The Tight-Fisted Boss

by admin on April 3, 2017

My boss gave me a $800 gift voucher to be spent at a department store as a gift for my new baby. I was pleasantly surprised because he is not normally a generous person. I was happily thinking for a few days about the things I could get on the voucher when he suddenly texted me asking if I could give him the receipts for the items I will be getting on the voucher so that he can use them as tax deductible expenses.

He owns his own small business and I have always been aware that he has to keep all receipts for his business accounts. While being my boss, he is also a friend of mine.

I texted back agreeing to give him the receipts, but later on I started feeling uncomfortable about the whole situation, and concluded that I felt weird about it because it feels cheap to give me a gift and then ask to use it for tax deductible expenses.

Can’t he just let the $800 go without having to gain something from it? I’m sure he got a receipt for getting the voucher in the first place, surely he can use that as a ‘gift for client’ cost or something?

It also feels like an invasion of privacy because he will be privy to what I’m buying on the voucher. What if I wanted a flat-screen TV instead of a bunch of baby stuff? It’s not a big deal that he knows what I buy, but it’s the principle of having no privacy to get what I want.

It makes me feel like I’d rather not have been given the voucher, I’m really not that fussed about it because I have everything that I need anyway. It was a nice gesture that was spoiled when I was asked to hand in the receipts.

A bit of background on him – when he gave me a pay rise once, he also asked if I could work extra hours from then on, so in my mind it was less of a pay rise and more of a change to my working hours. He also wouldn’t give me days off that I was due once because he ‘couldn’t afford it’. I guess in this context, it makes sense that he would do something like this, but I always wanted to give him benefit of the doubt and I thought this time really proved it. I guess I was wrong.

Is it tacky or am I just being nitpicky due to his history of being tight-fisted? 0317-17

I think your uncomfortable feelings are your intuitive guts telling you there is something hinky with this situation your boss has placed you in.   It appears he’s using you to possibly commit tax fraud.   Basically his business gave you an $800 gift voucher as an employee benefit and I can’t think of a reason why he needs your receipts other than to be a busy body.   His purchase of the voucher IS his receipt and that’s all he needs for his taxes.   I’ve been giving employee bonuses for decades and I have never once asked anyone what they did with the money nor needed receipts of any kind because my purchase of a money order, voucher or check is my receipt.    Where it gets hinky is if he was given the voucher by another person or company and he’s now using it to claim a tax deductible expense.

Why do you continue to work for a dishonest employer who manipulates you? He is not a friend and he’s using you.  Does he deny himself his accumulated vacation days, too?

{ 52 comments… read them below or add one }

Yasuragi April 3, 2017 at 7:31 am

Sounds like he’s trying to double dip for $1600 in tax deductions. I’ve never done taxes as a business but how doed one claim diapers, teething rings or rash medication as a business expense?


Cleosia April 3, 2017 at 7:36 am

Here’s another thought for you: Are you exempt from overtime? If not, he should be paying you time and a half for your extra hours. He basically kept the status quo by asking you to work more hours for the extra money and may be getting you to work more hours THAN the extra money that you are receiving for them.

And if you don’t get the days you’re entitled to, he’s paying you even less.

I agree with the Etiquette Guru. Why are you still there? He isn’t a friend. He’s a User.


Shalamar April 3, 2017 at 9:02 am

That reminds me of when a co-worker friend of mine asked for a day off. Her boss said “That’s fine, but I’d like to know what you plan to do with it.” He’d said that in an e-mail, so she forwarded it to HIS boss, asking “Do I have to answer this?” Big Boss replied “Absolutely not.”


Marie April 3, 2017 at 11:34 am

My grandfather was asked the same! This was a long time ago (as in: 50 years ago or even longer), and he had to fill in a form every time he asked for a day off, and the form required of him to write down what he was going to do.
My grandfather also felt like he didn’t need to tell his boss, so he wrote down “going to the prostitutes”. As you can imagine, he had trouble holding down jobs because he’d get in trouble with his bosses a lot.

