You are under pressure to set meetings with top executives, AT SCALE... using cold email.

Me too.

I've got to meet as many new prospects as possible. But CEOs and top decision-makers hit delete faster than ever. They're ruthlessly clearing inboxes from mobile devices. Marking unsolicited email as spam.

Send executive prospects 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.

Sending a meeting request to CEOs? Talking about your solution in the cold email?

Delete. Delete.

There is another, increasingly common "kiss-of-death" tactic I see sellers trying: using biased, "hook" questions inside the message.

This common (best practice) should be avoided. Never write cold email to a CEO this way. 

Pain points & hooks

Too often questions in cold email messages are marketing hooks. Whether you realize it or not. 

  • What are your biggest pain points? (hook: so I can sell to them)
  • What events are you attending this year? (hook: so I can stalk you)
  • Where do you see the biggest growth opportunities? (hook: so I can see if I can sell to you)
  • What's holding your team back from reaching your goals? (hook: so I can sell a solution)

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. They make your emails blend in with competitors'. 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 email messages starting with questions. Because questions usually make prospects feel vulnerable to being pitched. They sound like cheesy marketing hooks. Because they are.

Avoid "setting up" your buyer

Here's an example from my inbox:

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

I delete these immediately. Because no business owner can ever have enough new customer. This type of question is biased to what the seller wants---to open a discussion about what I want.

But I know better. I've been trained to delete these (by sellers who don't know better).

Sellers keep asking "telling" questions like this for one reason: To tee-up a benefit-laden, cut-and-pasted pitch about appointment-setting services. It's an obvious set-up.


Bottom line: Most questions are biased to answers the seller is looking to induce. Customers feel this and push back.


You've seen these questions in your inbox. They're telling and easy to spot-and-delete.

Be careful: Asking biased questions to executives can sabotage you. Unbiased, neutral questions can work as a strategy for a cold email message campaign. I'll give an example shortly.

2 types of questions in cold email messages

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 the status quo.

Compare this to a biased question—a "hook" making them feel vulnerable to your sales pitch. Hook questions are easy to detect. Especially if you're a CEO or senior decision-maker.

Because they see so many inbound questions biased to the answer sellers seek... to confirm their pain point. (and open the door for a sales pitch)

Unbiased questions are neutral. They avoid pushing on a pain. They avoid making the prospect feel vulnerable. Example from a member I'm coaching who calls on HR and Leadership executives:

"What would force you to consider helping managers find ways to embrace difficult conversations?"


Who benefits when employees don't address behaviors blocking peak performance?

The best way to use questions is to neutralize them; encourage the reader to introspect... to evaluate their situation at this moment in time.

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

"I never heard anyone put it that way before. Nobody benefits from that. What are you getting at?"


"Hmm...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 the 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?"

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 senior decision-makers and CEOs 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 I strengthen outreach to provoke conversations. 

No cheese, please

Don't push pains, ask for meetings nor seek to extract information

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

Equally damaging is asking people you don't know, or just met, to reveal their agenda. 

molander facilitative question example
facilitative question example

Instead, foster discussion on the status quo

Compare the lazy, cheesy "marketing hook" or "pain point" tactic to a question encouraging the buyer to introspect on a more complicated issue.

A problem they need to solve or situation they will soon need to overcome. (change)

Facilitative questions:

  • Are biased to the prospect; thus, are non-manipulative
  • Encourage introspection on status quo decision-making or satisfaction
  • Avoid “hooking” the prospect (helping them sense a pitch is coming)
  • Avoid making prospect vulnerable (via the hook)
  • Create neutral, safe environment for problem-solving dialogue (not solution yet)
  • Help you stand out from 95% of sellers pushing obnoxious, self-serving, seller-biased emails


"Do you have a way to understand when to negotiate your benefits brokerage fees?"


"How would you know when it's time to negotiate fees? What's your process?"

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. 

Marketing and cold email messages are not the same

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.

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

In 1999, I co-founded what became the Google Affiliate Network and Performics Inc. where I helped secure 2 rounds of funding and built the sales team. I've been selling for over 2 decades.

After this stint, I returned to what was then Molander & Associates Inc. In recent years we re-branded to Communications Edge Inc., a member-driven laboratory of sorts. We study, invent and test better ways to communicate -- specializing in serving sales and marketing professionals.

I'm a coach and creator of the Spark Selling™ communication methodology—a curiosity-driven way to start and advance conversations. When I'm not working you'll find me hiking, fishing, gardening and investing time in my family.

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