I'd suggest this is one of those "If you have to ask, don't do it" moments.
Even if someone might normally find things like this funny, the questions remain: What kinda of pressure are they currently under if sales are doing badly that might cause them to react badly?
If they're under a lot of stress this might make them feel very bad indeed.
What kind of impression will this give the rest of the company, if sales issues are well known - e.g. will everyone know it's meant to be a joke or will some people consider it a snub, and will everyone find it funny?
As others have said, it depends on the culture of the place... which to me means that none of us can tell you whether or not it would be ok as we don't work there.
And if you could tell whether or not it would be ok, you wouldn't need to ask us.
workplace.stackexchange.com/users/300/Rob Moir
Normally I wouldn't think twice about this sort of thing, but it's been made apparent that sales haven't been doing too well this year.
Does that make a gift like this [Sales for Dummies] a little too 'on the nose'?
I think it entirely depends on the personality of the Head of Sales, but I recommend not rubbing salt in the wound here.
It's likely the Head of Sales is taking a lot of flak for sale's poor performance and getting a book that insults his poor wounded ego just doesn't seem like a good idea.
I recommend another gift.
workplace.stackexchange.com/users/46398/jcmack
This is not a very fun joke if it comes at someone else's expense and also attacks their professionalism.
Only do this if you know the Head of Sales will also laugh and not feel embarrassed.
As a gift you are not too far off, though.
If the book is a well regarded "must read" in the field then the receiver might actually like it and read it.
Not "for dummies" but a real book where you did your research.
Then if someone else makes a joke everyone can laugh (including Head of Sales), or you can make the joke in a friendly manner.
The difference here is that a real book on the subject would not belittle them.
Take this with a grain of salt, of course.
You know the person and the environment better than any of us.
Just be aware that these kind of jokes can get out of hand and turn into workplace bullying .
There are no rules as long as it is all fun and games for everyone .
workplace.stackexchange.com/users/65552/Emil Vikström
Depends on the person's sense of humour, work atmosphere, your relationship to this person, their relationship to the rest of the company, whether they had an argument with their spouse this morning, planetary alignments, etc.
etc.
etc.
With the right person in the right circumstances?
Sure, it can be funny; perhaps even hilarious.
If you need to ask here however there's a decent chance
it's not, and probably wisest to avoid taking the chance.
workplace.stackexchange.com/users/8388/Martin Tournoij
I'd say first of all try to figure out if they take the bad sales personally.
If they think it's their fault or their problem and they're under a lot of pressure, it might not be a great idea.
However if they realize it's not just their fault and stuff like that can happen, they probably won't take offense from it.
Of course it'll still depend on their personallity and sense of humor.
But if you really don't know whether they will take it well, just don't do it.
A simple joke is not worth potentially insulting someone over.
workplace.stackexchange.com/users/95346/Dnomyar96
To add to @Emil
Vikström's great answer
might I suggest a book which is related to sales at least in an abstract way.
It would be treasured by the head of sales rather than thrown away.
Malcolm Gladwell - The Tipping Point is a great read which looks in to the psychology behind what causes things to suddenly become popular, such as the Hush Puppies craze in the 90s in America.
workplace.stackexchange.com/users/58406/Pixelomo
So it's secret santa time again at work, and I've drawn the Head of Sales. Secret santa is normally a jokey thing in our office, so I thought it would be amusing to buy him a 'Sales for Dummies' sort of book.  Normally I wouldn't think twice about this sort of thing, but it's been made apparent that sales haven't been doing too well this year. Does that make a gift like this a little too 'on the nose'?
Is a book on sales technique a bad idea for our head of sales in secret santa?
workplace.stackexchange.com
<professionalism><culture><gifts>
workplace.stackexchange.com/questions/123985
workplace.stackexchange.com/users/95294/reynardine
This might just rub salt in the wound. It depends on the person and the atmosphere in the company. Only do it if you think the person will find it funny. The answer to this question will be subjective and entirely depend on the person in question and your relationship with them. There is a risk that this could be received rather badly, so you should only do this if you're sure that it will go down well.
There is a risk that this could be received rather badly. You may wish to consider a different gift. The answer to this question will depend entirely on the person in question and your relationship with them. You should only really do this if you're sure that it will be received well.