Asking Questions More Effectively

Posted on Jun 6, 2010 | 127 comments


The ability to ask questions effectively is one of the most important skills in business as is the ability to actively listen.  Yet as important as these two skills are they really don’t seem to ever be taught in school.  I wonder if more college students ought to take a journalism course for a semester or do an internship at their school newspaper in investigative reporting.  It’s the only place I could imagine these skills being taught today.

Over the years I’ve been in many meetings where a group of people that I was with wanted to extract information out of a group of people with whom we were meeting and failed to do so effectively.  Witnessing this can be frustrating.

There are many different meeting types where asking different types of questions may be appropriate.  If you’re:

  • raising money you might like to ask how the investor makes decision
  • developing a product you might like to survey prospective customers without biasing their answers
  • interviewing a candidate for a job you might like to ask about his / her performance at the last job
  • trying to determine one’s math capabilities you might like to ask a detailed analytical problem to solve
  • doing a reference call on a prospective employee

There are many different question types dependent on the scenario you’re in.   But there is only one type that I want to focus on today because it’s one of the most important and most poorly executed question types I have seen.

The “Wide” (and uninterrupted) Question:

You ask a very broadly defined question and intentionally don’t try to offer specificity in what you mean by the question.  It is designed to get the person you’re asking to reveal more than they would if your question directed them toward a more narrowly defined path.  There are definitely times where a more narrowly defined question makes sense and where you want to guide the person you’re talking with to a narrow boundary to elicit a certain type of response.  For extracting the maximum range of information in an interview nothing beats “wide” and nothing beats silence from your side.

Some quick stories

1. FUND RAISING: I was once in a fund raising meeting.  There were a group of us and I wanted to know more about the individual with whom we were sitting across.  I wanted to know what made him tick.  I wanted to know what he liked and what he didn’t like.  I wanted to understand how he had arrived at his previous investment decisions.  We were not actually raising money yet, we were “pre marketing,” “relationship building” or whatever you want to call it.  At this time I wasn’t the senior guy on our team in the meeting so I wasn’t leading the charge.

We started presenting our company and talking about our views of the industry.  I noticed that the guy from our side doing all of the talking was a “crocodile(you know, big mouth and no ears).  We were selling and not listening.  I chalked this up as both a sign of nervousness, a certain social awkwardness / lack of confidence and a basic lack of interviewing skills.

I tried to do a real-time intervention.  I waited politely for a break in the conversation (about 20 minutes in) and then politely inserted, “I know I’m the least experienced in the room so I hope my question doesn’t come across as naive, but I really don’t know how you arrive at investment decisions.  I’d love to learn more about this and what your views on our industry are?”  This was a wide question and I could see a smirk from my colleague but the investor started talking.

It was golden.  It was as wide as you could get.  No real interpretation – just an invitation to talk.  And this is wise because most people love to talk.  In fact, in my experience the more they “inform” you the more they tend to have good feelings toward you.  Dumb, I know.  But I’ve found it to be true.  But more than anything I just wanted the nuggets of information to help me better target this individual in the future.  I wanted to learn.

Boom!  He started opening up.  He literally pulled out a list of all of his investments in the area and started walking us through why he had invested. I couldn’t believe it.  I was madly scrawling notes on everything he said.  I noticed my colleagues wrote nothing down.  He then started to get a little bit negative on our industry.  He was criticizing investments in our area that hadn’t performed relative to other areas and that some people were advising him to hold back on our area.  This was the most valuable bit.  I didn’t feel offended – I felt he was offering us a roadmap on how to avoid his “buying obstacles.”  And at a minimum he was giving us some data points about what the industry thought of our sector.

My colleague felt uncomfortable.  He couldn’t let those zingers about our industry go unanswered.  So he shot back at why we were different than others in the industry and then started selling our positive points.  He did it with a smile and with good data, but still: Crocodile, crocodile, crocodile.  I was infuriated because the flow of our conversation never returned to letting the guy inform us how to better sell to him.

I would have had let him speak for an hour if he wanted to.  A random walk down whatever path he wanted to take as I would have gotten to better know the man, his preferences, his biases, what excites him, etc.  A “wide” question has the beauty of sometimes veering off into unexpected and wholly valuable information.

You obviously can’t just walk into the meeting and start with a “tell me what you think about life” type question.  You need to establish some basic rapport first and I think this is always best done by doing (brief!) personal introductions and a quick overview of your firm.  But whether you’re raising money, selling to customers, looking to make an investment or whatever – listening pays more dividends than talking.  And a properly steered wide set of questions gives you facts you’d never expect.