I also sometimes ask my employees why they want the day off, but for a whole other reason. Where I work you need to ask two weeks in advance to have a day off (six if you want more than one day). However, I get a lot of requests that are for the same week. I often have people at my desk requesting the next day off. If I have enough people that are scheduled, I will give it to them without a fuzz. If it’s not possible to take the day off, I’ll ask them if they had something planned. If they tell me their kid has the flu, or they have a burst pipe at home they need to take care off, they know I’ll do my utmost best to get them their day off.
This hasn’t happened a lot so I don’t think people are taking advantage of it by lying. I think it’s ok for me to ask because they know they don’t have to tell me, and they also know that if they do I will help them if it’s needed, instead of just saying “no” by following company policy.


Rebecca April 4, 2017 at 12:24 am

Marie, this is a tricky one because I get that if there are a lot of requests for the same day, then some people’s requests are going to have to be denied, and if it’s “my parents’ 50th wedding anniversary party” vs “I’d like to have lunch with a friend” then it’s good to understand the degree of importance.

On the other hand, I’ve been an employee in retail with no set schedule, and if you wanted a specific day off you had to request it, otherwise you’d be scheduled for whenever. And as the single, unmarried person, I didn’t like that a supervisor got to assess how important my thing was to me vs how important someone else’s thing was to them. So “my kid’s soccer game” vs some event that I really, really wanted to do but didn’t involve kids – well guess who always ended up working? Despite it being written into the labour laws that there could be no discrimination based on family status.


Marie April 4, 2017 at 3:41 am

Don’t worry Rebecca! If people ask for a day (or days) off, it’s first come, first serve.
If the schedule allows it, it’s approved (and I certainly hope people have the mind to ask for important dates in time and not two days in advance).
I only ask when the schedule does NOT allow for a day off, and the request would otherwise be denied. The question would be: “it’s not possible to take that day off, did you have something important that came up?”
I am lucky enough with a team that will say “too bad, I wanted to go to the beach” and take their responsibility. But, if they say “a pipe has burst in my home and I was hoping to have the plumber over tomorrow instead of next week” – I will give them the day off, regardless of the schedule. They know they can come to me if they have a problem and I will try to help them by bending the rules a bit. In no way I am trying to pry, and if there is no scheduling conflict, no questions are asked.


NostalgicGal April 4, 2017 at 11:12 am

Exactly. Asking a reason is not unreasonable IF it has to help assist in why or why not the request is granted. IF someone needs the doctor appointment or has a home emergency, that does rate over the kid’s soccer game (sorry to the parent that misses the game, but). Most of the time though ‘why’ shouldn’t have to come into it, so it shouldn’t be asked every time.

ThetaMarie December 19, 2017 at 7:39 pm

Where I work there is an optional biton a day off request form to add a reason. Its partly so we can say ‘X wants to go to her old teacher’s funeral and Y wants to go to their third concert this month’ if we get two or more requests but also so we can assess ‘right, A wants to go to a wedding on the 12th and B wants to have a day off on that day to visit an event that runs for multiple days, so can we see if B would like another day that week?’. That way as many people as possible get the time they need on an appropriate date. You can leave it blank, at which point we’re likely to say J needs minor surgery and K didn’t say so J gets it’ or ‘neither T nor S said why they want the time, but T hasn’t had many days off and S just had a few extra days so T gets that day’. It’s not rude to ask generally what time is needed for if it HAS to be a specific day… I’ll sometimes book a few days off because I have a bunch of stuff to do and it can be done as easily on Wednesday as Saturday. Any response of ‘that’s personal’ is generally read as ‘important’ by me at least.

Shannon April 3, 2017 at 9:56 am

I’m far from an expert on tax law, but wouldn’t any tax-deductible purchases have to be business related? He’s definitely doing something shady. I would give back the gift card. $800 is a lot to pass up but I wouldn’t want to be involved in whatever he’s planning.


