How to Ask Good Questions

Asking questions remains the most powerful way to learn, but so often we hesitate or feel afraid to voice questions because we fear that others will see us as week, ignorant or unknowledgeable.

Most of us want to make a good impression when we meet someone, so we put pressure on ourselves to demonstrate strength, confidence, intelligence as ‘experts’ in our field. We assume that we should have all the answers - or at least come across that way - when in fact the greatest thinkers and leaders are constantly asking questions with a ‘beginners mindset’ that allows them to be more open to new ideas, perspectives and possibilities.

Another reason we hold back from asking questions is because we’re in such a hurry to get things done, to get the final result, or to have “the answer” - not realising that by taking the time to pause, ask thoughtful questions, and really listen - we can gain valuable information, inspiration and insights for the projects or initiatives we are working on and want to succeed in.

Being a good listener also helps you become a better questioner. Questions can help you to clarify your own thinking, be more creative / innovative in how you solve problems, to validate or invalidate assumptions, and to be a better leader - of yourself and others.



  • Simple answer: Anytime you want to learn or understand something more deeply.


  • In your workplace: Whether you’re starting a new job, participating in an internal meeting, speaking with clients, or managing and leading teams, asking good questions can help to:
    • Understand and align on what is expected of you in a new role / position / company
    • Clarify and align with your coworkers on goals and key deliverables for a project
    • Understand the needs and pain points of your customers / key stakeholders
    • Enhance team performance by uncovering challenges and generating better solutions
    • Provoke thinking, stimulate discussions, and arrive at an “aha” moment that leads to innovation and growth
    • Focus on learning instead of judging by looking to understand rather than jump to conclusions


  • In your career: Whether you’re exploring job opportunities, new business ideas, or potential collaborative projects, knowing how to ask good questions can help you to:
    • Gain deeper insights to an industry, company, or position you’re considering
    • Identify future trends and opportunities that can be leveraged in your profession or business
    • Make new and meaningful connections at networking events
    • Understand and align on goals for a collaborative project, or assess whether a prospective partner is a good ‘fit’ for your business or new initiative
    • Seek career advice and/or ask someone to be your mentor


  • In your personal life: Whether it’s with your spouse/partner, child, other family members, or friends learning to ask good questions can help you to:
    • Develop a deeper bond with family members or friends
    • Be a better spouse, parent, family member or friend
    • Empathise with and support the people who matter to you in difficult times - or positive ones



  • The type of questions you ask really depends on a few key factors…
    • Your intention - What is the purpose of your conversation / question - is it to gain factual information, general knowledge, insider insights to subject / area of interest, or to get to know someone better, or understand something on a deeper level? Is to gain more clarity and alignment with people you’re working?
    • Your desired outcome - How will the response to your question allow you to learn something new, do something better, or achieve something faster?
    • Your situation - What is the context of your line of questioning? Are you seeking guidance or feedback for something you’re working on or feeling stuck on? Are you trying to gauge whether a person or opportunity would be the right ‘fit’ for you? Or maybe you’re just looking to build your network, find your tribe, or make new friends.

Each of these factors would have an impact on the type of questions you ask and how you ask them. Whatever the case, try to be specific about your objectives for the conversation - either in your initial outreach email/call, or at the start of your discussion.

One of the most common situations in which you want to be thoughtful and effective in asking questions are job/information interviews or networking events. For a prospective employer, the questions you ask also a reflection of who you are - your personality, interests and preferences. Here are some examples of questions you might ask in these situations - adapted from the University at Buffalo’s School of Management webpage:


What Work is Like

  • Could you describe a normal day at work?
  • What are some of the key skills that have enabled you to succeed in your role/position?
  • What aspects of your work do you find more challenging / enjoyable?
  • Is there a ‘downside’ to your work / job?
  • What skills do you consider to be essential for success in this role/position?
  • How many hours do you work in a typical week?


State of An Industry​

  • Do you see opportunities for someone like me to ‘break into’ this industry?
  • What changes do you see in this industry? What are the prospects or trends - where do you see it headed?
  • In your view, are too many or too few people entering this profession?
  • How often are companies restructuring or laying off people in this sector - how do you think this is affecting employee prospects and/or attitudes?
  • Why do you think people leave this field or company?
  • Who are the most important people in the industry today?
  • What are some good resources or networks you would recommend to keep abreast of latest news, developments and insights to the industry?


Money and Advancement

  • What do you think would be a reasonable salary range to expect if I entered this field?
  • What is the long-term potential for professional growth + advancement in this field?
  • What has been your career path? Is it representative of most people in this field?
  • If you could start all over again, is there anything you would have done differently?
  • What is the background of most senior-level executives in this field?


