Asking Questions More Effectively

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.

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

    Agreed.

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

    Agreed.

  • http://andresiregar.com/ Andre Siregar

    This post is why I love to read this blog. It's full of good advice, but presented as sharing of personal experience.

  • http://andresiregar.com/ Andre Siregar

    This post is why I love to read this blog. It's full of good advice, but presented as sharing of personal experience.

  • http://www.johnexleyonline.com JohnExley

    Mark,
    This is really good stuff. While I enjoy your blog as a whole, this is a specific topic/series I am very, very excited to follow and learn about.

    My dad has reinforced many of the principles you highlight here to me throughout my life…listening and the art of asking questions. I think studying the way excellent interviewers ask questions can be a particularly useful exercise. My personal top 3: Andrew Warner (Mixergy), Michael Arrington (TechCrunch), and Matt Lauer (Today Show).

    While studying abroad in Singapore this past semester, I interviewed some entrepreneurs and investors to share on my blog this summer. If you have the time, I have a couple questions to you:
    1) Let's say you're in a 1-on-1 meeting. Is there specific etiquette on whether jotting down notes is appropriate while the other person is talking?
    2) When you were preparing for meetings to “build rapport” with investors/etc., would you make detailed lists of specific questions you wanted to ask or would you make a broader outline of topics you wanted to learn about and then be 'more natural/go with the flow'' in the meetings?
    3) In all the interviews you've done as CEO of your former companies, are there any specific questions that you were asked by potential hires that stand out in your memory as particularly effective?

  • http://www.johnexleyonline.com JohnExley

    Mark,
    This is really good stuff. While I enjoy your blog as a whole, this is a specific topic/series I am very, very excited to follow and learn about.

    My dad has reinforced many of the principles you highlight here to me throughout my life…listening and the art of asking questions. I think studying the way excellent interviewers ask questions can be a particularly useful exercise. My personal top 3: Andrew Warner (Mixergy), Michael Arrington (TechCrunch), and Matt Lauer (Today Show).

    While studying abroad in Singapore this past semester, I interviewed some entrepreneurs and investors to share on my blog this summer. If you have the time, I have a couple questions to you:
    1) Let's say you're in a 1-on-1 meeting. Is there specific etiquette on jotting down notes while the other person is talking?
    2) When you were preparing for meetings to “build rapport” with investors/etc., would you make detailed lists of specific questions you wanted to ask or would you make a broader outline of topics you wanted to learn about and then be 'more natural/go with the flow'' in the meetings?
    3) In all the interviews you've done as CEO of your former companies, are there any specific questions that you were asked by potential hires that stand out in your memory as particularly effective?

  • philsugar

    Totally agree. I remind myself and everybody with me if we're going into a meeting that we've asked for we establish rapport provide value, and ask wide questions, and we never, ever interrupt the person we've asked for the meeting.

  • philsugar

    Totally agree. I remind myself and everybody with me if we're going into a meeting that we've asked for we establish rapport provide value, and ask wide questions, and we never, ever interrupt the person we've asked for the meeting.

  • philsugar

    Totally agree. I remind myself and everybody with me if we're going into a meeting that we've asked for we establish rapport provide value, and ask wide questions, and we never, ever interrupt the person we've asked for the meeting.

  • ksrikrishna

    Mark – great advice with good specific examples. Many of the other commenters have said a fair deal – the thing I can add, is much of these “asking questions” and “listening” skills are equally important in other settings – be they engineering meetings (why is the ship date slipping) or internal sales review meetings (that big deal we were going to land) or marketing meetings (that new strategic direction we want to take). In many of these meetings, 'coz we know the people we tend to dive right in – and being “smart” people we are focused on getting to the right answers. The best managers and facilitators I have seen – even within the constraints of time that an internal review meeting may pose, did a phenomenal job of “going wide” – often unearthing assumptions, sacred cows or other rigid positions the players may have before helping the meeting arrive at consensus or a course of action. This in many ways falls into your “analysis” meetings category. So we don't have to leave what we learnt outside the company door :-)

