• Andrew Quagliata

Ask Better Questions

Updated: Nov 9, 2019



In the last few years more students than ever have asked me some version of the following question: “How do I ask good questions?” They want to know how to ask better questions in class, job interviews, to their colleagues, and in their personal lives. I have no data to explain why I’m getting this question more often, but it speaks to my students desire to develop stronger critical thinking skills.


Like all skills, learning to ask good questions takes practice.


  1. Listen. Don’t listen with the intent to respond. Listen with the intent to understand. Give the person you are speaking with your full attention. And don’t rush to ask a question; be comfortable with silence.

  2. Reframe how you think about questions. Asking a question doesn’t indicate a lack of knowledge on your part, it demonstrates your interest in the speaker and desire to learn more. Try not to worry about what other people think. Researchers at Harvard found that question askers are rarely perceived as rude or incompetent. In fact, they found asking questions increases interpersonal liking because it shows you are interested in hearing their perspective.

  3. Ask with genuine curiosity. Don’t make the question about you and don’t ask questions you know the answer to.

  4. Consider how you begin your questions. Questions that begin with “who,” “what,” “where,” “when,” or “how” tend to be stronger than those that begin with “would,” “should,” “is,” “are,” and “do you…” Also, "why" questions might make people defensive.

  5. Make your questions clear and concise. A good open-ended question doesn’t end with a list of options for the recipient to select, it ends with a question and silence. In other words, give the person a chance to think before filling the space. If it helps, write your question down before asking it.

The ability to ask better questions matters in every aspect of your life. What follows are examples of questions to help you develop the skill of asking better questions on your own. Bookmark this page and check back whenever you find yourself needing inspiration to ask better questions.


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Leadership

Some leaders mistakenly think the higher up they go in an organization the more answers they need to provide. However, the best leaders understand the higher up they go, the more important asking good questions becomes.


Empowering Others. Judith Ross, in Harvard Business Review writes, you can help your direct reports develop their ability to solve problems.

  • Can you explain more about this situation?

  • Instead of “Did you make your sales goal?” ask, “How have sales been going?”

  • What are the consequences of going this route?

  • Why did this work?

  • Can that be done in any other way?

  • What do you think you will lose if you start sharing responsibility for the implementation process?

  • Based on your experience, what do you suggest we do here?


Coaching Others. In The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever, Michael Bungay Stanier offers seven questions leaders can use.

  • The Kickstarter question: What’s on your mind?

  • The AWE question: And what else?

  • The Focus question: What is the real challenge here for you?

  • The Foundation Question: What do you want?

  • The Lazy question: What do you want from me?

  • The Strategic question: If you are saying Yes to this, what are you saying No to?

  • The Learning question: What was most useful for you?


Looking in the Mirror. In What to Ask the Person in the Mirror: Critical Questions for Becoming a More Effective Leader and Reaching Your Potential, Robert Kaplan shares seven areas where leaders can ask more effective questions.

  • Vision and Priorities: Have you developed a clear vision and key priorities for your enterprise?

  • Managing Your Time: Does the way you spend your time match your key priorities?

  • Giving and Getting Feedback: Do you coach and also solicit feedback from your key subordinates?

  • Succession Planning and Delegation: Do you have a succession-planning process in place?

  • Evaluation and Alignment: If you had to design your company today with a clean sheet of paper, what would you change?

  • Being a Role Model: Do you act as a role model?

  • Reaching Your Potential: Are you reaching your potential and being true to yourself?

Developing Strategy. In Seven Strategy Questions: A Simple Approach for Better Execution, Robert Simons suggests seven questions every manager should ask when developing strategy.

  • Allocating resources to customers: Who is your primary customer?

  • Prioritizing core values: How do your core values prioritize shareholders, employees, and customers?

  • Tracking performance goals: What critical performance variables are you tracking?

  • Controlling strategic risk: What strategic boundaries have you set?

  • Spurring innovation: How are you generating creative tension?

