These 5 Employee Time Off Hacks Will Help You Boost Productivity

Or How I Learned To Stop Worrying And Love It When People Took Time Off

For a long time at the non-profit where I worked in New York City, I toiled in the Finance Department and reported to the Comptroller.

He’s the fellow who, early on in my tenure, gave me the responsibility of maintaining the vacation book where I tracked everybody’s time off entitlement and availability.

He had a lot to do with my promotion to Operations Director, and it was he who insisted that I take the vacation book with me to my new department. Nevertheless, I still love Charlie and honor his memory.

That Crosswalk, Manhattan New York.
That Crosswalk, Manhattan New York.

My new boss was the Chief of Staff. One of our first official exchanges after my promotion was the first day I had the job, a Monday. John – the CoS – held a meeting of department heads every Monday morning.

Back in the day, such meetings were an accepted and efficient way to update everyone on the various projects and other activities that were going on, and I was going to attend my first one that morning.

Where the hell is Howard? Has he forgotten we have a meeting every Monday?

At the meeting, John looked around. “Where’s Howard? Where’s Eric?” He looked at me, his eyebrows raised. I guessed he was expecting me to answer.

I kind of shrugged, and he went back to conducting the meeting.

I thought maybe I’d gotten off on a wrong foot, a thought John confirmed when we got together in his office right after the meeting.

“If department heads can’t make it to the Monday meeting, I want to know, and I want to know why. I don’t want to come to a meeting and be surprised that people I expect to see aren’t there.”

By the end of the week, we’d instituted a relatively minor hack to our time off scheduling and approval program, except back then we didn’t know about hacks, so we called it a modification.

There was no way I was going to call 18 department heads every week to find out if they’d be at the meeting, and I wasn’t going to delegate such a crummy task to anyone in my department.

Instead, whenever a department head requested vacation pay, someone in Finance would call and alert me before the fact, and I’d alert John.

After a few weeks, we modified it again – I’d alert his assistant Rebecca, who started keeping a chart of all department heads.

It didn’t just track vacation time, it tracked all activity outside the office, so at a glance John could see not only who’d be out on vacation the next Monday, but also who’d be out of the building on business, which about a fourth to a third of our department heads always were.

Sick time was different – department heads who called in sick on Monday knew to alert John or his assistant that they’d miss the meeting.

Put more broadly, this first hack is to establish a system of tracking attendance of the people who matter in your job. If you’re a supervisor, that’d definitely include those you lead, plus whoever you report to, including all solid- and dotted-line relationships.

Include others you work with regularly or on whose work you or your people depend.

Ask them to let you know when they’ll be out, just so you can know. If anyone objects, tell them you’re not trying to exert any veto power over them, just that if you know when they’ll be out, it’ll be easier for you to work around them.

One of the problems with the manual system I maintained is that it was hard to get a picture of who would be in or out on any particular day — it was oriented more toward people’s time off eligibility and making sure nobody went over their entitlement.

Vacation notebook.
Vacation notebook.

Any attendance management system implemented today, of course, is best established digitally.

Who wants to spend so much time drawing charts and updating the personnel, whiting-out names and inserting new names when people are promoted or hired?

If you have digital time tracking software at your work, it should be easy to create your chart and access it whenever you need to.

The real beauty of such an approach is that you don’t need to enter any of the data – as soon as someone on your list is approved for time off, it gets entered in the system and is updated on your chart.

The larger and more complex your organization, the more time will be saved by managers and supervisors throughout the organization.

If there are privacy concerns, access to the data can be restricted to supervisors and above, and access to records of people outside one’s own line of authority might need to be approved.

Sorry, Boss, I can’t come in today – we just got back from vacation yesterday and we’re absolutely wiped out. Put me down for a sick day, okay?

I saw this happen fairly frequently in my first couple of jobs, but it never happened in any form when I was directing human resources at a vitamin factory. Here’s why:

the company had a firm policy of prohibiting sick or personal time the first workday after someone’s vacation, or any three-day holiday

The prohibition also applied to the last workday before a vacation, or a three-day weekend. It was designed to keep the production lines fully staffed, and it accomplished its purpose.

Or, put perhaps more cynically, it’s designed to prevent people from gaming the system by tacking discretionary time off to their vacation at the last possible minute.

I thought it was most effective prior to a holiday or vacation. I’m sure most people know someone – or of someone – who routinely calls in sick the day before a holiday or vacation, so they can “get a head start.”

This is different from changing the way you track time off. It requires a change in policy, and it might need ratification by your employees if they’re in a collective bargaining unit.

