One of the most famous questions ever asked in an ad was penned almost a century ago by copywriting legend Maxwell Sackheim. It read: Do you make these mistakes in English?

It was the headline for an ad that sold a rather pedestrian mail-order language course. Yet it worked so well, pulling in so much money, the company who owned it continued to run it for 40 long and successful years!

To be sure, a myriad of other headlines were tested, all using the same body copy, before that now famous winner was discovered. One competing headline even read: Do you make mistakes in English? Certainly close enough, you would think, but it failed miserably, as did all others.

It was only when that seemingly innocuous word “these” was finally inserted, that direct marketing history was made and a lesson for direct marketers was learned. Well, some endeavored to learn it, most never tried. They merely copied its form, without understanding why it worked so well. Even today, you’ll see that same headline in its innumerable permutations:

• Do you make these seven tactical mistakes on a first date?
• Do you make these errors when doing your own taxes?
• Do you make these blunders every time you write your own copy?

These copycat headlines will actually work... at least for a short while (particularly with those consumers who don’t get out very often). But as with most formulaic copy, it’s soon recognized as a trite, clichéd, over-used and unimaginative pitch that screams: Hey, look! Here’s my ad!

Nevertheless, the question remains, can asking a question in an ad increase sales? Some will argue vehemently that the use of a question is a non-starter, a pre-ordained copywriting disaster. Nevertheless, a question is a tool. And as with any tool, any copywriting strategy or tactic, if a question is not formulated and handled with proper caution, it could indeed do immeasurably more harm than good. Well, let me correct that: if you’re a direct marketer who tests you can measure precisely how much harm a poorly phrased question will do or how well a good one will work.

The secret to constructing a well-built, hard-working, money-sucking question:

For Max Sackheim the secret sauce in his brilliant question was intrigue and curiosity, both of which were lacking in: Do you make mistakes in English? This question failed because it was a yes or no question, and a yes or no question should never (with qualifications) be asked in sales copy. Why? Because either of the two possible answers, yes or no, will effectively end the conversation you’re trying to conduct with the reader.

If the answer to a question is no, the reader will assume there’s no further reason to continue reading your letter. In other words, you asked, I answered, now good-bye. Similarly, if the answer is yes, the reader responds with a big: Yeah, so? (And again, he’s gone.) A yes/no question does not sink the barbed hook in the fish’s mouth.

Why then “these”?

By inserting the word “these” in his headline, Sackheim prevented the reader from answering yes or no. And, because the reader didn’t know what “these mistakes” were, he had to keep reading in order to find out. And that was the key to the ad’s success.

The first objective of any sales copy, from the headline on down, is to compel the reader to keep reading. Otherwise, how else will you get the chance to prove your product’s worth and ask for the order?

Never give the reader time to think about the answer. You want to do all the thinking, and answering, for the reader. You want to direct the conversation and provide the conclusions - always!

For example, if you ask a question that doesn’t either hint or overtly state that the answer will only be revealed by reading further, sorta like in these questions:

• How many times a day do you dream of becoming rich?
• When are you finally going to tell your boss to take this job and shove it?
• How much money have you lost in the stock market this year?

You’re, in effect, asking the reader to step away from your ad and discover the answer elsewhere.  You have lost his attention and you’ve broken the connection.  For an ad to be successful it can never be laid aside. It must be read in its entirety with rapt attention, growing interest, and compelling desire.

But, since there are exceptions to all rules, here is the only time answering “yes” to a question will move a sales conversation forward and not end it: If you can pose a question or numerous questions in such a way, where you know, and want, the answer to always be yes. You will be leading the reader into a state of blissful acceptance of your argument or contention and ultimately of your offer.

If your question is more or less rhetorical where you and the reader know the answer is yes, sorta like in these questions:

• Couldn’t you use an extra $10,000 in your bank account starting tomorrow?
• Wouldn’t you like to be your own boss, and never have to answer to anyone else again while doubling your income?

You’re, in effect, positioning yourself as the reader’s good buddy, you’re agreeing with him, and prompting him to agree with you. You’re standing beside him, confirming his deepest beliefs and/or suspicions. The more he answers yes to your “leading” questions and to your similarly orchestrated statements and contentions, the more inclined he will be, by sheer force of habit if nothing else, to say “YES!” when you ask him to purchase your product or service.

Get it? Questions? Yes, no?