a green flag: 1) Unlimited PTO can come with unlimited expectations: When there are no set guidelines, people can feel unsure about what’s acceptable and hesitate, especially if no one else is taking time off. In high-performance cultures, unlimited PTO can quietly morph into no PTO, because rest can feel like a risk when work never stops. 2) Managers can make or break it: Your ability to take meaningful time off depends less on company policy and more on your direct manager. If your boss respects boundaries and encourages unplugging, you’ll likely feel safe taking leave. If they send Slack messages on weekends and make comments like “wow, it must be nice to take a break,” that same policy can feel like a trap. 3) Culture eats policy for breakfast: This is very true! It doesn’t matter how generous the policy is if the culture doesn’t support it. If leaders model non-stop hustle and subtly reward those who “push through,” you will quickly learn that rest is frowned upon, even if it’s not said outright. PTO becomes a theoretical versus practical benefit. If you are interviewing at a company with unlimited PTO and wondering if this is a perk, here are 3 questions I would recommend asking: 1) Do leaders and managers here take visible time off themselves? How many days off do people actually take here on average? 2) What’s your team’s approach to covering for one another when someone’s away? 3) Can you share an example of someone taking PTO and how was that supported? Unlimited PTO can be a wonderful perk, but only when the culture, leadership, and operations support it. Don’t just ask what the policy is but ask how it lives in practice (or not).

𝗧𝗢𝗫𝗜𝗖 𝗩𝗔𝗖𝗔𝗧𝗜𝗢𝗡 When did time off become such a hassle in the US?  Most US workers use about half of their paid time off.  One in three say they would take a pay cut to get unlimited time off.  However, other research shows that in organizations with unlimited PTO employees take less time off compared to workplaces that do not have that policy.  Last month in one of my newsletters, I shared this strip from my comic strip hobby: Cres: Mondays are the worst. Gwen: Nope. Days off. Cres: Explain.  Gwen: Monday is bad on Monday. Cres: And time off? Gwen: You pay before, during, and after. That is the American reality.  There is a strong workaholism vibe.  It’s driven both by our Protestant work ethic background and deteriorating economic realities that require more hours or jobs per person to make ends meet.  Professionals fear missing work will be viewed as a lack of dedication.  Many managers who don’t take enough time off themselves apply pressure resulting in employees who feel discouraged or looked down upon if they take time off.  People believe it will impact their performance reviews and future opportunities.        At a minimum, those who take time off experience a unique form of professional dread before, during, and after.  Before they leave, they stress about getting ahead, making sure others can properly cover them, and dealing with the comments or glances they are receiving from others.  During their time away, most are told not to untether, to stay reachable, and often to overtly do work while away from the office.  When they return, they find an inevitable pile up of work waiting for them to dig through. What used to be a chance to smile and recharge has become quite the opposite.  What results is guilt, worry, resentment, and ever creeping stress that pushes too many towards burnout.  So, what can be done about this? There are some good best practices for companies that care.  Leaders can openly take their vacation and encourage the same from others.  Unplugging when away should be normalized.  It’s easy to automate the process of ensuring people don’t work when they’re away.  I’ve even seen penalties for violating this rule.  Projects can initiate formal stopping points when key people step away so all constituents know about it, know who to call if needed, know when the relevant person will be back at work, and so on.  Formal tracking of PTO used and balances remaining should be communicated regularly to encourage use.  Mandatory minimums and rollover of unused time help.  Some even use incentives (including extra time off) if PTO is schedule early in the year.  I’m fascinated by business and how we can do business better… vacation should be fun time off!  What do you think?  Please speak up and share: What’s your view and what’s it like where you work regarding the use of PTO? #PTO #worklife #motivation #stress #leadership

Unlimited PTO sounds great, until you’re the one supervising it. I’ve heard from multiple leaders recently who are struggling with the same thing: Newer professionals taking large amounts of time off early in the job – mental health days, wellness breaks, personal resets – without fully understanding the ripple effect it creates for the team. One supervisor shared that an employee was out more than they were in during their first summer on the job. Another watched sick days pile up until project deadlines were at risk. Both had unlimited PTO policies. Both had organizational values that emphasized rest, balance, and whole-person wellness. But neither had supervisors who were clear from the beginning about how to uphold those values without compromising the work. That’s the tension. Unlimited PTO isn’t actually unlimited. The work still has to get done. Expectations still have to be met. And it’s not sustainable, or fair, to shift the burden to coworkers every time someone needs space to reset. Unlimited PTO might help an organization’s bottom line. But it puts more weight on supervisors to draw lines that are respectful, not rigid. Flexible, not fuzzy. Aligned with values but still grounded in reality. So, if you’re a supervisor under one of these policies, don’t wait for the work to fall through the cracks before you say something. Be proactive. Be specific. Be kind and clear. Time off can be part of the culture, but so is accountability.

