Recently I approached my manager to approve my 4 days leave (Paid Time Off). He said "Let's make it 3 days and take sick leave on the 4th day". He does this every time I apply for more than 2 days leave. His justification is that since Paid Time off (PTO) can be carried forward to next calendar year, why waste it when other types of leave are available.

We also have a payout policy for PTO's, so he makes his justification look more legitimate by quoting this also. (I am not sure about payout of sick leave. I'll update once I check my policies tomorrow.).

While I don't see any disadvantage for me to apply the leaves as he suggested, it is beyond my understanding what's in it for him?

  • 16
    Do you have any maximum sick policies (days or periods of absences). Consider what would happen if you were genuinely sick - would you exceed these?
    – Smock
    Commented Sep 17, 2019 at 13:18
  • 23
    Have you asked your manager directly why he suggests this leave time allocation? Surely there's a reason, and if you have a good relationship with him, he should be able to answer the question for you.
    – Milwrdfan
    Commented Sep 17, 2019 at 13:34
  • 33
    Some companies (mine for example) are very flexible about sick days, allowing you to take unused ones off for any reason. If that's the case there is no problem with what he is doing. He's trying to help you maximize your time off. Commented Sep 17, 2019 at 13:52
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    Be careful navigating this. If all your coworkers are doing this, and you check with HR and they quash it, you don't want word getting around that you were responsible for taking away everyone's free vacation days. Commented Sep 17, 2019 at 14:14
  • 11
    Which state/country are you in?
    – THiebert
    Commented Sep 17, 2019 at 16:58

9 Answers 9


This is a type of unethical conduct or workplace dishonesty which happens in hierarchical environments where there is little accountability of the greater good and huge accountability from your imminent relations. What it could be about:

  • As pointed by many: boss looking after his workers. He cares about the loyalty of his workers. Loyalty allows him to squeeze extra hours, possibly non-compensated, of his workers when needed even if the work policy does not allow demanding this or there is concerning regulation prohibiting this. Not necessarily bad for the greater good but indeed it is bending the rules and abusing human psychology of paying favours back.
  • It can be that the managers are rewarded by surveys. So he needs you to like him because people are not objective and value shady tips/approval for abusing the system. He is trying to be your guy. to get the good ratings.
  • Some kind of workday accounting may make it seem like he is achieving more with less which could affect his bonuses.
  • 32
    "Moral hazard" is not a random coinage, it is a term from economics with a highly specific meaning, discussed in connection with market failure due to asymmetric information. It does not typically include fraud, although it does include the agent acting in ways that harm the principal. I personally would not see this situation as a typical moral hazard problem, and don't immediately see any benefit of analysing it from that angle.
    – rumtscho
    Commented Sep 17, 2019 at 5:42
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    On the other hand, the manager may want to be accumulating documented evidence that you "always take some extra time off sick at the end of your holidays" - and the obvious reason for doing that is not going to benefit you when it is the reason you are fired.
    – alephzero
    Commented Sep 17, 2019 at 12:07
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    Maybe there is no financial gain for the manager for doing it. Maybe he seems there is no harm in the rule bending of sick days, and simply do it because he would like his boss to do the same for him. His gains may be of the personal satisfaction sort.
    – lvella
    Commented Sep 17, 2019 at 12:26
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    Your first bullet point seems to venture really far down the road of assumptions. Couldn't it just be the boss caring about his workers and their loyalty, without expecting to squeeze any extra time or work out of them; perhaps instead hoping that the morale will improve production.
    – JMac
    Commented Sep 17, 2019 at 14:36
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    @Octopus OP's very clear that his intention is to take vacations and their manager is telling them to book it as sick days (which they clearly are not). Telling you're sick when you're clearly not only is unethical in many cultures, it is labeled as fraud in many countries and can result in a for-cause termination. Commented Sep 18, 2019 at 9:14

While I don't see any disadvantage for me to apply the leaves as suggested by him

You are taking sick days when you are not actually sick. Maybe this is OK with and encouraged by your manager but what are the consequences of HR finding out? You need to read your employee handbook and find out if sick days at your company can only be used if you are actually sick or if they are more like personal days where it is any sudden unexpected excused absence. Your boss may be trying to help you out but this could backfire so I would make sure to fully understand your company's policies on PTO.

