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Sander Rossel wrote: Bring it so that his plan may have benefits IF it works out, and that you totally get his decision to do it this way, but (and don't use the word 'but') also tell him you have some concerns.
Not easy, I know, but he'll be a lot more susceptible to your concerns if he thinks you're on his side.
My parents told me that I should not tell lies... 
Skipper: We'll fix it.
Alex: Fix it? How you gonna fix this?
Skipper: Grit, spit and a whole lotta duct tape.
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Kornfeld Eliyahu Peter wrote: My parents told me that I should not tell lies...
They were lying!
I am not a number. I am a ... no, wait!
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Well, well - how dare you! 
Skipper: We'll fix it.
Alex: Fix it? How you gonna fix this?
Skipper: Grit, spit and a whole lotta duct tape.
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You can tell the truth in a non-committal way that will allow your boss see the information in his bias as confirmation of his ideas (you don't have to dissuade him) but that will also allow for criticism.
Decrease the belief in God, and you increase the numbers of those who wish to play at being God by being “society’s supervisors,” who deny the existence of divine standards, but are very serious about imposing their own standards on society.-Neal A. Maxwell
You must accept 1 of 2 basic premises: Either we are alone in the universe or we are not alone. Either way, the implications are staggering!-Wernher von Braun
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Then don't tell lies.
Actually it's better if you don't because most people are bad liars.
Tell him stuff like "if I were you I'd do the same" which technically isn't a lie, because he's doing it and if you were him you'd, well, do it too (or you wouldn't be him).
And "it's a good plan if it works", which also isn't a lie, because if it does it's really a good plan (just don't tell him the chances of it succeeding are pretty close to zero).
Also try to get into his mindset, why is he doing it? Perhaps it really does make sense, after all this guy is your (probably well paid) boss which means he's made some good decisions in the past. Perhaps he knows something you don't, or he has another view on things. If you get to see his point of view you can judge it from there and it might make sense in some twisted way. You might even praise him for it (you really got his attention now)!
Also tell him your plan in a way that he benefits from it. Maybe his plan is (short term) financially optimal, but technical (as in produced code) sub-optimal, maybe you could convince him that there's more money to be made in the long term when better code is produced. Don't tell him the produced code sucks and from a programmer's perspective that's unacceptable (like he gives a damn), tell him instead that more money can be made in the long run when the code that is produced now is of better quality (that's HIS money you're talking about!).
And if it's possible make him think it's his plan even when it's actually yours!
You: "Do you think our code quality should be better so we can make more money in the future?"
Him: *I don't know what he said, but it involved more money* "Of course we should!"
You: "That's pretty clever of you!"
I'm oversimplifying it, but you get the idea
Of course it's easier said than done.
You don't want to be a suck up, but you don't want to burn his idea either.
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Kornfeld Eliyahu Peter wrote: My parents told me that I should not tell lies
So, your parents don't have business sense. And in business, it ain't lying, its finding the correct turn of phrase to keep you employed.
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Sander Rossel wrote: I'm told that if you pay enough monkeys they'll reproduce Shakespeare!
I would hope not. He's been dead for hundreds of years, and I don't want to live in a horror story.
I wanna be a eunuchs developer! Pass me a bread knife!
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Quote: I'm told that if you pay enough monkeys they'll reproduce Shakespeare!
Only if you wait long enough for them to do it by complete accident. The monkeys then won't know what the hell they did or how to improve upon it without further waiting for another fortuitous accident to happen.
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So it's kind of like programming? 
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Sander Rossel wrote: I'm told that if you pay enough monkeys they'll reproduce Shakespeare!
- with infinite time, maybe.
but they will produce 99.9..% bad versions, leaving you with a search algorithm problem to find the best.
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With infinite monkeys (and infinite typewriters) they'll conjure up every work of Shakespeare (or every work ever written) soon enough, like before the end of the month 
Of course if you employ only one monkey it may take an infinity (then again, there's a change, small it may be, it'll write Hamlet on its first try).
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Sander Rossel wrote: if you pay enough monkeys they'll reproduce Shakespeare
Actually the quote is an infinite number of monkeys, so there will never be enough animals or typewriters. To type out all combinations of 10 characters limiting it to just the English alphabet, single case there are 141,167,095,653,376 ways the characters can be combined and that isn't close to the number of random words and spacing the monkeys need to produce. Shakespeare produced thousands of words.
I hate to think of the number of editors you'd have to hire to find the works of Shakespeare in 2x89a7 54C3 9Y2!$#a%^$^ sets of monkey produced text and the education needed to know the correct spelling of old English words.
That quote predates computers so you also need an infinite number of typewriters (an 11 character word) as well.
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That's what you tell your manager who wants to hire those monkeys.
He hires them anyway, and against all odds his monkey writes Shakespeare on the first try (the fun thing about chance is that it IS possible).
He visits you in your cubicle and tells you "see, I told you it would work, it's a little thing I call experience."
