Do You Want to be More Persuasive So You Can Sell More? (Be Careful When You Ask Questions in Copy.)

Filed under: Website Copywriting

Good attorneys are extremely persuasive. It’s part of their job description—especially when we’re talking about trial lawyers. In court, the attorney’s goal is to persuade a jury or judge to think a certain way and form a specific opinion.

Today we’re going to learn an exceptionally valuable marketing lesson from a lawyer’s playbook. This lesson can be applied to your tweets, blog posts, blog titles, article headlines, etc.—anywhere you’re working to pull people in and read more.

(Remember that one of the ultimate goals of our ongoing marketing efforts is persuasion: we want to persuade as many current or potential customers to take specific actions that ultimately lead to relationships, leads, and sales.)

Let’s set the stage for our marketing lesson:

In court, a lawyer asks questions during the cross-examination of witnesses. A competent lawyer ALWAYS knows the answer to the question he or she is asking. The answers buttress the lawyer’s argument.

Lawyer: Mrs. Jones. Did you see the defendant steal cash from the cash register at the coffee shop?

Witness: Yes.

Lawyer (pointing to the defendant): Is that the person you saw taking the wads of dollar bills from the till?

Witness: Yes.

Lawyer: Did the defendant also take some donuts?

Witness: Yes.

Lawyer: Did the defendant eat a pink donut, chocolate donut AND a maple donut without paying?

Witness: He did.

And so on.

Avoid These 2 Rookie Mistakes

Skilled web copywriters are extremely careful when asking questions in copy. In fact, they rarely ask them.

A big rookie web/marketing copywriting mistake is asking open-ended questions (questions without yes/no answers).

Another big rookie mistake is asking a question that a chunk of the target market might not answer in the desired way.

Let’s take a look at this email example from a real (and major) corporation. The question they’re asking isn’t open-ended, but is it highly likely most of their target audience will actually say “yes?”

After seeing this email, my answer to the question was a fast and resounding ‘NO’ — and yet the promotion is trying to get as many people as possible to say ‘YES’ and click through to the next step. I didn’t.  A potentially more effective question would have been: “Do You Want to Meet Your Favorite Musicians in Person?” I’m guessing a good number of people listening to satellite radio would answer…YES!  (However, in order to confidently create a really effective question, I’d need to learn about the demographics and psychographics of this email’s target audience.)

There’s Nothing Wrong with the Totally Obvious

Expert marketing copywriters will write a question-headline that’s carefully crafted to get as many people as possible to take the next step in the sales process. The questions are always simple and the copywriters are always confident they know how their audiences will answer the questions.

Questions in copy, especially in headlines,
work best when the answer is almost absurdly obvious.

 Let’s say you’re advertising to people with foot problems. Try this headline:
Do You Want to Walk Pain Free?

If you’re advertising a plumbing service that specializes in drain cleaning, try this:
Do You Need Your Drains Cleared Right Now?

Let’s say your company specializes in ski instruction. Try this:
Do You Want to Ski Like a Pro?

If you’re going to use a question in your online marketing copy, make sure the readers you’re targeting know the answer to the question. Doing so ensures you’re taking the first step in getting your readers’ attention and drawing them in to read more of your copy.

It goes like this:

  1. Your readers see the question, Do you want to ski like a pro?.
  2. Your readers answer/think “YES! I want to ski like a pro.”
  3. They feel excited.
  4. They’re eager to learn what it will take to ski like a pro.
  5. They attentively read through the rest of your copy—which of course works to persuade them to take a desired action (perhaps in this instance it’s booking with your ski school).

You grabbed your readers and pulled them in by getting them to answer an easy question without hesitation or thought.

It’s Not Too Basic.

It’s tempting to look at a question-headline with a painfully obvious answer and think it’s too simplistic or that it lacks creativity.  Remember though: we’re not writing serious literature here. We’re writing advertising, blogging, and social media copy with the ultimate goal of persuading our readers to do something.

Remember: those trial lawyers almost always ask basic and simple questions.  Imagine if the attorney in the earlier trial (above) had asked this open-ended question:

“So, what did you see that morning in the coffee shop?’

The witness could have answered with just about anything. “Oh, well…I ran into my uncle Bob who told me he was leaving for six months for New Zealand.” Not an answer that will keep the trial on-course or that will help the jury keep focused on the most important facts of the case.

So instead the lawyer asked, “Did you see the defendant steal cash from the cash register at the coffee shop?” The lawyer knows the answer. The answer is simple. The lawyer wants to emphasize the answer. They lawyer is guiding the process step-by-step down a specific path toward a specific end-goal or point.

Seems easy, but it can be tricky.

Interestingly, implementing easy questions in your copy can be much harder than it looks. Getting to simple can often be quite challenging.

Questions must be worded correctly and the words must be placed in the right order.

Writing the perfect (and perfectly simple) question headline or header or tweet that persuades your target market to take the next step typically requires research, knowing your market inside and out, several drafts and reviews, and then (hopefully) testing.

Bonus tip: One of the more important books in advertising copywriting is Million Dollar Mailings, which is a collection of direct mail packages that each produced over a million dollars in revenue in the early 1990s…yep, before the Internet. Look through the pages of this 501 page tome and you’ll see all of 14 question headlines.


Using easily-answered questions is a powerful technique that expert web copywriters use, and it’s one you can use too. Simply proceed with caution and keep in mind that it’s easy to come up with questions that don’t hit the target market and subsequently fizzle.

To Question or Not to Question. That is the Question.

Today’s key takeaways:

  • Don’t be afraid of using questions in your copy.
  • Don’t overuse questions in your copy.
  • Choose your questions carefully—just like the trial attorney working so tirelessly to nail down exactly what happened with the donut thief.