  • ksrikrishna

    Mark – great advice with good specific examples. Many of the other commenters have said a fair deal – the thing I can add, is much of these “asking questions” and “listening” skills are equally important in other settings – be they engineering meetings (why is the ship date slipping) or internal sales review meetings (that big deal we were going to land) or marketing meetings (that news strategic direction we want to take). In many of these meetings, 'coz we know the people we tend to dive right in – and being “smart” people we are focused on getting to the right answers. The best managers and facilitators I have seen – even within the constraints of time that an internal review meeting may pose, did a phenomenal job of “going wide” – often unearthing assumptions, sacred cows or other rigid positions the players may have before helping the meeting arrive at consensus or a course of action. This in many ways falls into your “analysis” meetings category. So we don't have to leave what we learnt outside the company door :-)

  • http://www.emergingenterprisecenterblog.com/ Dave Broadwin

    Great post. It is always good to be reminded of things like listening. Listening often leads to connecting: many times that is the real goal of the meeting (as opposed to say, convincing someone of your point of view).

  • http://www.emergingenterprisecenterblog.com/ Dave Broadwin

    Great post. It is always good to be reminded of things like listening. Listening often leads to connecting: many times that is the real goal of the meeting (as opposed to say, convincing someone of your point of view).

  • http://moneyandrisk.com Kim | Money and Risk

    Mark,

    Great post as always. I do have a question. I don't have problems getting people to open up. In fact, they share a lot of very personal and deep information on the first meeting. The issue is that I run out of time because they are opening up so much that I don't want to stop the flow. How do you deal with situations like this. I allot extra time on a first business meeting but I do have limited time and other appointments scheduled. I can feel the disappointment when I have to politely say, I have another commitment and need to leave in 15 minutes, would you mind if we circle back to why you wanted to meet with me. I do put in the transition of enjoying our time together and hearing more at another time.

  • http://moneyandrisk.com Kim | Money and Risk

    Mark,

    Great post as always. I do have a question. I don't have problems getting people to open up. In fact, they share a lot of very personal and deep information on the first meeting. The issue is that I run out of time because they are opening up so much that I don't want to stop the flow. How do you deal with situations like this. I allot extra time on a first business meeting but I do have limited time and other appointments scheduled. I can feel the disappointment when I have to politely say, I have another commitment and need to leave in 15 minutes, would you mind if we circle back to why you wanted to meet with me. I do put in the transition of enjoying our time together and hearing more at another time.

  • http://twitter.com/Baris Baris Aksoy

    Great post as usual. It's weird to see people asking questions just to show how much they know about the subject rather than really ask to learn anything. There are number of sales training programs which mainly focuses on some of the skills you mentioned i.e. build rapport -> ask high-level question on topic #1 -> listen –> then drill down -> switch topics & repeat.

    I also used to ask many specific questions to entrepreneurs to learn what exactly they're doing, etc. I guess it was kind of impatience. I noticed what I was missing until I was in a meeting with a great investor, who was asking wide questions, similar to the ones you asked @ interviews. She asked “why are you doing this?”. Entrepreneur was ready to answer what, how, when, etc. but wasn't expecting a why question. He was a bit surprised, but then he did well. I learned a lot about that CEO after listening his answer.

  • http://twitter.com/Baris Baris Aksoy

    Great post as usual. It's weird to see people asking questions just to show how much they know about the subject rather than really ask to learn anything. There are number of sales training programs which mainly focuses on some of the skills you mentioned i.e. build rapport -> ask high-level question on topic #1 -> listen –> then drill down -> switch topics & repeat.

    I also used to ask many specific questions to entrepreneurs to learn what exactly they're doing, etc. I guess it was kind of impatience. I noticed what I was missing until I was in a meeting with a great investor, who was asking wide questions, similar to the ones you asked @ interviews. She asked “why are you doing this?”. Entrepreneur was ready to answer what, how, when, etc. but wasn't expecting a why question. He was a bit surprised, but then he did well. I learned a lot about that CEO after listening his answer.

