Questioning Questions

Questioning Questions

People come to us for various reasons.  Some to chat, others to ask opinions and many to seek guidance.  In the work environment we are often too quick to answer questions rather than use the time to:

·       Train

·       Show interest &, concern

·       Delegate when appropriate

Questioning Questions allows the conversation to quickly get to the root of the questioner’s real need.

With a little practice, most employees recapture hours of time that were spent in well-meaning conversations that seldom delivered the results desired.

When a question is first asked or a conversation is in process, listen carefully for a key word or phrase that begs to have a questioned asked in return or as a response.  That question, if the right question, will cause the speaker to reflect and then clarify what they were trying to say.

Questioning Questions Technique

Questioning Questions allows Mark’s conversation to quickly get to the root of the Dave’s real need.  With a little practice, most employees recapture hours of time that were spent in well-meaning conversations that seldom delivered the results desired.

Below is a graphic that represents Dave asking Mark a question.  Dave goes on for a sentence or two when Mark interrupts and asks a question (Q1).  Dave answers the question, narrowing down the breath of his concerns, with the effect of bypassing unnecessary details.  Mark continues to interrupt by asking questions as needed (Q2-Q4) to allow Dave to think on his feet.  At some point, with clarifying questions and reflection, Dave has his answer and is able to articulate what he really needs from Mark

Questioning Questions Examples: Condensing Conversations

When a question is first asked or a conversation is in process, listen carefully for a key word or phrase (generous listening) that begs to have a questioned asked in return.  That question, if the right question, will cause the speaker to go down and reflect at a deeper level of detail, and then clarify what they were trying to say.

Dave asks a question, “Mark, is it possible for my group to get a budget increase this quarter?  My experience has been that even the act of asking can have a detrimental effect on following quarters.  Is that true?”

Mark Giving a Normal Reaction: “Yeh, I have never had any luck mid-quarter. What do you need it for?” (Dave would then go into more details, even though he has been told it is impossible).

Key Words: possible, experience, budget increase & detrimental effect

Mark Questioning Key Words:

1) “My experience is that there is always money available - if justified!  I would be interested in your experience of what you feel is possible in mid-quarter as it relates to budget increases?” (Dave is given the opportunity, invited into the conversation, to reflect and put into words what lies beneath his question).

2) “It would also be valuable to me to understand what kind of increase your thinking of for this quarter, and for what purpose?   Tell me about this.”

3) “What do you think the detrimental effects would be?”

P Listening for key words goes both ways. If Dave were consciously listening to Mark’s comments, he would notice Mark used the key word justified.  Asking Mark for detailed clarification of what he believes justifies getting a budget increase would increase his chances greatly. 

An important point here is that key words and phrases riddle all conversations.  What makes key words and phrases difficult to hear is our hardwired mind-set, emotional expectations, and reactions to other’s hardwired behavior?  In other words, hardwiring keeps most people semi-unconscious when engaged in risky conversations with others.  Thus we do not hear key words as portals into a deeper conversation 


As a reader of this chapter, you will have had many moments where you asked yourself, “How is he using that word - What does he means by semi-conscious? 

Who is Mark?  I don’t understand how this relates to his earlier point!”  These are “awakenings” to something missing, unclear or lacking in the author’s explanations and examples.  If we were in a conversation, these would be key words or phrases which could be used to get clarity.


If these “awakenings to something missing” are formed into questions for clarification, the tool of Questioning Questions has arises naturally.  We all do this to some extent in conversations at home and work.  The trick is to awaken during conversations that pose some risk or consequence with significant people and not to continue in a semi-conscious mode.  To be truly engaged, it is important to listen to every word attentively and ask for clarification when the “something’s missing” feeling prompts us to interrupt the conversation and ask a question.


Pulling or Pushing Questions


Pulling Questions:

  • Can interrupt by asking a question that deepens the employee’s conversation.
  • Invite the speaker to stay in the conversation by referring to the speaker’s behavior and core intentions (value).
  • Maintain the conversation’s behavior/intention balance through intentional language.
  • Give the speaker a feeling that we want them to continue, but at a deeper, more thoughtful level.
  • Pushing Questions:
  • Can interrupt by asking a question that stops the employee’s conversation.
  • Push the speaker out the conversation by only referring to what or to the way something was said, completely ignoring the speaker’s core intentions (value).
  • Disrupt the conversation’s behavior/intention balance by focusing on content or behavior.
  • Give the speaker a feeling that we do not want them to continue.
  • Can make the employee feel defensive, misunderstood or under valued.
  • Leave the employee with a sense of being wrong that is hard to pinpoint

Q the Q Summary – Time To Resolution

In the following timetable, we will look at the time savings as a result of using Deep Listening and Questioning Questions in the Solve process.  With out feeling interrupted or blamed, the employee is pulled into the conversation and helped to “language” their problem and act on suggestions for resolving the issue.