Rebecca April 4, 2017 at 12:26 am

I thought employee gifts were tax deductible but it must depend where you live. Either way, he’d have got a receipt if he purchased the gift card. He doesn’t need to see the individual purchases. If the gift card was given to him and he’s just passing it onto his employee, tough beans for him, he can’t deduct it as an expense.


Daisy April 3, 2017 at 10:02 am

You should check your own tax laws, but where I live, if your boss gives you $800 and then deducts it from his taxes, it’s not a gift. It’s income to you, and it’s taxable. That $800 “gift” may end up costing you money.


admin April 3, 2017 at 3:59 pm

Ooo, good point.


Nerokitty April 3, 2017 at 8:47 pm

Daisy, you are correct. A gift card is a taxable fringe benefit and should be included in your wages.


Anne April 4, 2017 at 6:24 am

Does his wife/girlfriend have a day care business? He could be using the receipts for write offs for her business, if the voucher is for use in a baby store.


Lindsay April 3, 2017 at 10:10 am

This sounds like he got the voucher as a gift then passed it on to OP. As such, in order to claim a tax deduction, he needs the reciepts from what she purchased. Is this tax fraud? Maybe. If the voucher was given to the company and he then transfered it to the employee, no, it wouldn’t be. That would be asset transfer. If it was given to him personally, then probably, yes, it would be hanky. Grey area, but hanky.

Either way, it was nice of him to give it to you. $800 is nothing to sneeze at. You would not be culpable in this instance either, should he get audited. Is it weird? Sure. Invasive? Could be. Still nice for an owner of a small business to give you an $800 voucher instead of a box of diapers? Absolutely.


Miss Herring April 3, 2017 at 8:19 pm

If he received it as an actual gift, he can’t take deductions for it no matter what. Unless it was a business gift and he is going to claim the $800 gift income, he doesn’t have any basis in it. No basis = No deductions


Anna April 3, 2017 at 10:42 am

This guy sounds like he is the kind of person who looks at every situation to see if he can squeeze anything out for himself. The receipt thing is super shady–I suspect he wants to both count the cost of the voucher AND the receipts for whatever you buy in order to double dip a tax deduction. He denies you vacation time you’ve earned because he “can’t afford” it? Vacation time is part of your compensation, which he apparently is stiffing you on. He’s also stiffing you on a raise by pretending you are getting a raise when what he really wanted was more work hours out of you. I bet if you do the math, he’s the one who is getting the benefit of that transaction. What a piece of work.

I would not comply with handing over the receipts, since it is dishonest and also really shows he did not give the gift in the spirit of generosity. I think I would reply “Is there a business reason why I need to give these receipts? I thought it was a gift. If this is a business transaction, I’m not sure I’m comfortable with that, and if that is a problem I’d be happy to return the voucher to you.”


thisgirl April 3, 2017 at 11:01 am

Be prepared to receive a 1099 at the end of the year, or see your wages increased on your w2 in the amount of the “gift”.


Bea April 3, 2017 at 9:19 pm

That’s my immediate thought as an accountant.

I also have a feeling he’s double dipping. He’ll write off the $800 as a employee relations expense. Then he’ll write off all the receipts as individual purchases because they are “extra” receipts he’s counting on.

That’s not how it works and I want the OP to run away from this situation. This person is doing other things wrong in terms of record keeping and I’m worried that he’s going to take her down with him when the auditors come knocking.


Dee April 3, 2017 at 11:08 am

The big question, of course, is why you aren’t honest with him and his out-of-line requests? When he gave you the “raise”, and it came with extra work hours, why didn’t you discuss your ability and willingness to change your job description at the time, since that’s what the “raise” was about? It sounds like you accepted the whole package without complaint, which is an odd thing to do, since most people would not be able to accommodate such changes without adjusting something in their off-work life (which may not actually be possible) and so such things need to be discussed AND agreed upon. And yet you just rolled over … so, the question is, why do you think you cannot say “no”?