  • 45
    Even if it's "any sudden unexpected absence", OP would still be violating that policy, since this absence is known in advance. And a pattern of taking sick days next to rec leave is going to look very suspicious if HR decide to check up.
    – G_B
    Commented Sep 16, 2019 at 23:12
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    @nick012000 taking a "mental health day" after each planned vacation would look really bad if I was the HR worker looking into this employee's history. I would not recommend using that term as a reason in this case.
    – Gertsen
    Commented Sep 17, 2019 at 7:40
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    @Geoffrey - it will look even more suspicious if everyone in that team does the same but that's a big indicator that the boss is responsible for the behaviour. I'd really want to check that he is encouraging the rest of the team to take sick days, and not just setting me up for a fall. Commented Sep 17, 2019 at 7:42
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    Even more cynical possibility: He attempts to create something that he can MAKE backfire on people at will. Commented Sep 17, 2019 at 20:31
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    It would look like alcoholism or some other substance abuse. He's not in shape for work the day after his vacation.
    – JollyJoker
    Commented Sep 18, 2019 at 7:46

It is not completely unusual for employees to view sick days as a commodity that are there to be "used up". This is an incorrect view of the world but just about common enough that it is likely your boss genuinely believes that you deserve the sick days as holiday.


It would be very unusual for this to be an actual company policy and as such you may be taking a significant risk by "spending" your sick days in such a manner. Amongst other things you are running the risk of actually getting sick and then not having any days left in your budget.

What is in it for your boss?

One possibility is that your boss wants you to break the rules because it will make it easier for him to break the rules also. This could be a benign or, if you are unlucky, it could be sinister.

  • 24
    or he wants to have something to use against the employee in the future if he wants to get rid of him. Fraud with sick days is a good way to get fired on the spot...
    – jwenting
    Commented Sep 17, 2019 at 7:51
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    @jwenting most likely he just wants his team to cover up for his own dishonest behavior as "every does it anyway". Commented Sep 17, 2019 at 12:20
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    Probably very regional. In some countries, sick leave intertwines with the healthcare system, and is not considered just a matter of employee and employer Commented Sep 17, 2019 at 20:35
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    @rackandboneman Careful there - "sick day" and "sick leave" are two very different things. Sick days are only between the employee and the employer, and is intended for short unexpected periods of leave (usually "I don't feel well today, so I'm going to get a bit of rest and come back to work tomorrow"). Sick leave usually involves health insurance and/or the government, and is intended for more serious issues, spanning multiple days or even longer. Sick days are a benefit paid for by the employer.
    – Luaan
    Commented Sep 19, 2019 at 8:24
  • 1
    @Luaan Where would that apply? I don't think you can assume this distinction or terminology to be universal. I can also name a country where the first few days of pay during sick leave are paid by the employer but still heavily regulated and must be reported to the government and another country where the employer is on the hook for up to 2 years of sick leave.
    – Relaxed
    Commented Sep 19, 2019 at 22:42

Just because this has not been mentioned yet, Assuming your company is larger, I have seen organisations where the budget for paid vacation comes directly from your team / manager's budget, but sickness comes from a central company medical expense budget.

It could be that your manager is trying to manipulate such a system to have a little more money for the department at the cost of the company's budget as a whole.

While it is probably harmless if used a few times I would not be surprised if you use it too much there may start to be questions centrally about if you have some kind of medical problem or are gaming the system. Unless you have what he said in writing do not expect to be able to blame him in case of any investigation, it would likely fall squarely on you.

  • 3
    This was my first thought too. I've worked at a university where nobody really cared about how or if I report vacation days (because the only thing that matters is that x % of my salary comes from the project where I report x % of my working hours) – but my boss told me to always report sick days when I'm sick, because we can save project funding that way.
    – JiK
    Commented Sep 19, 2019 at 11:33
  • The company could never prove later that you werent sick on that single day. If your manager routinely signs applications for four free days in a week, and makes no inquiries if workers dont turn up on the fifth, its his neck in the sling.
    – Karl
    Commented Sep 19, 2019 at 20:59
  • @Karl While I get your point, I happen to know my former employer as well as several other screen for employees who take significantly more sick days on Monday, Friday or the day before or after a vacation and begin investigating with HR.
    – Vality
    Commented Sep 19, 2019 at 21:01
  • Im sure, but the guilt still accumulates on their manager. ;) Of course Im judging from German work regulations, where such a case against a single employee would usually be as cold as a frozen duck.
    – Karl
    Commented Sep 19, 2019 at 21:21

While I don't see any disadvantage for me to apply the leaves as suggested by him, it is beyond my understanding whats in it for him?

There should be nothing for him personally here. He seems to be trying to build goodwill with the employee (you) by getting more monetary benefits available to you (by having PTO's cashed / carried over) by working the system.

However, if you work in a company with strict policies, such an action coming to notice of HR could lead to him getting a warning for such behavior. (As he sets the wrong example). Today he is bending one rule for subordinates, what if they start breaking other rules themselves by subjectively deciding what can be acceptable?

