The

Art of

Asking Questions
eREPORT

By Dr. Tony Alessandra © 2006 Dr. Tony Alessandra, All Rights Reserved in All Media

The Art of
Asking
Questions
What time is it?
What do you think about this project?
Can you support this decision?
What can I do to help you?
How would you deal with this problem?
What’s your objective?
How do you feel about this?
The world is full of questions – good questions, silly questions, important
questions, offensive questions. Questions can build rapport and trust or foster
suspicion and dislike. Questions can open up a conversation or slam it closed.
Questions can generate information or send the conversation shooting off on a
tangent. Questions are the heart of communication. They pump fresh life into
conversations.
Asking good questions is particularly important in organizations where
working well together depends upon everyone understanding each other clearly.
Asking questions about how things are done, why they’re done, who’s
responsible for doing them, and when they’re due form the basis of
organizational effectiveness. Imagine launching a new product, pu�ing together
a budget, improving a process, implementing a new policy, or reviewing
employee performance without asking questions. The Information Age couldn’t
exist without questions.
Because questions are so important, our education system takes great pains
to teach us the fine art of asking questions. ... No? ... Why not? Probably because
the average three-year old asks 4.2 questions per minute. Everyone assumes we
know all we need to know about asking questions by the time we learn what a
question mark is. A�er all, isn’t that what a question is? A group of words
followed by a question mark? That may be the definition of a question but
comparing that to the art of asking questions is like saying if you can spell “car,”
you’re ready for the Indy 500.
This report will help you understand how to use questions to improve your
communication, what types of questions to use and when to use them, and the
strategies and techniques of artful questioning. Being able to ask the right
question at the right time is a critical piece of the communication process.
Why Do We Ask Questions?

The standard response to that question is, “Because we want to know

something.” But questioning has a much richer payoff than just information
transfer. There’s an old story about a salesman who was scheduled to appear on
the Johnny Carson show. As he was si�ing in the green room, the producer
came in and started asking him about his approach to sales. The producer,
stubbornly skeptical, finally demanded: “Well, then, sell me something!” The
salesman looked around the room and spied a large ashtray on the table.
The following conversation occurred: Salesman: Do you like that ashtray?
Producer: Yeah, sure.
Salesman: What do you like about it?
Producer: Well, it’s big enough to hold all the ashes of the people who come
through here everyday.
Salesman: What else do you like about it?
Producer: Well, it’s a nice color and it matches the decor in here.
Salesman: How much do you think an ashtray like this is worth to you?
Producer: I don’t know... maybe $20.
Salesman: Sold!
With just a few questions, the salesman was able to find out why the
producer would buy the ashtray and what price he would be willing to pay for it.
While sales aren’t always this easy, the story illustrates how powerful questions
are a tool for ge�ing information. In fact, questions are the heart of any
information gathering process.
(If you are a salesperson and want to improve your selling skills, click here
to check out the Collaborative Selling 133-page eBook)
To gain the other’s views – When you need to know what someone else is
thinking, ask. “What do you think about...?” “Can you tell me how you feel
about...?”
To check agreement – What does the other person think about what you have
discussed? “Do you think we’re on the right track?” “Can you support this
decision?” “Are we in agreement?” “Do you have any objections?” “How does
this sound to you?”
To build rapport and trust – Rapport and trust are built by showing support
for the other person’s goals and objectives. How can I help you? What can I do
to help you meet your objectives? What would you like to accomplish? Tell me
about your goals/dreams/objectives.
To verify information – Sometimes what you hear is not what was meant.
Asking for feedback is a critical part of the communication process. Did I
understand you to mean...? Can I summarize this as...?
But questions can also be used for many other reasons. Here are just a few of
the reasons we ask questions:
To gain information – Information transfer depends on questions. Who, what,
where, when, why, how, and how much are all staples of information gathering.
To stimulate conversation – Imagine a�ending a social function where no
one could ask a question! No: “How are you?” “Have you heard...?” “Did you
see...?” “Can you believe...?” “What do you think...?” It would be a pre�y
strange gathering.