As far as the voucher goes, you could tell your boss that you are happy to accept the “gift” on behalf of you and the baby’s father, and the purchase of items will be decided between the two of you, and that may mean you’ll wait until the baby is older before purchasing new items for him/her. A year or two may pass. Someone may forget to save the receipts at that point. But that you appreciate the “gift” all the same and will think of him when you eventually use it. Nothing more needs to be said, and if the boss asks for those receipts at some future time then you can be vague and non-committal.

The boss isn’t your problem. There will always be people who will try to use you. In general, you cannot be used unless you agree to it. So why are you agreeing to it and then complaining about it?


TakohamoOlsen2 April 4, 2017 at 1:55 am

I agree there. Not only that, if you do complain to the relevant department with regards to your boss/workplace, they may wonder why you never questioned boss’s motives in regards to your payrise and extra hours. Could (may not though) go badly for you. May need to start recording this information just in case.


oregonbird April 8, 2017 at 9:03 pm

This is a great reply in a fair world, but that’s not here. Here we have people lined up looking for jobs, and the laws protecting us from unfair management are toppling daily. Most rights have become imaginary, rather than achievable.


livvy17 April 3, 2017 at 11:12 am

I agree with Cleosia, be sure to know your rights about your pay:

But other than that, Admin is right, I’m doubting what he is doing is right from an ethical or moral standpoint, and you really don’t want to work for someone like that.


Nan April 3, 2017 at 11:26 am

I don’t know how this particular voucher is set up, but is it possible that HE was given the voucher and is trying to turn something he might have to declare as income into something he can deduct? For someone tight with his money it sounds too generous to be true!


Kay_L April 3, 2017 at 1:44 pm

Sounds like tax fraud but I don’t think it will work.

He may have received the voucher in lieu of a cash refund for something he purchased–something he may already be deducting.

Any receipt generated from cashing in the voucher will likely say that it was purchased from a voucher and not with cash. If so, that protects the LW because she can turn the receipt over to him without worrying about contributing to tax fraud. He would have to alter the receipt to legally use it to back up a deduction.

Seems like an overly generous gift for an employee.


Aleko April 3, 2017 at 1:51 pm

Why don’t you give him a signed receipt from yourself, acknowledging that you have received this voucher as an employee benefit. If he really wants to prove that he gave you this bonus, that will actually ought to be better than the store receipts – how does a receipt for a baby buggy prove that?


Michelle April 3, 2017 at 2:19 pm

This sounds so sketchy. If it’s a gift, he should not need the receipts to file for his taxes. Even if this is considered a “business expense” the receipt of purchase should be enough. He doesn’t ask for receipts from clients does he?

I know you say this man is your friend, but from the descriptions you gave in your letter, he doesn’t seem to be a very good friend. Gives you a gift card/voucher but wants the receipts for his taxes, gives you a raise but asks you to work more hours and won’t give you the days off you earned because he couldn’t afford it? Unless he giving you great non-cash benefits, such as super flexible hours and ability to work from home, you might want to think about getting a job where you don’t have to provide receipts for what you spend gift card/voucher on, you don’t get asked to work more hours just because you were given a (presumably earned) raise and you can actually take off the days you earned.


Devin April 3, 2017 at 3:51 pm

It sounds as if this friend isnt a good friend and also isnt a good boss. Since its a small business, he is probably able to get around a lot of the federal regulations (only apply to businesses with over 25-50 employees in the states depending on the industry) regarding vacation, and pay (especially if you are salary).
Regarding the gift certificate, if you want to keep his nose out of your business use it to make a large purchase that is returnable, like an expensive crib or nursing chair or top of the line pump. Return the original purchase for a new gift card, then buy what you’d like. He’ll have a receipt showing you purchased something baby related, and you’ll get exactly what it is you want or need with the gift. Might be a little underhanded, but he shouldnt need individual reciepts for a gift.


