Should You Ask Questions in Your Copy?

  • Avoid Y/N questions
  • Ask questions intentionally
  • Ask questions that align the reader with you

Compare these 2 pop-ups side by side:

Should you ask questions in your copy?

They’re exactly the same – except for the headline.

Which one do you think converts better over at

I’ll tell you soon.

But to attempt to answer that question, we need to think through this:

  1. Should you ask questions in your copy?
  2. Should you “get personal” or establish familiarity in your copy?
  3. What happens when a button does or doesn’t reflect a headline? (take a look at the opt-out button above to see what i mean)

Should you ask questions in your copy?

Questions are tricky things.

The words you use to shape your questions are just as tricky.

So says science.

Researchers have shown that asking eyewitnesses questions in a misleading way can cause them to incorrectly recall what they saw. Not only does the way you ask a question impact the answer but the very act of asking a question can bias a response and change the respondent’s behavior. And even asking hypothetical questions can impact choice. (More about these 3 studies here)

I’ve said a handful of times – like on Page Fights – that the only questions you should ask in your copy are those that prompt your prospect to give the answer you want.

Put differently, you should never ask questions that could turn your prospect against your offer.

For example, this is a bad question: “Are you ready for the vacation of a lifetime?”


Because even good prospects could answer “no.”

In fact, it’s quite likely that the answer is “no” for nearly everyone.

Not because the vacation of a lifetime isn’t great.

But because the prospect isn’t ready for it.

A phrase I will never say.

A phrase I will never say.

And, to be clear, it’s not that the phrasing “are you ready” is universally problematic. Football fans who are ready for some football respond like lunatics to the phrase “are you ready?” The guy on the overhead asking an auditorium “Are you ready for Taylor Swift?” is bound to get nothing but mad wails in reply. Good mad wails. Yes, yes, they are ready.

The problem is asking ANY question that could easily be answered in a way that runs counter to your (and your prospect’s) goals.

Check out this example:

Asking questions in copy on Basecamp

Suddenly it’s easy to see how questions can fail us, isn’t it? No one’s hungry for more Basecamp “learnings.” So why would Basecamp, with their history of writing and advocating for outstanding copy, use such a question? As someone who’s written a lot, I’m answering that Q on experience: it is very, very convenient to ask a question to segue into the point we really want to make.

If you’re going to ask a question, don’t do it just as a segue. Do it intentionally. Start by following this clever advice from Erin at Followbright (formerly Time for Cake):

Questions in copy

Any question you ask is copy, after all, which means that it should be working to get your prospect that much closer to choosing you. If you ask a question, it should help the visitor get stoked about trying your software or hiring your team or submitting an order for a custom ugly Christmas sweater.

Here’s what that means, practically speaking…


Want to start managing projects in Flow? Click here to get started


Would you like to have a consultation with a life coach? Book a free call


Are you ready to upgrade to Buffer Premium? Upgrade now


Would your team like to do more in less time? Click here to get started


Wouldn’t you like to leave a legacy of happiness? Book a free call


Isn’t it worth $19/mo to dominate social? Upgrade now

We want our good prospects to give a resounding “YES!” as the answer.

Getting that means you’ve asked a good question.

Which brings us to this point: to keep things simple, ask Y / N questions.

BUT! Do not underestimate the power of the third answer, the one that exists outside of Yes and No. What is that answer, you ask? It’s the one most often given when reading any of these classic headlines:

Copywriting questions

Copywriting questions from olden days

Should you ask questions in copy?

The answer?

“I don’t know.”

What happens when we say we don’t know?

For most of us, the trusty ol’ curiosity gap kicks in, and we gotsta know the answer before we can move on with our lives.

(Remember, we’re talking about good prospects. Not the whole world. So if you look at “Is this the world’s easiest yoga?” and say “I really don’t care”, then that copy wasn’t written for you in the first place.)

When is it okay to ask an open-ended question?

One of the most famous headline formulas of all time is an open-ended question: “Who else wants __________________?”