  • http://www.hypedsound.com jonathanjaeger

    It's nice to occasionally have a post that is not directly and solely related to fundraising/investing. This post is applicable to a host of real-life scenarios, including outside the workplace.

  • http://www.hypedsound.com jonathanjaeger

    It's nice to occasionally have a post that is not directly and solely related to fundraising/investing. This post is applicable to a host of real-life scenarios, including outside the workplace.

  • http://twitter.com/KurtyD Kurt Daradics

    Mark, the skill of questioning is not valuable in business alone, of course. Asking the “wide question” of questioning reminds us that the “extraction of information” isn't where a question is born, but where it dies. I'd be curious to hear your thoughts about this conversation that my brother Chris hosted with former VP Brand at Nike and CCO (Chief Consciousness Officer) at Seventh Generation, http://bit.ly/aBeH9j, instigated by the question, “What can business accomplish?”

    I'm helping c0–produce these episodes and would very much love to have you on the program with someone that you admire.

  • http://seekingalpha.com mickwe

    Great stuff, thanks Mark.
    With the 'assumptive question' on the referral call, I see the advantages to you (it's hard to extract meaningful info on many of these calls), but aren't you concerned that you're spreading false rumors about the applicant to someone who's likely an important player in his/her industry?

  • http://seekingalpha.com mickwe

    Great stuff, thanks Mark.
    With the 'assumptive question' on the referral call, I see the advantages to you (it's hard to extract meaningful info on many of these calls), but aren't you concerned that you're spreading false rumors about the applicant to someone who's likely an important player in his/her industry?

  • dteten

    Great points! I made a presentation on this exact topic to the ACG Due Diligence Symposium, which you can view at http://www.teten.com/research

  • dteten

    Great points! I made a presentation on this exact topic to the ACG Due Diligence Symposium, which you can view at http://www.teten.com/research

  • William P.

    Excellent Post Mark. Thank you for your continued help in developing my skills through these wonderful posts. My personal growth is strongly influenced by these small interceptions of knowledge :) .

  • William P.

    Excellent Post Mark. Thank you for your continued help in developing my skills through these wonderful posts. My personal growth is strongly influenced by these small interceptions of knowledge :) .

  • http://www.lawforentrepreneurs.com John Horn

    Really enjoyed your post, Mark. It reminds me of the joke (which has a lot of truth to it):

    Q: What's the opposite of speaking?
    A: Waiting to speak!

  • http://www.lawforentrepreneurs.com John Horn

    Really enjoyed your post, Mark. It reminds me of the joke (which has a lot of truth to it):

    Q: What's the opposite of speaking?
    A: Waiting to speak!

  • http://terezan.tumblr.com/ Tereza

    Great post, Mark.

    I was very briefly a journalist and then a consultant for a long time. And in sales.

    Journalists are incented to just get the story out and done. It's transactional, and possibly adversarial. It was useful experience to learn how to gain rapport quickly with people, but that's pretty much it.

    A consultant who is smart and talented can become an effective interviewer with practice. It is helpful that there is supposed to be something that they “do” with the information. That is certainly the case with a lawyer, who is trying to win on behalf of his or her client.

    Sales people need to be patient and the best ones are.

    Because you spot-on. It's amazing what people will tell you when you shut up and let them vent.

    Also, it bears saying, listening is helpful for you to discern who you should spend LESS time with or disqualify from your sales or inquiry process. Is that “maybe” really a softened “no”? Pay attention to that. Prioritize your time. Give 'em space and wait to come back until something has substantially changed. Focus on the ones who are hot on your trail and have higher conversion potential.

  • http://terezan.tumblr.com/ Tereza

    Great post, Mark.

    I was very briefly a journalist and then a consultant for a long time. And in sales.

    Journalists are incented to just get the story out and done. It's transactional, and possibly adversarial. It was useful experience to learn how to gain rapport quickly with people, but that's pretty much it.

    A consultant who is smart and talented can become an effective interviewer with practice. It is helpful that there is supposed to be something that they “do” with the information. That is certainly the case with a lawyer, who is trying to win on behalf of his or her client.

    Sales people need to be patient and the best ones are.