Saucygirl April 3, 2017 at 5:00 pm

I agree with the people saying be careful of taxes. I worked for a company that one year worked out a deal with companies that owed them money to get gift certificates instead. Those gift cards were then given to us as Christmas gifts. And we were told that our next paycheck would be docked taxes for this “gift”. Needless to say, most people returned the cards.


bellini April 3, 2017 at 7:14 pm

The OP gave the amount of the voucher in dollars, but their language “pay rise” “wasn’t fussed” voucher instead of gift certificate/gift card …makes me wonder if they are in the UK and hence no one commenting from the US knows the tax implications of the boss giving this person such a large amount to spend and then asking for the receipts.

The whole thing seems weird to me too – go with your gut OP and don’t spend the voucher. This boss is not a friend.


ladyv21454 April 4, 2017 at 8:19 am

Since the OP did give the amount in dollars, my first thought was that she might be Canadian – like you, the language seemed more British than US.


Dee April 4, 2017 at 10:53 am

The language doesn’t trigger “foreign” to me but also doesn’t suggest familiarity, either, and I’m Canadian. Doesn’t mean this isn’t taking place in Canada, since accents and language are quite different across the country (but it’s only Americans who say “aboot”, in my experience); I would hazard a guess at Britain, too, based on the language, even though they don’t use “dollars”. But there are a lot of countries that use their own “dollars” as their currency so there’s a lot of potential here.


Pumpkin April 4, 2017 at 5:56 pm

Sounds like OP is Australia- we use dollars and more ‘British’ language…


Cat April 3, 2017 at 8:30 pm

I admit to being both old and rather old-fashioned, but an eight-hundred dollar gift from a man not your husband or your father seems a bit much. Maybe all he has in mind is a tax deduction, but I would be uncomfortable with a gift of that size from my boss/friend.
It’s not a year-end bonus given to all employees at your level. I’d return it to him and explain that I can’t accept such a large gift.


Miss Herring April 3, 2017 at 8:44 pm

Your boss doesn’t understand tax law well enough to try to work the tax fraud he is planning. What you purchase with the gift card matters not a whit. He gave it to you. If it was an employee benefit, then it must be included on your tax return as income (on which you will owe tax) and shown on the business tax return as an employee benefit expense. If it was a gift from him and his wife/spouse/pet cat to you, your spouse, and the new baby, then there are no tax consequences for anyone.

A few people have mentioned the overtime pay rules (for the USA). Assuming you are in the US, you might also find of use the updated rules for “exempt” (salaried) employees. As of December 1, 2016, the new minimum annual salary for an employee to be exempt from overtime pay is $47,476 per year or $913 per week. This is a huge jump from the previous amount ($23,660 per year or $455 per week) and has forced many employers to change certain employees to hourly (non-exempt) and pay them overtime.

If your boss is denying you earned vacation time, he is stealing from you. Unless you can choose to have the time carried from year to year or paid out (as an addition to your paycheck, you must be permitted to use your vacation time.

This man does not seem like your friend, and he is definitely not a good boss. I would suggest looking for a role with another business. If you want further advice on business non-etiquette issues, I would recommend Ask A Manager. She can help confirm that what this guy is asking is not reasonable or normal.


Devin April 4, 2017 at 2:18 pm

There was a federal injuction halting the new rules back in November. It is likely now this new rule will never go into effect, so it doesnt apply to this situation.


ALM April 3, 2017 at 9:21 pm

Am I the only one who thought an $800 baby gift was inappropriately high, particularly from an employer? Perhaps this isn’t in American dollars, but I would have found $100 more than generous.


NostalgicGal April 3, 2017 at 9:54 pm

Unless you are in a ‘salaried’ position, he may owe you a vatload of back pay for hours worked.

