As a kid, I was lucky enough to witness a close family friend build a company out of his garage into an everyday global brand.

It was the quintessential example of the American and Entrepreneurial dream, and helped spark my own entrepreneurial passion acting as a beacon of what’s possible.  As I later learned, what is even more impressive is that he was loved by his employees and customers alike along this journey.

So as I began my own attempts at more humbling endeavors, and continue to walk this entrepreneurial course, I often reflect back on advice that he gave me.  What he told me has stuck to with me to this day, and has been extremely helpful in business and in life.

His advice is also amazingly simple, he said:

“Ask Questions and Listen to the Answers”

At the time it sounded much too simple and obvious so I dug deeper. He went onto to explain (in more eloquent words)

Asking questions of your employees, managers, customers and friends does many things:

1 | Questions get people talking so you can listen. 

You’ll be amazed at the stories and answers that are right in front of your face that are simply waiting to be unearthed.  Many people, (not including the female side of my family) have a hard time starting conversations.  There is no better way to get someone talking then asking them a question about something they are have done recently or are around a subject they have a passion for.  But, remember to actually listen:

“When people talk, listen completely. Most people never listen.”
― Ernest Hemingway

“Long before I wrote stories, I listened for stories. Listening for them is something more acute than listening to them.”
- Eudora Welty, One Writer’s Beginnings

2 | Questions show you care.

To avoid the “Can you believe this weather?” moments. Challenge yourself to remember one or two things from the last time you spoke with someone, it completely changes the dynamic of a conversation. It shows you cared enough to not only listen, but to value their thoughts and opinions.  The same applies to follow up questions.  It’s important to fully engage in conversations.

“Most people do not listen with the intent to understand; they listen with the intent to reply.”
― Stephen R. Covey, The 7 Habits of Highly Effective People: Powerful Lessons in Personal Change

3 | Questions provide a wealth of knowledge.

Asking specific questions of people that have knowledge in an area of expertise allows them to speak on something they are comfortable in.  It seems obvious but if you try assigning a report on a topic that is with vague instructions, vs. directly asking the two or three specific questions the results will be night and day.  Yet we continue to assign vague projects and reports, and are “blown away!” when they completely underperform or missed the mark.

“The art and science of asking questions is the source of all knowledge.”
- Thomas Berger

4 | Questions advance and improve us.

Asking the type of questions like:  ”Can this be done better?” or “Could I have done this better?” are the type of questions that advance us as a society and as individuals.  It’s what drives us to improve.  As I’m writing this I’m using our Relaborate application to quickly ask questions of our team and my brother who was with me when we had these conversations.

“At the end of the day, the questions we ask of ourselves determine the type of people that we will become.” 
― Leo Babauta

5 | Questions are structured to uncover truths.

For some reason people open up in more direct ways when you pass the burden of expertise.  The simple prospect of asking them a question shows that you are looking to them (as a subject matter expert) for the best answer rather than telling them to do something.

In a business context, asking a question of your customers or employees allows them to feel comfortable to speak more openly on something because you’ve offloaded the burden of them having to come to you.  The majority of people will simply avoid the potential conflict or conversation altogether either because it is more work or because it could be a difficult conversation to start if it’s around something negative.

“A prudent question is one half of wisdom.”
-Francis Bacon

6 | Questions keep the ball in your court. 

Strategically speaking, asking a question and listening is usually a better strategy than talking.

“This is the problem with dealing with someone who is actually a good listener. They don’t jump in on your sentences, saving you from actually finishing them, or talk over you, allowing what you do manage to get out to be lost or altered in transit. Instead, they wait, so you have to keep going.”
― Sarah Dessen, Just Listen

With practice, and in the right context, questions can be amazingly powerful.  My favorite website: Quora, is built entirely on asking great questions and providing even better answers.  Since, we’re building Relaborate around a Q&A process for marketing, I’ve done quite a bit of research of how the most compelling questions are structured:

Here is a quick list of the top 25 style of questions I saw repeated on Quora by popularity. Collecting these wasn’t an exact science, but it’s still quite interesting and can help you ask questions that tend to elict great answers.  The most important thing however (and something we are working hard on at Relaborate in business content) is getting the correct question in front of the right person.  Quora has done an amazing job at this.

Top 25 “Quora style” questions that elicit great answers

(You can replace “x” with almost any abstracted entity: a keyword, occupation, company, person, location, etc)

• What is the best “x” ever?
• Why is “x” more popular than “y”?
• How do I get started with “x” ?
• Why did “x” do “y”?
• What did it feel like to be at “x” ?
• What are some tips for “x” ?
• What are “x” that fail consistently?
• How would you do “x”?
• What are the best “x” tools?
• What are some mind blowing facts about “x”?
• How would it be possible to become “x”?
• Whats wrong with “x”?
• What are the most important, iconic or beautiful “x”?
• What’s the difference between “x” and “y”?
• Where can I get “x”?
• How much did it cost “x” to do “y”?
• What is the worst piece of “x” ever?
• Is “x” a good idea?
• What’s the real backstory of “x”?
• Why does “x” use “y” instead of “z”?
• What “x” are hiring in “y”?
• Why hasn’t “x” disrupted or replaced “y”?
• How do I become a “x”?
• Which “x” needs and deserves “y”?
• How does “x” work?

To no surprise, the Quora questions that are popular are often people seeking knowledge about things that either aren’t publicly known, or questions that are designed to elicit great answers because they tease a subject matter expert to respond because there is a limited group that has that particular knowledge.

Update: I recently came across this excellent article “Are we asking the right questions?” that’s definitely worth the read.

What’s the most profound question / answer dialogue that you’ve had?

photo credit: Tintin44 – Sylvain Masson via photopin cc