    Because you spot-on. It's amazing what people will tell you when you shut up and let them vent.

    Also, it bears saying, listening is helpful for you to discern who you should spend LESS time with or disqualify from your sales or inquiry process. Is that “maybe” really a softened “no”? Pay attention to that. Prioritize your time. Give 'em space and wait to come back until something has substantially changed. Focus on the ones who are hot on your trail and have higher conversion potential.

  • http://madmediamonkey.com Choi

    Thanks for all of the information, great blog.

  • http://madmediamonkey.com Choi

    Thanks for all of the information, great blog.

  • http://loo.me pescatello

    Listening to your anecdote of a “wide” question reminded me of most first dates i used to go on. Instead of blabbering on about myself, i used to throw some softball questions over to the lady and let her ramble on. The more she talked, the more she believed that it was a good date. Of course, at some point women and investors need to learn about you but in the early phases, i found it was easier to “get in bed” if you ask questions better than you answer them

  • http://loo.me pescatello

    Listening to your anecdote of a “wide” question reminded me of most first dates i used to go on. Instead of blabbering on about myself, i used to throw some softball questions over to the lady and let her ramble on. The more she talked, the more she believed that it was a good date. Of course, at some point women and investors need to learn about you but in the early phases, i found it was easier to “get in bed” if you ask questions better than you answer them

  • the_real_fujun

    Very interesting points. When I was a consultant, I used to ask my clients provocative/seemingly obvious questions (in a polite way) and get really interesting answers. Have to deal with some strange looks from my coworkers sometimes, but they all agree the answer is interesting after the meeting.

  • the_real_fujun

    Very interesting points. When I was a consultant, I used to ask my clients provocative/seemingly obvious questions (in a polite way) and get really interesting answers. Have to deal with some strange looks from my coworkers sometimes, but they all agree the answer is interesting after the meeting.

  • http://twitter.com/txtechiplaw Nathan Roach

    You'd be surprised at how little emphasis is placed on these skills during traditional legal education. I've been fortunate to work with some great litigators over the years, and learned more from listening to the questions asked in trial and deposition than I ever did from formal education.

    The really great ones are able to mix multiple question types in such a way as to keep the pace constantly changing. One effective technique is to ask a series of “Yes/No” or leading questions that get the subject to agree with you in a serial fashion, then very casually drop in a wide question. Once you get someone talking, very rarely will they clam up or slam on the brakes to ponder a “hard” question.

  • http://twitter.com/txtechiplaw Nathan Roach

    You'd be surprised at how little emphasis is placed on these skills during traditional legal education. I've been fortunate to work with some great litigators over the years, and learned more from listening to the questions asked in trial and deposition than I ever did from formal education.

    The really great ones are able to mix multiple question types in such a way as to keep the pace constantly changing. One effective technique is to ask a series of “Yes/No” or leading questions that get the subject to agree with you in a serial fashion, then very casually drop in a wide question. Once you get someone talking, very rarely will they clam up or slam on the brakes to ponder a “hard” question.

  • http://twitter.com/mobilesymmetry Jim Patterson

    Great column. Did your colleagues in your fundraising example learn their lesson? Also, if you are presenting, how do you make sure that the presentation prompts listening to occur (as we can forget and “go croc” in the heat of the moment)? Definitely a “best of” column.

  • http://twitter.com/mobilesymmetry Jim Patterson

    Great column. Did your colleagues in your fundraising example learn their lesson? Also, if you are presenting, how do you make sure that the presentation prompts listening to occur (as we can forget and “go croc” in the heat of the moment)? Definitely a “best of” column.

  • http://twitter.com/joshuabaer Joshua Baer

    Great advice for interviewing, findraising, and sales! I need to ask more “wide” questions!

  • http://twitter.com/joshuabaer Joshua Baer

    Great advice for interviewing, findraising, and sales! I need to ask more “wide” questions!

  • Possibly Contrary

    Generally a good call but that last 'assumptive question' borders on and may well be unethical. You have run your candidate down and given him opportunity to distrust those he had put his faith in. I tend to respect you mark but clever doesn't prevent it from being a little gross.

