See title, but I am asking from a technical perspective, not

Take my 40 year old virgin niece on a date or you're fired.

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    If she's a 40 year old virgin, she's probably also an employee. Wouldn't that be against policy? – Tim Post Sep 9 '10 at 18:23
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    can you return her unopened next morning? – Mawg says reinstate Monica Sep 10 '10 at 1:49
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    Go read clientsfromhell.net – Pierre-Alain Vigeant Sep 10 '10 at 20:11
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    This whole Q+As is like Dilbert, but in real life. – Agos Sep 10 '10 at 22:40
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    Ah, the mods strike again against clear community interest (70 up-votes!). Sigh. You know, maybe if so many very popular questions are against rules, maybe rules need changing? – James May 13 '11 at 21:48

64 Answers 64


To market Neal Stephenson's sci-fi thriller Snow Crash, I was asked to write a "benign" computer virus. It would "benignly" pretend to take over the user's computer and replace the screen with snow, a.k.a., a "snow crash." After a minute or so of snow, the snow would fade out and be replaced by an advertisement for the book. This would be "benign," you see. The virus would spread through normal means, but nobody would mind because after taking over their computer "you'd just get a fun ad and then be relieved that nothing bad happened to your computer."

I was actually told to do this at a major worldwide corporation. I had to write a memo explaining all the laws this would break and all 17 bad things that could happen if they really made me implement this.

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    You were told to do this at Viacom ??? – Carlos Muñoz Sep 10 '10 at 3:37
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    Holy balls. That's the most perfect example of the "It's only evil if other people do it -- if WE do it it MUST be all right!" mindset I've heard in a while. – BlairHippo Sep 10 '10 at 14:15
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    Meh. It wouldn't have been any worse than the book itself... ;) – Mason Wheeler Sep 10 '10 at 16:37
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    That's awesome. We can sell it in a bundle with my 'benign' keylogger that serves up ads when users visit competitors sites, and we'll be rich. – µBio Sep 10 '10 at 17:21
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    @Neil G: 1. have something blatantly illegal done for you 2. profit! 3. blame employee when you get caught 4. more profit!!! (this worked for the Sony rootkit, IIRC) – Piskvor left the building Sep 13 '10 at 16:10

"This DLL you wrote is only 17kb. Can you add some code to make it bigger? The client is paying us a lot of money, and we want them to get their money's worth."

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    Easiest profit maximizing strategy ever. – Craig Walker Sep 10 '10 at 22:51
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    1) Embed a flight simulator easter egg. 2) ... 3) Profit! – Bill Karwin Sep 11 '10 at 5:15
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    Did you work for Oracle? – Sergio Acosta Sep 13 '10 at 22:55
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    HP printer drivers MUST do this. They're the only company who seems to think that 400 MB installs are normal for simple printers. Now, what key combination starts the flight sim? – JYelton Dec 27 '10 at 17:50
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    You call that crazy/stupid/silly? One client was doing this on a regular basis, because their customer was measuring progress by the size of the release files they got. – foo Jan 14 '11 at 19:28

Use Visual SourceSafe.

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    Nothing tops this. – Jaco Pretorius Sep 21 '10 at 20:02
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    Beats having nothing. – rjzii Sep 28 '10 at 2:55
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    @Rob - I'm not so sure. Having nothing, at least you know your source is "unprotected". VSS gives the illusion of protection whilst actually making things worse. It's a false sense of security of the worst kind. – CraigTP Oct 12 '10 at 14:13
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    I'm with Rob. It does beat having nothing. Although I no longer use it. Over my career, I've probably used it for a decade in total and never had any major data loss. @CraigTP, it may be unreliable, but it isn't 100% unreliable as you seem to be implying. A VSS installation that is backed up frequently (and a long tail of backups are kept) is indeed better than nothing. – JohnFx Nov 15 '10 at 17:09
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"You know this enormous 20-year-old Cobol program that contains piles and piles of hard-coded business rules that more or less defines our company? Would you mind converting it to .NET?"


We go live in a few weeks.

Wish me luck..