10 seconds into the initial conversation: 

Mark clarifies whether Dave wants a Listen or Solve conversation.  Since this time it is Solve, he asks Dave to gather the appropriate people at a specific time.  Mark does not ask for details from Dave.


Later, Mark sets the stage for the Solve conversation when Mary and Dave are present.  He wants everyone to assume good intentions so that they can focus on behavior without taking comments personally.  He then asks Dave a question.

10 seconds into Dave’s replies:

Mark interrupts Dave in mid sentence.  He asks Dave a series of questions based on a “loaded” word used in his first sentence – annoyed.   From Dave’s point of view, Mary seemed annoyed when he questioned the schedule.

Mark then asks Dave to give several other words that are like annoyed.  He does this to help Dave bring his unspoken feelings to surface regarding Mary’s behavior.   Dave comes up with preoccupied, angry and frustrated for three additional ways to describe Mary’s behavior.

2 minutes into the Solve conversation: 

Mark flips the conversation away from Dave by directly asking Mary to clarify whether she was upset with Dave, Dave’s behavior, or herself.  Carefully phrasing the question to direct Mary’s self-reflection, and then pull her into the conversation, Mark says, “Mary, are you preoccupied, angry, frustrated or annoyed with Dave personally, with Dave’s schedule questions or with your own work?”  Mary’s multiple answers allow Dave to reflect on a solution, rather than on reacting personally or defensively. 

5 minutes into the Solve conversation:

Mark allows Mary to complete her answers and is prepared to ask questions if necessary.  Mark then turns the conversation to Dave for his clarification of what he has heard Mary say in response to multiple behavioral descriptions. 

It should have become obvious at this point that asking Mary a question that requires multiple answers is important in resolving emotionally charged issues (i.e., “Mary, are you preoccupied, angry, frustrated or annoyed with Dave personally, with Dave’s schedule questions or with your own work?”).  Questions and answers with multiple responses move a potentially button-pushing reaction, in this case for Dave, to one that inclusively makes Mary and Dave feel like a part of the problem and the solution.  Achieving a mutual feeling of involvement is the key here. 

8 minutes into the Solve conversation

After Dave’s clarification, Mark has achieved enough room on the playing field so that the two employees are not bumping into each other when they talk.  Another way to express this is, Mark has sufficiently deepened the conversation container for the Dave and Mary to no longer push each other’s hardwired buttons before they get their common intentions on the table.

Mark now raps up the gathering by asking one last question, “Dave and Mary, what can the two of you do together to keep focused on the job to be done and remember to keep each other’s intentions in the conversation?”  Essentially Mark is formally handing off the expanded container to them.


When employees with relationship issues approach us, we normally go into either an automatic reactive or responsive way of listening.  If


, we may often find ourselves habitually repeating what was said to us earlier in our career.  These are often overused platitudes passed on with little effect on resolving real-time relationship conflict. 

If we are in a


mode, we may have the insight to begin a process that will not only efficiently solve the relationship issue, but also provide valuable training to the employee.  The Listen or Solve process gives us a way to respond to real needs, with viable options, that channel the employee’s productivity back to the job at hand and towards cooperative relationships with co-workers.  Options that will streamline conversations, minimize the time in conflict, and move the issue towards resolution and cooperation quickly.

The process of Listen or Solve is directly linked to the skills of

Intentional Language

, the



Generous Listening


Questioning Questions

.  Moreover, the successful integration of these options into an unforgettable, ultimately useful, real-time tool is to see that their common threads are pulled together by the art of questioning.  The art of questioning can be further simplified by understanding two types of questions: those that


listeners to react to our question and those questions that


listeners respectively into the conversation to continue the dialogue.  The bottom line to using the Listen or Solve process effectively, is to ask more responsive, pulling questions than using reactive, pushing questions – whenever, where ever or whatever the relationship situation.

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© Scott Taylor 2020