Why the Smartest People Ask Questions and What We Can Learn From Them

The work world is full of puffed up blowhards always spouting off about what they know, or worse yet, what they think they know.


Here’s some insight into the smartest people you work with and why they’re not telling - they’re asking.

My first meeting with Danny

Danny was recently hired and given the task of conducting discovery on a potential new technology platform designed to bring disparate data into one system. It was a complex set of requirements and Danny had a lot of very good exploratory questions.

During this first meeting, Danny demonstrated a genuine interest in trying to get to the heart of the problem and better understand the history of how we arrived at our current state. He never seemed judgmental, in fact, he seemed quite sympathetic to the complexities of the situation. He asked questions to better understand the history – knowing full well that internal politics might be a factor.

During this conversation it became clear to me that Danny knew how to solve complex technical problems and he never once told me about his work experience or qualifications. At the end of the meeting I remember thinking, wow, I have no doubt that this guy is going to get this done.

I began to re-think my assumptions


I had always worked under the assumption that the person sharing knowledge during a conversation is the one who instills confidence, is perceived as intelligent and helpful. At that point in my career I considered asking questions to be fraught with peril, fearing that I would look ignorant if I asked.

What I began to realize during this conversation—and many others while working with Danny—is that my assumption was wrong. It’s counterintuitive perhaps but I learned that the person asking the questions can impart confidence and project intelligence as well.

Someone who asks really insightful questions demonstrates intelligence and critical thinking skills. The answers lead to insight and knowledge, something those within earshot didn’t have previously. It’s a crucial element of workplace communication and team success.

Questions that got my attention


“What causes the most issues with the system? And would you please rate them - 10 being bamboo shivs pushed up your fingernails and 1 being a toothache.”

Are you laughing? I am, because that’s one of the very first questions Danny asked me. If you’re going to ask, why not have a little fun with it?

“Are we sure this is a system issue or is it a human capital issue that needs to be addressed?”

This question challenges the assumption that it’s a system issue and introduces the possibility that there may be other factors at play.

“What was the initial investment and how long have you had it running?”

He was trying to understand the political landscape which will lead him to a greater understanding of the bigger picture.

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Keys to asking questions that move you forward


There are many reasons to ask questions, first and foremost, you need more information in order to be effective in your job. Let’s go back to Danny asking me questions to understand what was needed in a new system - the simple truth is he couldn’t offer up the best technical solution until he fully understood all aspects of the problem. The only way to do that is to ask.

Don’t be worried about showing your ignorance on a subject. Push aside the fear that others will think you don’t know something. If you don’t ask, you may miss critical pieces of information that will later prevent you from doing good work. In that first meeting with Danny I was struck by how open and honest he was about not knowing the subject and I never thought he was ignorant.

Ask exploratory questions. Closed ended questions—those with yes or no answers—limit your ability to dig deep and explore the many nuanced aspects of a situation. Asking questions using “how”, “why” or “what” lead to answers that yield far more insight and open up the dialogue for further exploration.

Be curious. Don’t ask questions just to ask and fill the space. Ask because of your genuine curiosity about the matter at hand. Curiosity and critical thinking are closely linked. Danny is one of the most curious people I know. He asks questions that demonstrate his sincere desire to learn and understand. In doing so he demonstrates his critical thinking. He does not look inept in this process, quite the opposite. As our initial conversation continued, he was connecting the dots and I was sharing more complex information with him.

Always be ready to reframe the question when you get a circular answer. Sometimes people are unable or unwilling to answer questions directly. I once worked with a woman who would speak confidently for several minutes to answer a question and in the end nothing was there – it was a circle of babble. Because she had a position of power, co-workers were hesitant to question her further even though her answers were either nonsense or an obvious attempt to not commit to deadlines. This is when you have to reframe the question to acquire the information you need, for example, “Will I have the data from you by December 15th or not?” It may take a few attempts, be professional and don’t give up.

When you ask questions and seek answers in the spirit of teamwork and collaboration you introduce opportunities for colleagues to partner with you to solve problems or create something that didn’t previously exist. It’s an essential building block for successful teams and is a great skill to hone if you’re in a leadership role or aspire to be in one.

So listen closely to those co-workers who are asking questions. Get to know them a little better because they probably have a lot of knowledge to share.

All you have to do is ask.