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    Jeez, +1 just for sympathy! – Paddyslacker Sep 9 '10 at 18:37
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    Do you have a Paypal donate button somewhere? I'd like to buy you some aspirin. – Tim Post Sep 9 '10 at 18:38
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    If you accomplish it you'll be a programming God, and also lucky to get a "thanks" – Kevin Laity Sep 10 '10 at 22:08
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    Thank you for your support everyone. And just to let you know, we are now live! – CodingInsomnia Sep 21 '10 at 14:19
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    The worst part of this is that if you do it really really well, you'll get almost no credit. "Yup, it works exactly the same as it did before." – MatrixFrog Dec 11 '10 at 18:56

My brother and I were working on a multimedia heavy-website for a very famous rock star many years ago.

When the client saw the site he noticed some compression artifacts on some of the JPEGs and asked what was wrong with them. We explained that images need compression for bandwidth purposes and that the images were currently compressed at about 80% quality. He was offended and said something to the effect of

I haven't gotten to where I am today by doing things at 80%, set it to 100%.

We tried to explain how it would affect users, but he would have none of it. It resulted in the slowest "virtual world" website ever. This actually happened.

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    "All these computers and digital gadgets are no good, they just fill your head with numbers and that can't be good for you." - boston.com/ae/specials/culturedesk/2010/07/… – Evan Sep 11 '10 at 1:03
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    At least he didn't ask you to turn it up to 110%. – Barry Brown Nov 15 '10 at 17:38
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    John. It really was him. Trust me, if I wanted to dress fancy or play the electric guitar like a wizard, he would be the first person I would go to. But not for web design best practices. – jessegavin Nov 19 '10 at 2:16
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    At first I was reading it as wanting 100% compression, not 100% image quality! – Andrew Grimm Jan 14 '11 at 8:09
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    "I haven't gotten to where I am today by doing things at 80%, set it to 100%." That's actually an AWESOME quote. The person who said it is Prince right? not some manager or something? – Ziv May 14 '11 at 13:36

We need to delay the site launch by two weeks because Mercury is in retrograde and it's a bad time to start new things.

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    At least they didn't want to launch 2 weeks early. – Jeff Sep 10 '10 at 12:30
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    Ha! I have heard that one a lot in India – sabertooth Sep 10 '10 at 20:16
  • ha ha ha ... this is one of the coolest thing I have ever seen .. +1 to Gsto and Jeff. – Zerotoinfinity Sep 17 '10 at 6:53
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    If you were writing software for a space probe, this might make sense. – Bruce Alderman Nov 1 '10 at 5:32
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    Mercurial is always in retrograde. – Erik Reppen Jan 19 '13 at 16:44

Obviously after reading some business magazine on an airplane about how XML was the hot new technology (this was circa 2002), one of our executives asked me if our application used XML, when I said no he asked me if we could add it.

Now, I'm not talking about a feature to import/export files in XML format, he simply wanted it to be part of the architecture for no reason other than it was popular at the moment and would lend credibility to our app.

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    I had the same thing in 1998 - except the article was on Oracle, and our app was essentially a workflow diagram editor. We ported the file format we were outputting from disk to a table and took a dependency on Oracle licenses. Made version control very difficult as well. – Rob Fuller Sep 10 '10 at 20:45
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    Oh boy. I had the exact same thing (at around the same time) and it was also regarding XML. What was it about XML that made the execs start drooling? – CraigTP Oct 12 '10 at 14:16
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    That's pretty common. It's called "buzzword compliance". – Michael H. Nov 15 '10 at 15:21
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    @CraigTP I think it's the 'X'. It's dramatic and appealing. – Adriano Carneiro Jul 13 '11 at 20:26
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    Looking back I should have just appeased by saying. Even better, our web app uses HTML which has a whole extra letter in the acronym and the code is like a specialized version of XML that meets our exact business need! – JohnFx Jul 13 '11 at 20:42

"Right now, the usernames are required to be unique, and the passwords are not. Could we make it the other way around?"