Hamlet will look like a cute princess children story after what you do to him next
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Dunno, but my new boss seems to think that a system is "enterprisy" if it can be maintained by monkeys. Never mind that such a system will require more maintenance and have a higher TCO than the system I envision. It seems enterprises don't want developers who can think outside the box -- who'da thunk?
Meanwhile, a system I wrote for a smaller business a while back has been running flawlesly 24/7 for more than ten years and the only call I've had about it since I stopped working for them in 2009 was three years ago and that was just a question about configuration. But I guess that's not "enterprisy". :shrug:
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PIEBALDconsult wrote: It seems enterprises don't want developers who can think outside the box -- who'da thunk?
No, they want predictability. Workers who think outside the box aren't predictable. Nevermind that what they've come up with might be better, if it wasn't predicted, then it is to be feared.
We can program with only 1's, but if all you've got are zeros, you've got nothing.
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Yes, that's what I've begun seeing. The support staff all know how to use hammers, but not screwdrivers, and apparently they can't be trained to use screwdrivers, so I'm being discouraged from developing anything that requires a screwdriver. 
Never mind that a solution that requires a screwdriver would (in theory) require fewer staff and therefore have a lower TCO.
At least the deadline is still a couple months away...
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You got to find some angry (internal or external) client or problem employee to use.
Innocently mention your boss's plans at the perfect time when the dumb angry person will associate it with their ills.
If it comes back to you, what you said was innocent and it was the angry persons fault for misunderstanding. Everybody knows how that person is, anyway.
In the process some aspect of the boss's plan will be twisted and associated with a sh*t storm and he will now be battling misunderstandings the whole way.
modified 10-Apr-16 11:57am.
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Kornfeld Eliyahu Peter wrote: 2. To press on in a new field will lead to wrong roads
Is this your decision to make? If not, leave it to the people whose decision it is, because they are most likely privy to information that you are not.
By all means, give your opinion, but don't tell someone who has been working on something (that you haven't been working on) that he's wrong, because there's a good chance that he's not.
I wanna be a eunuchs developer! Pass me a bread knife!
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That's the exact problem...To give some background...We had in our company two groups (with a certain fading between them) one for the desktop development and one for the web...Now, with the new version we abandon the desktop and move all the functionality to the web...The leader of the desktop group try to ensure, he will not became obsolete (and this is foolish, as his knowledge of that part of system remains relevant) he picks subject that are relevant to the new technology stack and implements them (cache, authentication ans some) on his own, without knowing too much about the web (he got's his ideas from Google)...I do not want to dump him, so I have a big dilemma how to tell boos he has to stop it (as he not aware of the situation)...
Skipper: We'll fix it.
Alex: Fix it? How you gonna fix this?
Skipper: Grit, spit and a whole lotta duct tape.
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Granted, that's a sticky situation, but if you chat with whoever's in charge of the architecture, and discuss the idea of putting together "Grand Scheme" diagrams and white papers, it might help to nip off any wrong directions in a slightly nicer way than (what will look like) running to the boss.
If the guy's acting out of paranoia (or out of desire to improve his position) things are likely to get heated (or backstabby), if you don't work it with his feelings in mind.
Sit back and work out a rational approach toward, shall we say, getting everyone to pull in the same direction. There's always an intelligent approach that avoids anyone getting put down, and that allows everyone to feel secure in what they're doing.
I wanna be a eunuchs developer! Pass me a bread knife!
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Mark_Wallace wrote: Sit back and work out a rational approach
Exactly. And writing a rant here and getting calm-down responses, helps me calm down too and not to spit fire at the office...
Skipper: We'll fix it.
Alex: Fix it? How you gonna fix this?
Skipper: Grit, spit and a whole lotta duct tape.
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Windows form can rob company of vital data, unscrupulos users can steal windows form application .exe pirates. Or worse, decompiles the .net pseudocode. But from a risk standing, web application allows all user data and usage recorded to detained the cloud (opens new revenue stream from leveraging recorded usage), and disables stealing the executable.
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Kornfeld Eliyahu Peter wrote: 2. To press on in a new field will lead to wrong roads
This is probably going to come down to the way your boss likes to be communicated with, so it's difficult to offer a suggestion.
That said:
(1)Sometimes it's best to just mention your concerns, in person or by email, so that you are covered when and if it all goes pear-shaped. Sometimes the boss needs to be allowed to screw up so that they can become aware that they need to consult you more closely next time.
(2)Do a Columbo [^]and just drop the idea in as you leave a room or meeting, just when they are at their weakest - Mwahahaha!
“That which can be asserted without evidence, can be dismissed without evidence.”
― Christopher Hitchens
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Kornfeld Eliyahu Peter wrote: I have to
No, you don't.
What is the best that can happen if you bring it up, versus the worst?
Bastard Programmer from Hell 
If you can't read my code, try converting it here[^]
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I do have to!
It is for the good of the company I'm part of. It is my professional obligation. It is the very same reason I started to answer questions and writing articles here...
I do have to!
Skipper: We'll fix it.
Alex: Fix it? How you gonna fix this?
Skipper: Grit, spit and a whole lotta duct tape.
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