The biggest trap in corporates? Unlimited leaves. Sounds like freedom, right? But in reality, it’s corporate gaslighting at scale. Here’s how it plays out: The company announces “unlimited leaves.” Everyone claps. HR posts it on LinkedIn. But no one really takes them. Because there’s no baseline. No structure. Just guilt, quietly weaponized. With fixed leave, you knew what was yours. With unlimited leave, you have to ask for what feels “reasonable.” And suddenly, “reasonable” becomes a performance metric. The real issue isn’t the number of days, it’s the invisible pressure. In most companies, rest isn’t rewarded. It’s judged. And when the culture doesn’t back your break, no policy can protect it. No rules = No permission = No safety net. And the data proves it. Employees with unlimited PTO take fewer holidays than those with fixed plans. One study showed just 13 days off a year — versus 15 or more when boundaries are clearly set. That’s not flexibility. That’s fear in a shiny wrapper. What sounds like a progressive perk often turns into a cost-saving hack: No leave liability. No tracking. No accountability. So no, unlimited leave isn’t the revolution it claims to be. It’s just another way of saying: “Take rest, but only if you’re brave enough to risk it.” Until that mindset shifts, we’re not building healthier workplaces. We’re just rebranding burnout.

The most burned out employee I ever met worked at a company with unlimited PTO... Jenna hadn't taken a day off in fourteen months. Her company's careers page said all the right things: "Unlimited PTO." "Flexible hours." "Work from anywhere." She believed it when she signed the offer. Month one,  she asked about taking a long weekend. Her manager paused. "Now's not the best time. We're ramping up for Q2." Month three, she blocked off a Friday. Text message at 8 AM, "Quick question. Can you hop on a call?" Friday disappeared. Month six, she stopped asking. Nobody told her she couldn't take time off. Nobody had to. She watched a coworker request a week for his wedding. The eye rolls in the team meeting said everything. He came back to three "urgent" projects just dumped on his desk. The message was clear: Take PTO. Pay for it later. So Jenna stopped requesting. Started just... being available. Flexible hours meant she was always working. Remote work meant working everywhere. Unlimited PTO meant nobody tracked  how little anyone actually took. Her therapist called it burnout. Her company called it "high performance." One morning, she couldn't get out of bed. Not tired, really, just empty. She called in "done." Her manager was confused. "But you had unlimited flexibility here." "I had unlimited availability," Jenna said. "That's not the same thing." To leaders, it's flexibility. To employees, it's a ball and chain. You can put "unlimited PTO" on your careers page. But at least tell the whole truth about it: Unlimited PTO. Unlimited guilt for considering it. Unlimited work if you actually take it. Unlimited blame when you finally break. _____ Like my content?  Follow Bryan Howard and click the 🔔 on my profile. Find this useful? ♻️ Repost for your network. .

With employer healthcare costs projected to surge by 9.5% in 2026, the steepest climb in 15 years, many companies will simply absorb the financial blow. Strategic organizations, however, will use this as a catalyst to rethink their approach entirely. A recent Wall Street Journal report confirms what many CFOs and HR leaders are feeling. The increase is not a one-off event but a sustained trend driven by higher care prices, increased service use, and costly prescriptions. For mid-market companies lacking the negotiating power of giant enterprises, this presents a significant threat to financial stability and employee morale. Simply passing on these increases to employees or cutting benefits is a short-term fix with long-term consequences. Instead of reacting, leaders can take control with a more proactive strategy. This involves moving beyond a simple annual renewal and treating benefits as a core business function. Here are three levers that can be pulled right now: 1. Re-evaluate Funding Strategy: It may be time to explore alternative funding arrangements like self-insurance. As noted in the article, this gives companies more control over their plan design and can lead to significant cost savings by paying for employees’ actual medical costs directly, rather than paying fixed insurance premiums. 2. Aggressively Manage Pharmacy Benefits: Pharmacy expenses, especially for specialty drugs, are a primary driver of cost. A deep dive into your Pharmacy Benefit Manager (PBM) contract, formulary, and utilization patterns can uncover major opportunities for savings without compromising care. 3. Optimize Plan Design and Network: Steering employees toward high-quality, cost-effective providers is a powerful, yet underused, strategy. Implementing smarter plan designs that incentivize the use of efficient networks and care navigation tools can lower costs for both the company and its employees. Navigating this challenging environment requires a shift from a transactional to a consultative partnership. The companies that thrive will be those that build a sustainable, multi-year healthcare strategy, not just look for a quick fix for the next renewal cycle.

Both of his parents died unexpectedly last year, within six weeks of each other. He took time off. Not for a vacation. Not for a break. But to bury his parents, settle their affairs, and try to breathe again. His company has unlimited PTO. But apparently, unlimited doesn’t mean unconditional. In January, during their first 1:1 of the new year, his manager said: “You took a lot of time off at the end of last year.” She said it like he’d spent the holidays on a beach, not in back-to-back funerals. He didn’t miss deadlines. No one picked up his work. In fact, he earned a merit raise in March. But in May, she brought it up again. “I know we have unlimited PTO, but you’ve already taken two weeks this year.” Those two weeks? Probate meetings. Cleaning out his parents’ house. Helping his brother navigate paperwork that felt endless. He’s still grieving. Still showing up. Still delivering. And every time someone calls out sick or takes a day, she says it out loud “I know you missed a lot of time last week…” He’s leaving. Not for more money. Not for a title. But for peace. Because PTO shaming isn’t about time. It’s about trust. It’s about empathy. It’s about humanity. If your people have to earn the right to rest, you don’t have unlimited PTO. You have a culture problem. #PTO #ItsNeverReallyUnlimited #ResumeWriting