Learning how to ask better questions is like unlocking a superpower.
The skill takes time to build, but when you get the hang of it, you’ll be able to build stronger relationships, understand the people and world around you better, and advance your life goals with greater depth and satisfaction.
When it comes to schooling and career, the right questions can take you places. This is particularly true for folks working in sales, who rely on strategic questions from the first conversation to the close of the deal.
Many people don’t think about the questions they are asking others—or worse, they don’t ask any questions at all. This article will teach you how to ask better questions, whether you’re working in sales or just looking to improve your conversation skills.
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Curiosity is the key to asking better questions
When it comes to asking good questions, there is no trait you need more than curiosity. Even if you are using questions to drive your own agenda (like making a sale, for example), you still need your genuine curiosity behind your line of questioning.
When you want to know the answer, it shows. You listen more closely, and your next question builds on what the person just told you.
People can also tell when you’re asking a question to fill a silence or steer them somewhere. Your follow-ups get generic, and the other person starts giving you shorter answers.
The good news is that curiosity can be built like any other skill. If you want to ask better questions, start by getting curious about the people around you.
Everyone you meet knows something you don’t and has lived through things you haven’t. Try to learn one new thing about someone this week, like a coworker or the barista you see every morning.
Pay attention to what lights people up. When someone starts talking faster or leans in, you’ve found something they care about, and that’s the thread to follow.
How curiosity relates to sales
In sales, it’s easy to treat questions like a checklist you run through to qualify a lead. Prospects pick up on that quickly, and it makes them put up their guard.
When you’re curious about the person on the other end of the call, you learn things a script won’t surface, like what’s frustrating them and what they’ve already tried. That information helps you position your product as a solution to their actual problem.
Curiosity also builds trust, which makes the close easier when you get there.
Get comfortable with silence
Curiosity helps you discover the right questions to ask, but silence makes space for the right answers.
It’s normal to feel uncomfortable when there are pauses in a conversation—many people rush to fill the silence with more questions or their own statements.
Resist this urge, and instead, allow a few seconds of silence to pass after you’ve asked a good question. When you do this, one of two things will happen:
- You’ll give your conversation partner ample time to think of a thoughtful answer.
- Your conversation partner will sense the awkwardness and rush to fill it themselves—often giving a more honest, thoughtful, or surprising answer.
Either way, a moment or two of silence is worth the awkwardness for the results you’ll get.
How silence relates to sales
Silence can be hard to sit through on a sales call, especially when a prospect goes quiet after you’ve asked something important.
When a prospect pauses after a discovery question, they’re often deciding how much to tell you. If you jump in to rephrase the question or suggest an answer, you lose whatever they were about to say.
Silence matters even more once you’ve shared your price or asked for the sale. Newer reps tend to fill that pause by offering a discount or backpedaling, which signals they don’t fully believe in their offer.
Say what you need to say, then let the prospect respond first. Their answer will tell you whether they’re ready to move forward or have an objection you still need to address.
What are open-ended questions and why are they important?
Open-ended questions give the respondent opportunities to interpret the question in multiple ways and provide a more in-depth answer.
Closed questions do just the opposite—they limit the depth and diversity of the possible response, often to a simple yes or no.
Sometimes, the difference between a closed and open-ended question is subtle. Imagine you’re at a networking event, and you meet someone new. Making small talk, you ask them, “Is this your first time at this event?”
That question seems simple enough, but it doesn’t offer much in the way of response. They are limited, more or less, to saying “Yes, it’s my first time,” or “No, I’ve been here before.”
Now, imagine you asked them: “What do you like about these kinds of events?” This question is in the same vein as the first one, but the person you’re speaking with can respond with a whole range of answers, ones that will likely help the conversation keep moving.
Note that sometimes, a question can be too open—overly broad questions like “Tell me about yourself” can be difficult to answer thoughtfully.
You want your open-ended questions to strike a balance, giving people a place to start without closing off their answer.
Open-ended questions examples
Most closed questions can be opened up with a small change in wording. Starting with “what” or “how” instead of “do” or “is” usually does the trick.
Here are a few closed questions and how to open them up:
Closed: “Do you like your job?”
Open: “What do you like most about your job?”
Closed: “Did you have a good weekend?”
Open: “What was the best part of your weekend?”
Closed: “Are you excited about graduating?”
Open: “How are you feeling about graduating?”
