A Beginner’s Guide to Asking Better Questions

September 7, 2018 by
Tetra Prime Consulting, Aaron Garner

“So that office job is really different than your communications work,” said the interviewer as they skimmed my resume, “what was that – did you just like, need a job?”

Ouch. I was 20 minutes into an interview and every question this recruiter had thrown my way was similar to the one above – crass, interrogative, yes/no questions that derailed the conversation before it could get off the ground. As you can expect, we really didn’t get to know one another during our conversation, and I really didn’t have a desire to try. I called in a few days to withdraw my application.

Here’s the thing – I really don’t think this interviewer was an inherently rude or insensitive person. They were the head of their non profit organization, had a track record for organizing great work in their community, and had held their job for a long time.

I think they were just really really bad at asking the right questions, and, unfortunately, that can be just as detrimental to professional relationships as rudeness, insensitivity, and other tasteless qualities.

But asking the right questions isn’t a personality trait – it’s a skill that can be practiced and cultivated just like any other skill, and it’s worth the investment. Knowing how to to ask the right question will dramatically improve your networking abilities, strengthen professional ties, and can positively influence your career overall. We researched the surprising power of a good question and provide a few tips on how to form the right ones for yourself.

The Power of a Good Question

When was the last time someone asked you a really great question? Did it entice your brain cells? Challenge your current position? Invite you to expand on something you care about?

More importantly, how did you feel about the person who asked it? Chances are, you felt pretty good.

The article The Surprising Power of Questions (Harvard Business Review, 2018) references an interesting study conducted by author and assistant professor Alison Wood Brooks. Her research team studied questions in speed dating. Researchers asked some speed daters to ask a lot of questions (at least 9 in 15 minutes), while others were told to ask very few (no more than 4 in 15 minutes). Those randomly assigned to ask more questions were more liked by their conversation partners, learned more about their partner’s interests, and were able to recall those specific interests long after the date was over. They were also more likely to get a second date.

In short, asking more (and better) questions makes you likable. While storytelling inspires large groups of people to join your mission, asking good questions strengthens one-on-one relationships on an intimate level. That may seem trivial, but depending on who you’re talking to (especially in the workplace), these productive conversations are the ones that get big results. Whether it’s building a new relationship, recruiting for a new job, or trying to solve a problem, here are 3 big-picture tips to forming great questions.


Be Present and Listen

“But the biggest inhibitor, in our opinion, is that most people don’t understand how beneficial good questioning can be. If they did, they would end far fewer sentences with a period – and more with a question mark.” – professors Alison Wood Brooks and Leslie Kay John, The Surprising Power of Questions

Questions are powerful, yet the average person rarely asks enough of them. When she began researching questions, professor Brooks noted in The Surprising Power of Questions, “(..) the most common complaint people make after having a conversation, such as an interview, a first date, or a work meeting is, ‘I wish [s/he] had asked me more questions’ or ‘I can’t believe [s/he] didn’t ask me more questions.’”

So what’s the hold up? It could be a number of reasons. Maybe we’re egocentric? Nervous? Fear coming off as rude if we ask the wrong question? Shy? Preoccupied with something else? These mindsets result from failing to be in the moment, or in the moment, but focused wholly on our part in the conversation.

Combat this by actively making the other person the center of your attention. When your mind begins to wander or feelings begin to pop up that hinder your questioning, mindfully shift your attention back onto the other person. This practice gets you out of your head and ready to fully engage in the conversation.

Focusing your attention this way makes you a better listener. It’s an obvious reminder, but it’s from listening that you’ll gather the source material you need to create the right questions for the conversation.



If you can only form your questions from a single characteristic, make it empowerment. Empowering someone literally means to give them power – in a conversation setting, that means giving them a chance to show their own strength and knowledge on the topic discussed. Empowering questions convey respect and encourage innovative thinking in others. To ask empowering questions is a guaranteed way to get the most out of a conversation for yourself and the other person – especially in a professional setting.

In How To Ask Better Questions (Harvard Business Review, 2009) author Judith Ross provides this list illustrating what empowering questions can do along with some examples:


  • They create clarity: “Can you explain more about this situation?”
  • They construct better working relations: Instead of “Did you make your sales goal?” ask, “How have sales been going?”
  • They help people think analytically and critically: “What are the consequences of going this route?”
  • They inspire people to reflect and see things in fresh, unpredictable ways: “Why did this work?”
  • They encourage breakthrough thinking: “Can that be done in any other way?”
  • They challenge assumptions: “What do you think you will lose if you start sharing responsibility for the implementation process?”
  • They create ownership of solutions: “Based on your experience, what do you suggest we do here?” 

 – How To Ask Better Questions (Harvard Business Review, 2009)


Keep It Open-Ended

No one likes to feel interrogated – especially from someone they just met. Forming open-ended questions vs. firing off a series of yes/no ones counteracts this and keeps the conversation flowing. In The Surprising Power of Questions, professors Brooks and John write, “Open-ended questions (…) can be particularly useful in uncovering information or learning something new. Indeed, they are wellsprings of innovation—which is often the result of finding the hidden, unexpected answer that no one has thought of before.”

For a quick review, MediaCollege.com defines an open-ended question as “designed to encourage a full, meaningful answer using the subject’s own knowledge and/or feelings. It is the opposite of a closed-ended question, which encourages a short or single-word answer.” Open-ended questions usually start with “Why,” “How,” and “Tell me about…,” but don’t have to follow this pattern.

Other examples include:

“Do you get along with your manager?” vs. “Tell me about your relationship with your manager.”

“Who will you vote for?” vs. “What do you think about the candidates?”

“Are you feeling better today?” vs. “How are you feeling today?”

Sometimes close-ended questions are necessary and more productive in certain situations (closing a deal for example, setting a meeting time, planning the details of an event, etc.), but more often than not, open-ended questions are the best choice for creating productive conversations.

When it comes to asking the right questions, this is not an exhaustive list. Our tips are the big-picture ideas that prime your mind for constructing great questions, no matter the situation. As with any skill, practice is key. Try these tips at your next professional event, and you’ll be well on your way to mastering the subtle, but powerful  art of asking great questions.

Tetra Prime Consulting, Aaron Garner September 7, 2018
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