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  • Julius de Jong

How to Ask Better Questions (Episode 2-39)

Updated: Jul 30, 2021

New Perspectives on Ourselves, Others, and Any Problem Through Better Questions.

Questions are greatly underestimated, I believe. Intuitively, I recognize that if I know the right questions to ask, life will become much simpler. Questions can help me understand myself better. Similarly, questions can open up and deepen relationships with other people. The right questions can help us tremendously in business too. No matter if the relationship is private or business, asking good questions help people connect and understand each other better. Questions, finally, also help us solve difficult problems. Asking the right question, I believe, is more than half the solution to any problem.

However, society doesn’t necessarily value questions. Most schools, and corporates too, often smother the instinct to ask questions. Most education and training teach people what to think (Vaughan, 2015). Not how to think. As Tim Ferriss said, ‘thinking is largely asking yourself questions and answering them [in your head]’ (Ferriss, 2017). Good questions therefore, are critically important. As is learning how to ask better questions. In this post I share some of my learnings on the topic, enjoy!

Questions can shift our mindset

The right type of questions can shift our mind from being a victim with a ‘judger mindset’, into a positive person with a ‘learner mindset’ (Adams, 2004). Every new moment in life offers us an opportunity to be open and inquiring, or closed and judgmental. In most cases however, we are rarely conscious of this fact because of our habitual ways of being. We don’t recognize how many choices we make. Nor do we recognize the internal questions we ask ourselves in the process. We can’t choose what happens to us. But we can choose how we respond. We choose the questions we ask. Learners deal with problems positively. They ask open, information-gathering questions. Judgers ask closed and judgmental questions. We can’t entirely eliminate judger behavior, but we can learn to minimize it in favor of learning patterns and questioning. (Adams, 2004). Asking questions enables us to learn.

Three main areas for asking questions

During my research, I have found principally three broad and main themes in the literature dealing with questions. Questions to better know and understand yourself, questions to better relate to others (be it private or in a work setting) and questions to help solve problems.

1. Questions to better know and understand yourself

As individuals, we make sense of our story by asking questions about who we are, where we’re going, and what drives us. These are important questions we shouldn’t leave to chance, according to Steve Hobbs of Asking Better Questions Ltd. whom I interviewed on the topic of asking better questions. Good questions open us to a world of possibilities. The right question can expose you and me to a new consciousness about novel options. This in turn result in an opened mind and increased creativity and inspiration. The more we are able to become present in the here and now, the more susceptible we will become to questions that bring us forward. As I will touch upon later, slowing down, noticing, and learning to be still, are very useful tools. They enable deep questioning, to better understand ourselves.

2. Questions to better relate to others (be it private or in a work setting)

‘Questions are our way to connect with other human beings. Asking shows our interest in the other. Questions help us build relationships because they make us put others’ needs before our own (Schein, 2013). ‘Inquiry, not imitation, is the sincerest form of flattery’ (Senso, 2007). When inquiring with someone, give them the gift of your presence. Stay focused on listening and asking. As journalist Frank Senso has beautifully written, ‘[k]eep your questions like your eyes, locked on that other person, on the project you’re discussing and on [your] shared goals’. One practical suggestion for this is made by psychiatrist Mark Goulston. As he says, one of the best ways to connect with people is to talk and ask questions while you’re participating side-by-side in a shared activity together. Another suggestion he makes is golden: asking, ‘Do you really believe that?’ This simple question often diffuses a situation of stress or helps someone zoom out, and see the bigger picture. When asking questions, always be sure for there to be enough time to answer. Get comfortable with the silence. Let the silence do its work, and allow the answers to surface.

3. Questions to help solve problems

Journalist Warren Berger, a seasoned expert at asking questions, has identified in his book A More Beautiful Question three levels for asking questions to help solve problems:

1. As he states, ‘The first step in solving a problem is asking why a situation is the way it’. This is what he calls the “The naive questions: why?” This is the most open and expansive question. Forget everything you know. Be like a curious child. Adopt the beginner’s mind. Approach things as if you meet them for the first time, with surprise, curiosity, and wonder. As Zen master Shunryu Suzuki said, ‘in the beginner’s mind there are many possibilities, but in the expert’s, there are few’. Asking ‘Why?’ allows you to step back from your assumptions and things you think you know. It allows you to see things anew. Fresh. With a beginner’s mind. For example, car company Toyota for decades has used the practice of asking ‘Why?’ five times in succession as a means of getting to the root of a particular problem.

