The Benefits of Deeper Questions

Why don’t you ask deeper questions? Are you more afraid of the questions or the answers?

Deeper questions

  • Uncover concerns
  • Shift the conversation
  • Invite transparency
  • Shift the mood
  • Provoke deeper thinking

Asking Deeper Questions

“Live your questions now, and perhaps even without knowing it, you will live along some distant day into your answers.”Rainer Maria Rilke

Asking Deeper Questions of Yourself

It starts by asking yourself deeper questions. In her TED Talk Christine Comaford, shares the importance of finding “your one big question.” The finding (and answering) of this “question” is a way to “intentionally evolve. She invites listeners to 1) reveal yourself 2) stand for yourself and 3) get still as you look for your questions.

Asking Deeper Questions Of Others

When, asking questions of others, pause and give yourself time to formulate the best question. Proactively plan your deeper questions as you plan your day. Make a point of asking at least one deeper question in any significant meeting you attend.

Power Questions by Andrew Sobel and Jerold Panas and StoryCorps are great resources to help you plan deeper questions for a variety of circumstances.

I asked Andrew Sobel to share the best questions for three of the most challenging topics for frontline leaders: dealing with disengagement, building confidence, and helping someone feeling overwhelmed.

“Sometimes the simplest question is the best. For example, ask your people often, ‘What do you think?’ Or, ‘How can I be helpful to you right now?’ Ask personal questions–‘How did you get your start?’ Turn statements into questions. Instead of, ‘We really need to burn the midnight oil if we’re going to hit our targets this month” ask “Here’s what we’re up against. What are your thoughts?”
~Andrew Sobel

Addressing Disengagement

  1. What is the one thing we could do to make it easier for you to do your job effectively? 
  2. What can I do to help you be more effective in your job? 
  3. What makes you proud—or not proud—to work here? 
  4. What’s the most and least engaging part of your work? 

Building Confidence

  1. What options are you considering right now? 
  2. What do you think are the pros and cons? 
  3. What do you think you should do? 
  4. What is most puzzling or difficult about this?
  5. What have you done in the past in similar or analogous situations? 
  6. What’s your biggest unanswered question about this situation?
  7. Who do you think has the right experience to help you with this? 

Helping the Overwhelmed

  1. What’s something that’s very hard to do for you but which would really help you be more successful? If there were no constraints—what could help make it happen? 
  2. How can I help you right now?
  3. What people or resources would be helpful to you right now? 
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Karin Hurt

Karin Hurt, is CEO of Let’s Grow Leaders and a former Verizon Wireless executive. Karin was named on Inc.’s list of 100 Great Leadership Speakers for Your Next Conference, the American Management Association List of 50 Leaders to Watch, and as a Trust Across America Top Thought Leader in Trust. She’s the award-winning author of two books, Winning Well: A Manager’s Guide to Getting Results— Without Losing Your Soul, and Overcoming an Imperfect Boss. She’s regularly featured in business publications including Fast Company, Entrepreneur, and Inc.

16 Comments

  1. The overwhelming majority of managers/leaders have a very hard time asking questions. They’re always in the mode of “fixing.” There are many implications, not good ones, for this way of thinking.

    Favorite question? I don’t have one. When I first became an executive coach, almost 10 years ago, I looked for books on great questions. I purchased one or two. I didn’t get to far with either read. Why?

    I came to realize the “best” question is the one that happens in the “moment.” Spontaneously. Extemporaneously. The one that hits the client like a blind right cross. The question they never saw coming. The one that lands, sticks, paralyzes, etc.

    How do I know I’ve asked a good question? The client, says “that’s a great question.” How do I know I’ve asked a Great question? I hear silence. This means they’re giving their response serious thought. That’s when I go to the fridge to get a celery stick.

    p.s. Second week of my 21 day plant based challenge is going better than week one. Searching for tantalizing foods to marry my taste buds has been fun.

