7 Suggestions for Asking More Powerful Questions

When I started out in my career, the key to success was having the right answers. If the boss had a question, he expected me to have the answer—or know where to get it. Those who advanced in their careers the quickest were seemingly the ones who had the most answers.

Questions Flow Chart Being Drawn by a Businessman - Photo courtesy of ©iStockphoto.com/matspersson0, Image #16588175

Photo courtesy of ©iStockphoto.com/matspersson0

But as I began to ascend the corporate ladder, I discovered that the key to success began to shift. It became less and less about having the right answers and more and more about having the right questions.In the age of Google, answers are the easy part. You can look up virtually anything and have the answer almost instantaneously. But this only happens if you know how to ask the right questions.

If you are going to be a successful leader, you are going to have to learn how to ask good questions. Here are seven tips for taking this skill to the next level.

  1. Ask open-ended questions. Questions that can be answered “yes” or “no” are closed-ended questions. They don’t generate discussion and they rarely yield any insight. By asking open-ended questions, you get far more interesting insights.

    For example, instead of asking, “Are you happy with your results?” you might ask, “Why do you think you got the results you did?” The first question can only be answered “yes” or “no.” The second question invites reflection and starts a discussion.

  2. Get behind the assumptions. Every business decision is based on assumptions. If you don’t understand these assumptions, you may, in fact, make a bad decision. It’s often helpful to ask yourself first—and then your colleagues—“What are we assuming in this scenario?”

    Then you need to keep peeling the layers off the onion until you get comfortable with the assumptions. This is where people often make mistakes. The logic may be impeccable, but if it’s built on faulty assumptions, you’ll end up with a faulty conclusion.

  3. Get both sides of the story. It is so easy to hear one side of the story, act on the information, and then be embarrassed when you find out that you only had halfthe facts.

    I have done this hundreds of times, I’m sure. I think I am getting better at getting both sides of the story, but I still consider myself “in recovery.” I have to constantly remind myself, There are at least two sides to every story.

  4. Ask follow-up questions. Avoid the temptation to comment on every question. Sometimes I like to see how many questions I can ask in a row without commenting. It’s amazing what you can learn when you do this.

    And it makes your comments or decisions much more informed. Often you don’t get to the real meat of an issue until you’ve gone several questions deep.

  5. Get comfortable with “dead air.” Most people get uncomfortable when things get quiet. They feel the obligation to fill the space with chatter. You can let this work to your advantage by just keeping your lips locked and your ears open.

    When you do, you will often find that people volunteer amazing amounts of information that you would have never obtained any other way.

  6. Help people discover their own insights. One of the best ways to mentor others is to ask rather than tell. Yes, you can pontificate to your subordinates, but your insights will not be as meaningful to them as they are to you. You can accomplish far more by leading them with good questions.

    One of my favorite, especially in the wake of a mistake or disappointment, is this: “What can we learn from this experience that might be useful to us in the future?”

  7. Understand the difference between facts and speculation. One of my former bosses once told me, “Make sure you tell me what you know and what you think you know, and make sure I know the difference.”

    People make all kinds of statements that they think are based on the facts. These should immediately cause your radar to go off. Often you will have to ask, “Do you know that to be a fact?” If so, “How do you know?” or “Can you provide me with the source for that statistic or claim?”

Finally, when you are asking questions, take notes. It communicates tremendous respect for the the person you are interviewing. It is also very helpful when things get quiet. You can go back over your notes and discover new questions you haven’t yet thought about or asked.

Question: What are some questions you have found useful as a leader? You can leave a comment by clicking here.
Want to launch your own blog or upgrade to self-hosted WordPress? Watch my free, twenty-minute screencast. I show you exactly how to do it. You don’t need any technical knowledge. Click here to get started.

Please note: I reserve the right to delete comments that are snarky, offensive, or off-topic. If in doubt, read My Comments Policy.

  • http://theordainedbarista.com/ Barry Hill

    I especially appreciate #2. I love the idea of really dealing with, and talking about, the assumptions before you move on.  Then you can clarify what people are thinking about the past, present, future, expectations, roles, trust that it will be completed.