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    ha.. I made the mistake once where both the username and password needed to be unique. short lived mistake thankfully – WalterJ89 Sep 22 '10 at 22:16
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    What the heck were they trying to accomplish? – Jason Baker Nov 23 '10 at 5:38
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    As I recall it was something to do with a client sharing email addresses at a company. Emails and usernames were 1:1, so the idea was to create multiple accounts with the same username and use the passwords to differentiate them. – Craig Walker Nov 23 '10 at 15:30
  • In that case, they might as well drop the usernames entirely and look up the account based on the (unique!) password. Sheesh... did they tell you anything else about why they wanted it that way? – foo Jan 14 '11 at 19:32
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    @Craig Walker Amazon used to have this. I created one account with my yahoo email address, and then another account using a different password with the same email address. I don't know when they fixed this, but depending on the password I used, I'd get a different account. – Yahel Jul 7 '11 at 4:58

About 7 years ago I worked at a bespoke software shop that decided to sell one of its products. It was an end-to-end operations suite for some industry. Well, this industry wasn't known for being super technological, so somehow we ended up providing third-party technical support for their servers and IT infrastructure instead of farming it out to independent small business IT consultants.

One day, a customer's server encountered disk corruption. The server we had sold them was configured with an Adaptec RAID controller, set up for a RAID 1 mirror. Their application database was toast. They hadn't performed backups in months. The backups they had performed were unusable. They ended up losing 8 months of data. They hired an IT consultant to handle this investigative work.

Phone calls ensued, and the sales manager (known for promising impossible features) apparently told them it would be taken care of, and wrote it up in a contract.

The sales manager promised the customer that we would ensure that the application database and any other application-related files would never be replicated by RAID controllers if the files were considered to be corrupt. No configuration should be necessary either. Yep. We were told to deliver this functionality in 2 weeks, or the customer would fire us.

So the program manager -- who had some large enterprise CRM products, and other serious development successes, under his belt -- and I had a meeting with the COO, and the sales manager. The program manager was detailing how insane, impossible, and insanely impossible this was. The sales manager (military background) would simply scream in his face (literally!), "I don't care! How hard can it be to make the RAID thing not RAID?! Their data would be fine on the other drive if the RAID thing hadn't screwed it up!"

At the end of that meeting, the program manager quit with a zero-day notice. So I was now tasked with this. Over the next week, I petitioned both Adaptec and LSI Logic to provide an engineer for a conference call, simply to laugh in the face of the sales manager.

Ultimately, they obliged, and held up their end of the bargain. And they went into detail how ridiculously unfeasible it was. The guy from LSI was particularly harsh - he didn't sugar coat anything.

I didn't have to implement the feature. One I did have to implement was a custom security scheme requested by a customer, that would allow them to toggle any of the application's controls - on a control by control basis - as visible, disabled, enabled, read-only, or read-write. In theory, there were 146,000 combinations. And if you accidentally screwed up by say... disabling a control group, you'd have inadvertent side effects. Needless to say, when I was given the ultimatum that it had to be implemented, I also quit with a zero-day notice.

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    +1 for "quit with zero-day notice", because sometimes you just have to leave, and some people never get that and keep muddling on. – sbi Sep 13 '10 at 11:56

They asked me to search a Commercial Product that could find and fix source code bugs automagically.
Still searching..since 2001 :).

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    Why can't you use an open source product to do this task? Do they just love spending money? After all, it'll be expensive! :) – alternative Sep 10 '10 at 0:37
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    "Could we have a list of all the unexpected errors, please..." – Evan Sep 11 '10 at 0:56
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    Imagine if a client doesn't need a developer to develop his application. He himself can write anything and debugger will solve it automagically. Let me google it, Ill let u know if I find anything like this :-) – Zerotoinfinity Sep 17 '10 at 7:00
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    I actually have such a tool. The problem is that it takes several weeks or months depending on the problem at hand, tremendous amounts of interaction with your team, lots of coffee, and is very expensive. – Michael Haren Nov 22 '10 at 18:11
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    @Michael send me two copies please, I need to getting job done. – systempuntoout Nov 22 '10 at 20:17

I once had a client specification that literally called for code capable of traveling backwards in time.

My employer harvested data for the client, and we were to deliver it in file format X at ten-minute intervals between 9 AM and 5 PM, save for the final delivery, which was in format Y (just X with a different footer). I did just that ... and they freaked. We were collecting low-volume data, and really only had one or two data points to deliver on any given day.


Okay. So, my code checked every ten minutes, and only delivered if there was anything to deliver. Fair enough.