  • Building commitment: How committed are your employees to helping each other?

  • Adapting to change: What strategic uncertainties keep you awake at night?

Solving Problems at Work. In Managing the Gray: 5 Timeless Questions for Resolving Your Toughest Problems at Work, Joseph L. Badaracco writes, “When you face a gray-area problem, you should work through it as a manager and resolve it as a human being.” He suggests using five questions as guidelines for making gray-area decisions:

  • What are the net, net consequences?

  • What are my core obligations?

  • What will work in the world as it is?

  • Who are we?

  • What can I live with?

Leading Meetings

  • How does this align with our purpose?

  • What problem are we trying to solve?

  • Whose perspectives are we missing in our discussion?

  • Is there another option we haven’t considered?

  • Who else should we speak with?

  • What do you think? [great when asked to the person who hasn’t spoken]

Human Resources


Informational Interviews are an excellent way to learn about a specific job, field of work, company, or industry. The following questions are pertinent if you are trying to learn about a new field of work.

  • What are your main responsibilities as a...?

  • What is a typical day (or week) like for you?

  • What do you like most about your work?

  • What do you like least about your work?

  • How do most people get into this field? What are common entry-level jobs?

  • What steps would you recommend I take to prepare to enter this field?

  • What qualities, abilities, and skills are essential to success in your field?

  • What advice would you give someone who is considering this field?

  • Is there anyone else you can recommend I speak with?

Interviewing Job Applicants. In the Harvard Business Review article, 7 Rules for Job Interview Questions That Result in Great Hires, John Sullivan provides a handful questions you should add to your list the next time you are hiring.

  • Provide the candidate with a description of an actual problem that they will face on their first day. Then ask, “Walk me through the broad steps you would take in order to solve the problem.”

  • What 3–5 major trends should we anticipate in our industry, and how will top firms need to change over the next few years to meet those trends?

  • What steps would you take to continuously learn and maintain your expert status in one important technical area?

  • What are the top factors that you’ll use to assess a job offer?

Interviewing A Prospective Employer. If you find yourself on the other side of the interview table, here are some questions you could ask at the end of an interview:

  • What do you like most about working for this company?

  • How would your direct reports describe your management style?

  • How do managers and employees share feedback?

  • What are the qualities of the ideal candidate for this position?

  • What have past employees done to succeed in this position?

  • Can you give me an example of how employees live out the company values?

  • In three months, how will you know whether you hired the right person?

  • Can you walk me through the next stages of the hiring process, and what I can do to show you that I'm the right person for this position?

Checking References

  • How long have you known [the candidate]?

  • What was the most significant contribution that [the candidate] made?

  • What was the greatest challenge presented to [the candidate]?

  • Can you tell me what it’s like to work with [the candidate]?

  • What else do I need to know about [the candidate] that I didn’t already ask?

  • Is there a question I should have asked that I didn’t?

  • Who else should I speak to about [the candidate] that can provide different insight?


Personal Life


Building Interpersonal Relationships. The following list of questions is from a 1997 article by Arthur Aron published in Personality and Social Psychology Bulletin. You can also find these questions in a more interactive form on the following site. Go through them in order with you want to get to know better.

  1. Given the choice of anyone in the world, whom would you want as a dinner guest?

  2. Would you like to be famous? In what way?

  3. Before making a telephone call, do you ever rehearse what you are going to say? Why?

  4. What would constitute a “perfect” day for you?

  5. When did you last sing to yourself? To someone else?

  6. If you were able to live to the age of 90 and retain either the mind or body of a 30-year-old for the last 60 years of your life, which would you want?

  7. Do you have a secret hunch about how you will die?

  8. Name three things you and your partner appear to have in common.

  9. For what in your life do you feel most grateful?

  10. If you could change anything about the way you were raised, what would it be?

  11. Take four minutes and tell your partner your life story in as much detail as possible.

  12. If you could wake up tomorrow having gained any one quality or ability, what would it be?

  13. If a crystal ball could tell you the truth about yourself, your life, the future or anything else, what would you want to know?