  • http://sidekickgraphics.com/ George Gregory

    A great reminder. I’m a great one for telling people what I think, and am constantly reminding myself to ask questions and LISTEN in a deliberate way. When you do, it tells the person that they are important and shows you respect them. 

    You have to genuinely want to know what they think, with an open heart willing to consider their views.This is quite an adjustment, because it requires true humility on our part to become good listeners.

    I really liked the part about open-ended questions. Sometimes answers are messy, but taking the time to understand the nuances of a situation is important. Simple answers are often glib and don’t carry a lot of weight.

  • http://soulfari.blogspot.com/ Jay Cookingham

    Actively listening is a powerful relational tool, it helps us tune in the person we are trying to understand better. Great post brother!

    • http://www.timpeters.org/ Tim Peters

      Active listening is huge.  

  • http://www.jeffrandleman.com Jeff Randleman

    This post couple be reposted almost exactly as-is with the title “How To Communicate With Teens In Youth Ministry.”

    These principles all translate really well to what I do working with youth.  I’ve learned how to communicate in ways that allow teens to open up instead of closed, uneasy communication.

  • http://www.volunteerfringe.com/ Marney Mcnall

    Your post made me think of the book I’m currently reading called, ‘QUIET: The Power of Introverts in a World That Can’t Stop Talking’. The author, Susan Cain, discusses how simply asking questions is a method to give strength to a more introverted, mild-mannered person. 

    From QUIET…”And she tended to ask questions–lots of them–and actually listen to the answers, which, no matter your personality, is crucial to strong negotiation.”

    • Jim Martin

      Marney, good comment!  I have heard of this book but actually know very little about it.  I just downloaded the free sample onto my Kindle.

  • Wendy Claussen

    I believe when questions are asked using “WE” instead of “YOU”
    it builds a sense of community between all those involved in the discussion.
    Using YOU sounds like blame. Using WE sounds like teamwork. Thank you, Michael,
    for using WE throughout your post! :-)

    “What are WE assuming in this scenario?”
    “What steps can WE
    take to make sure WE understand both sides of the story?”

    “What can WE learn from this experience that might be useful
    to us in the future?”

    “Can you provide me with the resource for that statistic so
    WE know WE have our facts straight?”


  • Josh Glaser

    Working with a lot of ministry people, sometimes we’re too prone to only offering positive or “nice” feedback. This leaves us at a disadvantage if we’re ever going to grow or get better at what we do, so I’ve learned to also ask questions that require my team to look at our areas for improvement: “What could we do differently next time?” “How would you do your part differently next time?” “How can I serve you better on future projects?”

    • http://www.jmlalonde.com Joe Lalonde

       All great questions Josh, and ones that need to be asked. I like to ask the “What could we do differently question.” It leads to great follow up and growth.

  • http://www.learningalongtheway.com/ Lisa

    Great points for work relationships and really all relationships!  Engaging people and inviting their thoughts and contributions really are marks of a great leader; giving them space in the silence to contribute can be challenging (especially for an extrovert!) but very worthwhile.   Thanks for laying out these suggestions in a clear, practical way.

    • http://www.timpeters.org/ Tim Peters

      I agree Lisa.  Great questions for all relationships.

  • http://deuceology.wordpress.com Larry Carter

    My boss today asked me a question I didn’t have the answer for.  I had the opportunity to have gotten it before he asked, but I missed it.  He then gave me the opportunity to learn from that that and get the answer.  Just by asking me a question.

    • http://www.jmlalonde.com Joe Lalonde

       Sounds like a great learning opportunity Larry! Glad you were able to grow from the experience.

  • http://danblackonleadership.com/ Dan Black

    While in college I took some counseling classes which really helped when it come to asking listening and conversation skills (asking question skills). I believe it would benefit any leader/manager to take a counseling/conflict resolution class, because it will sharpen your skills in this area. Great post. 

  • Pingback: Monday Morning Musings | Old Testament 101

  • Kelly Williams

    One of the best questions I have found to ask us a variation of “What’s important about this?”. It adds a further dimension to the discussion and leads to greater insight.

    • http://www.jmlalonde.com Joe Lalonde

       Great question Kelly! I can see that leading to knowing the person’s heart.

    • Jim Martin

      This is a very good question.  I can see how this might be very insightful at times.

