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3-Minute Guide 
to Asking Outstanding Questions
Too many salespeople think selling is about 
pitching, pitching, pitching. In reality it is about 
asking, listening and developing solutions to 
customer needs. Asking questions is an art form 
understood by few. Here are some tips on how to 
ask great questions:
ASK 
Open-Ended Questions
Open-end questions have a large number and type 
of potential replies. Closed-end questions are yes-no, 
multiple-choice, etc. While you’ll want most of 
your questions to be open-ended, you should also 
feel comfortable using closed-ended clarifying 
questions that check your understanding and 
demonstrate reflective listening.
ASK 
Easy-to-Answer Questions
Questions that are focused, limited, and specific 
are generally easier to answer than those which 
are not. This does not apply so much to the 
subject matter, as to the structure of the question. 
For example: “What is the one thing you spend 
more time on than anything else?” is more 
focused and easier to answer than “How do you 
spend your time in this job?”
ASK 
Enjoyable-to-Answer Questions
As a rule, questions that are interesting and 
engage the mind are more effective than those that 
are dull, shop worn, and call for no new thinking. 
Try to pose questions that are a little different, a 
little out of the ordinary, perhaps a little 
challenging...your clients will find themselves 
enjoying the conversation, giving you more time 
with them, and increasing their trust and value of 
you.
ASK 
Timely and Topical Questions
Give the prospect the opportunity to talk about 
what’s hot right now... issues of importance, 
relevance, and urgency. Not every question can 
have that feel, but if your needs analysis isn’t 
loaded with questions like that, the prospect may 
get the feeling he or she is helping a student with 
a term paper, rather than talking shop with a 
professional colleague who has a lot of problem 
solving savvy.
ASK 
Questions that Build Trust and 
Establish Value
Every question you ask will either enhance or 
impair your credibility, especially during the early 
stages of a relationship. Choice of appropriate 
topics, correct use of language, attention to 
jargon, and your demonstration 
of empathy, all play a key role in building trust and 
establishing value 
as a problem-solver. Remember: using their jargon 
correctly will build your credibility; using it 
incorrectly will destroy it.
ASK 
Non-Threatening Questions
Be very careful with threatening topics and 
questions that are structured in a threatening way. 
Potentially threatening topics are: finances 
(revenue, profit, budget), personal information, 
competitive strategy, trade secrets, etc. Keep in 
mind you may have to ask questions about some of 
these topics at some point during a needs analysis. 
Be sure to do this after you have established trust 
and value in your relationship.
CONTRACT 
Your Way Around Sensitive Topic 
Areas
It’s human nature that people like to know where 
they’re going, and dislike being led into the 
unknown... especially by a salesperson! Use your 
knowledge of contracting to introduce sensitive 
topics. Explain why you are asking a question about 
a topic, and what the benefits to the prospect are 
in answering.
ASK 
One Question at a Time
Avoid complex, multi-part, or compound questions. 
Take ’em apart and ask them one at a time to make 
your questions easy to understand.
LISTEN 
Actively
Maintain eye contact. Reflect. Clarify. Ask follow-up 
questions. You’re not listening when you’re busy 
forming the next question while the prospect is still 
answering the last one. It's OK if there is some 
“dead air” while you ponder and digest what was 
just said. Also, take some notes to demonstrate 
you are listening to their answers.
PRACTICE 
Empathy
If you want to discover the client’s needs from the 
client’s point of view, you have to pose your 
questions from the client’s point of view! Clients 
will sense quickly—and react poorly—if your line of 
questioning is designed to define their problems 
from your point of view or if it’s a thinly-veiled 
attempt to lead them down the path toward your 
pitch. Drop the leading questions, and don’t 
accidentally telegraph the desired or expected 
answer.
PRACTICE 
Flexibility
Allow the prospect to take the conversation into 
areas of the client’s interest. Follow the 
conversation where the client takes it and ask 
follow-up questions.
BE 
Genuine and Sincere
Questions always sound 100% better when you 
really want to know the answer! Be genuinely 
interested. When you are, you’ll find yourself 
naturally asking a lot of good follow-up questions.
ADJUST 
To Their 
Behavioral Style
Pay closest attention to their pace (is it quick or 
laid back?) and priority (whether they want to 
handle the task first or build a relationship first) 
and adjust your style to theirs.
LAST 
But Not Least
When great salespeople work with a customer, an 
unbiased observer can’t tell which of the two people 
is the seller and which is the buyer. Don’t place the 
client on the witness stand and don’t conduct a cold 
Q&A. Instead, aim for a lively, interactive, and 
creative conversation between two peers... one of 
whom would like to able to offer real help, and the 
other of whom will always gladly accept real help.
