6 Unexpected Questions That Reveal What Your Prospect Is Really Thinking

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Aja Frost
Aja Frost




“What’s keeping you up at night?”

“How important is X to you?”

“What do you know about our company?”

Most prospects get the same questions from salespeople over and over again.

Using any of these cliché, routine questions harms your credibility. Rather than seeing you as a trusted advisor, the buyer associates you with all the other reps they’ve ever spoken to. It’s usually not a positive association.

In addition, your prospect will go on autopilot and recite the same answer they’ve given on previous sales calls. You’ll lose the chance to get information your competition doesn’t have; furthermore, it’ll be hard to re-engage them in the conversation.

To maintain authority, keep the buyer’s attention, and find out what they’re really thinking, ask questions they’re not expecting. These six inquiries will come in handy throughout the sales process.

1) “It’s [date two months from now]. You haven’t purchased [product]. Why not?”

This question dives directly into your prospect’s concerns and surfaces potential internal obstacles.

It’s a version of the traditional question, “What would stop you from buying [product]?” But because your prospect hasn’t heard the question in this form before, they’re likelier to share their honest, unfiltered thoughts with you.

Giving a specific date is effective as well. The buyer immediately pictures themselves on that day in the future -- giving you a good segue into the risks of doing nothing.

2) “What’s your objective for this [conversation, meeting]?”

The buyer usually has different expectations for the discussion than you. Maybe you’re hoping to learn more about their situation, demonstrate your product’s value, or get their support as an internal champion.

However, your prospect might be interested in getting advice or insights, learning more about the product category, seeing how knowledgeable you are about the product and the space, or figuring out how much your solution costs compared to their current provider.

Once you’ve gotten their goal onto the table, you can do two things.

First, you can actually fulfill that goal. If the buyer wants to know your price, give it to them. You don’t want to drag out a sales conversation with someone who can’t afford the solution.

Second, you can create an upfront contract. Let’s say your prospect wants to get your suggestions on building a referral program. Before you delve in, say, “Do I have your commitment that we’ll schedule another call if you’re satisfied with the tips I give you today?”

At the end of the call, ask if they’re satisfied. If they say yes, you’ll have already secured a follow-up conversation.

3) “What do you need to accomplish to [get a promotion, receive X award, secure funding for Y, get Z campaign off the ground]?”

Tying the solution to the buyer’s personal career goals can accelerate the deal. After all, if they see a clear connection between buying your product and moving forward professionally, they’ll be eager to sign.

Before you can draw that link, however, you need to know more about their objectives. Use this question to figure out the milestones or steps they need to hit.

4) “Why?”

Most salespeople respond to objections by telling the buyer why that concern is invalid. However, this approach can backfire. Prospects often end up more convinced than ever their worry is legitimate.

Instead of arguing with them, get them to convince themselves. If they say, “That price is too high,” ask, “Why?”

They might respond, “Our most expensive machine to date costs half that,” at which point you can reestablish your product’s relative ROI.

Or perhaps the buyer tells you, “My boss will never approve this purchase.” It’s tempting to immediately offer case studies and compelling arguments your prospect can use to persuade their boss. Simply saying “Why?”, however, is usually more effective.

The prospect might give you an answer you hadn’t anticipated, such as, “She bought a similar solution at her former company and hated it,” or “She’s trying to redirect our budget toward X objective.”

Once you have the details, you can help the buyer overcome the internal obstacle -- or alternatively, decide they’re not a good fit.

5) “Can you [help me understand something, give me a little more context]? You’ve said [solving X, doing Y, pursuing Z] is a major priority for you. Why haven’t you already [taken action, addressed this issue]?”

Pursuing deals when you can’t answer “Why now?” is dangerous. Your prospect might sound committed to overcoming an obstacle or capitalizing on an opportunity, but something has been stopping them from doing so. You need to know why they’ve finally decided to act. Maybe they’re not truly invested, in which case it’s a waste of time and energy to continue humoring them.

This question lets you dig into their timeframe and desire to change without being overly aggressive. Most buyers won’t anticipate such a direct approach, so they tend to give you a genuine reply.

6) “What’s your best alternative?”

If the buyer is seriously considering your offering, she’s also looking at other options: Other vendors, the choice to build an in-house solution, or even the decision to do nothing.

Rather than pretending these alternatives don’t exist, bring them out into the open. You’ll have a much better sense of how to position your product. For instance, if your prospect is reviewing two other companies in your space, you can highlight your solution’s unique strengths. If, on the other hand, her top alternative is building an internal version, you might bring up the opportunity cost of waiting for a development team versus installing the product immediately.

You need to establish trust before you ask this, or it may make your prospects bristle.

These questions are designed to catch prospects off-guard -- not enough to harm the relationship, just enough to provoke an authentic response. Your conversations will become more valuable and memorable as a result.

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