  • http://www.brendonwilsoncreative.com/ Brendon Wilson

    When I was younger .. not that I am old now, I had the extreme privilege to go through a number of the Dale Carnegie Courses and it has allowed me through the years to really ‘re-look’ at the way we ask questions. In fact, my mentor over at Dale Carnegie – Michael Crom (Carnegie’s Grandson) was famous for dead space …… Thanks for the great post – I will be sharing it with my team. 

    • http://www.jmlalonde.com Joe Lalonde

      I’ve been thinking about the Carnegie courses. This just pushed me one step closer!

      • http://www.brendonwilsoncreative.com/ Brendon Wilson

        I would say who I am today in leadership, people development and public speaking would have a lot to do with those courses …… not cheap but I literally use the Leadership Training for Managers Manual every week to help people go to a higher level. 

        • http://www.jmlalonde.com Joe Lalonde


  • Miranda

    Here’s what I always say when I notice a person’s (or an organization’s) success: “There’s no magic about it; they went about things in a manner that resulted to success.” So I ask questions like “What DID they DO right, and DIDN’T they DO wrong?” Observing such people or organizations as a case study, and asking the right questions – What are the things they DEEMED right to do? And, What are the things they made every effort to AVOID? – gives greater insight than one could possibly imagine. With these at the back of my mind, I get ready to be practical about what I discover, and to work hard as well.

    Another thing, do not decide to throw away a seemingly good idea because it appears ‘difficult’ to accomplish. This is where optimism (along with the right dose of realism) plays a huge role. If history has taught us anything, is that, what the mind can conceive, it can achieve. We can take a few lessons from history!

    • Jim Martin

      Miranda, good point!  Asking good questions can give so much insight and information.

  • http://cavemanreflections.blogspot.com/ Michael Mulligan

    I like the onion peeling idea.  At the center of the onion you find the heart.  I’ve learned people will share their hearts when you learn to ask questions like “how to you feel about this?” or “why is that important to you?”  Great post.

  • http://talesofwork.com/ kimanzi constable

    I think these questions are right on and if more leaders asked them, they would have better results. Most of the time leaders are too willing to bark out orders instead of asking the right questions.

  • http://www.learntodobusiness.com/ Kenneth Acha

    Great post. Nothing reveals a person’s depth of understanding of a subject matter like the questions that person asks. The ones that he answers only reveal a little bit. The ones he asks tell much more about his depth of understanding or insight. But of course, this is true only when people ask honest questions. When they ask to know more about a situation etc.
    So when I talk to someone that I shepherd, I prefer to have them ask me questions than asking them questions. (Now this won’t work if you are doing an interview or something like that.) The key is to create an environment where those questions are spontaneous. If you make them feel pressured to ask you questions, you dilute the revelatory strength of this technique.

    • Jim Martin

      You make a good point, Kenneth, about questions revealing the depth of a person’s understanding.  That is so true.  When I teach a class, I know that my questions are better if I have a good grasp of the content.

  • Carlos Gutierrez

    Premises are use to find out assertive answers.

  • http://www.andrewsobel.com/ Andrew Sobel

    Great list. I like to ask several other types of questions as well:

    Empowerment questions: “What’s the best way for us to use this time together?”  “What have you tried already? What worked/didn’t work?”  “What do you think is the right decision?”  “What did you learn”

    Passion questions: “Why do you do what you do?”  “What are you doing in your work that you are the most excited about?” “Outside of your major in college, what did you study?”  “If you hadn’t become a lawyer, what would you have done?”

    Aspirational questions: “You’ve had a great career…what else would you like to accomplish?” “You’ve achieved significant improvements in the last two years–where do think future growth will come from?” “If you had additional time and resources, where would you put them”

    And finally, the ultimate question that Jesus asked his disciples before entering Jerusalem for the final time: “Who do you say I am?”

    (Matthew 16:15)
    . In other words, 

    As a leader, do people know who you really are and what you stand for? Do they know what your values are and what drives you? When you are gone, will the organization be able to carry on?

    Many of these are drawn from my new book, Power Questions (Wiley). I’ve been using these–practicing, really–with my own senior business clients and I’ve seen that the impact of the right question at the right time can be transformational.

    • http://www.timpeters.org/ Tim Peters

      Andrew – I like these questions.  Very good.  