It also needs to account for people who really are sick. From the perspective of compassion, for instance, if someone comes down with the flu or some other illness the day before they take off for vacation, they often have to cancel or at least modify their vacation plans.

Isn’t it adding insult to injury to not pay them for sick time they would otherwise have been paid?

So some employers have modified their policies even further, to allow for paying sick time for the day before or after a holiday or vacation if they can document a real sickness, primarily through a doctor’s note, together with documentation of cancellation of vacation travel.

It’s my impression, though, that most employers with that policy of no paid sick leave before or after a holiday or vacation just leave it alone or deal with them on a case-by-case basis.

Incentivize Taking Time Off

You’d think that taking time off would be its own incentive. But the fact is that most salaried employees only take about half the vacation available to them.

You know the problem – or perhaps you’re not yet familiar with it. Employees want vacation time for a variety of reasons, but from the perspective of your business, there are two main reasons to give paid vacation time.

The first is that it’s what your employee wants – so much so that the promise of more paid vacation is a meaningful incentive both for employee retention and attracting new employees.

Another reason is to give employees some real time away from the job – time to rejuvenate, to unwind, to get their minds off work and refresh themselves.

If you’ve been fortunate enough to take a vacation of two weeks or more, you know what I’m talking about – when you get back to work, there’s actually a sense of change, both in the organization, and in yourself.

And you don’t just go to your desk and pick up where you left off – you need to be updated on all the things that have happened while you were gone.

Full of cheer at the start of the 36 hours.
Full of cheer at the start of the 36 hours.

This is how I know that I’ve really had a good vacation. And people who have that opportunity to relax and refresh periodically wind up feeling better on the job and about the job, and they do better work.

The problem, though, is that some people don’t take off even a full week at a time.

I knew one fellow who, one summer, arranged to spread his vacation over three months of Fridays – for 15 weeks in a row, he took off every Friday

He’d been used to taking just a week off in the summer and another in the winter, and then using the other five days on a piecemeal basis.

He told me a few months later he wished he’d taken two or three weeks off in a single chunk – the string of three-day weekends didn’t really refresh him the way he thought they would, and by the time Halloween came along, he was feeling really burned out.

He was actually in the minority, because even though he spread it out, he took all his vacation time every year.

According to a Glassdoor survey discussed in the Huffington Post, the average American is entitled to just 10 vacation days per year – which is half – or less – of what workers are guaranteed by law in many European countries.

Even worse, the average American only takes about half of what he or she is entitled to every year.

Some people can’t afford to take vacation – their pay is enough to pay the bills, but there’s not enough left over to fund a vacation trip.

These folks take what are called “staycations” – they stay at home and often remain in close touch with the office

I had a switchboard operator who knew before I did when her replacement was going to call in sick, and she’d call me from her staycation and volunteer to come in and cover for the person who was supposed to be covering her while she was on vacation.

Work from home...
Working from home…

Other people can afford a vacation, but for whatever reason, they don’t take much time off, but let it accumulate.

Some of these folks say that they’d rather be in the office working than staying at home doing basically nothing.

Still others do take their time off, but they bring their computers and phones with them and stay connected to the job while they’re vacationing.

These folks are often concerned that if they really disconnect, even if just for a week or two, their employers will decide they’re not really necessary.

They look for ways to prove themselves indispensable, and indispensable people don’t take vacation – they can’t.

Because there are proven benefits to employees taking at least a week off,

and preferably two or more, some employers give bonuses to employees who take at least a week of vacation at a time.

Evernote, for example, a high-tech firm headquartered in California’s Silicon Valley, provides a stipend of $1,000 to any employee who takes an entire week off. Another company, FullContact, headquartered in Denver, Colorado, has a program it calls “Paid, Paid Vacation.” It’s both simple and difficult.

What’s simple about it is that the firm, which offers employees a minimum of 15 vacation days per year, also offers them a $7,500 annual stipend to take vacation – enough for a family of four to take a very comfortable vacation in a tropical location.

The catch? Employees must actually go away – no staycations – and they must completely disengage while they’re away – they can’t work and they can’t be in contact with the office. It’s almost a joke nowadays, but actually difficult.

The emphasis on disconnection is critical. Some employers have noted that many of their salaried employees take work with them on vacation and remain in regular contact with the office.

They try to participate with their family in a regular vacation while simultaneously keeping on top of things at work.

When they return to the office, according to FullContact’s CEO Bart Lorang, they’re fried.