2. THE ANALYSIS MEETING: I once was doing some due diligence work on an industry.  I was interviewing the founder of a prominent company of which many of you would have heard.  I was honored to be meeting him and I was deferential.  My goal was to learn as much as I could to help inform my analysis.  After building some rapport by discussing my background and listening to his, I started by asking really wide questions.  I figured I could do more specific “deep dive” questions later in the meeting.  We knew the specific details we wanted to get about the company we were researching but we had an hour so I didn’t want to rush there.

I asked him, “What makes consumers want to use your product?”  It was totally vague.  And intentionally so.  I know that I could have asked him, “Why would they use your product when it actually seems to not be in their financial interest?”  or “Your supplier (the company we were evaluating) is in an industry seen as a bit shady yet you give them a lot of business.  Does the industry just have them pegged incorrectly?” Those would have been good questions and I certainly wanted to know.  I had intended to go down that line of thinking later on in our conversation.  If I would have asked questions this way he would have given very different responses.  It would have been defensive and a rebuttal of the true value they provide.

So I kept my question wide.  The CEO started talking and rattled off for about 5 minutes with awesome information when my colleague jumped in for clarification, “But our research shows that while the conversion rates on that type of campaign are 3-4x what we’ve seen elsewhere the offer is of such low quality that it leads to a high long-term churn rate.  Is that your experience?”  I was gutted.  The guy had been serving up unsolicited information that was valuable to us.  By my colleague having asked a “clarifying question” he ruined the flow and got the guy off track.  If he had written his question down to return to it at a later time he could have still asked it without interrupting the meeting flow.

The only reason I could think that he asked the question that way was to try and establish personal rapport with the CEO by showing that he was knowledgeable on the topic – that he was smart.  As in scenario 1 above I think it came from a lack of self confidence.  I felt perfectly comfortable asking the “dumb” questions since the CEO is clearly more informed on his industry and letting him teach me a thing or two.

What both of the scenarios above (and countless more meetings) have taught me is that to effectively employ this strategy I either need to be alone in the meeting or I need to be the lead and have agreement from others not to interrupt answers or to take my cue when to join in on the questioning.

3. THE JOB INTERVIEW: Me: “What makes you tick?”  Silence.  No guidance.  Just a smile.  If asked a clarifying question like, “what do you mean?” I respond, “Interpret the question however you like.  I just want to hear how you think.”

4. THE REFERENCE CALL:  Reference calls are hard.  The person you’re calling has been prepped by the candidate you’re considering hiring and in many cases the questions you ask will be passed back to that candidate after your call.  This is why I hate referencing only from the people that the candidate has asked me to call.  Here is an example of the need for both wide and narrow questions.  I always start wide, “so tell me about the circumstances in which you worked with Bob Smith?” “Yeah, how’d it go?”  ”Was he a good employee?”

Sometimes you pick up more than you expect in these wide questions but in this type of call you usually don’t.  So I begin to narrow more quickly than I might in other meetings, “I’m very fond of Bob.  We’ve obviously had a great experience interviewing him or we wouldn’t be doing reference calls.  But I do want to be sure I hear any potential downsides.  One thing we picked up from another reference call was that Bob has at times fought with co-workers.  When this happened at your firm, do you think it was at Bob’s instigation?”

That’s pretty narrow.  And I’ve applied a “assumptive question” as in “we know there was conflict with Bob at your firm” even if I didn’t know whether it was true.  In this case I’m looking for the reference to deny my statement or to provide evidence that Bob didn’t cause conflicts.  I only point this out because as I said at the start there are many question types and “wide” is only one type.

Conclusion

As with the reference call question above, wide questions will never yield you all the information you need in a meeting.  Wide questions are to be used early in a meeting to learn as many unexpected facts as you can.  Answers to wide questions can give you lots of nuggets to drill down into later in the meeting.  But resist the temptation to seek clarification for a nuggets at that exact time or the “random walk” answer gets taken off course.

Wide questions lead to narrower and narrower of questions later in the meeting.  I’ll likely write about other question strategies at a later time.  There are many types I employ including “assumptive” questions, the “awkward” question, etc.  But think about how you can use “wide” and “uninterrupted listening” with your customers, employees, business development partners and investors.  You might be surprised how much you learn.

  • http://twitter.com/L1AD LIAD

    Mark, ever looked into NLP ? It goes into these kind of meta language patterns and open vs closed questions. It's interesting stuff

  • http://twitter.com/L1AD LIAD

    Mark, ever looked into NLP ? It goes into these kind of meta language patterns and open vs closed questions. It's interesting stuff

  • spencer wendt

    Nuggets of Gold! Love your stuff Suster! Even enjoyed watching your flirt schtick with Femme VC on TWiVC last week :)

  • spencer wendt

    Nuggets of Gold! Love your stuff Suster! Even enjoyed watching your flirt schtick with Femme VC on TWiVC last week :)

  • http://www.metamorphblog.com Matt Mireles

    Ahh yes, the human psyche. Of it, some are masters, others not so much.

