Why questions often backfire
(and how to fix them)
You are under pressure to start discussions -- during difficult times -- AT SCALE.
Me too.
Questions are often used to start, re-start and advance conversations with:
- Inbound leads from trials, webinars, downloads (demand generation)
- Outbound prospecting efforts (call, voicemail and email scripts)
- Customers who are actively considering engaging / investing with you
In the email & voicemail contexts, prospects hit delete faster than ever. They're ruthlessly clearing inboxes from mobile devices.
Questions—at any point in the message—are often used.
But biased questions can be a kiss-of-death to an otherwise strong email or voicemail.
Pain points & hooks
Beware of pushing pain points, trying to get customers to qualify immediately and set a meeting. You need to get into the conversation first.
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 them as relevant. They see it as bait for a hook they aren't biting! Especially during uncertain times.
Questions are often lazy. They can make 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 messages 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.
In cold emails I 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.
Delete!
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.
Instead, un-biased, neutral questions can work. I'll give an example shortly.
2 types of questions
Ever ask a question you're not able to answer?
There are two flavors of questions often appearing in email messages, calls or customer meetings. Those helping a buyer think ...
- I gotta get out of here ... or ...
- hmmm...
It's the "hmm" we're after.
These are un-biased questions—designed to help prospects reflect on their situation, status quo. (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 push a pain. This is why they stand out (earn attention) and provoke replies.
Provoke introspection
The best way to use questions is to encourage the reader to introspect... to self-evaluate their situation at this moment in time.
Example: Ask your prospect a question they are most likely NOT asking themselves—but should be!
This can stop people cold.
What comes back at you (from prospects) often looks like this:
"Good question. I never heard anyone put it that way before."
or
"hmmm... I'm aware this situation could hurt me (personally or 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 making that decision?"
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.
Asking questions which you cannot answer is often the key to provoking conversations. Different from conventional questions, facilitative questions help customers to reflect on their difficult situation.
That's why the ask-er (you) often cannot know the answer. That's why they get noticed and provoke conversations.
Bottom line: Beware of 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 in the upcoming workshop. I'll provide more examples and get more specific.
Otherwise, here's a quick example.
Avoid this kind of 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 dead.
If your question feels like you're leading them to a conclusion you want—boom. Delete.
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 provoke thought and trigger response.
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.
Thanks,
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?
Instead, ask this way
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 a question that helps me realize, "hey, dummy, you don't have a way of knowing when that time will be!"
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? Join us online and I'll provide examples and get more specific.
Otherwise, here's a quick example.
It's not your fault
Sales copywriting 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. Hooks.
When we get stuck ("what should I write? how can I press a pain point to grab their attention?") we turn to marketing concepts.
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 when cold prospecting this kind of messaging fails. Instead, we need messages that earn—and 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.
Ready to provoke response with better questions? Join a small group of us in the upcoming workshop. I'll provide more examples and get specific.
With your success in mind,