The Two Major Types of Questions

There are only two basic types of questions

– closed and open. Each type is very important to the communication process.
Closed Questions
Closed questions are generally simple, information gathering questions.
Response to a closed question is usually a “yes” or “no” or a very brief answer.
Typical closed questions are:
What time is it?
Did you finish the project?
Are you going to the meeting?
Can you work overtime tonight?
When did you first discover the problem?
Closed questions perform the following functions: They allow specific facts
to be gathered.
Which color do you prefer?
Open questions have the following
characteristics:
They cannot be answered by a simple “yes” or “no.”
How do you think we could make this process work be�er?
Not: Do you think we could do this process be�er?
They are easy to answer and seldom intimidating. Will you be finished by 5:00
p.m.?
They usually begin with “what” or “how.” What do you think about the new
benefit policy?
They are useful in the feedback process, where someone wants to check the
accuracy or completeness of the communication.
Have I got the information right?
 They do not lead the answer.
Where could we make improvements in the new marketing plan?
Not: How much do you like our neat new marketing plan?
They are used to gain commitment to a position. Does this seem right so far?
They can be used to reinforce positive statements. This seems like a good plan,
doesn’t it?
They draw out ideas and feelings.
How do you feel about the reorganization of the department?
They can be used to direct the conversation to a desired topic or concern.
Do you have time to talk about the budget?
They encourage elaboration on objectives, needs, wants and problems.
What do you think about the new employee review system?
Open Questions
Open questions are generally more stimulating, with longer, more complex
answers. Open questions are used to draw out a wide range of responses on a
broad topic. They o�en ask for opinions, thoughts or feelings. Typical open
questions are:
How did you feel about the meeting? What could we do to make this project
be�er?
How can we meet our objectives?
What’s your opinion on the new marketing plan?
How important is it to you?
They promote self-discovery.
How do you think the new process will work for your group?
They stimulate thinking about your ideas. Where do you think we might run
into problems with this idea?
They allow a broad range or responses and styles.
How would you change the policy?
(For more on resolving conflict with others, please click here to see my
Resolving Conflict 23-page eReport)
It’s important to know which kind of question
– open or closed – to use to achieve your goals. Both are useful and can help you
achieve several different purposes, including:
about your first item?” “Couldn’t we postpone the decision for a week?” With
these questions, you want to direct the conversation to a different topic or to lead
the person to a particular decision.
Fact-finding – If you are looking for specific information and data, use
closed questions that ask for the detail you need. “What did you accomplish on
the project?” will generate more detail than “Did you get a lot done?” Take notes
and verify that you understood the information correctly.
Feeling-finding – To understand a person’s feeling about a subject generally
requires an open question. Are you happy about the project? doesn’t get the
same response as the open-ended question: How do you feel about the project?
Used properly, feeling-finding questions generate a lot of information about
a�itudes, convictions, and motivations. These questions are extremely powerful
because they are so seldom asked ... and the answers are listened to carefully less
frequently.
Clarifying – Closed questions are used to verify your understanding of a
conversation. “Do I understand you correctly...?” “Are you referring to...? Do
you mean...?” are examples of questions you can ask to make sure you
understand the information being given to you.

Questioning Strategies

All forms of communication are improved by planning and understanding

the focus of the communication. Questioning is no exception. If you intend to
ask someone a question, you should know what you’re trying to accomplish by
asking the question. If you’re trying to find out how someone feels about an
upcoming change, slapping them on the back and saying, “Sounds great, doesn’t
it?” will probably not meet your goals.
Too o�en we think we’re asking a question for one reason when we really
want something else. For instance, if you ask someone what he or she thinks
about the budget, you may actually want to know if they will support it. A
question such as “Is there anything in the budget you couldn’t support?” might
be�er accomplish your objectives.
Funnel Technique
Expanding – Open questions are used to draw out further information on a
topic. “Can you give me an example?” “Would you tell me more about that
point?” “What else might be causing a problem?” are questions that continue to
generate information about the subject.
Directing – Directing questions are generally closed and point the
conversation toward a particular goal. “What was the other point you wanted to
make?” “Can we go back and talk One of the most fundamental questioning
techniques is to start with broad, open questions and build on the speaker’s
responses by asking narrower, more specific questions. This is called the funnel
technique. It’s like painting a picture. You start with a blank canvas and begin
filling in the background with broad-brush strokes. Gradually you add more and
more detail until you have a complete picture. With questions, you start out at
the top of the funnel with a broad question and 5 then as you move down the
funnel, you “paint with a finer brush”– by asking closed questions that demand
more exact answers– and fill in the details.
(For more on learning how to relate with others, please see The Platinum Rule
50-Page eWorkbook.)
With the funnel technique, you actually begin exploring the other person’s
needs and expectations, problems and opportunities by using your questioning
and listening skills. You start with, “Tell me about your business” or “What are
your long-range goals in this position?” or “What’s important to you?” A typical
computer salesperson might ask a prospect what kind of computer system he
currently has or what his computer needs are. The hotshot salesperson who has
learned the funnel technique starts out by asking about the prospect’s business or
operation. A manager trying to locate the cause of a recurring problem could say,
“Why does this switch keep failing?” An artful questioning manager would start
on a broader level saying something like, “Tell me about the overall process that
surrounds the switch.” A supervisor trying to deal with a tardy employee could
ask why the employee is late again. Or he could sit down with the employee and
ask, “How are you feeling about your job?” begins to build rapport, the artful
questioner builds on the responses and adds to his understanding of the
information being transferred. Our computer salesperson might have a client
who says, “I need more control over our order system.” He then builds on that
response by asking a question using the most important words in the answer –
control and order system. For instance, he might ask, “What aspects of your
order system would you like to have more control over?” or “Could you tell me
more about your order system?” When the client responds, he builds his next
question around the response to that question and so on.
(To improve your persuasiveness when speaking with clients, please read
Becoming More Persuasive Becoming More Persuasive page eReport)
The broad, open questions at the top of the funnel are easy for the speaker to
answer. They give the speaker the freedom to tell you whatever he wants. By the
time you get to the more specific questions, he can see where you’re heading
with your questions and he’ll be willing to share more information with you. Not
only that, most people’s level of trust and willingness to share information is
related directly to how much information they have previously shared.
Broad brush questions give you a lot of information about the situation,
including important clues as to where to direct more specific followup questions,
and give the other person a chance to relax and tell you what he thinks is
important.
 Broad, open-ended questions show your interest in the other person’s
situation. They o�en start with “Tell me,” “how,” “who,” “what,” or “why.”
They are much more powerful than closed questions that require a simple answer
such as “yes” or “no” or a specific piece of information. A�er the broad
question opens the conversation and Here’s another example of building on
previous responses.
Imagine two people meeting on an airplane:
“Hello, my name is Ellen. What do you do for a living?”
“I’m a writer.”
“A writer ... what kind of writing do you do?” “Mostly humor. Occasionally I
write something serious or philosophical but people seem to laugh at that too.”
“Humor – I’ve always thought that must be the hardest kind of writing to do.
Tell me how you do it.”
“Well, for me, it’s one part sarcasm, two parts irreverence, and a dash of
creativity. I shake the whole thing up and hope it doesn’t explode in my face!”
Notice how the intelligent use of the funnel technique has guided the
conversation from a simple, non-meaningful declaration, “I’m a writer,” to a
fairly detailed, very personal expression!

