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The place where I work, my manager enters manually the casual/sick leaves. He approves it by email sometimes verbal, but we cannot enter it into the time tracking system as he has only access to it.

My boss keeps approving my casual/sick leave requests for appointments and casual kinds of stuff but twice he has forgotten to enter it into the system. I still get paid but it doesn't get counted against my leave bank.

Do I tell him he's forgetting or reap the benefits of additional time off since we only get so many days a year?

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    Yes, but do it via email. This way, if he replies that it's ok, or if he doesn't enter it a second time even after being reminded, at least you have a time-stamped written record of trying to do the right thing. – Stephan Branczyk Jan 21 '20 at 12:21
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Do I tell him he's forgetting or reap the benefits of additional time off since we only get so many days a year?

  • It might entirely be possible that the manager is just keeping a separate note somewhere for all the leaves applied by all the employees (which are approved) and updating the system only once in a while. Though not very common, it's possible.
  • It might be possible that they had simply forgotten.
  • Another possibility is there is some problem in the system because of which they are not able to update the data in recent past and waiting for that problem to be fixed.

If you ask, you'll get to know for sure. I'm sure most people appreciates when you help them to do their work. Send an email saying

Hey Boss, I was just checking the timesheet entries and noticed that my previous leaves for dates X and Y are not reflecting in the system, are they already updated or shall I check back later?

If you don't ask and receive some undue benefits out of that, later for any audit purpose if someone counts the leaves and pay - you'll certainly be in trouble - at least you'll be known for someone who wanted to "steal" from the company. Do you want to be known as that person?

The answer to the above question is the same as the answer to the question whether you should keep mum about the case.

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Do I tell him ?

Yes, but do it in writing. You want to create a paper trail that clearly shows that this is not your error or even malicious intent.

Not logging time-off correctly is a potentially serious offense that can be interpreted "stealing from the company" or "fraud". You want to make crystal clear that whatever happened is not your fault and that your own behavior is squeaky clean.

A simple e-mail with the specifics is sufficient

Hey boss, I have taken time off on xxx (8 hours) and yyy (16 hours) but that hasn't been deducted from my vacation time yet. Would you mind logging this in the time management system? Thanks

If he doesn't follow through, keep doing this on every new instances of missed time-off capture and keep your own private list. If this ever blows up you can simply show your list and the correspondence and demonstrate that you have done due diligence.

I also recommend to NOT spend the extra vacation. If that gets ever cleared up, you may have to pay this back out of pocket. If it never gets cleared up, you would typically be eligible for payout of accrued vacation time (depending on jurisdiction and company policy, that is). In this case you can point out the discrepancy and ask them to not pay out extra amount. This is going to hurt a bit, but it's the right thing to do.

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Do I tell him he's forgetting

Yes, but in a nice way. Something like:

Hello boss, do you remember that you approved me a sick leave on ... (date). I see that it does not appear in the system, and I worry that ... (reason; e.g. you will not have enough vacation days) Will you please verify and eventually enter the info again?

You might continue:

Maybe it would be helpful if we could enter the data ourselves, to make sure that it is there, and you will only need to verify and approve it.

With the above approach, you help your boss save face. The idea presented is that the system is bad, not the memory of the boss. Moreover, you get to be proactive, and try to release him from the work of introducing the data into the system.


Of course, the boss might reject all your requests, but his "anger" will be kept at a minimum.

Imagine the following going on:

Hey boss, it seems that you forgot again to enter the data into the system. Are you going to do it any time soon?


On the other hand, you always have the option do not protect your interests, to give up your benefits - and tell nothing to the boss. If you can live with it, this will work as well.


Should I ask my Boss to add my Previous casual leaves?

Well, it depends on how long ago was previous. It is best to keep an eye on the system regularly, and report any missing information as soon as you find it missing. If there are more than two months, the situation might get trickier to fix, depending on a number of factors (including national laws, company rules and regulations...).

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  • I think OP is more coming from the angle that he wants to keep the benefits of the boss not entering it! – Gamora Jan 21 '20 at 12:05
  • I added to the answer while you sent the comment. Please see if it is better. I will be glad to improve the answer. – virolino Jan 21 '20 at 12:07
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Do I tell him he's forgetting or reap the benefits of additional time off since we only get so many days a year?

I'm sure you know what the right thing to do is.

I can tell you that most managers would appreciate the honesty.

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Do I tell him he's forgetting or reap the benefits of additional time off since we only get so many days a year?

Another option is: do neither. Maybe you are not on best terms with your boss, or are afraid to be misunderstood or don't want to be seen as complaining. And that's okay. What is not okay is using the mistake to your own advantage by unfairly gaining more days than in your contract.

If you have an allowance of X days, then taking exactly X days should not get you into any trouble. It does not matter whether the system says you took less. If someone complains at the end of the year that you did not take all your leave (believe it or not, that happens) then you can still say "I believe I took my complete allowance, that must be an oversight in the system".

Don't talk to anybody and just keep your own actions fair and in compliance with your contract and you should be fine.


I'm not really advocating doing nothing, it's certainly fine to talk to your boss, I'm just saying minding your own business without cheating is an option too. Just because you could cheat does not mean you have to.

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From an ethical standpoint, you agreed to work a certain amount of days for a certain amount of money. So yeah, you should go to (reasonable) amount lengths to remind your boss.

From a more cynical, practical standpoint, you should also tell him. It would be fairly easy for your boss to find out if you've been taking too many days off. While he might think you forgot, or suspect you took advantage, in both cases you lose some of his trust. Also, you may have to pay back the extra days in some way.


Virolino came up with good diplomatic ways to tell your boss.

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  • Well the one to forget is actually the boss. If these leaves were approved by email, it's not up to the OP to check whether their boss did their job correctly, and one could legitimately tell they've not checked and expected it to be done correctly. – Laurent S. Jan 21 '20 at 13:23
  • It's not just about whether your boss can prove you took advantage. Do you really want your boss thinking they have to check up on you because you're "forgetful"? – ObscureOwl Jan 21 '20 at 14:20
  • We're not talking about the OP forgetting to mention their day-off, we're talking about the boss forgetting to register these day-offs. The boss is being forgetful, not the OP. As a general rule although I appreciate people not taking advantage of me or my mistakes, I usually don't blame them for this. – Laurent S. Jan 21 '20 at 14:56

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