  • http://www.metamorphblog.com Matt Mireles

    Ahh yes, the human psyche. Of it, some are masters, others not so much.

  • http://brmore.posterous.com/ brmore

    Stuff like this works great on prospecting calls too, which I suspect are much like the “funding” conversation you describe. If you open the door wide and go for rapport over “the sale” you'll find people really do want to talk about their problems … to the point of confiding in you how the other guy's dropped the ball in their pitches and what you need to do to solve their problem (NOT SELL THEM SOMETHING). Sorry for shouting.

  • http://brmore.posterous.com/ brmore

    Stuff like this works great on prospecting calls too, which I suspect are much like the “funding” conversation you describe. If you open the door wide and go for rapport over “the sale” you'll find people really do want to talk about their problems … to the point of confiding in you how the other guy's dropped the ball in their pitches and what you need to do to solve their problem (NOT SELL THEM SOMETHING). Sorry for shouting.

  • http://twitter.com/philmichaelson Phil Michaelson

    Great post. I always ask investors to talk about the “why” of some of their past investments and past rejections, and their decision making process. definitely helps to understand roadblocks.

    on the reference call, i learn a lot with this broad question:
    * How would you manage this person?

    Which I sometimes narrow down with something like…:
    * I want he/she to be motivated to have a quick win upon joining our company. What would be the type of project he/she excels at? How would you set them up and motivate them to have this win?

    * Personal development matters a lot to me. I want he/she to learn while working with us. What are his/her opportunities for development?

    Phil Michaelson
    http://kartme.com/phil

  • http://twitter.com/philmichaelson Phil Michaelson

    Great post. I always ask investors to talk about the “why” of some of their past investments and past rejections, and their decision making process. definitely helps to understand roadblocks.

    on the reference call, i learn a lot with this broad question:
    * How would you manage this person?

    Which I sometimes narrow down with something like…:
    * I want he/she to be motivated to have a quick win upon joining our company. What would be the type of project he/she excels at? How would you set them up and motivate them to have this win?

    * Personal development matters a lot to me. I want he/she to learn while working with us. What are his/her opportunities for development?

    Phil Michaelson
    http://kartme.com/phil

  • http://twitter.com/wojciech_jawor Wojciech Jawor

    Great post. Luckily it's not in my nature to talk a lot, so I never get to be the crocodile, but this will help me ask questions even more effectively. Can't wait for the rest of the series.

  • http://twitter.com/wojciech_jawor Wojciech Jawor

    Great post. Luckily it's not in my nature to talk a lot, so I never get to be the crocodile, but this will help me ask questions even more effectively. Can't wait for the rest of the series.

  • http://www.linkedin.com/in/rajatsuri rajatsuri

    useful post, thanks

  • http://www.linkedin.com/in/rajatsuri rajatsuri

    useful post, thanks

  • http://cloudcomputing.blogspot.com/ Chirag Mehta

    Great post Mark! You are absolutely spot on about lack of training on listening skills. It is ironic that most people believe the communication skills are about talking and presenting and not listening.

    I have coached quite a few people on active listening skills as it relates to a specific type of an end user interview called contextual inquiry. One of the causes for poor listening skills is the “knowledge curse”. The people on the receiving end believe that they know a lot more and cannot just shut up and listen. They have unstoppable urge to interrupt, talk, and share what they know. Before I start coaching people on active listening skills I make them go through a small exercise. Each person has to listen to another person's story for 5 minutes without interrupting that person. The five minutes feel like five hours and people get an empathy for what it is to stay quiet – not easy. People tend to do much better after going through this exercise. What you refer to as a “wide” question is essentially an open ended question that I strongly encourage people to ask. It does make people open up and talk about all kinds of stuff. The answers move from “what it is” to “how I feel about it”.

    Active listening is priceless and I hope people acquire these skills early on in their careers.

  • http://cloudcomputing.blogspot.com/ Chirag Mehta

    Great post Mark! You are absolutely spot on about lack of training on listening skills. It is ironic that most people believe the communication skills are about talking and presenting and not listening.