Question Formation

Here are some general strategies to help you formulate your questions:
1. Have a plan – Know what you want to accomplish and what type of
questions you will need to use. You don’t have to have the questions wri�en out
in advance but you should be clear about your objectives.
2. Keep the question simple
– It’s best to ask
for one answer at a time. A question like: “What do you think about the
marketing plan and will the new ad campaign confuse customers and would that
confusion actually be beneficial to the long-term product growth?” will not
produce a meaningful answer. If you ask a two-part question, people tend to
either answer the second part only or only the part they were interested in or felt
safe with. One question at a time!
4. Stay non-threatening
– Trust is essen
tial in communication. The wrong question can quickly destroy trust and the
relationship. Why didn’t you...? How could you...? Aren’t you...? are all
questions that generally make people defensive. Once someone throws up a wall
of defense, the opportunity for exchanging information and building a
relationship goes away.
5. Ask permission – If the area of questioning is sensitive, explain the need
for the questions and ask permission before proceeding. The application requires
some detail about your financial condition. Would you mind answering...?
6. Avoid ambiguity – Ambiguous questions generate ambiguous answers.
“Could you support the budget?” does not tell you whether the person would
support it.
7. Avoid manipulation
– Keep the relation
ship as a primary focus. Tricking someone into giving you an answer you
want destroys trust and rapport. “Would you prefer to work overtime tonight or
tomorrow night?” does not give a person the chance to say that he doesn’t want
to work overtime at all. Explaining the need for the overtime and asking if he’s
available has a totally different feel. Manipulation is an a�empt to take away a
person’s control.
Mastering the art of asking questions will help you gain the information you
need, build trust, stimulate the views and opinions of others, and verify
information.
3. Stay focused – Keep the questions on track and follow a topic to its
conclusion. Any question that starts with By the way ... is probably going off on
a tangent. Hold the question for later.
Tony Alessandra, PhD, CSP, CPAE
Building Customers, Relationships, and the Bo�om Line
Dr. Tony Alessandra helps companies build customers, relationships, and the bo�om line. Companies
learn how to achieve market dominance through specific strategies designed to out market, outsell, and out
service the competition.
Dr. Alessandra has a street-wise, college-smart perspective on business, having fought his way out of
NYC to eventually realize success as a graduate professor of marketing, an entrepreneur, a business author,
and a keynote speaker. He earned his MBA from the University of Connecticut and his PhD in marketing
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Dr. Alessandra is president of Online Assessments (www. OnlineAC.com), a company that offers
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Dr. Alessandra is a widely published author with 14 books translated into 17 foreign languages, including
Charisma (Warner Books, 1998); The Platinum Rule (Warner Books, 1996); Collaborative Selling (John
Wiley & Sons, 1993); and Communicating at Work (Fireside/Simon & Schuster, 1993). He is featured in
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Dynamics of Effective Listening (NightingaleConant); and Non-Manipulative Selling (Walt Disney). He
is also the originator of the internationally-recognized behavioral style assessment tool The Platinum
Rule™ (www.PlatinumRule.com).
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Dr. Alessandra was inducted into the Speakers Hall of Fame in 1985. He is also a member of the Speakers
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