  • Possibly Contrary

    Generally a good call but that last 'assumptive question' borders on and may well be unethical. You have run your candidate down and given him opportunity to distrust those he had put his faith in. I tend to respect you mark but clever doesn't prevent it from being a little gross.

  • http://www.piqqle.com/blog/ Daniel Kim

    Great post Mark. Being a listener and trying to ask questions the evoke varying emotions without leading is a skill that I continually work on. Your advice works well as people in general enjoys talking about themselves, but sometimes I forget that I too enjoy talking about myself, ideas and dreams as well. I need to constantly remind myself to let the other party drive the conversation in directions they want, and for me to just provide the vehicle and get out of the way. As an executive recruiter, I often start meetings with job seekers with this very open ended question “What do you want to do when you grow up?” Whether someone is a new grad or a 30 year veteran, the question elicits answers that allows me to determine whether someone is a dreamer or realists, shows organized thought or distorted, ambitious or contentment, loyal or fickle, leader to follower etc. This one line question usually gets followed by a very informative 5 minute response.

  • http://www.piqqle.com/blog/ Daniel Kim

    Great post Mark. Being a listener and trying to ask questions the evoke varying emotions without leading is a skill that I continually work on. Your advice works well as people in general enjoys talking about themselves, but sometimes I forget that I too enjoy talking about myself, ideas and dreams as well. I need to constantly remind myself to let the other party drive the conversation in directions they want, and for me to just provide the vehicle and get out of the way. As an executive recruiter, I often start meetings with job seekers with this very open ended question “What do you want to do when you grow up?” Whether someone is a new grad or a 30 year veteran, the question elicits answers that allows me to determine whether someone is a dreamer or realists, shows organized thought or distorted, ambitious or contentment, loyal or fickle, leader to follower etc. This one line question usually gets followed by a very informative 5 minute response.

  • http://www.piqqle.com/blog/ Daniel Kim

    Great post Mark. Being a listener and trying to ask questions the evoke varying emotions without leading is a skill that I continually work on. Your advice works well as people in general enjoys talking about themselves, but sometimes I forget that I too enjoy talking about myself, ideas and dreams as well. I need to constantly remind myself to let the other party drive the conversation in directions they want, and for me to just provide the vehicle and get out of the way. As an executive recruiter, I often start meetings with job seekers with this very open ended question “What do you want to do when you grow up?” Whether someone is a new grad or a 30 year veteran, the question elicits answers that allows me to determine whether someone is a dreamer or realists, shows organized thought or distorted, ambitious or contentment, loyal or fickle, leader to follower etc. This one line question usually gets followed by a very informative 5 minute response.

  • andyhunn

    Great post as always. This will be somewhat self-serving unintentionally, but i've found the folks who have learned this style best are startup bus dev / corp dev guys who have put together partnerships with big companies successfully, done m&a, investments etc. – nothing like knowing other guys motivations to figure out how to put a meaningful deal together. I'm sure this relationship is partially personality type that drives these folks to this role in the first place, and real world experience of bites in the ass of realizing after the fact that you neglected to ask the right questions at deal time… self included.

  • andyhunn

    Great post as always. This will be somewhat self-serving unintentionally, but i've found the folks who have learned this style best are startup bus dev / corp dev guys who have put together partnerships with big companies successfully, done m&a, investments etc. – nothing like knowing other guys motivations to figure out how to put a meaningful deal together. I'm sure this relationship is partially personality type that drives these folks to this role in the first place, and real world experience of bites in the ass of realizing after the fact that you neglected to ask the right questions at deal time… self included.

  • http://twitter.com/timroberts Tim Roberts

    Also a great strategy for meetings challenged by conflict. Sincere inquiry and listening can be disarming, show respect, provide great context for counter argument and come at little to no cost. Classic 7 habits stuff – seek first to understand and then be understood.


Mark Suster is a 2x entrepreneur who has gone to the Dark Side of VC. He joined GRP Partners in 2007 as a General Partner after selling his company to Salesforce.com. He focuses on early-stage technology companies. Read more about Mark.

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