Closed: “Was the class hard?”
Open: “What was the class like?”
Closed: “Did you grow up around here?”
Open: “What was it like growing up where you did?”
Closed: “Do you have plans this summer?”
Open: “What are you hoping to do this summer?”
Examples of open-ended questions in sales
In sales, closed questions can end a conversation before it gets going. If a prospect can answer with a quick “no,” they often will.
Open-ended questions get prospects talking about their problems in their own words. That tells you what they need and how to position what you’re selling.
Closed: “Are you happy with your current provider?”
Open: “What would you change about your current setup?”
Closed: “Is this a priority for you right now?”
Open: “Where does this fall on your list of priorities this quarter?”
Closed: “Is budget a concern?”
Open: “How does your team usually make budget decisions?”
Closed: “Are you the decision-maker?”
Open: “Who else will be involved in making this decision?”
Closed: “Would this be helpful for your team?”
Open: “How do you see your team using something like this?”
Closed: “Do you have any questions?”
Open: “What would you need to see to feel confident moving forward?”
Closed questions still have a place in sales. Once you understand what a prospect needs, a direct yes-or-no question can confirm details and move the deal toward a close. But during the earlier stages of the sales process, open-ended questions are one of the best sales techniques you can master.
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The art of the follow-up question
A good open-ended question can ignite a conversation, but it can’t keep it flowing on its own. Eventually, the person will finish answering the question you asked, and to keep the momentum, you’ll want a follow-up question ready to go.
The best follow-up questions come from the answer you just heard. This is where active listening skills come in handy, because if you’re paying close attention, you’ll likely pick up on a detail the person mentions in passing, which you can then use as fodder for a follow-up question.
Going back to the networking event, say you ask what they like about these kinds of events. They tell you they enjoy meeting people outside their field, and that last year they met someone who got them volunteering at a local nonprofit.
That answer gives you plenty to work with. You could ask what kind of work they did at the nonprofit, or what made them want to get involved in the first place.
Either follow-up shows you were listening, and it gives them a reason to keep talking about something they care about.
When you get stuck, a simple prompt like “What happened next?” or “How did that go?” can keep the conversation moving while you find another thread to pull.
Common mistakes when asking questions
Open-ended questions and good follow-ups will help you keep conversation flowing. But even when you know the basics of questioning, there are still pitfalls to watch out for.
Here are a few good rules to keep in mind, whether it’s an everyday conversation, a first date, a networking event, or a sales call.
Keep the conversation balanced
Asking better questions is an important skill, but too much questioning in a conversation can start to feel like an interrogation.
A good conversation is balanced—you’ll ask questions, listen to answers, and share your own thoughts and reactions. Ideally, your conversation partner will also be skilled at asking good questions, but even if they aren’t, you should still try to break up the conversation with your own responses.
Avoid leading questions
A leading question nudges the other person toward the answer you want to hear. “Don’t you think that movie was overrated?” makes it awkward for someone to admit they loved it.
People can usually tell when they’re being steered, and it makes them less likely to give you an honest answer. Ask “What did you think of the movie?” and let them form their own opinion.
Ask one question at a time
When you’re nervous or excited, it’s easy to fire off a few questions in a row. “Where did you grow up, and what brought you to the city?” sounds natural in the moment, but it puts a lot on the other person.
Most people will answer whichever question they remember, usually the last one, and the other gets lost. Ask one question, let them answer fully, and come back to the second one if it still fits.
Be careful with “why” questions
“Why” questions can come across as a challenge, even when you mean well. “Why did you choose that major?” can sound like you’re questioning someone’s judgment.
Rewording with “what” or “how” gets you the same information with less pressure. “What drew you to that major?” gives them room to tell you the story behind their choice, without sounding accusatory.
Make sure you want to hear the answer
Some people use questions as a setup to talk about themselves. They ask about your weekend so they can tell you about theirs.
People notice when a question is really a lead-in, and it makes them less likely to open up. Sharing your own story is part of a balanced conversation, but give their answer some room first.
Better questions come from curiosity and close listening, and both get easier the more you practice. Try a few of these tips in your next conversation, whether it’s with a friend or a prospect, and notice how much more people open up.
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Want to practice asking better questions in a professional setting? Vector sales reps learn presentation skills, how to respond to objections, how to actively listen, and how to ask the right questions. Request an interview today.
