Why questions rarely work

John Doe UI/UX Designer

By Jeff Molander

Sales Communications Coach

Trusted by brands like ...​

You are under pressure to start discussions AT SCALE.

Me too.

We are trying to meet as many new candidates as possible. But targets are hitting delete faster than ever. They're ruthlessly clearing inboxes from mobile devices.

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. 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.

Starting with a question rarely works

Are your cold prospecting InMails / emails starting with a question? Have you tried using "quick question?" as a subject line—and then asked your question?

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

Potential buyers increasingly delete cold emails that start with questions ... because they signal "terrible pitch ahead."

Be careful: Asking questions can sabotage you.

Especially when the message within the template also:

1) Takes longer than 15 seconds to read.

2) Includes web links or attachments.

3) Presents a solution, rather than provoking the buyer to hit reply and talk about their problem.

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

These are just a few characteristics that work against you. There are a half-dozen more that I'll discuss in an upcoming online workshop. Join us. It's fun. If the Clinic isn't for you, no worries. We also have a private, low-cost Online Academy.

The root cause of your cold email being deleted may be that silly question you are asking. The one you are asking to appear relevant. That's a good instinct.

Trouble is, it's a dead give-away.

It's lazy. Sorry but it is. And it's like 95% of your competitors' emails pouring into your buyers' inbox. Highly delete-able.

The 2 types of questions

There are two flavors of questions appearing in email messages. Those that help the buyer think ...

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

- hmmm...

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

There's a lot of talk about making sure to "add value" in your email messages right? Well, questions can add value. But they're super tricky. Thus the best way to use questions, in a cold email, is to encourage the reader to introspect... to evaluate their own situation at this moment in time.

The provocation looks like this: "hmmm... I never heard anyone put it that way before." or "hmmm... I'm aware that could hurt me personally/our company but have been putting off addressing it." 

Or even an occasional, "yikes! I didn't realize I was overlooking that ... this sounds important for me to, at least, know about ... if not act on."​

These provocations earn replies that ask 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. Your success isn't about getting a meeting.

You need to get into the conversation first.

Thus, help your prospect reach their own conclusions ... in your cold email and every email in your sequence.​

In this way the urge to meet (with you) is a natural extension of the email exchange.

The type of question that earns deletion? These are the questions YOU delete all-the-time. ​(in your inbox)

Here's a quick example.

Example: A torpedo question

Opening your cold email with a question is dangerous. If the reader perceives it as a "leading question" you're deleted. If your question feels like you're leading them somewhere? That's trouble. Because these feel like a set-up to a sales pitch.

This provokes deletion, not response. Don't let questions torpedo you.

If it is odd... has tension within it... and provokes introspection it may work. But questions are risky.

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

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.

[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? And do you see how someone like me would just roll-eyes and hit delete—without hesitation?

If you'd like to see how to improve on this in our private, online Academy of sales geeks. It's tons of fun.

I know it's obvious, but are you doing this?

My sales training hero, John Barrows, puts it bluntly. Marketing is typically good at writing content that drives brand awareness and attention for inbound lead flow. You know, for people who have expressed interest in the product. Case studies, pitch decks, etc.

"The problem comes when providing the Sales team messaging they can use to keep attention when making calls and engaging with people who haven’t heard of the company before.

In today’s world, we literally have seconds to get someone’s attention which is why the typical elevator pitch that Marketing develops fails when using it to make calls. It’s usually way too long, too general and filled with buzz words that are not natural for a sales rep (or any normal human being) to say."


This is where sales reps need the most help but get the least support

John Barrows

Sales Trainer 

Beware: Most questions I see my students writing are marketing-driven. Marketing departments often encourage sellers to ask them. DON'T!

If you're in marketing (or were) no offense. It's just not the same as sales prospecting. Not at all.​

Are you asking questions this way?

One of my students was using, “Did you know that printing is typically the 3rd highest office expense behind payroll and rent?” He sells managed print services to CEOs, COOs and IT managers at small and mid-sized businesses. I want this guy to succeed. And he will. But this question hasn't been working for him.

Generally, it won't—no matter how many emails he sends.

Rather than be provoked to reply, his prospects are thinking, “I know why you're asking…” (roll eyes) and hitting delete.

Many, many marketers and sellers have (against their interests) trained buyers to detect this approach. We've all seen it so many times. It signals “sales pitch ahead.” Thus, sabotaging your provocation—even if you have written a good one!

If the only obvious answer to your question is yes or no it may risk insulting the buyers' intelligence. "Did you know printing is expensive?" is an obvious yes.

This approach is risky as compared to a question that forces the buyer to introspect on a more complicated issue.

Use a 'grabber' technique

Templates do not work.

But a formulaic approach to message design—that is mostly template-able—does.

Customization is key.

In the above example from Homer, what might be important to me are weaknesses. What if Homer brought to light my current learning management software's weaknesses?

That's a grabber.

It encourages (forces?) me to stop and think, “am I doing everything possible to be sure customers can easily participate in my training?” In my case, it forces me to realize, “am I even paying attention to device compatibility!?”

It makes me want to read on. It provokes me.

This kind of approach also shows me the seller:

1) Did homework on me (he knows what I sell and to whom; this is probably not spam)

2) Is smart enough to know the important issues I'm facing

3) May have invested time researching my current technology (prompting his question)

Have you made it this far down the page? Nice work. One of these days, hit reply to the email I send you. 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. 

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 & speaker

Photo credit: Markus Spiske