  • 8
    "if you work in a company with strict policies" - worth also noting that every company can become a "company with strict policies" overnight and without warning.
    – user81330
    Commented Sep 17, 2019 at 12:53

Your boss is messing with your professional reputation

I don't know if that is their intention, but it is certainly the end result. Taking sick leave straight after a planned holiday generally carries a negative connotation - it is not a good look. Your boss might think they're doing you a favour, but it could give other people in the company the impression that you're slacking off.

Have you ever had this conversation at work?

P1: Wasn't Greg supposed to be back today?
P2: Yeah his leave ended yesterday. I guess he came down with a case of the "holiday blues" because he called in sick today!
P1: Wow, how unprofessional.
P2: Yeah, this isn't the first time either. He does this every time he takes leave.

Even putting the interpersonal aspect aside - it will make your attendance/leave records look off, which businesses tend to check in performance reviews and other scenarios - would you put "Greg the slacker" up for a raise or promotion? If you needed to lay off 50 people today, who's top of the list?

Only your boss will know why he is doing this. Maybe he genuinely believes he's doing you a favour. Maybe he's setting you up to look bad for some reason. My point is, don't let it continue. You need to tell them to enter your leave exactly as you requested it; it's not worth whatever benefit he thinks he's giving you.

Tell your boss you want to save your sick leave for when you are actually sick.

  • 7
    1) OP didn't do the calling in. 2) Outside of the boss and maybe admin, no one needs to know that OP is using sick leave instead of holiday leave, and 3) Such a petty work environment sounds horrible
    – Mars
    Commented Sep 18, 2019 at 8:15
  • 3
    Another issue is if your HR department uses a Bradford factor to check sick days.
    – PeterI
    Commented Sep 18, 2019 at 8:22

Honestly I'd guess there's a greater than average chance that what's happening here is not legitimate. I think you probably realise that it would take some extraordinary reason for it to be.

Key seems to be this line

why waste it when other types of leave are available

Well, because the different types of leave are for different purposes. There's exactly one type which can be legitimately used for paid time off, and it's your... contractually agreed PTO days.

This looks to be a classic case of too good to be true - what your manager is suggesting making sense and being legitimate as per your contract defies reason. If your company wanted you to use sick days to boost PTO days because [reasons], why not simply give you more PTO days or make [reasons] apply to PTO days?

In these cases, ignorance is generally not an excuse for culpability, even if someone senior is enabling you. It's you who'll take the ultimate blame. The risk is yours as much as if you did it 100% yourself.

When presented with such an offer, if you ever feel the slightest ambiguity, always just say "No thanks. I'll just do things in the standard way", until you've officially cleared it as something legitimate. If it does turn out to be a legitimate thing, by definition it won't go away as an option for next time, so you've not really lost much.


Sounds like your manager is trying to cut you a break. My old shop had sick days that you could roll over because we were union. But some places don't, so it sounds like hes trying to help you stretch your time. So long as HR doesn't complain, it looks like he's just being nice. I wouldn't worry too much, because sometimes you get someone who isn't just in it for themselves.

  • 4
    I had this 'workday accounting' thing in my mind also. He may claim that he allowed less PTOs for his subordinates in a year. I strongly feel that he gets some sort of benefit out of it. Since no one has control over sick leaves whereas he may claim that he convinced his subordinates to reduce their PTO duration. That manager is cunning which makes me doubt on many actions he takes. Hence I asked this question. Commented Sep 16, 2019 at 19:48
  • 1
    @chrono_tachy My cousin is cunning but he uses it to help people. Luis can arrange anything to work for him but he likes to help people. What makes you think your manager is out for himself?
    – Tina_Sea
    Commented Sep 16, 2019 at 20:41
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    I had a manager that would adjust my whole teams time to maximize PTO savings in a similar fashion. On the other hand, he strictly enforced our timekeeping. It felt like he was maximizing the team and business interests at the same time—I respected him for it. He had a "don't be petty" motto. I was eligible for a reward and completed the needed steps, but unable to report it to HR until the following (expired) day due to work emergencies. He fought HR until they gave in, saying that anyone could have walked my paperwork in and I pick up the prize after the expiration. Commented Sep 17, 2019 at 18:52
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    @NathanGoings we had this one boss who didn't care about anything if you got the job done so if things got ahead we could take long breaks or leave early so long as if things got rough we'd jump in and stay late or work through breaks and we didn't mind because he was cool whe things were slow.
    – Tina_Sea
    Commented Sep 19, 2019 at 12:13

I don't know where you are in the world, but i have seen sick days taken used in redundancy matrices.

So even if it is not immediately apparent it could have detrimental long term effects.

What happens if you do catch an illness that requires lots of sick days, you will now be over and HR will be on your back, with a possible warning.

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