The voucher and receipts sounds massively shady. If I was you I’d round up all proof of hours worked, all ‘reimbursements’ that he claims are salary, and any ‘benefits’ he claims to provide.

I’d also be looking for another job pronto. I’d also give the gift card back lest it become ‘income’ at the end of the year and you be forced to pay taxes on it. This just so smells.


NostalgicGal April 4, 2017 at 11:19 am

Adding. A long time ago, on the Dilbert cartoon website, they would hold submissions for this or that topic, that could then be voted on by the readers. A woman that won for worst boss and best retaliation… her boss had managed to get two weeks in Maui at the height of tourist season. When the travel agency called to confirm, she cancelled it. Because she had not been able to take a single day off in six years. No vacation, no sick time, nothing. Also not paid or otherwise reimbursed for that missing leave time. She was too ‘indespensable’ to the place and the boss wouldn’t let her go. An attorney that seen the submission contacted her as she had a HUGE legal issue there, and she ended up owning the company after about a year of court.


sunnydi84 April 3, 2017 at 10:15 pm

This does seem very shady. It’s like giving someone a gift card and then asking for the receipts for what they purchased with it. It’s one thing to send a thank you note and let the giver know what you bought with the card/voucher. It’s another to ask for the receipts from the purchases!
One time the company I worked for gave us all $50 US Savings bonds. We all thought, ‘what a nice gesture’. Come tax time, those $50 bonds were taxed at the gift tax rate of 40%!! So, it really wasn’t that great of a gift having to be taxed at 40%. It even pushed a few people into a higher tax bracket, costing them more money! Most of us returned them. Who wants to pay $20 (or more) for basically a $30 ‘gift’ for yourself?? I don’t know where you live, OP, but I would definitely ask if you will be taxed a gift tax on this voucher and also see if it puts you in a higher tax bracket. This $800 ‘gift’ could wind up costing you quite a bit.


Mags April 4, 2017 at 12:28 am

I agree with everyone else about the situation being shady on the boss’s end. But I am also put off by OP’s comment “What if I wanted a flat screen TV instead of a bunch of baby stuff?” Whatever his reason for giving OP the voucher, it was given with the expressed intent that it be used for baby stuff, not toys for OP, and I don’t think it is tacky in itself for the boss to want to know what was purchased with his substantial gift.


Dee April 4, 2017 at 10:58 am

I don’t think the boss is out-of-line for simply asking what his gift has bought, for curiosity’s sake, and OP could lie about some crib or baby swing while purchasing that new TV instead. The problem is the boss demanding OP prove what she’s bought. Once a gift is given it’s out of the hands of the giver and the receiver is free to do whatever he/she likes with it, even to the extent of not letting the giver know what has actually happened to that gift. This instance, though, sounds like anything BUT a gift.


Mags April 5, 2017 at 2:48 am

I know that the receiver gets to do whatever they want with the gift, but I would have a pretty poor opinion of anyone who spent money intended for the baby on a TV, regardless of whether they had the legal right to do it.


Margo April 5, 2017 at 6:51 am

With vouchers, there are very good reasons why you might spend the actual voucher on something different.
If the voucher is for Store A, but the products I want / need for the baby are cheaper/only available at Store B then there is no reason at all not to chose to buy baby stuff at Store B and spend the voucher on something else at Store A.

Equally, you might already have bought the baby stuff you need so you spend the voucher on something different instead of having spent the voucher on baby stuff and your own savings on the other thing .

I think it would only be reasonable to be aggrieved or let it change your opinion of someone if they were spending the voucher on non-essential items for themself AND they don’t have essentials for the baby.


Dee April 5, 2017 at 12:04 pm

If you really want to give a gift that is specifically for the baby then you need to buy a baby gift and not give a voucher or certificate or card or cash or whatever. It is rather lazy to give someone the equivalent of money and expect them to buy their own gift, and so the giver can’t complain about how that money is spent. In any case, there is no need for the giver to know what the money was spent on unless they harass the recipient, and then they deserve whatever answer they get.