2. Moving on, follow-up with the dreamer’s question: what if? Consider any possible solution, no matter how unusual or outlandish. Asking ‘What if?’, will help you bridge from the present to the new field of thought which your “Why?’ questions have unveiled. Asking ‘What if?’ questions allow you to dream and brainstorm without limitations. Freeing your imagination from current constraints and practicality. When brainstorming, see if you can match or make new combinations of existing and seemingly incompatible concepts. Many fresh ideas emerge from this process. Also, this forces you to think outside of your current scope. ‘What if?’ questions are creative and aspirational in nature.

3. Finally, ask how you can turn this ‘What if?’ scenario into reality. This is the realist question: how? The ‘How?’ question helps to narrow down your ‘What if?’ ideas and helps make things practical again. ‘During this “slow, and methodical” stage, test ideas, watch them fail and learn from the failures’ (Berger, 2014). During the ‘Why?’ and ‘What if?’ stages, it’s often beneficial to ignore conventional wisdom. Contrary, during the “How?’ phase, it is advantageous to seek out specialists and expert advice.

What makes a good question?

Steve Hobbs identifies two key elements of a good question. Firstly, a good question fits with-, and illustrates awareness of-, its context. This means, for example, that a question is appropriate for the time constraints in the moment of asking the question. Tim Ferriss gives an example of this context element in this video, when considering what question to ask someone you’ve just met in a lift. Because of the limited time together, a concrete question such as ‘What book have you gifted the most to other people?’ is appropriate in the context of the elevator. The very broad question ‘What is your favorite book?’ would not be suitable as it doesn’t consider the context sufficiently: limited time for answering. Secondly, good questions are congruent with their intent. This means the question is in line with the purpose you’re trying to achieve. Is the question actually meeting that goal? Awareness of the context is important for answering that question. Intent also relates to the psychological impact of the question. Are we asking a question because we are sincerely interested in better understanding the other person? Or is there perhaps an element of ego involved?

Listening, noticing and humility

Asking (good) questions is critical. But questions are wasted when we don’t allow for space and presence to listen to the answers. As Steve Hobbs says, ‘listening demonstrates care and love for the other person’. If you want to build rapport and trust, actively listening is a crucial required element. For that we need presence in the here and now. We need to be able to notice. When we slow down, we become more mindful and develop a greater awareness to our surroundings. This helps us practice humility, according to retired MIT professor Edgar Schein who is an advocate of what he refers to as humble inquiry. This can be summarized as ‘asking questions to which you do not already know the answer’ and ‘building relationships based in interest in the other person’ (Schein, 2013). Finally, when listening, ‘Don’t let your preconceived notion of other people influence the way you listen’ (Goulston, 2009).

Speedbump questions

It is interesting how in my research on writing a lot of times the importance of noticing was mentioned. Again, with my research about asking better questions, this concept surfaced again. Steve Hobbs also mentioned it during our interview. How it is crucial to widen the gap between our stimulus and response (Hobbs, 2021). He also shared a great tool for this which he had learnt from Dr. Matthew Duncombe, an expert in Ancient Greek Philosophy, including Socrates, Plato, Aristotle, Stoicism, and ancient skepticism. Duncombe’s goal is trying to get people to pause, reflect and ask themselves some questions. A concept he refers to as speedbump questions. Putting a temporary halt in your thinking. Speedbump questions force us to pause and ask ourselves to reflect on what we are listening to. Steve gives some very interesting example speedbump questions: ‘[w]hat am I being asked to believe or do? Am I being given a good enough reason to believe or act?

