May 19, 2021

How to Ask Better Questions

These days, it’s rare to interact someone who knows how to ask better questions. But when you do, you can tell the difference. It’s that experience of feeling truly seen and heard by a person who’s genuinely curious and engaged. They’re able to inquire about things in a way that draws you out and goes deeper than small talk.

Want to know how to ask better questions yourself?

The ability to ask better questions is becoming more and more of a unique superpower. This is especially true for leaders who want to build influence and empower others.

Here are 8 tips for improving your skills of inquiry:

1. First, get present. We all have an active internal monologue – it’s the mind chatter that’s continually running through our heads. It helps us evaluate and navigate our experiences, but our thoughts can also get in the way and pull us out of the present moment. This can be problematic when interacting with others. So what can you do? Practice working the “muscle” of catching where your attention is focused. You can get better at shifting your attention from the internal monologue to the external dialogue happening right in front of you. This is a foundational prerequisite for how to ask better questions.

2. Listen actively. Once your attention is directed to the present moment, you can activate listening skills that’ll inform and strengthen question-asking. What does active listening mean? It’s listening fully, at multiple levels, to catch all of the following: the actual words being said, their context and meaning, and even the tone and emotions underneath the words. In practice, it involves using responsive and focused body language such as head nods, eye contact, and facing the other person. Verbally, it might include some simple “uh huh” or “yeah” type responses, in addition to the skill of repeating back what you just heard as a way to confirm understanding.

3. Be really curious. This seems basic, right? You’re probably thinking “I’m already a pretty curious person.” But I’m challenging you to go even deeper by…ready for it?…mimicking the curiosity of a small child. That might sound a little odd, but think about it – Children are completely open and fascinated by what’s around them. They’re a blank slate, an empty cup. No assumptions, judgements, or “I already know that.” Tap into this type of curiosity and more powerful questions will start to come naturally.

4. Make them open-ended. If you only implement one of these strategies for how to ask better questions, this would be the one! It’s probably the most impactful. Open-ended questions deepen and extend conversation, while close-ended questions stop conversation. How do you know which type you’re asking? Close-ended questions can be answered with a simple “yes” or “no,” and typically start out with words like “Is there…,” “Do you think…,” and “Did you…”. Open-ended questions, on the other hand, start with words like “how” or “what.” Consider the difference it would make to alter a question like “Did you enjoy your trip?” to “What did you enjoy most about your trip?” How would the answers to those questions differ?

5. Keep them short. This might seem counterintuitive, but many of the most powerful questions are short and simple. They’re like ninja moves—small actions with lots of impact. Some examples include questions like “What else?,” “What are your options?,” “How come?,” and “How would you start?”. What makes these powerful? Their shortness creates maximum openness. And you don’t risk “leading the witness” by baking-in your own assumptions, interpretations, or biases.

6. Use their words, not yours. To take your question-asking to an even higher-level, experiment with this trick — take the exact words or phrases your discussion partner just used and put them into your question. I admit it kinda feels like cheating or taking the easy road, but it actually makes for better questions. For instance, let’s imagine you’re talking with someone at work about a challenge they’re facing and they say “Yeah, it’s just hard to know which thing is the biggest priority!” Using their words, you could simply ask them “How would you know which thing is the biggest priority?” Contrast that to a question like “How would you be able to tell whether one project is more important than the next, or maybe you really can’t tell, I guess, ya know?” This second version introduces words and terms that could actually mean slightly different things, and it also ends up being leading and close-ended.

7. Combine them with an observation. In some cases, proceeding a question with an observation can make the subsequent question more powerful. Observations are brief statements that share what you’ve heard or seen about the other person’s situation. For example, you might say “It sounds like you’re feeling stuck,” and follow that with the question “What do you think is causing that?”. Such an observation can help your conversation partner gain new clarity and awareness about their situation, and naturally sets up the open question to follow.

8. Listen to your intuition. Some of the best questions you can ask don’t come from trying to analyze or problem-solve the other person’s situation. They can come from listening to your gut. Let’s say you have a gut feeling that someone is hesitating to speak up in a challenging situation at work. Instead of just asking “Do you think you can do anything?” you might share your intuition as an observation and combine it with an open question, such as: “I have a sense you want to speak up but aren’t. What do you think is holding you back from saying something?”. But beware that your intuition isn’t always right. You have to be open and unattached enough to let go of what your intuition is telling you if it’s not accurate. But, even if it doesn’t land with the listener, it will likely bring more clarity and awareness to the surface.