Amydkw April 4, 2017 at 11:03 am

It is one thing to say “thanks for the great gift, I got …….”. It is another to be asked for the receipts for said items


Kat April 4, 2017 at 1:22 am

Do you work for my mom’s old boss?

He promised her a week of paid vacation every year. So something comes up and she lets him know she’d like her vacation. Oh no, she can’t take it now, he said, she’d leave him in the lurch. She needs to take it the week of Christmas when the office shuts down anyways. So she waits for Christmas and asks for it, and he says there’s no money coming in to pay her with.

He repeatedly said she was the best office manager her ever had – hard-working, organized, etc. But he ripped her off for four weeks’ worth of paid vacation time. She took 6 weeks off to have back surgery. He hired someone to fill in during her absence (who of course my mom had to spend weeks training). When she was ready to go back to work, he wanted her to just be a substitute here and there for the new girl when she needed time off (I call her a girl because she was very young). New girl made less money, of course, so he wanted to pay her instead. That didn’t go over well with my mom who still wanted to work full time. The kicker is that we heard that less than 3 months later, the new girl had gotten to take a week of paid vacation. That man prides himself on being a Christian but I don’t know how he sleeps at night, cheating people. Utterly cheap.


TakohamoOlsen2 April 4, 2017 at 1:44 am

When the twitchy gut feeling tells you that something is amiss… usually is.


Princess Buttercup April 4, 2017 at 1:23 pm

On the one hand, he already has the receipt, why does he want double receipts unless he’s going to claim he gave you 1600$?
On the other hand I know if someone gives me money as a gift I write a thank you note and try to say what I did with the money. So telling what I bought with it wouldn’t bother me.

In general it sounds like this guy doesn’t know how to run a business. I’d be worried about working for someone doing so much shady stuff.


InTheEther April 5, 2017 at 12:09 am

I have to ask about the “raise”. Was he legally required to provide your raise vie the employment contract or something? Even if it was just a carrot he was using to get you to work for him or doing something special (Like “Hey OP, could you do X. If you do I’ll make sure to budget a raise for you after MONTH”), it’s kinda a dick move to go “Hey, here’s your raise. Now, to make up for it you’ll need to work more, so its entirely possible you could even be making less per hour.”

It sounds like he may very well be committing a federal crime even outside of the gift voucher thing. I know that I’ve had bosses who had to actually get on to employees over not clocking out for breaks or clocking out late. The laws are pretty strict as to how much certain types of employees can work (fulltime vs part time vs PRN vs seasonal) and also very strict on what benefits an employer must provide for their employees. With the extra hours to offset the pay raise it sounds like he may be fudgeing the books to make it look like you’re working less than you are, and thereby denying you benefits. And I know he can get in trouble if you’re not getting your vacation time. My mom’s a manager and I know that every year near fall she has to start bugging a few employees about taking vacation time (or arranging to redeem the hours for cash) so that they don’t wind up in December with half the employees being owed a week or more.


Margo April 5, 2017 at 6:47 am

On a practical level, i think I would send him a nice thank you note in due course and if he brings up the receipts just say “oh, sorry, I forgot. But don’t worry, I’m sure that the receipt for the card itself is all you need for your taxes”.

If you frame it as a reassurance rather than an implication that he is doing anything shady then there is nothing for a reasonable person to object to.


@LizaJane April 5, 2017 at 11:11 pm

I know part of this was in the original response but not only is this not tax deductible for him-you’re an employee, not a client – but it could actually be considered taxable income to you.

He doesn’t need the receipts for tax purposes either way. Does he ask you to provide receipts for everything you spend your paycheck on? No? Same thing.

The guy is nosey, weird, stupid or possibly all of these.


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