​Skills and Experience

  • What are some relevant skills, experience or educational/training areas would you recommend for someone who wants to advance in this field?
  • What do you look for in a new hire?
  • How do most people enter this profession?
  • Are you a member of any professional networks / associations? Which ones do you feel are the most important to belong to?
  • Can you recommend any courses I should take before proceeding further with my job search?
  • Which companies or industries would you suggest I should target or contact?
  • Is there someone you would recommend I talk to next? May I mention that you referred me when I reach out to them?

Fitting In

  • Do you think my background, skills and experience are a suitable ‘match’ for this company/profession/role? Are there other paths/directions you’d suggest I explore?
  • Do you think my current career objectives are realistic and achievable?
  • Would working at your organisation involve any lifestyle changes - e.g. frequent travel, late-night calls/meetings with overseas clients, overtime/weekend work?

But asking good questions isn’t only important for job-seeking. It is also an essential skill for building relationships in your personal or professional life because it’s about understanding people, hearing their stories, finding connection, and learning from their experiences.

Constructing good questions is pretty important for our work at The Change School too, for: ​

  • Connecting with potential collaborators or partners
  • Engaging with career shifters and prospective students on/off line
  • Taking client briefs for training programs / workshops
  • Interviewing guests on Change School TV to share their journeys with our viewers

​In all of these situations, the goal is to understand their dreams, key objectives, pain points, and what success means to them, in order to find alignment points that build on our shared values, interests, and respective strengths.  

Some examples of questions we might ask include:

  • What drives you to wake up every morning? What inspires the work that you do?
  • What are your personal/professional goals?
  • What’s most important to you in your work and working relationships?
  • What type of work do you enjoy the most, and least?
  • What do you look for in a partner / position / leader?
  • What are your personal likes / gripes?



Some of our questions are pretty ‘out there’. Like - What’s your spirit animal? What would your ideal work day look like? Write your ideal job description for yourself. These questions help us get to know the people we’re considering to work with in a more meaningful way. More than just superficial questions, it’s about digging deeper to the person’s core - their personality, values, and preferred working style.

While it’s good to ask a lot of questions, in some situations, it can come across as being overly inquisitive, intrusive, or even agenda-driven (leading someone to a certain answer/response). So it’s important to ask questions in a thoughtful, friendly and non-threatening way - HOW you ask questions is often more important than WHAT you ask.

 Here are some PRO tips to keep in mind…


  • Ask open-ended questions. Everyone loves to tell and share stories. Asking open-ended questions invites the person you’re speaking with to share their story, give broad answers, and go deeper into matters that they feel engaged and passionate about. Simply asking “what”, “how” or “why” is a good way to prompt further reflections and dialogue with someone.

 Here are some examples of open-ended questions:

  • Why do you think that happened?
  • What are the reasons you think that might have caused this problem?
  • How do you think we could avoid this situation next time?
  • What do you think worked well and didn’t work well?
  • How would you make improvements / do things differently in future?
  • Why do you think you (or someone else) feels that way?

By contrast, closed questions are questions that limit your responder to short / stalk or “yes” or “no” answers. This happens when we are sometimes too quick to form opinions, make judgements, jump to conclusions or proposals without necessarily having the full picture of a situation or person - or when we ‘fill in the blanks’ before giving the other person a chance to do so.

Here are some examples of closed questions you want to try and avoid:

  • When did this happen?
  • Were you (or someone else) feeling __________ (a certain way)?
  • Did you do _____________ (something)?
  • Where is ______________ (a person / project / situation) right now?
  • Did you _______________ (take a specific action)?
  • Would you like to ______________ (a specific activity) on ______________ (a specific day / time)?


  • Be engaged in your conversation. There’s no point asking questions if you’re too distracted or disinterested in listening to the response. This not only comes across as being disingenuous, but it can also make the other person feel neglected, unheard, or unimportant. To avoid potential misunderstandings, actively demonstrate your interest with positive facial expressions,  body language and by listening attentively.



  • Stay curious. Most of us have likely experienced conversations where someone is obviously more interested in talking, offering advice, and giving the final answer than hearing all the other views or opinions in the room. How annoying is that? Allowing more time to pause, process and observe and reflect on what someone is saying (or not saying)  makes for deeper and richer dialogue.


  • Dig for details. Think of a time when someone asked you to share more details about a memory or story you’re recounting. How does it feel when someone takes a genuine interest to know more? Even if it is a negative or unintended situation, it is always appreciated when someone demonstrates the desire to understand what happened, why, and how things can be improved instead of assuming, accusing, or blaming. Try to be the kind of person you would want to meet or engage in conversation with. Chances are, they will greatly appreciate those attributes and reciprocate your thoughtfulness during your interaction. Even if they don’t, you can choose to be practice better habits and lead by example.

For tonight’s episode, we’ve got a great list of sample questions curated from different career sources to help you craft more incisive questions for career exploration or job seeking. To get your hands on that Cheat Sheet - head on over to