The Art of Asking Good Questions (Pt.2)

Since the first part of The Art of Asking Good Questions sparked such a great discussion I thought it was only suitable to write a follow up post. In part 1 of the post we discussed how we can implement open-ended and clarifying questions to better connect and strength our relationships during a conversation. 

Thomas Berger said, The art and science of asking questions is the source of all knowledge.” Good question asking is about asking the right question, with the right tone, at the appropriate time. This can be challenging (That’s why it’s an art) however like any skill it can be learned and mastered. It’s something worth focusing on because it will allow you to become a better leader. Below are 2 more questions you can implement into your conversations:

1. Inward life questions- Asking inward questions can help you reveal the inner workings of a person; it allows you to identify their personality, character, and deep heart qualities. The questions can help you learn about a person’s values, beliefs, and convictions. Though it takes time to learn about who a person is on the inside their actions and attitude can be a great indicator of their inward thoughts and life. This is because the person on the inside, good or bad, shows through in their behaviors and attitude.

Ask questions that will help you learn about what drives and motivates them as well as ones that will reveal their attitude about life. Examples of these questions include:

  • “What drives you forward or toward success?”
  • “How have you overcome the obstacles life throws at you?”
  • “What do you think about ________?” (Something going on in the organization, like a major change).
  • “What do you want to achieve in your career and personal life.”

2. Passion questions- This is personally one of my favorite types of questions. Asking a question similar to, “If money or time where not an issue what would you do?” This can help you learn about the other person’s passions, ambitions, and dreams. If you follow this question with open-ended or clarifying questions you will dig deeper into what the person’s personal passions include.

 If you’re able you should allow the person to work in areas of personal passions while at work (if at all feasible and appropriate). For example, if one of your team members is passionate about connecting and building relationships with other people but they are behind a computer all day, if possible you should move them into a different department or allow them to spend some time in front of the customers or clients if it is possible. This will not be feasible in every situation, but if your able to have your people work in areas of passions you will see an increase of energy and enthusiasm from them. At the very least you should support and encourage them to focus on their passion outside of work.

Questions: Have you used either of these types of questions in your life or leadership? Can you add to the list?

Please note: I reserve the right to delete comments that are offensive or off-topic.

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46 thoughts on “The Art of Asking Good Questions (Pt.2)

  1. Excellent thoughts, Dan. Questions are my favorite way to engage people and learn their stories. Sometimes, I will ask people where they see themselves going in the future or where they will be in five years. I love to get a feel for whether they are even thinking along these lines.

    While we’re on the subject, what are some obstacles you have had to overcome in developing your voice and platform?

    • Thank you Chris:) Those are also some great questions to connect and learn about someone else.

      Disciplining myself to consistently write and publish good content has and is an ongoing struggle, especially with a 17 month old. Writing in turn will allow us to find our voice.

  2. Both of the above questions have played major roles in my life. As a result, I’m able to engage with both God and the people around me. Engaging questions will also help. A good example of this will be – How can I help to better benefit you and/or others? – Hope this helps!…:-)

    • Hello Micky,

      Great point about engaging with God through questions. It’s important to ask then listen to His response. Great example!!! Thank you for reading and sharing.

  3. All of the time. These are the kinds of questions I would ask a potential partner, my child, or a friend I’m counseling. I also often ask these questions of students to help them choose speech topics. I think it’s also important to ask these questions of ourselves.

  4. I definitely use both very often because I love those profound conversations. Superficial conversations only hold my interest for so long that I often fall back on the deeper ones and I find that people love those as well. Why? Because they’re not used to being challenged to think like that. It’s a refreshing change of pace.

    • That’s great Vincent. I hear you, “Superficial conversations” only go so far. To really connect and learn about someone we have to ask deep heart questions. Thank you for adding to the topic.

  5. Dan, sometimes we do something on our team called “Blue sky thinking”. Basically we ask the question, “if there were no limits how would we do this?” It’s always a fun and rewarding process.

  6. Not only asking questions, but really getting to know people can do so much with regards to where they like to be, but also how to deal with them in specific times and trials that come along all too often. It’s fascinating to ask questions and get to know the story of the life… While we’re all similar, we’re light years different.

  7. Dan, you wrote:”Good question asking is about asking the right question, with the right tone, at the appropriate time.” You are so right about the tone and the timing being critical. In terms of tone, we need to be honest with ourselves as to our intent for asking questions. There have been times when I’ve asked the “right” question but with less than honorable intent–and it’s impossible for that to not come out in tone or body language. If I’m primarily asking a question to get someone to see how their mistaken or wrong in some way, I might win the battle but I’ll certainly lose the war.