    • Jim Martin

      Andrew, these are very good questions.  Also, you are so right.  The right question at the right time can be so significant.

  • http://www.jmlalonde.com Joe Lalonde

    Here are my top three questions:

    1. This worked well this time. What could we do next time to make it even better?
    2. What stuck out to you in this experience? – This helps you to see how others viewed a situation. It may be the same or you could be shocked at how different your team member saw  it.
    3. What are you reading this week?

    • http://www.timpeters.org/ Tim Peters

      Great questions, Joe. 

      • http://www.jmlalonde.com Joe Lalonde

         Thanks Tim. Do you have any questions you would add to the list?

    • Jim Martin

      Joe, I really like your questions!

  • http://bbcjc.com/ Randy Dignan

    Great article!  I immediately thought of how many times you see the question mark after the many Words of Christ!  Jesus answered many questions with questions and was never afraid of the dead air!  I sure love the article!  Thank you much!

    • Jim Martin

      Randy, you are so right!  Jesus had a way of asking the kind of questions that challenged others to wrestle with the heart of a particular matter.

    • http://michaelhyatt.com Michael Hyatt

      Yes, Jesus is such a great example of this.

  • http://blog.higherpixels.com/ Brian

    I think one of the most important things to do after asking these questions is to think “gray.” 

    Steven Sample, former president of USC, had this great book for leaders called “The Contrarian Guide to Leadership,” and in it he talked about the difference between managers and leaders. Managers are often valued with how quickly they can react to the new data (answers) they get from their customers/employees, but leaders should practice slower, more measured responses.

    As humans, we seem to strive for a black & white sort of world where the questions we ask and the answers we seek are simple and straightforward. The art of practicing “gray” thinking though, encourages us to think more freely about the data being retrieved before making a conclusion.

    Great article! Thanks for sharing!

    • Rachel Lance

      Love his thoughts on grey thinking! And I can definitely see how that concept would help a person grow the ability to ask meaningful questions.

  • Shawn Callahan

    I met a senior leader of a bank and written in bold letters of his notebook was “DON’T ASK WHY.” He said that when he asks Why? people get defensive. But by asking all the other types of questions “Why” emerges.

    • Rachel Lance

      Very interesting rule. Seems like a great addition to the onion peeling illustration.

  • http://www.liveitforward.com/ Kent Julian

    I have found “if only” questions to be great focusing questions in leadership. For instance:

    1. If you could change only one thing in our organization, what would it be?

    2. If you could target only one customer, who would it be?

    3. If you could invest your life in only one pursuit, what would it be?

    • Rachel Lance

      I like your idea, Kent. It’s a helpful framework for building a stronger question-asking muscle. Thanks!

      • http://www.liveitforward.com/ Kent Julian

        “Stronger question-asking muscle” – I like that phrasing, Rachel!

    • http://michaelhyatt.com Michael Hyatt

      These are very good, Kent. Thank you for sharing.

      • http://www.liveitforward.com/ Kent Julian

        Thanks for starting this discussion, Michael. Excellent!

  • http://uma-maheswaran.blogspot.com/ Uma Maheswaran S

    Mike! I have seen in my experience that anyone who wants to grow as a great leader must be walking towards wisdom. In order to succeed in that objective, he/she must learn to ask profound questions always.  I feel putting the right question is a great plus for a leader.

  • http://relationships-relationshiptips.blogspot.com/ Njut Tabi Godlove

    just the right article for me at the right time. getting into a new career. it never gets better. http://rhapsody-of-realities.blogspot.com

  • http://www.creativehogg.com/ Josh Hogg

    This post could be the some of the most valuable to beginning and veteran professionals alike.

    I especially like the suggestion contained in #4 – Seeing how many times you can ask questions without commenting. This is so important to a leader, not to mention a service provider. It allows you to find both sides of the story before you pick a direction; and it helps make sure you understand everything you need to go forward.

    One of the biggest parts of my job is assumptions. Everything I do is based off assumptions, and when I give someone the results of my work, I explicitly state my assumptions to them, so there is no confusion. Often, most of the work is evaluating what assumptions to make (do we be conservative or not?).

