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Once again, y'all can blame my boss. Well, him or Captain Picard. He (my boss, not Picard) has the annoying habit of saying "Make it sure that", instead of "Make sure that". No matter how many times I correct him (usually via a post-it note thrust in his face while he's on the phone), he keeps making this mistake.

Today, he clarified the root of his confusion: if there's an it in "Make it so" (he's a big ST:TNG fan), then why shouldn't there be an it in "make sure that", also? As a native speaker, the best I can come up with is "because it sounds wrong", and that's never enough to appease my boss. Help? How can I explain the difference to him? Is there logic behind it, or is it merely idiom?

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Yes, it's idiom, which is not 'mere' but overrides all other considerations. The catchphrase "make it so" is irrelevant; in any case it apparently derives from military usage. – StoneyB Sep 28 '12 at 17:28
Whoever voted to close this as general reference, pretty please provide that mythical "single link to a standard internet reference source designed specifically to find that type of information". Really. If you can't provide such a link, it's not general reference. Just because the correct usage is utterly natural to native speakers doesn't mean this question is easy to answer. – Marthaª Sep 28 '12 at 18:06
@StoneyB: yes, but why is "make it so" irrelevant? – Marthaª Sep 28 '12 at 18:33
Because it's a different idiom. A)It has a different meaning. I'd say Do it! - does that mean your boss should say Do it that ...? B)It's drawn from a different discourse community. Clearly your boss wants to sound like J-L Picard; does he want to sound like a hard-ass marine, too? C)It's a different structure. that ... is the object of make sure; but in Make it so, the object is already in place, videlicet it. He could say *Make this sure: that ...", but that probably wouldn't satisfy him nearly so much. – StoneyB Sep 28 '12 at 19:30

Make sure is an intransitive verb in that context, that’s why. Your boss would not, I imagine, use its synonym, ensure, in that way and say Ensure it that . . .

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If so, why must one say "Make it obvious that I know the truth" instead of "Make obvious that I know the truth"? If there's a difference in transitivity between this and the "Make sure" cases I'd like to know. See my answer below. – Merk Sep 28 '12 at 20:58
It's because make on its own, as in your example, is transitive. – Barrie England Sep 28 '12 at 21:29
But make isn't on its own, it's followed by an adjective + that clause, just like in the other kind of case. Reducing the OP's question to a question of transitivity is question-begging unless you can coherently explain your principle for attributing transitivity. The ultimate problem is that transitivity is too coarse a distinction to explain the grammar of verbs that can take multiple complements. – Merk Sep 28 '12 at 21:33
Actually, I would bet even money that my boss would be fully capable of saying "ensure it that". – Marthaª Sep 29 '12 at 3:35

The reason is that by including an "it" you are creating a reference to a specific thing.

therefore the meaning of "make sure that" which means to be certain that changes to mean make the certain thing sure meaning to change its sureness from not sure to sure

for example had you been discussing a robot you could say "make it sure that you are in command" its

it would be like saying "make dave sure that you are in charge" which doesnt work for named items, however for a non specified, but implied specific entity it works, but you cant use a regular noun in that position... it just doesnt work...

whereas "make it so" means make the command "it" so and even that can only be used after an order has been discussed... which is why you will notice that picard never says "make it so" without an order or objective being discussed

"what do you think no 1, should be investigate?" "i think we should captain" "helmsman make it so"

without the discussion, you couldnt say "make it so" else the response from the helmsman would be "make what so"

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Creating a reference doesn't matter. Sometimes you have to create a reference before you use it. Example: "Make it obvious that I know the truth." It would be ungrammatical here to leave the 'it' out. – Merk Sep 28 '12 at 21:03
I'm sorry, I can't make heads or tails of your first few paragraphs. Please add some italics or something to distinguish use vs. mention. Please? – Marthaª Sep 29 '12 at 3:37

I think the explanation is that "make sure" is a phrasal verb distinct from "make", and that the phrasal verb "make sure" can only take one complement, but that "make" can and frequently does take two complements (e.g., Make a boy a man; make yourself available).

Compare "make sure" with "make obvious":

Make it obvious that I won't talk to him.

is correct,

Make obvious that I won't talk to him.(*)

is not.

So it appears that "make obvious" is not a phrasal verb, and that when the verb "make" takes the complement "obvious" it must take another complement as well. Indeed, "Make sure!" and "Make certain!" are valid commands, but "Make obvious!"* and "Make available!"* are not.

As for "make it so", that one's a bit trickier. Is it (a) a set phrase, (b) the verb 'make' with the pro-adverb 'so' (similar to 'do it like so'), or (c) is 'make so' a distinct phrasal verb of its own?

If you believe (a), then you will simply say that 'it' is part of the set phrase and therefore need not teach any grammatical lesson. If you believe (b) or (c), then you need only explain that the verb construction requires a(nother) complement to be grammatical, just like "Make obvious!"* or "Make available!"*.

By the way, (a) may be undermined by the fact that it seems okay (?) to say things like "It was made so by the actions of the first king of France."

PS Notice another way to add a complement to "Make obvious": "Make obvious our objections to the decision."

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Could "make it so" be explained as use of simple make with two complements, it and so? – Marthaª Sep 29 '12 at 3:40
I think it depends on whether you think so is an adverb or not. In a sentence like "I did it willingly", willingly plays no role in making the sentence syntactically correct, and the meaning of 'did' is the same whether willingly is there or not (unlike "make him a man" vs. "make a baby", which are two different meanings of "make"). If you think "so" is like this, then it I don't think it is a complement. But if you think "make it so" is closer to "make it so that he tells the truth", then maybe not. "So" is complicated: english.stackexchange.com/questions/19394/is-so-a-pronoun – Merk Sep 29 '12 at 4:09

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