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The saying “never ask a barber if he thinks you need a haircut” means “don’t ask a person about their own activity, because they are in a conflict of interest and can only answer in one way”. Thus, it is an equivalent to “don’t ask silly questions”.

Looking it up on Google Books, I’ve found that the oldest occurrence dates back to 1998. It is therefore quite recent, if we are allowed to give some credit to this piece of information. I would like to know if this saying is actually used and established in everyday language, and if it can be understood by any native speaker.

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    I've never heard it, but its meaning is clear. Often in response to silly questions, people will say (if the answer is yes) something like "Is the pope Catholic?" or "Do fish swim?" One common way to refer to someone with a conflict of interest is "He's like a fox watching the hen house." Off-hand, I can't think of anything else that works exactly like your example, but, again, its meaning is clear. – user66965 Dec 2 '15 at 20:49
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    I have just found a source that includes the following: "Daniel S. Greenberg wrote “Don’t Ask the Barber Whether You Need a Haircut” for the November 25, 1972 Saturday Review, popularizing the saying. Variations of the saying date to at least 1909. " The link is: barrypopik.com/index.php/new_york_city/entry/… Learn something new every day. – user66965 Dec 2 '15 at 21:03
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    A similar phrase from 1834: "Ask a barber how to make your hair grow and he will bid you shave it off." – JEL Dec 2 '15 at 21:09
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    Why do you call it a "proverb"? (a short popular saying, usually of unknown and ancient origin) The earliest written instance I can find is 1998. But anyone who's never heard it before (such as me) would obviously understand the intended meaning, even though it has negligible currency and even less history. – FumbleFingers Dec 2 '15 at 21:29
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    @FumbleFingers I see, “proverb” is improper. Thank you for your correction and for your reply. – Ferdinand Bardamu Dec 2 '15 at 23:28
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Although I wasn't familiar with this saying, it appears in Charles Doyle, Wolfgang Mieder, Fred R. Shapiro, The [Yale] Dictionary of Modern Proverbs (2012):

Don't ask a barber if you need a haircut.

1972 Daniel S. Greenberg, "Don't Ask the Barber Whether You Need a Haircut," Saturday Review: Science 55, no. 48 (Dec.) 58 (the article is subtitled "Greenberg's First Law of Expertise"). 1973 Arnold H. Vollmer, "The Numbers Game," in Environmental Impact: Proceedings of the ASCE Urban Transportation Division, Specialty Conference ... 1973 (New York: American Society of Civil Engineers) 85: "One of the basic laws of reasoning, discourse o argument can be summarized as 'Don't ask the barber whether you need a haircut.' Try though we may to be completely objective, there is no denying that an engineer has an an inherent bias toward and a vested interest in engineering." ...

So the expression goes back to 1972 (at least), is sometimes credited to Daniel Greenberg, and has attained the status of a modern proverb in the estimation of the Yale modern proverb collectors. I would caution you, however, never to ask someone who is publishing a collection of proverbs whether a particular saying is a proverb.

Malcolm Berko, "Broker Not to Blame for Bad Stock Picks" extends this advice to other fields:

I have a philosophy: never ask a painter if your house needs painting, never ask a lawyer if you should sue a defendant and never do business with a lawyer who advertises for business in newspapers, radio or TV.

Nevertheless, you should have no qualms whatsoever about asking strangers at English Language & Usage questions about English language and usage.

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    I am afraid that the difference between a proverb and a saying is wasted on me. Isn’t the antiquity a necessary condition for a saying to be pigeonholed as a proverb? As for this particular [saying? proverb? pick whichever you like], I think that it lends itself to a lot of variants, as long as they entail a conflict of interest. The concept in itself might as well be “ancient”, regardless of the “characters” that embody it. – Ferdinand Bardamu Dec 2 '15 at 23:39
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    @Ferdinand Bardamu: I was joking about not trusting proverb collectors when they call something a proverb. The definition of proverb in Merriam-Webster's Eleventh Collegiate Dictionary (2003) does not require a proverb to be nearly as venerable and hoary as you might suppose: "proverb n (14c) 1 : a brief popular epigram or maxim : ADAGE 2 : BYWORD [in the sense of 'a frequently used word or phrase']." Those definitions provide strong support for concluding that your epigram or maxim about barbers may legitimately be called a proverb. – Sven Yargs Dec 3 '15 at 0:48

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