(* -- It is possible I'm misremembering portions of the conversation.)

"So, I'm only to deliver the file if there's fresh data to deliver."


"And the final delivery for the day is supposed to be a different file format."


"Except I have no way of knowing which file will be the last of the day until the end of the day."


"So the only way for me to implement this is to write code that goes backwards in time at the end of the day to redo the format on what turned out to be the final delivery."


I refused, in part because violating causality is an unethical programming practice, in part because CPAN.org didn't have a module that would let me do it. (I checked.) In the end, they allowed me to send a file in format Y at the end of the day, regardless of whether or not it had any actual data. I'm pretty sure their bandwidth survived the hit.

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    +1 for "violating causality is an unethical programming practice". Now there's a rule that needs more attention. – sbi Sep 13 '10 at 18:43
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    And you didn't consider sending a file every day at 11:59:59 in format Y containing "This is the last file of the day"? – DJClayworth Sep 13 '10 at 19:38
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    This reads like The Oatmeal. – Kyralessa Sep 29 '10 at 1:55
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    You could've withheld the last piece of data for each delivery to roll it over to the next one. This way at the end of the day you will always have at least one piece to send in format Y. :) – Fixpoint Oct 2 '10 at 0:45
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    @Joey Adams: On the internet, nobody knows you're a snail. – Alan Pearce Mar 10 '11 at 11:49

Without any discernable cause, I was brought into a private meeting, and told not to check if my computer was being monitored - including, never ever checking my task manager for any reason. I asked if they were monitoring my computer, and was told (roughly) "this is just a preventative thing -- you know, our lawyer told us to tell the employees about this -- but you know, we can't really say -- but I'm not monitoring it now."

(nudge, I think they were monitoring my computer, just not while they were telling me not to look for any monitoring programs. In fact, a few weeks later, I came in early and literally watched the mouse moving around my screen as if by remote -- so I looked through the window of the CEO and saw him remotely clicking around on my computer from his laptop.)

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    I hope you don't still work there. – finnw Sep 10 '10 at 19:32
  • Sounds like a winner of a company... If you're still there, I'd say bolt. – Pwninstein Sep 10 '10 at 20:48
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    What he wants to do ??? Let him code for you ... – Zerotoinfinity Sep 17 '10 at 7:02
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    1) Open up notepad 2) Type "hi boss" 3) ... 4) Profit! Also, a good surveillance program would hide itself from Task Manager. – Note to self - think of a name Sep 21 '10 at 19:35
  • Sounds illegal. I hope you got a lawyer. – Old account Nov 22 '10 at 16:57

I once had a long "discussion" with a pointy-haired boss who insisted that we could store a 2 in a bit datatype because it was "only one digit."

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    You can definitely do this. As long as the variable is named "IsATwo" – JohnFx Sep 10 '10 at 14:37
  • just map null to 2! – dotjoe Sep 13 '10 at 21:46
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    bool true,false,file_not_found (apologies to DailyWTF) – Martin Beckett Sep 15 '10 at 20:10

The stupidest thing I've been asked to do is probably a ground up rewrite of a very large project. It was about 350k lines, all C (with a little perl mixed in for 'helper' scripts) and worked well no matter what clients did to it.

Almost a year later, we had:

  • Lots of functions that basically did the same thing as the old functions
  • No real improvements in speed or functionality
  • A slightly smaller memory footprint
  • A much larger executable
  • Annoyed clients

Basically, we accomplished nothing that sensible refactoring could not have accomplished. But my boss was happy, we got rid of the helper scripts.

I consider it to be the most egregious waste of time and existing code that I've ever seen.


Client: We've been using your database software for a couple of years, developing our own applications with it, and calling you from time to time for help.

Me: Yes, we appreciate doing business with you.

Client: Yeah. Every time we call, you tell us how to use a new feature, or you help us debug our usage, or provide a workaround for some issue.

Me: Sure, we're always happy to be of assistance.

Client: Occasionally, your product has an actual bug in it, and your company fixes it and gives us a software update.

Me: We do our best.

Client: Well, what we need from you now is some assurance that we won't have any more issues.

Me: . . .

