How to get more value out of open-ended sales questions

But being a good listener isn’t enough on its own. Salespeople need to know how to get prospects to share valuable thoughts and opinions. And there’s no way to get those insights than with open-ended questions.

Let’s take a look at the advantages of open-ended questions for sales. Then we’ll get into how you can teach your salespeople to ask better questions.

Open-ended questions are a staple in discussions of establishing rapport, developing charisma, and closing deals.

Why? Because they get the prospect thinking.

It’s easy to quickly answer a closed question like “How’s your sales performance this year?” But a prospect will have to spend more time thinking about the open-ended question, “What would you like your sales process to look like in three years?”

The second question takes a lot more thought to answer. Here are some advantages of open-ended questions:

Thoughtful answers give you information that helps your sales pitch.

There’s an important difference between the two questions above. The prospect can answer the first question with “they’re not too bad, but they could be better.”

But the second question gives you deeper insights into what the prospect is looking for. They’ll tell you about their aspirations for their company. That does two things.

First, it gives you a lot more information.

Second, it opens up the prospect’s thinking. Now, instead of thinking about their current sales, they’re thinking about what they’d like to create, because of the sales question. That’s a bigger mental space, full of potential and interesting ideas.

Those ideas and thoughts give your sales rep a lot of information to work with. They can suggest solutions based on goals, address potential issues the client sees, or talk about previous clients who have set out to hit similar targets.

And there’s always a possibility that the answer to an open-ended question will surprise you.

Heading off on tangents can be surprisingly valuable.

You might be surprised by the things you hear when you ask open-ended questions. If something is on your prospect’s mind, it may come out quickly when they get the chance to talk.

It might be a business concern they’ve had on their mind. Or an aggressive goal they’ve been mulling. Those are valuable pieces of information for a salesperson and can be explored through open-ended sales questions.

When a prospect starts going off on a tangent, your first instinct might be to tune out or direct them back to the topic at hand. But great salespeople know how to listen and pick out the most interesting information from a prospect’s answer to a sales question.

We’ll talk more about active listening and useful follow-up questions a bit later. Before that, we need to talk about one of the subtle benefits of asking open-ended questions:

Open-ended questions make people like you.

There’s a lot of disagreement over whether the old sales adage “people buy from people they like” is actually true. But you can bet that the converse is accurate when it comes to open-ended sales questions: if someone doesn’t like you, they won’t buy from you.

Research shows that people who ask more questions—especially more follow-up questions—are more likable.

Even if liking someone isn’t a prerequisite for making a purchase, establishing that connection is a great way to start a sales relationship.

With all these benefits to open-ended questions, you might wonder why you’d ever ask another closed question again.

Open-ended questions are great for getting people to open up. But sometimes that’s not what you want. Sometimes you just need information.

Here are some things you might need to know if you’re selling a piece of software:

• Whether the prospect already has a solution.
• If they’ve talked to your competitors.
• What their budget is for your type of software.
• The size of the company.
• Whether the person you’re talking to is a decision-maker.

You could get those pieces of information with open-ended questions. But you could also waste a lot of time listening to your prospect talk about irrelevant things if you let them.

So when you need specific information, ask a closed question to get it.

Sometimes you’ll find that the answer to that question is worth pursuing, in which case you can follow up with a more open question. We’ll talk about that more later.

Asking open-ended questions is a practiced skill. Some people are naturally charismatic and great at asking questions—but it’s something any salesperson can learn and develop as a habit.

Here are some practical tips on how to encourage your sales team to ask open-ended questions.

Emphasize the value of prospects’ knowledge and feelings.

Asking a question about the state of things won’t get you much information. It’s easy to answer “Does your company struggle with closing deals?” with minimal information.

It’s much harder to answer “What factors are holding your salespeople back from meeting their potential?” with a short sentence.

The first example is a question about the state of things. A company either does or does not struggle closing deals. The second question requires the prospect to draw on what they know about the company and what they feel is holding their salespeople back.

Questions about a prospect’s feelings can be especially useful, as showing an emotional benefit to a product or service is a great way to emphasize its value.

For example, “Tell me about some of the frustrations you face on a daily basis” gets people to open up about what vexes them. And that positions the salesperson to provide a solution.

Master the art of the follow-up question.

Following up the answer to a question with another relevant question is a sure way to build rapport (and it works if you want to build rapport with existing customers too). It’s also a method for digging deeper into an interesting topic.

If salespeople can come up with more specific follow-up questions, great. But sometimes they’ll have a hunch that they’re on the right track, even without knowing exactly what to ask next.

This intuition is valuable, and it should be pursued.

Here are a few ways to follow up on questions that a salesperson thinks might be valuable:

• How do you feel about . . .
• Tell me more about . . .
• What brought you to . . .
• What do you think . . .
• Where do you see . . .

If salespeople can fall back on these types of questions during sales calls, they’ll instantly improve the quality of information they get from prospects.

These questions are great ways to save a conversation from heading down a dead end. If a prospect gives a “yes” or “no” answer, a follow-up question can get them talking again.

Be careful with “why” questions.

You might think that “why” would be a great way to start open-ended questions. And in some cases, you’re right. But it’s important to understand the drawbacks of “why” questions.

Kay White, a career and communications mentor, points out that asking “why” can put people on the defensive. It encourages prospects to answer with “because,” which makes them feel like they’re justifying their decision to you.

Let’s say that your prospect just told you their company is looking to switch from their current CRM provider. You could ask “Why are you looking to switch?” But that might get your prospect thinking defensively.

Instead, ask “What led to the decision to switch?” That encourages your prospect to lay out a sequence of factors that led to their current situation.

It’s subtle, but it can make a difference in the way your prospect feels during your conversation. If they’re feeling defensive, they may be in a negative mindset. And salespeople should avoid that at all costs when coming up with open-ended questions.

Practice active listening to supplement open-ended questions.

When you’re talking to your salespeople about open-ended questions, be sure to include some discussion of other active listening skills.

For example, it’s a good idea to reiterate what your prospect has just said, both to confirm that you heard it correctly and to make your prospect feel validated. If reps can put the statement into their own words, even better.

Listening actively often leads to asking open-ended questions. It gets the salesperson thinking like the customer. And that gets back to the knowledge and feelings we discussed before.

When salespeople are expected to have all the answers and provide a lot of information, it’s easy to forget to listen to what the prospect is saying. But that’s where you get the best information for closing the sale.

Now that you’ve seen the power of open-ended questions, you might be wondering exactly what to ask. To help you out, here’s a list of open-ended questions to get you thinking:

• What inspired you to get in touch with us?
• What are your company’s goals for the next three years?
• What are the biggest challenges in your business right now?
• What do you hope to accomplish with our product/service?
• What are your top business priorities right now?
• How will we measure success on this project?
• How would you like to see this process proceed?
• Who else should I talk to about this issue?

You can also use “tell-me” statements in place of some open-ended questions. For example:

• Tell me about the difficulties your business is facing right now.
• Tell me what worries you about your business.
• Tell me about your professional goals.
• Tell me about the systems we’ll use to measure success.
• Tell me more about that.

There’s an infinite number of ways to get the information you’re looking for. With these examples of open-ended questions, you can create others that fit your sales process.

Talking to your team about open-ended questions is a good place to start. But listening in on actual sales calls is the best way to find out what kinds of questions your reps are asking.

Next time you’re listening to a sales call (or a recording of one), be sure to keep an ear out for open-ended questions. See where your reps are already putting them to good use. Take notes on where they could be doing better.

Encouraging active listening starts with a single conversation. Make a point to schedule at least one listen-in today!