Questions are the most important tools in the salesperson’s arsenal. Too many reps dominate the conversation with product pitches, long feature lists, and rambling explanations.

But guess what? Your prospects don’t care! They care about their problems, their businesses, and their lives -- not your product, your company, or your prerogative.

In order to gain the prospect’s trust and earn the right to connect your offering with their problem, you have to first ask about their problem. I sometimes play a game in sales training sessions that I call “Question Marks and Periods.” It’s simple -- two people have a conversation, and the first one to use a statement that ends in a period loses. When you’re speaking in only questions, the conversation gets interesting fast. Try it sometime -- it’s more instructive than you’d think.

Thoughtful, attention-grabbing sales questions get the conversation flowing and deepen the relationship between salesperson and prospect. Here are 22 of my favorite questions to pose in a sales call, along with explanations of when to use them.

Getting to Know You Questions

1) How did we get together?

This question will uncover any trigger events or referrals that might have led the prospect to you. Listen carefully for the pain the prospect is feeling -- whether they’re aware of what’s causing it, or not.

2) How did you get in this business?

Ask this question to start building rapport with your prospect, and get a sense of their background, career, and personal goals.

3) How did this happen?

Does the prospect know what led to their problem? Ask for their explanation and thoughts before you leap to diagnosis.

Questions to Fully Understand the Problem

4) Are you holding back?

Sometimes prospects have been telling themselves “it’s not so bad” for so long that they don’t fully realize or want to admit to the havoc the problem is wreaking on their business. Pull out anything they might be holding back with this question.

5) How long can you stay in business if it stays this way?

Help them truly get a handle on the ramifications of the situation.

6) Can you repeat that?

Pose this question to help the person listen to their responses from your point of view.

7) Has it always been this way?

Get the prospect to reflect on how things used to be before this problem cropped up. This might change their attitude toward their current situation.

8) Zero to death, where is it?

Get a sense of how important solving this problem is to the prospect.

9) Why isn’t there a line of people waiting to buy at your front door?

Deploy this question after giving the prospect a (genuine) compliment. The compliment helps them to drop their guard and the question will make them scratch their head and share their problems with you. This query is especially helpful if you’re selling to agencies.

Questions to Keep the Conversation on Track

10) How am I supposed to react to that?

Sometimes prospects play games. Don't answer. Don't answer seriously. Don't answer fully. Draw on your experience from the “Questions and Periods” game and keep turning their questions back on them with more questions.

11) Is this fun for you?

For a prospect who’s giving you a particularly hard time. This question can lighten the mood and possibly get the prospect to drop their guard.

12) How would you answer that question?

This is a fail-safe question I use when I don’t want to answer the prospect’s question. Ask them how they’d respond, and then play off their answer.

13) May I ask you a question?

When a prospect asks about price or another feature of your offering directly, they expect an answer. But the salesperson might not be able to give an accurate response due to inadequate discovery at this point in the conversation.

Instead of ignoring the question and angering the buyer, simply ask, “May I ask a question?” Then continue on with discovery questions, and offer an answer when you have enough information.

14) Usually by now, I start feeling synergy, but I'm not. Would you mind if we stopped?

If the prospect is giving you the runaround, ask this question to determine if they truly want to work with you. If not, end the call, and devote your energy to a more serious opportunity.

Questions to Understand the Decision Process

15) Am I the first person you’ve told about this?

If the answer is yes, follow up with the question “Who else is going to care, and why?” The prospect will then reveal the other decision makers as well as each of their individual motives.

16) How will you decide if we work together?

It never ceases to amaze me how few sales reps ask this question. Is the prospect looking for the cheapest option or the best value? Does the length of time your company has been in business matter, or is it irrelevant? Who needs to approve the decision? You won’t know the answers to any of these important queries unless you ask this simple question.

17) Who’s your favorite salesperson? Your favorite supplier?

Not only does this give you a feel of who the prospect likes to buy from and why, it also sets the stage to ask about the possibility of a referral.

Questions that Challenge the Prospect

18) Does anybody ever say “no” to you?

Some executives aren’t used to being opposed, but a yesman salesperson isn’t going to be able to solve the problem. To truly get to the heart of the issue and remedy it, the rep needs to ask tough questions and earn the respect of the prospect. This question sets the tone that you aren’t afraid to confront or oppose the prospect.

19) Did I just cross a line?

In some cases, you’ll ask a question, and the prospect will fall silent. By following up with, “Uh oh. Did I just cross a line?” you’ll salvage the relationship while establishing that you’re not afraid to ask tough questions.

20) Please don’t be upset, but what if we do all this digging, and we find out you’re the problem?

If they can’t admit there’s even a remote chance that they might be the problem, chances are you’re not going to be able to affect the changes you need to affect.

21) What if it was free?

Use this question to navigate around price objections, and establish the amount of value the prospect sees in your product.

22) I've been asking questions trying to find something to talk about, but haven't found anything. Can I assume that life is perfect?

Get a reticent prospect to cop to their issues.

The Role of Questions in Role Plays

Sales managers: pick a question and ask your salespeople for examples of when it could be used, with whom, and under what circumstances. This is one of the most effective team coaching strategies I’ve discovered over the years. 

Remember that it’s okay to be creative in role plays. It helps when prospects decide that they want to get “creative."

Carole Mahoney and I conduct several group coaching sessions with their clients every week. If you'd like to be invited to one, send me an email

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Originally published Apr 29, 2015 7:00:00 AM, updated October 30 2019


Sales Qualification