    And finally, one of the best things for questions I find is directing them at certain people, to make sure the introverts give their input. Introverts aren’t necessarily shy, they are just thoughtful people that think in their mind rather than out loud like most extroverts. This can create a problem when the extroverts are all speaking and brain storming and the introvert gets no input because this isn’t his thought process. A well directed question at an introvert will ‘quiet’ the extroverts, long enough for him/her to speak.

  • http://traceembry.com/ Joshua Wallace

    As a leader I am constantly challenged with knowing how to ask the right questions. Often times I forget this important concept. Great post! Thanks for a practical reminder!

  • http://twitter.com/PepperVA_Grace PepperVA_Grace

    Practicing these seven suggestions, would take time
    depending on each leader’s personality.
    Based on my experience, I would always make a habit of asking open ended
    questions and to ask follow-up questions. I believe that once you apply these
    seven suggestions effectively, you can communicate more with your colleagues,
    bridging the gap and to feel better as a leader. 

  • Katy Field

    “How would you define your different constituencies in this group you’re trying to work with?” seems to elicit enlightening responses for my high school students and for me as I try to teach them experientially about leadership through the medium of a group collaborative endeavor. I tend to ask this question when they come to me one-on-one because they’re frustrated with trying to collaborate without an auhoritarian in charge. Usually I learn something about how they see each other, and they realize there’s an untapped group of people who could potentially be turned into allies more easily than the 1 or 2 people who were causing them the most consternation.

  • Pingback: 7 Suggestions for Asking More Powerful Questions « Todd Stocker's Blog

  • Pingback: Leadership Lessons from Potty Training via Mad Gravity

  • Pingback: TLW 84: Question, Question, Who’s Got the Question?

  • Pingback: Asking Better Questions | John Carroll's BLOG

  • Pingback: Twitter Highlight Reel | TonyMorganLive.com

  • Pingback: Strategic Questions Mind Map | IQ Matrix Blog

  • Al Weinberg

    What’s so good if we do this? And. What’s so bad I’d we don’t?

  • Pingback: WorkingAtTheEdge.org Daily Links 04/08/2012 | Working at the edge

  • http://www.halfabubbleout.com/ Natasha Hawkins

    At Half a Bubble Out we often ask “Is that helpful, or has this been helpful for you?”  If something we said or did wasn’t helpful to a client or co-worker then we missed our target. Questions are treated like gold at HaBO, great blog! http://www.halfabubbleout.com/blog

  • Pingback: Worship Service Review: Asking Powerful Questions « creativeworshipideas

  • Pingback: Friday Link Round-Up

  • Janice

     I have found that by regularly asking “What tools do you need to do your job better?” and “How may I support you?” demonstrate a leader’s commitment. Especially when there is a commitment to hear and then act.

  • Pingback: Networking 101: Schmoozing Like A Pro!

  • Erwin Pfuhler

    I have heard the first time about powerful question from Charles M. Savage (5th Generation Management). Luckily he lives in Munich, Germany and I met him at a Toastmasters meeting. There is one point I miss in your compilation. It is motivation and inspiration. These two aspects, at least one of them should be tackled by a powerful question. The hard part is applying this knowledge in a natural manner while being in a conversation. Thanks for sharing your insights with us!

  • http://www.think2ool.com/ Scott Pickard

    The Art of the Good Question: 
    the right content,
    asked in the right way, 
    at the right time

  • Pingback: 5 Great Leadership Posts For The Week • Leadership Done Right

  • Pingback: Why Is It Important For Your Career To Ask Questions On The Job?

  • Rafi Qallander

    The main point is giving importance to the questioner’s question. Although i am freshman in university but when i was in 1oth one of my teacher have told me that :”the more you are listening to someone, the more you pursuing him to talk.” i have always tried to look and keep aye contact with the person who is talking to me from which i found a special attention of speaker even if i don’t know too. I really like it and it contains more things special.

  • http://sacramentolocalseo.blogspot.com/ Jay Williams

    As a business leader, community leader and a father, I am constantly challenged with knowing how to deal with all sorts of different types of people and personalities and ask the right
    questions the right way is more then half the battle. Often times I find myself forgetting the importance of concept in the question. Also to use the good old KISS system.

    “LOCAL SEO Guru” http://sacramentolocalseo.blogspot.com/