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    My face twitched a little while reading this. – Daenyth Sep 16 '10 at 21:07
  • @Daenyth, I got that too! – DaveDev Sep 17 '10 at 12:21
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    This is a true story. The client above was a manager at an company who developed air-traffic control software for logging flight data. The sole developer on the project (who had no one reviewing his code) called to report a "bug" frequently, but it turned out to be an error on his part 9 out of 10 times. He didn't know about his own errors because he refused to check error statuses returned by our API. Why? Because he said any error must indicate a bug, and our library should have no bugs. – Bill Karwin Sep 18 '10 at 0:49
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    @Bill, sounds like you library should fail badly and loudly including the last 10 error codes returned to calling code. – user1249 Nov 28 '10 at 14:09
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    @NimChimpsky: Some of the client's "issues" were cases where they wanted the software to do something it was not designed to do, or when they made fat-finger mistakes (like misspelling SQL keywords). They reported these cases as "bugs". – Bill Karwin Aug 4 '11 at 16:16

I have been asked to write in a presentation of our software to a major multinational potential customer that we used "spaghetti code" coding technique.

Of course, we're in Italy... sounds good.


Do some work for free.

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    I've been asked that too. "We've run out of funding, can you work unpaid for a couple weeks until we get some customers?" – µBio Sep 15 '10 at 20:46
  • There is no free lunch – Chris Jul 28 '11 at 11:09

Changing my syntax highlighting colors to match the ones used in the version control system.

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    haha, a sadist boss/client – µBio Sep 9 '10 at 19:26
  • We so had this... and a requirement that EVERY LINE be commented, in the 79th column, so that the code was down the left and comments on the right. And all of this was enforced by an IDE add-in. – Tevo D Nov 30 '11 at 13:55

Let's see:

Write programs in C++

  1. without the use of version control,
  2. no refactoring,
  3. no Boost,
  4. limited STL (I argued and won on this one),
  5. use unverified subcontractor libraries,
  6. without a memory profiler (to help fix subcontractor work),
  7. no unit testing,
  8. stick to 3 letter names for member function names,
  9. no test environment (VM not allowed either) just push to production
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    Wow. What's your company score on the Joel Test? – DJClayworth Sep 13 '10 at 19:31
  • When I first started, 2, I think. Now that I've been there a while I can say group A: 4 and group B: 8. Guess which one I'm trying to join and guess which one won't let me. – wheaties Sep 14 '10 at 0:13
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    Clearly, your boss was of the opinion that 'Real' programmers program with a magnetized needle and a steady hand. ;) – brice Sep 21 '10 at 15:17
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    @brice Don't make me bust out the butterflies... – Note to self - think of a name Sep 21 '10 at 19:36
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    No one can ever force you to work without version control. Use whatever you want (I'm an increasingly big fan of git, personally) on your own machine, and gradually other developers will follow along. Hopefully. – MatrixFrog Dec 11 '10 at 19:04

Can you take this 10-page report that I asked you to prepare as a word document and make it into a powerpoint presentation because I am really a visual thinker and won't actually read the written report I asked you to make?

  • may be this is a way of ensuring that you are doing genuine work and all the important aspects are covered in all the steps and finally the most concise lucid idea is conveyed in the end. – Aditya P Mar 10 '11 at 15:02
  • Quit job, if he say "Do it by E.O.D." – Chris Jul 28 '11 at 11:07

Ok, I want you to scan this picture of a house, when I come back, you should be able to show me the back portion of it.

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    ZOOM...ENHANCE! – Jon Purdy Sep 22 '10 at 4:48
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    oh CSI how I hate you – WalterJ89 Sep 22 '10 at 22:41
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    Enhance... enhance... enhance... OH JUST PRINT THE DAMN THING! – James Dunne Oct 13 '10 at 2:12
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    @WalterJ89 maybe that's where he got the idea – setzamora Oct 13 '10 at 18:35
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    Was there an address? I would have run out and taken a picture of the back of the house and showed it to him. Then explain how you have the ability to walk into a photo as if it were another dimension. The print your resume in case he doesn't laugh. – Jeremy Heiler Jan 14 '11 at 18:01

"I don't like the way this Oracle database works. Why don't we just write our own database?"

(Admittedly, this was over 15 years ago, but still!)