For more information on conducting a needs 
analysis that delivers value to the customer and the 
seller, download The Hourglass Needs Analysis 
Method and learn the secrets employed by world-class 
sellers!

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3-Minute Guide to Asking Outstanding Questions

  • 1. 3-Minute Guide to Asking Outstanding Questions
  • 2. Too many salespeople think selling is about pitching, pitching, pitching. In reality it is about asking, listening and developing solutions to customer needs. Asking questions is an art form understood by few. Here are some tips on how to ask great questions:
  • 4. Open-end questions have a large number and type of potential replies. Closed-end questions are yes-no, multiple-choice, etc. While you’ll want most of your questions to be open-ended, you should also feel comfortable using closed-ended clarifying questions that check your understanding and demonstrate reflective listening.
  • 6. Questions that are focused, limited, and specific are generally easier to answer than those which are not. This does not apply so much to the subject matter, as to the structure of the question. For example: “What is the one thing you spend more time on than anything else?” is more focused and easier to answer than “How do you spend your time in this job?”
  • 8. As a rule, questions that are interesting and engage the mind are more effective than those that are dull, shop worn, and call for no new thinking. Try to pose questions that are a little different, a little out of the ordinary, perhaps a little challenging...your clients will find themselves enjoying the conversation, giving you more time with them, and increasing their trust and value of you.
  • 9. ASK Timely and Topical Questions
  • 10. Give the prospect the opportunity to talk about what’s hot right now... issues of importance, relevance, and urgency. Not every question can have that feel, but if your needs analysis isn’t loaded with questions like that, the prospect may get the feeling he or she is helping a student with a term paper, rather than talking shop with a professional colleague who has a lot of problem solving savvy.
  • 11. ASK Questions that Build Trust and Establish Value
  • 12. Every question you ask will either enhance or impair your credibility, especially during the early stages of a relationship. Choice of appropriate topics, correct use of language, attention to jargon, and your demonstration of empathy, all play a key role in building trust and establishing value as a problem-solver. Remember: using their jargon correctly will build your credibility; using it incorrectly will destroy it.
  • 14. Be very careful with threatening topics and questions that are structured in a threatening way. Potentially threatening topics are: finances (revenue, profit, budget), personal information, competitive strategy, trade secrets, etc. Keep in mind you may have to ask questions about some of these topics at some point during a needs analysis. Be sure to do this after you have established trust and value in your relationship.
  • 15. CONTRACT Your Way Around Sensitive Topic Areas
  • 16. It’s human nature that people like to know where they’re going, and dislike being led into the unknown... especially by a salesperson! Use your knowledge of contracting to introduce sensitive topics. Explain why you are asking a question about a topic, and what the benefits to the prospect are in answering.
  • 17. ASK One Question at a Time
  • 18. Avoid complex, multi-part, or compound questions. Take ’em apart and ask them one at a time to make your questions easy to understand.
  • 20. Maintain eye contact. Reflect. Clarify. Ask follow-up questions. You’re not listening when you’re busy forming the next question while the prospect is still answering the last one. It's OK if there is some “dead air” while you ponder and digest what was just said. Also, take some notes to demonstrate you are listening to their answers.
  • 22. If you want to discover the client’s needs from the client’s point of view, you have to pose your questions from the client’s point of view! Clients will sense quickly—and react poorly—if your line of questioning is designed to define their problems from your point of view or if it’s a thinly-veiled attempt to lead them down the path toward your pitch. Drop the leading questions, and don’t accidentally telegraph the desired or expected answer.
  • 24. Allow the prospect to take the conversation into areas of the client’s interest. Follow the conversation where the client takes it and ask follow-up questions.
  • 25. BE Genuine and Sincere
  • 26. Questions always sound 100% better when you really want to know the answer! Be genuinely interested. When you are, you’ll find yourself naturally asking a lot of good follow-up questions.
  • 27. ADJUST To Their Behavioral Style
  • 28. Pay closest attention to their pace (is it quick or laid back?) and priority (whether they want to handle the task first or build a relationship first) and adjust your style to theirs.
  • 29. LAST But Not Least
  • 30. When great salespeople work with a customer, an unbiased observer can’t tell which of the two people is the seller and which is the buyer. Don’t place the client on the witness stand and don’t conduct a cold Q&A. Instead, aim for a lively, interactive, and creative conversation between two peers... one of whom would like to able to offer real help, and the other of whom will always gladly accept real help.
  • 31. For more information on conducting a needs analysis that delivers value to the customer and the seller, download The Hourglass Needs Analysis Method and learn the secrets employed by world-class sellers!