Why 97% of Sales Email Messages With Questions Don’t Work

Two of the most popular writing strategies in B2B sales email messages fail to provoke desired behaviors. Especially replies. Instead, they put your customer in a vulnerable position.

sales email messagesTwo of the most popular writing strategies in B2B sales email messages fail to provoke desired behaviors. Especially replies. Instead, they put your customer in a vulnerable position.


I’m talking about asking prospects questions and/or offering persuasive research.

Both tactics fail or under-perform. Because both result in tipping-off customers to your motive:

To sell … before they’re ready to be sold to.

These tactics reek of persuasion. While marketers think persuasive copywriting is good, it’s not.

Copy that openly allows customers to persuade themselves — if, and when, they’re ready for it — delivers consistently more value to both sides. Especially if you are trying to get a meeting with the CEO using email.

Are You Asking Customers to Become Vulnerable?

Are you asking prospects to:

  • Answer questions leading to an outcome you want?
  • Be persuaded by third party research to form a conclusion you want?

If so you are asking customers to become vulnerable. Nobody likes feeling vulnerable. Hence, your email (or even website) copy may be under-performing or not performing at all.

Because your persuasive tone screams, “I’m trying to persuade you … answering (at all) will entrap you!”

Example: I recently received this response after requesting a demo from a software provider.

Thank you and Communications Edge for your interest in learning about our award winning [software tool]!

I am eager to hear from you and what you are looking to get out of your LMS package.

In order to give you a more detailed pricing quote, do you mind answering a few questions:

  • Are you training staff or external partners?
  • If external, will you be selling the courses?
  • How many learners are you expecting on a month to month, year to year basis?

Who says I want — or am qualified to request pricing?

Why would a seller communicate, “I’m going to ask these questions specifically to size-you-up for a quote” before discovering if a price quote is appropriate?

Wouldn’t it make better sense to ask me (a potential buyer), “What is your current LMS solution and/or why would you not build your own LMS?”

Of course it would.

But this solution provider’s rep didn’t ask me that. Because in his twisted world it wouldn’t serve him. After all, I just requested a demo.

I must be ready to buy! Or I’m darned close.

Wrong and wrong.

Those conclusions are both foolish and blindly abundant thinking.

Perhaps you may not think “Why would you not build your own tool?” is smart. But have you considered how this question is neutral? It pushes against making a quick sale.

Therein lies the power. Sound like David Sandler’s “negative reverse” technique? Indeed! It can be very effective.

Effective at qualifying a purchase for both buyer and seller? No. Effective at qualifying a discussion about a potential purchase … if and when the purchase is right for the buyer.

The Role of Questions

The role of questions in effective cold email messages is to serve. The client! In doing so you serve yourself: Clients “qualify-out” themselves. Customers will gladly tell you if they’re going to purchase, when and why … if you will kindly not rush it.

Too often we see questions being used to qualify buyers and/or entrap them. Both cause your email messages to fail or under-perform.

Another rep recently sent this question to me, paragraph No. 1, cold:

“Hi, Jeff. Would you like to increase distribution of your training modules? I am contacting you because I would like to bring [company] to your attention.”

Of course I’d like to, you dope. But then it gets worse … he tells me his intention is 100 percent about his need to place a solution. This isn’t about my need at all. Just to be clear!

First this rep tries luring me with a question that, if I answer, obviously makes me vulnerable to a sales pitch. But just in case I miss his intention he spells it out clearly for me!

The above reps want to sell LMS software to me … more than they care if this is, at all, a fit for me. Prefacing questions with “I’m asking you these questions to push a quote on you” literally screams “I’m going to jam this sale through as fast as I can … game, Jeff?”

In the first example, exploring the nature of my demo request could be saving him time. Time is money. (if you’re this reps’ boss this should trouble you!)

There are a myriad other problems with this message. For example, how does communicating, “I’m eager to show off” benefit me, a potential customer?

BANT Is Killing Us

Rather than a servant leadership mentality (and practice model) there is a pervasive “BANT mentality” (Budge, Authority, Needs and Timeline) dominating sales email messaging. Especially inside sellers.

It’s giving us a bad name, wasting resources and losing accounts.

All by promoting a communications technique which helps customers feel vulnerable to pitches that want to happen way, way too soon.

Help the prospect see your questions as neutral to your bias to sell. In other words, don’t help them feel your question is self-serving. Instead, aim your question at their decision-making process … to spark curiosity.

What is your experience with questions? How are you using them to serve customers and your lead qualification process?