This is what inspired the paid paid vacation, and its requirement that employees must pretty much go off the grid for their vacation time. The firm incentivized relaxation.

Give Time Off as a Reward

Some employers have standard time-off policies that provide for a certain number of vacation days, etc., for all employees.

However, they also give people bonus days for a range of accomplishment.

For instance, if a project is completed successfully, or under budget, or before the deadline, the participating team members are given a few extra days off.

Of course, in most workplaces, there are employees doing great work in administrative departments who wouldn’t generally get special recognition for doing their jobs well, unless that was somehow built into the system – making it not really a special incentive.

Stop Limiting Time Off

Yep, you read that correctly. It may sound like a pipe dream, but the fact is, some companies are experimenting with getting rid of all limitations and giving their employees unlimited paid time off.

Of course, there’s a catch there too – you can take all the paid vacation you want, but you’ve got to get your job done. So obviously, this won’t work in many traditional employment venues, like factories.

Many high-tech companies, though, work much differently, and some are more project-oriented, so that the time between projects is basically down time during which employees could come to work and do makework, or take paid vacation.

Even when a firm is constantly busy, most projects don’t need 100% participation from all team members all the time.

Of course, the needs of the business must still come first, and vacation requests must be presented for management approval.

However, it’s a fascinating idea, and not surprisingly, it’s controversial

Some people insist that without any limits, employees will take that unlimited vacation and drive their employer into bankruptcy.

Others, though, say that without guidelines, employees will be reluctant to take advantage of such a policy, especially in a struggling economy.

Even with a policy of unlimited vacation, so the argument goes, nobody wants to be the person who’s taken the most vacation in a still-shaky economy.

Working From the Hammock.
Working From the Hammock.

One of the reasons more employers are shifting to unlimited vacation policies is the recordkeeping involved.

It’s easier today than it was when I was maintaining the vacation book, but it’s still another step in the recordkeeping chain, as well as another opportunity for human error.

There’s a hidden benefit for employers as well. Once people accrue vacation time, it’s like money in the bank.

They can take the paid time off, or they can leave it in their vacation bank and let it grow. It doesn’t earn interest, but it does grow.

Consider – someone making $500 a week banks a week of vacation and takes it the following year, after his pay has gone up to $520. He gets paid $520 for the week he banked, not $500.

Many employees routinely bank a portion of their annual time off accrual and let it grow to the maximum permissible.

They only cash it out when they leave employment or when they retire – sometimes dozens of weeks of pay that are a nice supplement to their severance or retirement package.

Unlimited vacation time solve another vexing problem – “use it or lose it.”

Many employers limit the amount of vacation time that can be banked, leading to situations where employees who have banked that limit effectively aren’t permitted to earn any more time off until their bank “balance” is drawn down.

Take it from personal experience – people get very irritated when you tell them they aren’t currently earning any vacation time because their bank is full.

Then when they try to take a few weeks off to draw down the balance, their managers don’t like to approve long vacations on short notice.

Without caps on how much vacation a person can take, there’s nothing left over to accrue.

But wait – there’s more! All that accrued vacation must be carried on the company’s books as a liability, from year to year.

Establishing a policy of unlimited vacation means no more liability for accrued vacation pay, a befinite benefit for the employer both in terms of the balance sheet and the time spent tracking these figures.

There’s even more. Many employees’ retirement benefits are calculated based on their earnings during their final two or three years of employment.

Accrued vacation time that’s cashed out upon retirement usually gets added to that equation as earnings during the final year.

This has caused sometimes dramatic increases in many retirees’ pension benefits.

Can We Wrap This Up Already?

So there you have it – five hacks to the way you run your vacation tracking and policy in your shop that should contribute immensely to your staff’s morale and productivity.

The first – installing a good system to track people’s time off – is easily done, as you don’t really need any sort of buy-in from other stakeholders.

Time off tracking software CakeHR.
HR management software CakeHR

The others – not paying for sick days that butt up against vacation or holidays, incentivizing taking time off in meaningful chunks and using time off itself as a reward may take some more selling, depending in the size and nature of your shop.

The final hack –

establishing a policy of unlimited paid time off – is a major change

that might take a lot of selling just to help others get over some of their stereotypes and preconceptions.

Companies that have it, though, including Netflix, credit card payment processor Gravity Payments, and insurance company GoHealth, all seem to be doing quite well.

While unlimited vacation time isn’t quite yet a trend – the Society for Human Resource Management says about 1 percent of all employers have adopted the policy – it seems to be an idea worth serious consideration.


Written By

Dale Marshall

Human Resources Manager.