One of the most successful letters in history starts with a
question: "Do you make these mistakes in English?"

so I think your underlying assumption is proved false.

The truth is you have to test. No one can tell you one way
or another for a particular copywriting problem.

One of the best ways to begin a sales letter is with a question. Sales
people know that asking their prospects questions, not only builds
trust, but also extracts important information on which to base their
appeal.

Consider this opening of a sales letter for a fictitious product that
restores hair in bald men:

Dear Friend,

Are you worried about your present hair loss? Have you already
tried hair restoration products that didn’t live up to their claims?
Are you embarrassed to look in the mirror? Are you about to settle for
the myth that ‘this is just genetic and nothing can be done about it?

As you read through each question you can see how the copywriter tries
to enter a conversation with the reader by showing that he knows what
concerns him. The prospect also assumes that since you raised the
questions that you have the solutions to his problems.

In the case of a sales letter you cannot ask the prospect questions
expecting to get a live answer, since the letter is a one way
conversational tool. But asking the questions that the prospect is
already asking helps build rapport and gets his attention.

Some of the greatest thinkers and philosophers asked the correct
questions that led them to discover some of the laws of nature that we
take for granted today. Asking questions early in the sales letter can
also cause the reader to think in the direction you want him to
follow.

Since you are trying to build rapport at the beginning of the letter
you want to ask questions with a definite ‘yes’ answer. Questions such
as, “Do you want to make more money than you are making now?” will get
the client nodding in agreement with you. The answer to the questions
should also be the main benefits that is offered by your product or
service.

Questions also help to engage the reader early in the sales process
because he is forced right away to think about the answers. The
copywriter must assume that readers come to the letter with a
preoccupied mind and the only way to break through this natural
barrier is to tune the mind to a different frequency. Questions are
therefore great attention-getters.

Another effective way to use questions in the sales letter is to raise
objections in the form of questions and then answer them one by one.
This is one of the ways that I have used the Frequently Asked
Questions (FAQ) for clients and incorporate these into the main sales
letter. If people keep asking these questions this means that your
sales message is not answering them and these questions are really
objections to buying your product.

For example, if you are selling a software product that helps people
create videos to be uploaded to YouTube and prospects keep asking how
large are the video files output from your software, then this
question is one objection you must meet squarely.

In that case I would suggest that you raise the question: “Does you
software produce high quality videos with small file sizes?” I would
then immediately answer that question by illustrating the file size
inputs compare to the output and comment on the quality versus the
file size.

Questions are powerful sales tools that are frequently taken for
granted and not used often enough. Asking a question can often engage
a reader more than simply sharing facts with them. And getting
attention these days is one of the toughest battles to be fought
online.

-Ray Edwards

-Ray Edwards

Try turning your question around.

Put the burden of proof on yourself.

That'll give you your answer.

You're one guy on a forum who thinks it sends up a red flag.

Meanwhile, thousands of successful advertisements over the last several decades have started with a question.

Your post starts with a question.

Anyway, what you personally like, what you "imagine" - there are billions of people on the earth. Thousands in your market. If you cast them as feeling and imaging the same way you do, then you're only selling to yourself.

What is this woman doing?

Seen here:

Bud Weckesser: Master of Case Study Marketing

It sold millions of dollars of books.

The question as a headline depends on the TARGET. And probably more important, where the target meets the promotion.

In print media, it is a good stopper. Slows down the eye, arouses curiosity.

Yes, use the question...when it works. HOW to know? Test.

gjabiz

Sales pitches should be natural.

You should be looking to support or help others with your ideas. When they ask how you know so much you tell them. It just so happens that you work in the field that is why you know so much. When you help people they are more likely to trust you and want to deal with you at a later date.

So to answer your question I feel you are over thinking it, be natural.

Alright so here's my take Jared,

I do believe that using a question in the first sentence makes it look like a sales letter.

Because, i myself think of it that way.

So, instead of using a generic question in the first sentence, you must use a pattern interrupt question.

A question which basically gets the attention of the reader.

Now, a pattern interrupt can be done in many ways.

Either through using an controversy, or a statement which has no real relationship with the letter.

This works wonders.

Anyways do your testing.

And let us warriors know the results.

Ab

Btw you can use Pattern Interrupts like

"From the desk of:-
so so so"

This works as well.