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The Two Most Insightful Questions

If you really want to get a current pulse on someone, whether that’s your employee, boss, client, child, or friend, here are the two questions to ask:

  1. So, what’s going on?
  2. How’s that working for you?

Ask the first question. Stop. Listen.

Ask the second question. Stop. Listen.

The challenge is to stop and listen. And I mean, really listen.

I received this information from a Rabbi who has done private counseling for over 30 years.

This simple concept works – not only in a counseling situation, but also in your everyday life. Try it.

Any Questions? The Art of Asking & Answering Questions


One of my beloved uncles just passed away.  I asked my cousin-in-law, “How’s Beth coping with the loss of her dad?”  He replied, “She’s doing fine.  She’s already gone through the grieving process.”  Later I asked Beth directly, “How are you coping with your loss?”  She sighed, “I haven’t processed it yet.  I can’t believe it’s happened.  I’m sure it will hit me soon.”

Same question about the same issue to two different people with two vastly different responses.  And they’re even married!

Does that make their answers “wrong”?  No.

Does that mean that questions, and their accompanying answers, go through personal filter systems with personal slants of perception?  Yes.

Does that infer that asking questions and analyzing answers become tricky?  Yes.

According to The Teaching and Learning Laboratory (TLL), a think tank designed to improve the quality of teaching and learning at MIT, the craft of asking and answering questions is one that is built upon several different skills.   These skills include:

  • phrasing and sequencing questions effectively;
  • responding to questions so that time is used efficiently;
  • keeping questions from leading into digressions (unless those digressions are a worthwhile investment of time and energy);
  • using the right tone and delivery when asking questions or responding to them; and
  • dealing with the personalities and methods of interaction as questioners and respondents.

In the spirit of “practicing what you preach,” this article will attempt to ask and answer questions about asking and answering questions, keeping MIT’s approach in mind.

What makes a question effective?

A good question is relatively short, clear, and unambiguous. Ask only one question at a time. Pouring out a string of questions (even if they are on the same topic) is likely to confuse your prospect or client, who often won’t know where to begin an answer.

Pay attention to the responses you get because they will tell you how effectively you have phrased the question. Sometimes when prospects don’t respond or respond poorly, it’s because the question has been worded either too vaguely or too broadly. It may help to think backwards: Begin with the answer you want to get and then devise a question that will lead to that answer.

What are the different kinds of questions to use?

MIT suggests that the best way to categorize questions is to think of them along a continuum of relatively closed to relatively open.

Closed questions ask for a very specific answer.  An example would be the 3 questions I posed near the beginning of this article that asked for a yes/no response.  Another type of closed question is the “Are-you-with-me?” question that asks the listener to acknowledge their buy in.

Open questions require more thought.  (“How’s Beth coping with her loss?”)  These questions will provide greater insights.  The trick is to be quiet and listen to the responses.

After you ask a question, how long should you wait for a response?

Hold out as long as possible. Many people, if they don’t get a response right away, immediately rephrase the question, repeat it, or even answer it themselves. The latter is a particularly bad strategy since the listener will be even less inclined to make the effort to answer a question.

Let at least five seconds go by before you say anything.  And that is hard to do.  A study of college physics classrooms found that increasing wait time to five seconds had a positive effect on class participation, not only during that particular class session, but also for the course as a whole. Be patient.

What can you do to get your prospects to ask questions?

Give your prospect a chance to frame their questions. The silence that follows your earnest, “What questions do you have?” may be uncomfortable, but it’s important. Convince your potential client with your tone of voice and body language that you are receptive to their inquiries.  Do this from the very first interaction, and be enthusiastic when you receive questions.

How can you best manage the process of answering prospects’ questions?

  • Be sure you understand the question that’s being asked. This challenge can be easily handled by repeating the question. If you’re not sure what the prospect asked, rephrase the question in your own words, and check to make sure that’s what he or she wants to know.  
  • Be as direct as possible with your answer.  Questions get asked out of confusion or curiosity about something. Therefore, it’s usually a good idea to be concise and honest with your response.
  • Be aware of your eye contact.  If you are answering questions from multiple people at one setting, such as a husband-wife team during a home presentation, look at both people when answering your question.  The passive participant may be the decision-maker.  Be inclusive through your eye contact.

How do you know when you’ve got the best answer?

Izzy Gesell, a personal and business coach, says, “The first answer rarely identifies the underlying cause or motivations.”  His rule of thumb is to go to the second and third levels.  His example:

Level 1:  “Why are you hesitant to make this decision?”   “I’m overwhelmed.”

Level 2:  “Why are you overwhelmed?”    “I think I’m confused about the insurance appraisal vs. your numbers.”

Level 3:  “How is this confusing you?”    “My neighbors had a bad experience…”

Gesell says, “It’s HERE that you’ll get a valuable discussion.  The root of the issue is at this third level.  A much more potentially productive conversation will happen now, rather than just answering ‘Don’t be overwhelmed’, which is one of the choices at the first level which doesn’t get to the essence of the situation.”

Gesell emphasizes, “You know you have the best answer when the issue gets resolved or the prospect is able to challenge their own limiting assumptions.”

Any questions?  Call or email me.


  • Teach Talk Library, Teaching and Learning Laboratory at MIT
  • Izzy Gesell, CSP, www.izzyg.com.

The Columbo Method – How to diffuse any situation

Remember Peter Falk? He’s an actor best known for his role as Lieutenant Columbo in the TV series Columbo. As the star of that 1970’s show, he was “everyone’s favorite rumpled television detective”, writes historian David Fantle. The beauty of Columbo was watching how he unraveled the mysteries and crimes.

His method – asking insightful questions in a humble manner.

Yesterday I had lunch with a very successful client. He said, “Karen, I use the Columbo Method to negotiate, sell, and diffuse any situation.” I commented, “I’ve watched Peter Falk wearing his wrinkled raincoat in Columbo and always liked him.” He said, “Exactly! He solved the crime, and got people to tell him everything. Even the bad guys trusted him… until they lost the game.”

My client explained, “Columbo got the job done by asking these three questions. And I use those same questions to diffuse anger, get agreement, get the sale, talk to my teenage daughter …whatever.”

Here are my client’s Columbo Method Three Questions:
1. What did you mean by that? (Allows the other person to further explain the situation)
2. How did you come to that conclusion? Or – What makes you think that way? (This allows you to really get inside the other person’s head)
3. Have you ever considered __________ Or – Another way to look at this is ___________ and you fill in this blank with your alternative solution.

Good luck in solving your next crime or negotiating your next deal!

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