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    Well, why not? Some people actually did this, and that's how we got OODBMS. Imagine Amazon or Google using Oracle as DB backend... and then think about what impact speed has on their business. – foo Jan 14 '11 at 19:43

I was asked to load articles from a competitor's website inside an iframe that would be inside our website's skin, making it look like it came from us.

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    Yes ! The same thing happened to me when I was in the training and I was asked to copy contents from various website and paste it into ours and make it look like the original article. I can't give the name of website here but it is still on the internet and grabing thounds of user evreyday.. – Zerotoinfinity Sep 17 '10 at 7:14
  • Ebuyer was well-known for this a few years ago. – njd May 16 '11 at 11:35
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    Yep. Somebody wanted me to help them build their own version of Craigslist that did this at first until they got "their own content." I explained that I was pretty sure this was illegal by digital millenium act standards but they didn't think it would be a big thing. I didn't take that contract. – Erik Reppen Jan 19 '13 at 17:01

For me, the craziest (and quite possibly, funnest) was

See this 10 million lines of code in (out-dated web technology)? Write a compiler to convert it to a working Asp.net site.

It never spit out a working version (of course, I tried to tell them it was impractical), but it was fun anyways.

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    Its nice of Joel S. to let his employees post about WASABI. ;-) – Donny V. Sep 10 '10 at 21:03
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    @Donny V. haha, I wish. It was much, much, much crazier than that. Dynamic inline sql used server side to generate mass quantities of dynamic server side code, leading to giant buckets of javascript and html with embedded server side code, that executed sql queries that... – µBio Sep 10 '10 at 21:09

One major feature of an application our company developed was the ability to search large amounts of documents by the full-text of the document. A competitor made the following claim in a marketing presentation to one of our clients,

Our search technology is superior because it doesn't just search the text of the documents, it also searches the 'bits and bytes' of the actual file in binary form.

They gave a ridiculous example of how the decimal ascii repersentations of the words "boot" and "boat" were much less similar than the same words in binary form, when you compared the actual numeric digits in the representation. So searching based on the 1's and 0's more accurately reflected how similar those two words appeared visually, and thus improved recall.

Naturally I was tasked with researching this technique, which I assume was the result of a marketing guy completely misunderstanding a programmer somewhere, and drafting a response that we could include in our proposal.

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    I'm afraid I can think of a couple of search techniques that might (just) have made sense of the claim. – DJClayworth Sep 13 '10 at 19:34

Can you write a simple time entry and billing system for our new foreign office that uses a different language, currency and tax laws?

  • That's a good one :) – µBio Sep 9 '10 at 19:10

Small team of programmers, boss wants us to do a ticket reservation system for a small airline (in a very short timeframe, of course). Team says:

-- as you can imagine, we will need some testers for this project

Boss says:

-- don't worry, learn from the car industry. They recall cars from time to time: users will do the testing.

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    Crash test comes to mind... – brice Sep 21 '10 at 15:33
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    Sounds good, if airline has only 1 plane with 6 seats. – Chris Jul 28 '11 at 11:12

I was a part of a mainframe support team that did shifts with other support teams in a data center. After the shift we would usually have a briefing with managers and the team of the next shift. One day our new director showed up and asked the question: "Why average CPU load during your shift was only 72%, while previous shift shows near 95%? I think if we try real hard, we could eventually achieve 100% CPU load!"

  • 1
    Sounds like a 6 month project in Hawaii... – user1249 Nov 22 '10 at 9:23

About 12 years ago when I was in college I worked on a data modelling application for Windows. The project was nearly complete after about 60,000 lines of Win32 code, you know, code targeting the Windows platform. Then the client said the application also needs to run "on the web". She had a hard time understanding how this one "minor little" requirements change could have such a big impact on the project. I started over from scratch in Java but ended up quiting the project before it was ever finished.


I was working on a big project in 1996 where we were scoring live sporting events. This conversation happened:

Boss: Go out to the venue for the next event.

Me: What do you need me to do.

Boss: Be there just in case.

Me: Just in case what?

Boss: In case the tech lead loses it. He's way too stressed out and I don't know what he might do.

Me: And if he loses it, what do you want me to do?

Boss: Just get him out of there so everyone else can continue working. I don't care how you do it.

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