Skip to main

5 Killer Questions to Woo Prospective Customers

Authors: Jack Vincent Jack Vincent
Posted Under: Digital Marketing
Listen to this Article
5 Killer Questions to Woo Prospective Customers
Image via

It’s hard to trace a sale back to any single action—your online submission form, your social media activity, a face-to-face meeting, a video conference. Every component of marketing and sales comes together somehow, and then we convert prospects into happy customers.

How do you pull ideal customers or qualified leads into your marketing and sales funnel? Create intrigue, then ask killer questions. And to do both of these things, I recommend the following:

Keep It Simple in Marketing, Go Deeper in Sales

Most psychologists believe that attraction and curiosity are emotions. They are spontaneous. Humans are not aware of that spark, that moment when our jaws drop open and we lean forward with interest.

Emotions are only sparked with simplicity. Something strikes us in the heart, even more than the head, and we become curious… desirous.

Bang! The hook has been set. Your prospective customer is convinced, at least initially, and wants to learn more.

Keep it simple in marketing. Go deeper in sales. —@jackvincent (Tweet This)

But to Convert

…we usually have to then address other issues. By nature, most sales become more complex in the middle and latter stages, so one simple message does not a deal maketh.

Probably the most underrated trust-builder in life and the most persuasive skill in sales is listening, especially in the middle stages. The most persuasive way to listen is to ask killer questions!

You must be prepared to open a first engagement with a prospective customer. You shouldn’t, however, open with the purpose of presenting more material, but to confirm in the prospect’s mind that her time is well-spent by having a helpful conversation with you.

The purpose of opening a first meeting, therefore, is to earn the right to ask questions.

I’ve developed a five-step questioning model for asking the right questions at the right time and for pulling the buyer through their purchase.

S.C.O.R.E© Conversion Questioning


The answers to SCOPE Questions are fact-based, and are easy for the customer:

How many people did your last campaign bring into your funnel?or How long have you been using social media?

The benefit of SCOPE Questions is that they get the conversation going. The danger is that they can alienate the buyer.

Did we bring this guy in for a Harvard education?

Use SCOPE Questions economically. Plan them judiciously.


With CHALLENGE Questions, you’re not challenging the customer, but you’re asking them about their challenges… in areas where you can add value, of course.

CHALLENGES can be problems that need to be solved. They can be opportunities that should be exploited, but exploiting them effectively could be the customer’s challenges:

What keeps you and the CEO up at night?or Are your channel partners concerned about this? Why?

CHALLENGE Questions are the raw materials from which sales are made. They uncover the diamond in the rough. Spend time here. Actively listen and go deeper. Resist the temptation to offer a solution the moment you hear the Challenge. Show the love, and go deeper.


There’s a lot of talk about “buyer pain.” But customers may not take immediate action if the pain grows a little every day. It doesn’t feel acute.

OUTCOME Questions, therefore, are not focused on the OUTCOMES customers want to achieve—that comes next! Instead, they focus on the outcomes of the customer doing it wrong or of not addressing this issue:

Where will you be a year from now if you do nothing?

This makes buyer pain more acute, which often prompts them to take action. Timing is important, here, so use an OUTCOME Question only after you’ve really listened and understood their Challenges, and only ask this OUTCOME-type Question once or twice, and then…


With RETURN Questions, you focus the customer on the positive Returns of working with you, or perhaps going to the next step.

Essentially, by answering this, the buyer will present you with your value proposition, which you can use in your proposal.

How would it help if we?or How about if we prepare (this and that), and then we re-group next Tuesday to see how to move forward?

You know your business. You know your value-add for your ideal customers, so you can fill in the rest of the RETURN Questions above.


This is essentially the “close” question. Closing should feel as natural to you as it as it does to the buyer. It should never feel like pressure, because that is the ultimate trust-killer. Again, timing is important. With EXECUTION Questions, you’re simply asking the customer how they’d like to move forward:

It seems like weve covered everything, Theresa. How would you like to proceed?

Customers want to feel in control, too. The EXECUTION Question leaves them in control, but prompts them to move forward. The customer may say:

“Let’s do this. How do you normally proceed from here?”

Great! (Be ready to answer that!) If they’re not ready to move forward, they’ll tell you why, and you can move into handling objections (subject for another post). But often, objections are usually great buyer signals. They just need to see a bit more light and feel a bit more love!

The beauty of questions is that the answers come out of the customer’s mouth. They will believe them! You telling them is simply less persuasive… and it’s pushy.

Pull your customers through the middle and latter stages of their purchasing cycle.

Pull them into your funnel with simple, compelling messages. Then go deeper in sales with killer questions.

What killer questions did you wish you asked your last customer? What type of questions have you found work best on your social properties vs. in person?

Article Banner Image

Get our best tips. Join the smartest marketers who receive our twice monthly update.

B2B Marketing Just Got Easier.

Everything you need for your B2B Content, Influencer Marketing, and Lead-Generating Research Strategies.

b2b influencer

Ready to Get Started?

I am looking for...