How to Ask Questions That Will Always Inspire Thoughtful Answers

I ran an experiment the other day where I decided to count how many questions I asked during a single day. It didn’t matter to whom, or how important they were, I just wanted a rough estimate of how many questions we ask as normal operating people in society.

My number: 38

The questions I asked ranged from, “can I have room for cream” to “in your opinion, is social media killing journalism or enhancing it?”

Clearly, some were deeper than others.

The point is you don’t have to be a reporter or interviewer to ask questions. We all ask, and we all want the best possible answer.

It really is an art form that needs to be continually enhanced and refined.

When Asking Questions Really Matters

One of the most important places for someone to ask questions is when they are being interviewed. We've all been there, you go through the gauntlet of a 3-hour job interview and then your would-be-boss looks across the table and says, “do you have any questions for me?”

Exhausted after hours focused on nailing the interview, most people say, “Nope, I think we covered everything.”

Wrong answer.

One hiring manager I know told me that if someone doesn't have intelligent questions ready to ask them, then they aren't a good fit for their company. That’s it.

Their premise, while extremely harsh, is that if someone is really passionate about this job and their industry, then their mind should always be churning with questions. Furthermore, they assessed, anyone can prepare for an interview and study up on the industry, but if they don’t ask questions in the moment, that shows they can’t process what is happening right then.

I interview about 3-5 people a week, and I get a thrill every time someone starts their response with ‘good question’, it shows I've made them think and when someone has to think quickly you usually get their most honest responses. No planning, no consulting, just honest.

I ask some terrible questions too, so that is why I always analyze after each interview. After years of questioning these are the principles I adhere to in order to get the best results.

Learn the Open-Ended Principle

Open ended questions force a response, while closed-ended questions can often be answered with a simple “yes”, “no” or one-word answer.

It’s not as simple as just starting with who, what, when, where, or why, to automatically get an open-ended question. You still need to put some thought into it.

For example:

• What is your best quality? My thighs. Closed question.


• What is the reasoning behind switching from Quantel editing suites to Avid media composers? Expect a detailed response…Open!

Think of how you would answer your question before you ask it. Could you get away with a one word answer? If so, re-craft it to dig deeper.

Be Quick About it Already

This is where I can run into trouble sometimes (as I mentioned, being self-analytical is important). The longer your question the more likely someone will get confused, disengaged or distracted.

I call this the sports talk radio conundrum.

Sports talk radio hosts are responsible for filling so much air-time and are therefore trained to talk forever and ever. Often when they get interview subjects they don’t adapt their style to the moment, they remain in their time-filling mode and ask monolithic questions.

I laugh every time I hear an interview on sports talk and some host goes on and on with a question comprising of parts A, B and C and then next thing you know the interview subject has this long pause as if to say “I have no idea what they just asked me”.

Be clear, be concise, be specific and…

Be a Good Listener

The only way you can ask good questions is to listen and be engaged in the topic being discussed. If you daydream or lose focus, you will fall out of rhythm and possibly even ask something that has already been answered. Big no no.

“Stop thinking about what your next question is going to be and listen to what their answer is,” says Fox Sports Reporter Laura Okmin.  “That's when an interview stops and a conversation happens.”

It doesn't matter of you are questioning Robert Griffin III or the HR rep at your interview, listening and being connected starts a conversation, and conversations can get great results.

If All Else Fails Just Start With Why

Dr. Craig Allen, associate professor at the Walter Cronkite School of Journalism and Mass Communication at Arizona State University has a very simple philosophy, “Just begin every question with the word “why” I tell students this all the time.”

It’s not quite as universal as Dr. Allen suggests, sometimes valuable questions need to be asked that can’t really start with why…but if all else fails why is a pretty good starting point.