Why questions rarely work

Jeff Molander

Sales communications coach & Managing Partner, Communications Edge Inc.

Trainer to brands like:

You are under pressure to start discussions AT SCALE.

Me too.

I've got to meet as many new candidates as possible. But targets hit delete faster than ever. They're ruthlessly clearing inboxes from mobile devices. Marking unsolicited email as spam.

Send them what they're already seeing—or have been trained (by experience) to delete—and you're dead.

Fail to personalize? (at least a little bit) You're done. Deleted. Canned templates don't work.

Ask for the meeting? Talk about your solution at all? (in the first touch)


But there is one, increasingly common, "kiss-of-death"​ tactic I see sellers trying. Starting the message with a question.

Pain points & hooks

Too often questions are marketing hooks. Whether you realize it or not. 

Sometimes we ask questions to appear relevant. That's a good instinct.

But customers don't see it as relevant. They see it as bait for a hook they aren't biting!

Questions are often lazy. What I mean is this: It makes you look like your competitors' emails. Everyone is asking the same "pain point" questions. These are pouring into your buyers' inboxes.

Highly delete-able.

Even if you are starting with questions—and having success with it—be advised:

Prospects increasingly delete cold emails starting with questions. Because questions usually make prospects feel vulnerable to being pitched. They sound like cheesy marketing hooks. Because they are.

We often see,

"Are you getting crushed with new leads, Jeff?"

Heck no. What business owner can get enough leads? They keep asking stupid questions like this for one reason: To tee-up a benefit-laden, cut-and-pasted pitch about appointment-setting services.


Most questions are biased to answers the seller is looking to induce. Customers feel this and push back. Hard. You've seen these questions in your inbox. They're telling and easy to spot-and-delete.

Be careful: Asking biased questions can sabotage you. Un-biased, neutral questions can work. I'll give an example shortly.

The 2 types of questions

There are two flavors of questions appearing in email messages. Those helping a buyer think ...

- delete this email (rapido! rapido!) or ...

- hmmm...

It's the "hmm" we're after.

These are un-biased questions—designed to help prospects reflect on themselves. (rather than think about answering in a way you want them to answer... and "confirm their pain point.")

Un-biased questions are neutral. They don't try to push a pain. 

Example: It's important to add value in cold email messages. We know this. Questions can add value and provoke conversations. The best way to use questions is to encourage the reader to introspect... to evaluate their situation at this moment in time.

What comes back at you (from prospects) sometimes looks like this:

"I never heard anyone put it that way before."


"hmmm... I'm aware that could hurt me personally/our company but have been putting off addressing it. What are you suggesting here, exactly?" 

Or even an occasional,

"I didn't realize I was overlooking that piece. This sounds important for me to, at least, know about ... if not act on. How can I get more details on that?"

These provocations earn replies asking for more details—about the thought you just provoked, not your solution. If this sounds like Challenger methodology it is very similar. But it is also part Sandler.

Bottom line: Stop pushing pain points, trying to get customers to qualify immediately and set a meeting. You need to get into the conversation first.

Ready to start? Join a small group of us online as Jed Fleming and I strengthen outreach to provoke conversations. 

Otherwise, here's a quick example.

A torpedo question

Opening your message with a question can torpedo you. It can be done effectively. But if the reader perceives it as a "leading question" you're deleted. 

If your question feels like you're leading them to a conclusion you want this provokes deletion. 

However, if your question is unusual (compared to biased questions they see every day) you've got a strong chance. If your questions has tension within it... and provokes introspection... it may work.  

The below example recently hit my inbox. It is a popular (and ineffective) template. I'm obfuscating the company's name to protect the innocent :)

Hi Jeff,
Would you like to generate more revenue from your training modules? I am contacting you because I would like to bring [company] to your attention.

[company] provides all the resources you need to create and sell online training modules:Create, distribute, analyse and sell your modules all within [company]. Your modules will run on any device and can be used in any language.

Last month we welcomed our 15,000th customer. In case you want to give [company] a try, you can sign up for free at [Web site].

If you’d like to know more about how [company], let me know, I am always happy to show you [company] possibilities for your business.