    I have coached quite a few people on active listening skills as it relates to a specific type of an end user interview called contextual inquiry. One of the causes for poor listening skills is the “knowledge curse”. The people on the receiving end believe that they know a lot more and cannot just shut up and listen. They have unstoppable urge to interrupt, talk, and share what they know. Before I start coaching people on active listening skills I make them go through a small exercise. Each person has to listen to another person's story for 5 minutes without interrupting that person. The five minutes feel like five hours and people get an empathy for what it is to stay quiet – not easy. People tend to do much better after going through this exercise. What you refer to as a “wide” question is essentially an open ended question that I strongly encourage people to ask. It does make people open up and talk about all kinds of stuff. The answers move from “what it is” to “how I feel about it”.

    Active listening is priceless and I hope people acquire these skills early on in their careers.

  • http://erica.biz ericabiz

    Listening is definitely the most underrated skill in sales. I used to let potential clients talk as long as they wanted about their businesses. Then ask simple questions about what type of web hosting solution they needed. I closed 90% of those meetings with contract in hand in less than 2 hours. Some of them were for multiple thousands of dollars a month. All because I listened.

  • http://erica.biz ericabiz

    Listening is definitely the most underrated skill in sales. I used to let potential clients talk as long as they wanted about their businesses. Then ask simple questions about what type of web hosting solution they needed. I closed 90% of those meetings with contract in hand in less than 2 hours. Some of them were for multiple thousands of dollars a month. All because I listened.

  • http://lmframework.com/blog/about David Semeria

    …And this is wise because most people love to talk. In fact, in my experience the more they “inform” you the more they tend to have good feelings toward you. Dumb, I know.

    Dumb? Perhaps.. But it's a secret known only by the very best salesman (and the odd blog commenter!)

  • http://lmframework.com/blog/about David Semeria

    …And this is wise because most people love to talk. In fact, in my experience the more they “inform” you the more they tend to have good feelings toward you. Dumb, I know.

    Dumb? Perhaps.. But it's a secret known only by the very best salesman (and the odd blog commenter!)

  • http://rbeale.com RBeale

    Great Post, Mark. Asking questions is fundamental in every aspect of business and life. A wide question that I use on a daily basis in my job as a Sales Rep calling on inbound leads (a website visitor that has provided my employer with personal and business information in exchange for any number of marketing offers – free trial, demo, e-book, kits etc) is “What are you looking for help with?”

    Very simple, but very effective. The goal of every sales call is to qualify prospects and see if they are a good potential long term customer. By simply asking, “what are you looking for help with,” many prospects in fact uncover business problems/needs on that “initial connect” that prove valuable when it comes time to close the deal.

    I love the crocodile metaphor “big mouth and no ears” HA!

  • http://rbeale.com RBeale

    Great Post, Mark. Asking questions is fundamental in every aspect of business and life. A wide question that I use on a daily basis in my job as a Sales Rep calling on inbound leads (a website visitor that has provided my employer with personal and business information in exchange for any number of marketing offers – free trial, demo, e-book, kits etc) is “What are you looking for help with?”

    Very simple, but very effective. The goal of every sales call is to qualify prospects and see if they are a good potential long term customer. By simply asking, “what are you looking for help with,” many prospects in fact uncover business problems/needs on that “initial connect” that prove valuable when it comes time to close the deal.

    I love the crocodile metaphor “big mouth and no ears” HA!

  • http://www.facebook.com/people/Bill-Davenport/1151410841 Bill Davenport

    One of the best posts I've read on any blog this year. Many thanks!

  • http://www.facebook.com/people/Bill-Davenport/1151410841 Bill Davenport

    One of the best posts I've read on any blog this year. Many thanks!

  • http://www.aarlo.com Aarlo

    This is a great post, thanks! Would love more like it.

  • http://www.aarlo.com Aarlo

    This is a great post, thanks! Would love more like it.

  • http://asable.com/ Giang Biscan

    Love this post, Mark. You address such an important topic but often overlooked. Asking questions is a great way to get invaluable information and to bond with others.

    The crocodile metaphor is hilarious – and so true.

    Looks like you're on the road. Have fun & be safe!

  • http://asable.com/ Giang Biscan

    Love this post, Mark. You address such an important topic but often overlooked. Asking questions is a great way to get invaluable information and to bond with others.

    The crocodile metaphor is hilarious – and so true.

    Looks like you're on the road. Have fun & be safe!

  • http://www.chaosprg.com/blog irv

    The absolute best person I ever met for getting both the broad outlines and specifics of a situation was a lawyer. I've also known a couple law enforcement professionals who could get a lot out of someone without even seeming to try. Not everyone in those fields is good at interviewing, but it IS taught there for obvious reasons. I also once saw a description of a course (which I did not take so I can't speak to its effectiveness) on interviewing and investigating for social services workers. This specifically stated it was not a legal type investigation but an attempt to do fact gathering for specific agency related purposes.

