Flip your prospect's questions to close more deals

Flip your prospect's questions to close more deals

In my recent post on how to ask powerful sales questions, I talked about the importance of listening and asking questions.

But there's another way to utilize questions to close more deals: flip them.

Here's how flipping questions works:

When your prospect asks you a question, you flip it back on them. You ask them the same question they just asked you

Answering a question with a counter-question can come across as a bit confrontational. You can soften it with a buffer phrase like: "That's an excellent question, and before I go ahead, allow me to ask you..."

Then ask them one of these questions:

  • In an ideal world, what would be the answer? What would you want me to say?
  • What would you want the answer to be?
  • What would be the ideal answer?
  • Why is this important to you?
  • How does this play into the larger context?
  • What's your workflow like?
  • Why do you want it to be that way?
  • What are you looking for?

Flipping questions helps you uncover deeper wants and needs of the prospect.

Find out why they ask that question, why they are curious about this, why they care. You'll better understand how your solution can be a good fit for them. Or how it isn't a good fit, in which case you can save yourself and your prospect the time to keep this sales conversation going for much longer.

Scenario 1: Answering questions bluntly

Prospect: "Does your product have feature X Y Z?"

Sales rep: "Yes, we do indeed!" or "No, we don't!"

You might think that "No, we don't" is a bad answer - but both of these answers are bad! Superficial responses like these don't lead to great sales conversations. You won't be able to advise your prospect in the best way possible and uncover ideal opportunities.

Instead, you dig deeper. (If you're a regular reader of my blog, you've already read this a thousand times. I keep saying it because people keep missing out on it).

Scenario 2: Flipping questions & digging deep

Let's use a specific example here for the sake of clarity. You can apply this to whatever product or service you're selling. Since we're selling sales software, let's use that as an example.

Prospective customers often ask us about reminders or tasks. These are often customers that have previously used certain CRMs (which shall remain unnamed!). As they've increased their lead flow, they're sinking deeper and deeper into CRM hell. (CRM hell is that painful place where you spend more and more time managing your CRM, and less time doing actual work).

Prospect: "So, does your product have reminders or tasks?"

Sales rep: "I'm glad you asked that question! Now before I answer it, let me ask you, in an ideal world, what would the answer be? How should reminders or tasks work?"

Prospect: "Well, we need a reminder to when someone doesn't respond to our email."

Sales rep: "I see. Why is this important to you? What's your workflow like?"

Prospect: "We send cold emails to product managers. When they respond, we then send them another email to set up an appointment, and sometimes they go silent at that point. So we would like to add a reminder to get back in touch with them if they don't reply at that point."

Sales rep: "Ah, I see. So there's two ways to answer that question. First, yes, you absolutely can add a reminder in Close to any lead. In our app, we call them tasks, this is what it looks like."

Sales rep: "You can also connect tasks with your calendar, Google, Apple Outlook, whatever you use. And you'll get reminders."

Prospect: "Aha, good."

Sales rep: "Now that was the first part of the answer. But here's the part you will really love. We've got something much better than tasks and reminders for a case like yours. You see, you can automatically generate a list of all leads who have responded to your initial cold email, but then went silent. So normally after how many days of silence would you follow up?"

Prospect: "After 7 days."

Sales rep: "Are you using a cold email template, or do you write each cold email from scratch for each lead?"

Prospect: "We use a prospecting template."

Sales rep: "Ok, now look at this. In Close, you won't ever need to add a reminder manually for a thing like that. Instead, you just use our search function to show you all leads that a) have received your prospecting template, b) have sent you at least one email, and c) where the last email interaction that took place was an email that you sent them more than seven days ago."

"Close automatically logs all your email activity associated with your sales leads. Within less than 30 seconds, you have a list of all the leads you need to follow up on. Let me show you."

How to manage your pipeline in our sales crm software by creating a custom lead list

Prospect: "Wow, nice!" (The more tailored to their specific workflow we make this, the more impressed they are).

Sales rep: "Even better, you can just save this as a SmartView, so you can access it with just one mouse click or share it with your team."

If a prospect has previously managed their sales pipeline through manual reminders and tasks, and we show them this, it's always a big aha moment. It will save them plenty of time wasted on a pretty dull repetitive task. And the data in their CRM is a lot more accurate because we've eliminated that room for human error, so leads just don't slip through the cracks anymore.

Now, if our sales rep wouldn't have flipped the question or dug deeper, he could have just said: "Yes, we have tasks and reminders."

This opportunity to educate the customer that there's a much better way to do it, a possibility to improve their workflow would have been completely missed.

You've probably heard that the best sales people are like trusted advisors. That's great right? Every sales rep and their mother nowadays will tell you: "If you decide to do business with us, we won't think of you as a customer. We will think of you as a partner.

And when you hear it, that little bullshit alarm in your head starts to go off.

But by flipping questions and digging deeper, you actually can turn yourself into a partner, a trusted advisor, a professional who creates value for the prospect. You help them to discover opportunities for optimizing their business, overcoming obstacles, achieving objectives more efficiently. That's the kind of sales person businesses want to deal with.

This is harder than it sounds. So practice!


When asked a question, we instinctively feel propelled to answer. When I was a small boy, I got taught that when someone asks me a question, I need to answer it. My guess is, you were too.

When your parents asked you a question, you were supposed to answer, right?

Later in school, when your teacher asked you a question, you had to answer it. It's one of these basic things we all learn as we grow up.

So to answer a question with a counter-question goes against that conditioning, and you might have to remind yourself to flip their questions.

Don't overdo this

Use this technique carefully. If you overdo it and just flip every question a prospect asks you, it'll just become irritating.

Sometimes the best way to answer a question is to do so in a straightforward, direct manner.

Sometimes the best way is by asking a follow-up question.

And sometimes the best way is to flip the question back on them.

So when should you flip questions? Gut instinct, a bit of practice and common sense are good enough guidelines. Think about the direction the conversation is taking if you respond straightforward - and the possibilities that could open up when you flip it.

With a bit of experience, you'll add this to your repertoire of sales skills and use it to close more deals.