14 Questions That Will Convince Prospects to Change From the Status Quo

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Leslie Ye
Leslie Ye





Whether you’re working a competitive deal where your prospect is considering four other vendors or you are the only provider in the picture, your biggest enemy in the sales process is the same: The status quo.

Cognitive biases and fear of failure can significantly delay purchase processes. We’re psychologically uncomfortable with uncertainty, and investing in an expensive product that doesn’t work out isn’t a decision that can be easily reversed -- it has real implications for your prospects’ jobs and promotions.

That’s why creating urgency is an essential part of the sales process. But moving prospects to buy can’t involve tactics that manufacture fear or pressure prospects to act before fit or benefits have been established. The 14 questions below help prospects see they need a change without veering into aggressive, old-school tactics.

14 Questions That’ll Move Prospects to Abandon the Status Quo and Buy

1) What is your process for [business area] right now?

This question sets the stage for the following 13. Before you can convince your prospect to shake things up, you have to understand what they're doing right now. Get them talking about everything they’re doing now to support a goal or business driver, or else you won’t have a strong foundation to build a compelling argument for change upon.

2) What kind of results are you trying to achieve with this process?

Asking about results right after will keep them top-of-mind for your prospect. The most sophisticated-sounding process in the world is useless if it’s not getting prospects the results they need. Your sales conversations should keep your buyers’ processes tied closely to their goals so you’re keeping them focused on their process’ impact rather than specific tools or practices.

3) Why are these results important?

This question knocks down what you’ve set up with the previous two. It’s not enough to understand what the goals are. To create a true sense of urgency, you need to understand how these goals fit into your prospect’s larger business context.

Will failure in this area cause layoffs? Or is it simply an experiment with no larger implications? These two diametrically opposed endpoints could easily be serviced by the same process and goals, so dig deep to make sure you have the full picture.

4) How is it going?

Ask this question and hit the mute button. You’ve just had your prospect tell you what they’re doing and why -- now have them explain what’s not working. Presumably, they wouldn’t be spending time with you if everything was perfect (see #6), so be direct and find out what’s wrong.

Don’t cut in until your prospect is done -- not only will this approach ensure you get all the essential information, it also allows your prospect to talk through every aspect of the problem, which will amplify their pain in their own mind.

5) Is there anything about your current process that you wish was easier?

Of course, fear by itself isn’t useful. Pair it with hope -- in your prospect’s ideal world, how would this process work? What do they want automated or taken off their plate? With this answer, you’ll start seeing where your product fits into their world and the specific benefits you can call out.

6) Why did you take this call today?

You won’t always encounter prospects who are willing to open up and share their fears, hopes, and dreams with you. So if they’re waffling or ducking your question, just pose it to them this way. They’ve taken time out of their day to speak with a stranger about spending their own money on something -- why?

7) What’s the implication to the business if you don’t meet your goals?

This is another way to ask #3. The more precise wording can help focus prospects who are unsure how to answer. It’ll also give you a read on whether your prospect is the right point of contact -- someone who has no idea what the larger implications of success or failure probably won’t have the influence or authority to sign off on a purchase.

8) What will happen to you personally if you don’t meet your goals?

It’s not always smart to get personal in sales, but this question is a perfect way to do so. After you’ve zoomed out and learned about how your prospect fits into the whole business, zoom back in and focus only on their world. Are they up for a promotion? A bonus? Is this project their first major initiative in a new role, or a last-ditch attempt to turn things around?

Although every employer would love if employee decisions were made 100% rationally, this just isn’t the case -- emotion influences every choice we make. So get personal and figure out exactly what your prospect stands to gain (or lose) from this situation.

9) Why wouldn’t you buy?

This might seem counterintuitive. Don’t you want your prospect to focus on why they would buy, not why they wouldn’t?

Yes and no. But hiding from objections and pretending they don’t exist won’t do you any favors. Instead, get them out in the open so you can assess whether your buyers have real doubts or just need more answers. What is your prospect worried about? Are there any particular challenges they don’t believe your product will solve?

Asking this question early also surfaces potential blockers to the deal. If your product requires two full-time employees to ensure a successful implementation and your buyer is a team of one, it’s best to learn this as early as possible so you’re not wasting time on a bad fit.

10) Take me through your day.

Understanding your prospect means understanding everything they do. Presumably, they’re not just working on one project at once. And although your product might only be able to help with one part of it, understanding everything that’s on their plate will help you best position your product by showing them where they san save time or effort.

11) What is the hardest part of your day?

There are two potential answers here: It’s a process related to your product, or it’s a process that’s not. Either way, you’ve got options. If their biggest hairball can be cleared away with your product, go in for the kill. If it’s something else, figure out how your product can free up more time to work on their most pressing priority.

12) What is the most important thing on your plate right now?

It might be the business area you serve, or it might not. But you have to ask this question to assess where your product falls in the hierarchy of other things your buyer is working on.

13) Where is your process lacking right now?

Before you start making any recommendations, have your prospect self-identify what they wish was more effective. Having them kick off this part of the conversation not only demonstrates what’s most important to them, it eliminates the need for you to guess what’s hard or try to get the buyer to see your point of view -- they’ll just tell you what matters.

14) If those parts of the process were fixed, how would that affect your day?

Ask this as a follow-up to #13. As in question #5, you’re juxtaposing a negative emotion (fear, stress, frustration) with a positive one -- hope. Once you understand what your prospect’s “better tomorrow” looks like, you can figure out whether your product will actually get them there, or whether you need to try a different tack.

It’s always easier to get someone to do what you want if you’re able have them reach the conclusion they need to take action on their own. These 14 questions are designed to do just that. By teasing out the nuances of your prospect’s situation and having them self-identify what they’re looking for in a solution, you’ll convince them to change from the status quo without ever having to employ dirty tricks.

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