Homer Simpson

See that first sentence? See how someone like me would just roll-eyes and hit delete—without hesitation?

Of course I would like to generate more revenue. It's what feeds my family, after all. But the first sentence here is such a terrible marketing hook why would anyone read further? And if one does "I would like to bring my company to your attention" is just awful. 

I get dozens of these each week. Why would I hit reply? 

A grabber

Instead, what if Homer asked me this question?

"Noticing your Spark Selling Academy's video tutorials, Jeff. How will you know when it's time to distribute the training beyond your own website?"

Do you see how this question is just plain different than what I get in my inbox every day?

See how the structure forces a mental stop? It makes me think, "Hmm... how will I know when it's time? What will happen in my business—to make me think 'NOW is the time to expand?' Interesting question." 

It's a question that grabs. It's a question that helps me want to read what might be coming next. 

It's what we call a "facilitative question" because it facilitates a conversation by focusing the reader to think inward. 

See how it's different than asking a question that baits?

Another torpedo example

One of our coaching students was using this leading sentence. He sells managed print services to CEOs, COOs and IT managers at small and mid-sized businesses...

“Did you know that printing is typically the 3rd highest office expense behind payroll and rent?”

I want this guy to succeed. And he will. But this question will continue to sabotage him. No matter how many emails he sends he's going to fail. Consistently. 

Because his prospects are thinking, “I know why you're asking…” (roll eyes) and hitting delete. Nothing provocative about it.

Many marketers and sellers are (accidentally) training buyers to detect this approach. You've seen it, right? So many times. It signals “sales pitch ahead.” Sabotaging your provocation—even if you have written a good one!

(If you're still writing messages—and not blunt provocations—get that sorted with us quickly.)

No cheese, please

Remember: If the obvious answer to your question is yes or no it risks insulting the buyers' intelligence. "Did you know printing is expensive?" is an obvious yes. It's an obvious set-up. D

Instead, compare this lazy, cheesy tactic to a question encouraging the buyer to introspect on a more complicated issue.

It's not your fault

This is where sellers need the most help, but get the least support.

I don't like the blame game. But most questions our students are writing reek of marketing. Bad marketing. When sellers get stuck ("what should I write? how can I press a pain point to grab their attention?") they turn to marketing materials. 

Don't. Resist. 

If you're in marketing (or were) no offense. Writing marketing copy is not the same as sales prospecting copy. Not at all.

Marketing is typically good at writing content driving brand awareness and attention for inbound leads... for people who have expressed interest in the product. Case studies, pitch decks, etc.

But sellers don't need this kind of messaging. Instead, we need messages that earn---and then keep---attention when making calls and engaging with people who haven’t heard of the company before.

We literally have seconds to earn attention. The typical elevator pitch (that marketing develops) fails. It’s usually too long, too general and crammed with buzz words that are not natural for a sales rep to say.

Quick tips to get started

Help your prospect want to read your email. Help them get curious. Keep it super-short. Provoke them.

Once they agree to chat, allow them to end the chat whenever they want. Say as much. Don't need the conversation so much.

This is the most important part: Never use words that sound persuasive. Don't posture. Don't try to appear credible. Instead, let them reach their own conclusions ... in your cold email and every email in your sequence.

Help your prospects convince themselves they need a meeting. Imagine: The urge to meet (with you) is a natural extension of the email exchange. Sound crazy? Sound impossible? It's not.

Less is more. Brief, blunt, basic. Provocative. 

Make sure your message:

1) Can be read in less than 15 seconds.

2) Includes NO web links or attachments.

3) Does NOT present a solution, talk about your benefits.

4) Avoids asking a question that screams "lazy sales person asking me a question making me vulnerable."

Have you made it this far down the page? Nice work. One of these days, hit reply to the email I send. Be in touch. I'll be glad to understand more about you, your challenges and what you think of the news I'm reporting ... and advice I'm providing. 

Or join a small group of us in an upcoming workshop as Jed and I strengthen a volunteer seller's outreach methodology.

Or comment below.

Are you experiences different? I am all ears and will enjoy learning from you. Be in touch!

With your success in mind,

Sales communications coach & Managing partner