Be more interested than interesting

The next advice I had to read a few times over to let the magnitude of the words sink in: “[b]e more interested than interesting”, according to the advice of psychiatrist Mark Goulston. He also says: ‘don’t think of conversation as a back-and-forth game of one-upmanship. Instead, let the other person dominate the dialogue. I really like this. We’re somehow taught that if we have people’s attention, it must mean we are doing something right. However, in case we actually shut up and listen, there is a world of learning opening up for us. It’s not an accident we have only one mouth, yet two ears and eyes.

What the top performers do

Most questions are safe. They service what is already know. Top performers ask questions that go deep and inspire creative thinking. Going from automatic and reactionary thinking, to deep thinking. They ask questions that spur people into action. Questions, that make the unknow know. To do this, MIT professor and leadership scholar Hal Gregerson suggest adopting the perspective of childhood. As a child, our curiosity is natural and isn’t met with suspicion. ‘Great questioners are like kids in that regard. They have a “beginner’s mind”’ (Gregerson, 2018). ‘Top performers develop the ability to ask good questions’ (Vaughan, 2015). They suspend their judgement just long enough to understand someone else’s perspective. This leads to reduced conflict, a common language and a shared vision and understanding between people. Through this, when a situation evolves, so did the thinking of these top performers (Vaughan, 2015). Would you like to become a top performer in asking questions? Study the pros. Watch and listen to what they do. And ask questions, many, many questions. As with everything, practice makes perfect. What will you ask yourself?


Examples of good questions to ask:

When you want to understand a situation:

  • ‘What’s happening?’

  • ‘What brings you here?’

  • ‘Can you give me an example?’

In case you desire to understand cause and effect:

  • ‘What may have cause this?‘

  • ‘Why do you suppose this happened?’

When wanting to be action oriented, ask:

  • ‘How did you get here?’

  • ‘What have you tried already?’

  • ‘What do you suggest we could do to get X?’

Ask systemic questions when wanting to understand a complex situation:

  • ‘How do you think she felt when you did that?’

  • ‘What do you think he will follow through?’

Instead of asking ‘Why are you defensive?’ or ‘Why are you upset?’, try:

  • ‘Have I gone too far?’

  • ‘Is this too personal?’


  • ‘What could we do?’ instead of ‘What should we do?’

  • ‘How am I going to get this done?’ instead of ‘Why am I always lazy?’

Seeing the bigger picture:

  • ‘Do I/you really believe that?’

Speedbump questions:

  • ‘What am I being asked to believe or do?’

  • ‘Am I being given a good enough reason to believe or act?’



To learn how to ask better questions, I interviewed Steve Hobbs from Asking Better Questions Ltd. Steve is an expert on questions and builds on a vast, eclectic and interesting foundation of experience. It was a beautiful and inspiring conversation where my views on how to ask better questions were greatly expanded. I learnt a lot.

Steve Hobbs is a facilitator and coach who enables powerful conversations that create clarity and help get things done. His purpose is simple; helping clients achieve their goals and objectives. He does this through group facilitation, coaching and asking better questions.

Steve has over 40 years of experience under his belt in a range or roles, responsibilities and industries. A red thread through all this has been his continued curiosity and powerful conversations, which he rightfully considers the precursor to effective action. I hope you will enjoy watching the interview as much as I enjoyed conducting it!

Find more information on Steve and his company Asking Better Questions Ltd. via:



Adams, Marilee, 2004, Change Your Questions, Change Your Life.

Berger, Warren, 2014, A More Beautiful Question.

Carpenter, Alissa, 2020, How to Listen and Be Heard.

Ferris, Tim, 2017, “How To Ask Better Questions” Youtube,, accessed on June 30 2021.

Goulston, Mark, 2009, Just Listen.

Gregersen, Hal, 2018, Questions Are the Answer.

Pyle, James and Karinch, Maryann, 2014, Find Out Anything From Anyone, Anytime.

Ross, Judith, 2009, “How to Ask Better Questions”, Harvard Business Review,, accessed on June 30 2021.

Senso, Frank, 2007, Ask More.

Schein, Edgar, 2013, Humble Inquiry.

Turkle, Sherry, 2015, Reclaiming Conversation.

Vaughan, Mike, 2017, “How To Ask Better Questions” Youtube,, accessed on June 30 2021.

Suzuki, Shunryu, 2006, Zen Mind, Beginner’s Mind.

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