  2. I think you would enjoy Ken Coleman’s new book, One Question: Life-Changing Answers from Today’s Leading Voices. I haven’t read it (yet) but I have heard him interviewed about it and it sounds right up your alley.

    http://www.amazon.com/gp/product/145167502X/ref=as_li_ss_tl?ie=UTF8&camp=1789&creative=390957&creativeASIN=145167502X&linkCode=as2&tag=legalearsyst-20

    It’s all about questions…

    My favorite is after a project goes miserably bad, to ask:

    What did we do well?
    What did we get right?
    How can we repeat that and add on to it?

    And similarly,

    What can we use from this in a positive way?

  3. Karin,

    I noticed most of the deep questions begin with WHAT ….
    Sometimes the deepest questions begin with WHY.

    Thanks for the great post. Thought provoking.
    Thanks for sharing.
    Lolly

    • Karin, What questions are future focused. Why questions tend to look back. Sometimes it’s a matter of semantics. I try to stay with the “What.”

    • Lolly and Steve, LOVE the conversation. Lolly, I agree with you, some of the best questions are “why”. And Steve, yes, “what” questions are awesome at narrowing down to action. Of course there are also some good future-headed “why” questions… “why do you want to do this?” etc.

  4. Karin
    Thank you for another insightful post
    In today’s fast paced world, one of the best things managers can do for their teams is help them reflect by asking powerful questions. I read somewhere ‘The quality of questions we ask ourselves determines the quality of our lives’ and that has stayed with me since. “How can I” is an example of a great question and I coach my clients to use it. Time and again they have come with good ideas where none existed using this one question.

  5. Karin. I have questions for you. What motivates you to respond at length to some comments? How do you select your titles? How important to you are attracting titles? What concerns do you have post publishing? How do you feel when a reader makes a comment? Have your ever said to yourself what a silly comment? What are your rewards from writing? When do you write? Have your ever had the thought why do I write? have your considered quitting sometimes?

    • Wow, Ali… what a challenge. Here you go.

      Q: What motivates me to respond to comments?
      A: I am working to build a community where we can grow as leaders together. The engagement and conversation is the richest part. My favorite is when the community begins to interact and respond to one another.

      Q: How do I select my titles?
      A: This one is tricky for me… I don’t think this is my strongest area. I am tempted to find something cute and fun, like my “diaper genie feedback” post… however they are not easily searchable via google, and end up not gettting as much traffic. I try to mix some of the cute with some of the more searchable.

      Q: How do I feel when a reader makes a comment?
      A: Wonderful. Sometimes the silliest comment are the most fun.

      Q: What are my rewards for writing
      A: Introspection. Connections. Relationships. Contribution. Growing leaders.

      Q: When do I write
      A: Early mornings. Weekends. Airplanes. Hotel rooms late at night.

      Q: Do I ever question why, or want to quit?
      A: Not yet. Sometimes, I get overwhelmed with the pressure to continue the daily practice… but i’m always glad in the end.

      Thanks for asking. Namaste.

      Why do you produce your great presentations?

  6. Karin-careful readers shall notice that none of your motivators is money. Genuine leaders are like that.
    As for the titles, I give you my secret. Read my presentation below and check the links in the slides. The presentation shows why I selected the chosen title in detail.
    http://www.slideshare.net/hudali15/juicy-titles-do-not-lose-readers

    I write when I have all the needed information ready. I feel propelled to write. During writing, I focus and nothing distracts me. Mornings are the best times for me to write.

  7. The comments here are so inspiring. I had a phone interview yesterday for a intriguing position. At the end of the interview, I was asked if there was anything else I wanted to add. I had some notes on my pad & I reviewed two significant bullets. Their open ended question led to me sharing more about me. Now I read the questions here and realize the last question of any interview can be an opportunity to find out about the organization or the individuals on the other side of the table or phone line. The opportunity is to connect. Their apt question could have led to more connection. I don’t regret I pulled out my trust two bullet points at the end, but another option would have been to engage — and ask a question & show that I am interested.

  8. Pingback: Let's Grow Leaders | Real Leaders, Better Business | How to Encourage the Lazy and Disengaged

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