Do Questions Work as Headlines?

One of the biggest benefits of being a copywriter is I get to learn while I earn. I learn something new from every single client I work with. This was especially true when I recently wrote a sales letter for Ed Oakley.

Ed is the co-author of two books: Enlightened Leadership and Leadership Made Simple. As part of my research, I began reading the latter of the two. Then, on page 27, I came across a “gold nugget” of insight.

Nothing redirects people’s thinking better than a well-phrased question.

This really struck a chord with me because of a few “coincidences” that all happened around the same time.

For one, I started using questions as post titles on my blog. Based on Alex King’s Popularity Contest plug-in, I’m able to see which posts are most popular. Currently, on this blog, my post titled “Eight Months to Write a Letter?” has been the most popular.

On another blog, the most popular post was a blog carnival I hosted (the people who participated in the carnival linked back to the post, which produced a lot of out-of-the-ordinary traffic).

But the second and third most popular posts both use questions as post titles. The second most popular post is “Are Cars Worth It?” and the third most popular post is “Should You Tithe When You’re Broke?”

And yet it seems using questions as blog post titles isn’t the only place they’ve been proven effective. They’ve also worked extremely well in direct response sales letters.

Examples from sales letters.

  • One of the greatest copywriters of all time, Bill Jayme, is most famous for this headline that was used to promote Psychology Today magazine: “Do You Close the Bathroom Door Even When You’re the Only One Home?”
  • And Gary Bencivenga got good mileage out of this famous headline phrased as a question: “Has This Man Really Discovered the Secret of Inevitable Wealth?” (Kudos to Ben Settle for digging this one up.)
  • One of Maxwell Sackheim’s most famous headlines was for a space ad that advertised the Sherwin Cody School of English. The headline said: “Do You Make These Mistakes in English?” (Note: If you have the AWAI Hall of Fame book, you can read the entire ad on page 257.)
  • Eugene Schwartz made his mark selling a unique type of rose plant that produced incredibly large quantities of blooms throughout the entire growing season. To sell this plant, he asked a poignant question: “Who Ever Heard of 17,000 Blooms from a Single Plant?”
  • And perhaps the most imitated headline on the entire Internet was a question written by John Caples. It was originally to sell a laundry detergent: “Who Else Wants a Whiter Wash–with No Hard Work?”

The bottom line: questions
definitely work as headlines.

So, in light of all this proof, does it make sense to always phrase headlines as questions?

The answer, clearly, is no. I believe questions as headlines are some of the riskiest types of headlines you can write. Many times the question simply won’t be compelling enough to capture your readers’ interest. In most cases, you will be better off with a statement or promise of some kind.

But I also believe the right question used as a headline can have the biggest payoff. My recent experience has proved this to be true.

Recently, I conducted a headline split-test for an upcoming real estate conference. The headline that won by a long shot was a question: “Would You Like 2008 to Be the Year in Which You Build the Foundations for Long-Term Real Estate Wealth?”

(I actually thought this headline variation would lose the split-test. But the actual results proved otherwise.)

Anyway, the whole point of this article is this: Whenever you are brainstorming headlines for blog posts, sales letters, articles, etc., always consider headlines that are phrased as questions.

You may ultimately decide to go with a statement or promise, but occasionally you will happen upon a well-phrased question that outperforms all the other “normal” headlines you can possibly think of.

-Ryan M. Healy

Ryan M. Healy

Ryan Healy is a financial copywriter and the author of Speed Writing for Nonfiction Writers. Since 2002, he has worked with scores of clients, including Agora Financial, Lombardi Publishing, and Contrarian Profits. He writes a popular blog about copywriting, advertising, and business growth, has been featured in publications like Feed Front magazine, and has been published on sites like,, and

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