    By contrast, the journalists I knew when I worked at the newspaper, tended not to be good at digging for information. They were too busy transcribing bullet points (who, what, when, etc) to be good listeners. I guess that's built in to the medium.

  • http://www.chaosprg.com/blog irv

    The absolute best person I ever met for getting both the broad outlines and specifics of a situation was a lawyer. I've also known a couple law enforcement professionals who could get a lot out of someone without even seeming to try. Not everyone in those fields is good at interviewing, but it IS taught there for obvious reasons. I also once saw a description of a course (which I did not take so I can't speak to its effectiveness) on interviewing and investigating for social services workers. This specifically stated it was not a legal type investigation but an attempt to do fact gathering for specific agency related purposes.

    By contrast, the journalists I knew when I worked at the newspaper, tended not to be good at digging for information. They were too busy transcribing bullet points (who, what, when, etc) to be good listeners. I guess that's built in to the medium.

  • http://www.skmurphy.com/ skmurphy

    “to illicit a certain type of response” s/b “to elicit a certain type of response.”

  • http://www.skmurphy.com/ skmurphy

    “to illicit a certain type of response” s/b “to elicit a certain type of response.”

  • http://www.repeatablesale.com/ Scott Barnett

    “In fact, in my experience the more they “inform” you the more they tend to have good feelings toward you. “

    Even more than that – have you noticed that it's really important when selling enterprise software that the technical folks all want to be “smart”? Well, the more they “inform” you, the smarter they think you are, essentially because you were empathetic, agreed with them, or generally showed interest in what they had to say, nothing more. And in reality, how is somebody really going to “get” how smart you are in a 2 hour meeting? Can you really compress years of experience and knowledge into 2 hours?

    I'm surprised nobody here said the obvious – we were given 2 ears and 1 mouth for a reason.

  • http://www.repeatablesale.com/ Scott Barnett

    “In fact, in my experience the more they “inform” you the more they tend to have good feelings toward you. “

    Even more than that – have you noticed that it's really important when selling enterprise software that the technical folks all want to be “smart”? Well, the more they “inform” you, the smarter they think you are, essentially because you were empathetic, agreed with them, or generally showed interest in what they had to say, nothing more. And in reality, how is somebody really going to “get” how smart you are in a 2 hour meeting? Can you really compress years of experience and knowledge into 2 hours?

    I'm surprised nobody here said the obvious – we were given 2 ears and 1 mouth for a reason.

  • http://bothsidesofthetable.com msuster

    Yes, I have. And you're right. Hadn't thought about it.

  • http://bothsidesofthetable.com msuster

    Yes, I have. And you're right. Hadn't thought about it.

  • http://bothsidesofthetable.com msuster

    Thanks, Spencer. Flirt? Er, not so much. Dana is a good friend.

  • http://bothsidesofthetable.com msuster

    Thanks, Spencer. Flirt? Er, not so much. Dana is a good friend.

  • http://bothsidesofthetable.com msuster

    Agreed. But to get it right you need to earn the right to ask questions. I think people are annoyed when sales people just come in and say “tell me your problems.”

  • http://bothsidesofthetable.com msuster

    Agreed. But to get it right you need to earn the right to ask questions. I think people are annoyed when sales people just come in and say “tell me your problems.”

  • http://bothsidesofthetable.com msuster

    Thanks, Chirag. Sounds like a great training program. The reality is that most conversations in life consist of one person talking and the other waiting and looking for the opportunity to jump in and start talking.

  • http://bothsidesofthetable.com msuster

    Thanks, Chirag. Sounds like a great training program. The reality is that most conversations in life consist of one person talking and the other waiting and looking for the opportunity to jump in and start talking.

  • http://bothsidesofthetable.com msuster

    ;-)

  • http://bothsidesofthetable.com msuster

    ;-)

  • http://bothsidesofthetable.com msuster

    That's a great way of phrasing the opening line from an inbound query. Thank you.

  • http://bothsidesofthetable.com msuster

    That's a great way of phrasing the opening line from an inbound query. Thank you.

  • http://bothsidesofthetable.com msuster

    You're right. Not enough journalists are good at it. The best are. But it ought to be bread-and-butter to any good lawyer.

  • http://bothsidesofthetable.com msuster

    You're right. Not enough journalists are good at it. The best are. But it ought to be bread-and-butter to any good lawyer.

  • http://bothsidesofthetable.com msuster

    Doh! Thank you. Typing too fast. Fixed it.

  • http://bothsidesofthetable.com msuster

    Doh! Thank you. Typing too fast. Fixed it.