    • It’s certainly important to have the right motives when asking questions. Luckily we can learn from and correct any of the wrong motive or bad questions we have asked in the past. Thank you for taking time to share your wisdom on this topic.

    • That’s great! These types of questions also have great value when it comes to coaching or mentoring someone. They can assist us to better help other people. Thank you for taking the time to read and share.

  8. Those are great questions to ask Dan. They dig deeper into the issue and let you clarify what’s going on.

    Another type of question is the Improvement Question – What can be done to improve this aspect of my life? How can we better serve our customers? Etc…

    • Glad you enjoyed them Joe:) I know it would be beneficial for you to use them with the youth you work with. That’s a great additional question. Thank you for sharing it.

  9. I asked and answered the passion questions several years ago. I had the pleasure of living my passion at work, ministry and home. Right now I am struggling at work. I am the person you are talking about in your last paragraph. I am working to live my passion in full time work and ministry.

    • Great point about asking our self’s these questions. I know as you move toward your purpose and dreams the area of work will be better. Thank you for reading and sharing.

  10. Never used the inward life questions Dan. I am going to add this to my list of Interview questions for those seeking to join our team. Its great to connect and know people better. We have a survey that includes personal development, Life, Business, Family questions to see if they would be a good fit for the Organization.

    • That’s great! I think it would really help you connect and learn about the people you interview. Survey’s are a great tool to determine if they would be a good match. Thank you for adding to the discussion.

  11. These are two powerful types of questions that leaders should put in their arsenal. One of the greatest questions I’ve came across comes from Jim Collins in his presentation to next generation leaders:”If you woke tomorrow morning and discovered you inherited $20 million, and had discovered you also had terminal disease with 10 years to live, what would be on your stop-doing list?” (

    This isn’t honestly an easy question to answer. It penetrates into what matters most in your life and galvanizes you to take action.

  12. To me, these are really the only types of questions worth asking. At least, if you’re really trying to get to know someone. Because superficial questions can only ever lead to a superficial understanding of someone.


    • I agree:) It’s all about connecting with the person on a deep level and these types of questions really help. Thank you for taking the time to read and add to the discussion.

  13. Hi Dan,

    These inward life questions and passion questions are brilliant. Thank you for sharing them.

    I loved the approach you talked about of encouraging people in organisations to work in areas, which really bring out their best.

    One question, which I love to ask people in order to determine what they value is “what does this mean to you?” Getting information from people at the meaning level, usually helps in bringing out the inner world of individuals.

    Thank you.

    • Hello Hiten,

      Glad you enjoyed them:)

      They can really help us when it comes to placing people in different roles or departments. Thank you for reading and adding to the conversation. I appreciate it.

  14. Dan this really stands out for me “Good question asking is about asking the right question, with the right tone, at the appropriate time.” So great a statement to dwell on. I can think of tonnes of time when I’ve asked questions with one or two “ingredients” missing, (esp the tone : ) ) . Thanks for this food for thought.

    • Thank you Ngina. Yes, when it comes to conversations and asking questions those three elements are so important. I know I have failed with my tone at times, especially with my wife:) Thank you for sharing.

  15. These are the type of questions I love asking. When people ask superficial questions that don’t dig into personality and point of view, it just seems like you’re not really getting to know the person. These are when you get to the heart of what makes someone unique.

    At the same time, you can’t just start off with these questions, you have to build up to them. I learned this is in a communication class. You have to build up with small questions to get to know the other person. Once you’ve gotten to know each other a little and built some trust, you can then dive into these types of questions. But I do think the passion and inward life questions are the best way to truly know another person.

    • Great points Steve,

      After talking with someone for several minutes about general things I usually work one of these types of questions into the conversation. I have found when I do people love talking about themselves and what they enjoy (Most times) which allow the conversation to stay alive and the other person feeling good about my interest in them. It just depends on the persona and conversation. Thank you for reading and adding to the topic.

    • This is especially true if you want to go really deep. Often you have to take the first step and share something vulnerable about yourself first before you earn that right to ask similar questions.

  16. Great questions, Dan. I think they would also be fun to ask at the dinner table. We often ask, “What was your high (point) of the day,” and, “What was your low”? It’s great to hear the different perspectives of my husband and the kids.

  17. An exhilarating post, Dan! Good questions make the world, or at least good conversation, go round. And I think you did a fine job of elevating them to their proper status by calling it an ART.

  18. I think that your perspective is deep, its just well thought out and really fantastic to see someone who knows how to put these thoughts down so well.