That headline is powerful – and reused ad nauseam – because it suggests that a lot of people are already getting X, that a consensus exists among a growing number of people that X is good. So why wouldn’t you join in? But unless you’re really trying to show off your copywriting skills, is there any reason not to stick with closed questions?

K, now, should you get familiar in your copy?

If we think back to Tim’s pop-up split-test, one of the two headlines was this: Hi, I’m Tim Grahl. 

That headline is, at its core, dialogue marketing at work – or a sort of “dialogue copywriting,” if we wanted to go there. The headline is engaging the reader in a personal conversation, one that could be desirable and one that is certainly different from most interactions with brands off social media.

(We’re all trying to converse on social media, of course.)

But let’s go deeper than that.

What is the word “hi” doing in this headline?

Here’s what Tim says he intended when he used that word and this entire familiar headline:

I’m one guy trying to teach things I’ve learned and people tend to like me when they hear me talk, read my writing, meet me, etc. So I was just trying to play up on that.

At its essence, it’s trying to bridge the space between – the space that separates Tim from his visitor. (This TEDx talk explores this subject in a very emotional way. You should watch it.)

Further, when we’re writing copy, we’re always considering tone – and the word “hi” is simply quite tonal. It’s informal, friendly, used commonly when speaking, used less commonly in written copy, and unlikely to cross a line (except in cultures and situations where formality is required on first meetings – like in Jane Austen times or in Japanese business).

So consider this. Studies with fMRIs have shown that:

The brain takes speech and separates it into words and “melody” – the varying intonation in speech that reveals mood, gender and so on. … [W]ords are then shunted over to the left temporal lobe for processing, while the melody is channelled to the right side of the brain, a region more stimulated by music.

As the guys at Buffer put it: our brain uses two different areas to identify the mood and then the actual meaning of the words.

What might the brain do when it encounters the arguably melodic phrase, “Hi, I’m Tim Grahl”? Might such phrasing – and the tone implicit in it – be a new ‘way in’ to the prospect’s mind, a mind we’re always trying to slip into? Could it set a mood?

…And is that mood good or bad, problematic or helpful?

And – last but not least – what does button copy have to do with headline copy?

I could talk endlessly about buttons. And I have – at Rainmaker (then Authority) 2014 and here on Copyblogger.

Last year, I spoke at CTA Conf about the need for buttons and headlines to work together. This was based on a handful of split-tests that showed – again and again – that as powerful as the headline continues to be, call-to-action buttons are creeping up and, in my experiences, even overtaking the headline due to the fact that the button is the very site of conversion online. You can read a headline and not convert, but you can’t convert without interacting with a button.

I broke down my findings (on tests I ran with the help of Jen Havice) in this post.

A key takeaway was this: when a button is in close proximity to a headline, it can be beneficial to make the button copy closely reflect the headline copy, especially the action in the headline. Here’s an example of how doing so has performed in the past:

Headlines and buttons

In the Schedulicity case above, when the button didn’t closely reflect the headline, clicks were lower than when it did.

So now let’s look at this truncated view – headlines and CTAs only – from the Tim Grahl test in question:

Tim Grahl pop-up case study on Copy Hackers

The opt-in button copy “Download Now” doesn’t reflect either of the headlines.

The opt-out button copy “No, I’m selling enough” doesn’t reflect “Hi, I’m Tim Grahl” but does come close to matching “Want to sell more books?” That is, the opt-out copy seems to be part of the same conversation as “Want to sell more books?” but not part of the “Hi, I’m Tim Grahl” convo.

Where does that leave us?

It leaves me asking this: If the opt-out is a better “fit” as a button – if it’s following the rules and is thus optimized to be clicked – might that drive opt-outs up, thus driving opt-ins down? 

Which brings us to the results of Tim’s two-way split-test:

Let me repeat the contenders for you:

Should you ask questions in your copy?

Based on what you’ve read above, which of the two do you think is bringing in more sign-ups?

One converts at 4.28%.

The other at 2.92%. 

The winner?

“Hi, I’m Tim Grahl.”

Are you surprised? Weigh in below, and let’s talk.