  14. Is there something that you’ve dreamed of doing for a long time? Why haven’t you done it?

  15. What is the greatest accomplishment of your life?

  16. What do you value most in a friendship?

  17. What is your most treasured memory?

  18. What is your most terrible memory?

  19. If you knew that in one year you would die suddenly, would you change anything about the way you are now living? Why?

  20. What does friendship mean to you?

  21. What roles do love and affection play in your life?

  22. Alternate sharing something you consider a positive characteristic of your partner. Share a total of five items.

  23. How close and warm is your family? Do you feel your childhood was happier than most other people’s?

  24. How do you feel about your relationship with your mother?

  25. Make three true “we” statements each. For instance, “We are both in this room feeling ... “

  26. Complete this sentence: “I wish I had someone with whom I could share ... “

  27. If you were going to become a close friend with your partner, please share what would be important for him or her to know.

  28. Tell your partner what you like about them; be very honest this time, saying things that you might not say to someone you’ve just met.

  29. Share with your partner an embarrassing moment in your life.

  30. When did you last cry in front of another person? By yourself?

  31. Tell your partner something that you like about them already.

  32. What, if anything, is too serious to be joked about?

  33. If you were to die this evening with no opportunity to communicate with anyone, what would you most regret not having told someone? Why haven’t you told them yet?

  34. Your house, containing everything you own, catches fire. After saving your loved ones and pets, you have time to safely make a final dash to save any one item. What would it be? Why?

  35. Of all the people in your family, whose death would you find most disturbing? Why?

  36. Share a personal problem and ask your partner’s advice on how they might handle it. Also, ask your partner to reflect back to you how you seem to be feeling about the problem you have chosen.


Getting Married Buy The Hard Questions: 100 Essential Questions to Ask Before You Say "I Do", sit down with your partner, and answer all of them. Here’s ten to get you started:

  • Who is responsible for keeping our house and yard cared for and organized? Are we different in our needs for cleanliness and organization?

  • What is our ultimate financial goal regarding annual income, and when do we anticipate achieving it? By what means and through what efforts?

  • How ambitious are you? Are we comfortable with the other’s level of ambition?

  • Do we eat meals together? Which ones? Who is responsible for the food shopping? Who prepares the meals? Who cleans up afterward?

  • Is each of us happy with the other’s approach to health? Does one have habits or tendencies that concern the other (e.g., smoking, excessive dieting, poor diet)?

  • What place does the other’s family play in our family life? How often do we visit or socialize together? If we have out-of-town relatives, will we ask them to visit us for extended periods? How often?

  • Will we have children? If so, when? How many? How important is having children to each of us?

  • If we have children, what kind of relationship do we hope our parents will have with their grandchildren? How much time will they spend together?

  • Do we share a religion? Do we belong to a church, synagogue, mosque or temple? More than one? If not, would our relationship benefit from such an affiliation?

  • Does one of us have an individual spiritual practice? Is the practice and the time devoted to it acceptable to the other? Does each partner understand and respect the other’s choices?

Raising Children

Here are five questions I like to ask my children:

  • What is something that happened today that you are grateful for?

  • How did you spread kindness today?

  • What is something you learned today?

  • What is something that challenged you today?

  • What is the best question you asked today?

Dr. Laura Markham has 230 Conversation Starters for Family Discussions.


Asking Yourself Deep Questions

  • Am I a better person today than I was yesterday?

  • Am I living the life I want to be living?

  • How can I live in this moment?

  • Are my actions aligned with my values?

  • How do I want to be remembered?

If you want to develop the ability to ask meaningful questions with people you trust, consider reading Honest and Open Questions as a Spiritual Practice by Marcia Eames-Sheavly.


Asking Better Questions [In the Classroom]

  • Could you elaborate further on that point?

  • Could you give me an example?

  • How could we find out if that is true?

  • Is there another point of view we haven’t considered?


What other categories of questions I should add to this list?