10 Career Questions I’d Like to Ask Just About Everyone

It’s an occupational hazard — I love to hear details about people and their work. When meeting someone at a conference or gathering, career related topics always flood my mind. Most questions on this topic consist of the garden variety; Who do you work for? How long have you been with your organization? Do you travel much? But, these aren’t the questions I’d like to pose. I’d like to know much, much more and hear the “unabridged” story. The successes, the failures, the wrong turns, the U-turns  — all of the highs and lows.

They all meet and mingle to tell a real-life career story.

Most of us become so busy with our everyday work lives that we fail to carve out a moment to reflect on our own paths. That process would take time and the right frame of mind. However, I encourage you to do so.

So — here are the questions that I would really like to ask you. You can consider them when you have a moment:

  • How did you choose your line of work (be completely honest)?
  • Would you make that same choice today?
  • When you think about work, do you feel energized?
  • If you could create your dream role, what would that be?
  • Who was your most challenging boss and why?
  • Who was your most aggravating co-worker and why?
  • Are you most creative alone or on a team?
  • What kind of work spaces motivate you?
  • What is your most memorable failure?
  • What single thing would you change (if you could) to improve your work life?

I’d love to hear some of your answers and what you might do with the information. Feel free to share that here.

Dr. Marla Gottschalk is a Workplace Psychologist. She also writes for Talent Zoo and  Linkedin.

15 thoughts on “10 Career Questions I’d Like to Ask Just About Everyone

  1. Dear Marla,
    1) Recently, i started a job, i am working because i still want to give myself a chance to see how the legal industry is like, as i studied law as my undergraduate.

    2) I am not too sure how to answer this question, i did not really have a choice, as this position was the only available job that I had at that point in time.

    3) Not particularly.

    4) If i could create my dream role, I would like to work for myself , have my own control to the things I do. IE: an entrepreneur

    5) Not applicable (atm)

    6) Not applicable (atm)

    7) A mixed of both, I would like to gather the ideas myself and share it with the team, and they could give me further feedback.

    8) A friendly and laid back environment

    9)The most memorable failure, was I did not pass the necessary qualification to be a lawyer, and from time to time, i still think whether if i should re-take the qualification, the fear of failure is taking over me than the attempt to move on to try.

    10) If i could improve my work life, i hope that i actually get to like my work more.


  2. Hi Marla,
    My current role is a bit difficult to describe, as I think it is unique to our organization. It is kind of like a business analyst, but not completely. My organization is going through major changes with a senior manager that does not really see the need to support people through it. So at this stage I kind of keep on making suggestions to him of how we can assist the team and reap the benefits. I also volunteered to do some things to up engagement, so I do a newsletter, etc. Officially this is not part of the role, but since there is a gap and I love things like that, I kind of gave myself that responsibility. With regards to the change: I have some wins with the boss, so I am optimistic.
    How did I realize that I am interested: I am currently studying Organizational Psych. – still a far way to go….Psychology in general has always interested me but I don’t see myself as a counsellor. I think it is the perfect job to include both people and my love for analysis and stats.

    PS: I love reading your articles both here and on LinkedIn


  3. Corne – Thank you for sharing your perspective here – it is greatly appreciated. I noticed that you would like to incorporate Change Management into your current role. How did you realize this? I’m also anxious to hear how you are developing your role to accommodate this. (I also love that you do not dwell on negative co-workers – a challenge for many of us.)


  4. Gordon – Thanks you so much for your answers. It is obvious that you have found a way to weave your collected experiences into a very well rounded (and tolerant) perspective of work life. Your answer to #9 – was really very intriguing. Thanks so much for sharing them with us.


  5. •How did you choose your line of work (be completely honest)? – My work kind of chose me. I started work after school, as that is what I had to do, not want to do. After years in the organisation, I slowly progressed to the position where Im now, and for the first time I feel that I have found my purpose. This is what I want to do.
    •Would you make that same choice today? – Most probably. When I was younger I never would have guessed I love this job so much. I had to find it out by myself.
    •When you think about work, do you feel energized? – Yes
    •If you could create your dream role, what would that be? – I would love to incorporate Change Management a little more into what I do now – I’m working on that.
    •Who was your most challenging boss and why? – challenging as in “difficult”: My previous manager. Set in her ways, not open to change and did not understand that the world is changing so processes change. Challenging as in “challenging my mind” My current manager. He constantly challenges me to do better, learn more, be more.
    •Who was your most aggravating co-worker and why? – I don’t really know. I tend to not focus on them.
    •Are you most creative alone or on a team? – Alone. My thinking process is different than those of my colleagues. I prefer things my own way.
    •What kind of work spaces motivate you? – flexibility, honesty at all times, trust
    •What is your most memorable failure? – all big failures were because of emotional decision-making
    •What single thing would you change (if you could) to improve your work life? – get a little more flexibility from my managers.


  6. Great Read! Really provokes thoughts. So here is some feedback from me:

    1) I chose my career, because I like building business engines. Having them progress, make money, and flourish in the economy. I started out with developing improvements in gruntwork, accross all aspects. First hand knowledge of running businesses.

    2) Looking back, I don’t know if there was another record that should have played. So, I don’t know what else I would have done.

    3) I can get very energized when Im building and planning work.

    4) I think my dream role would be today, to build and manage a firm that specializes in “Design and Control” Systems for CEO’s. A firm that puts reality into their lives,so they can guide their ships to great successes.

    5) I had two that came to mind, 1- Early in my career, a non-college grad
    that taught me how to blend college know how, with good common sense. 2- In my later consulting career, someone that challegened me to dig out the best within me, to bring my light to a shine.

    6) Ones that “Don’t do their own work”. There were several. They just never grasped the concept of “Original Work” and therefore were never able to be trained to do much. Clients paying $ 300+ per hour per man, meant I had to hustle 10 times as hard, to produce the work to cover their time.

    7) Can be either! I can blend in with a team, or create on my own, the end result is that it “has to work for the customer/ client/shareholder.

    8) I have had workspaces from small and tiny, to huge and spacious. I like to have space to do my work, and good board room props to do my professing and sharing. If its permanent, an office big enough to allow some freedom, surrounded by books (Texts and famous reads), paper, printer, and a good MS computer. Of course a Telephone.

    9) I don’t know if any mis-steps would have been the most memorable,
    but they all reduce down to knowing your “Core of Consciousness”. Several times in my life, I had more than I knew, and in hindsight some of it, I still don’t know at what point, I could have been a more positive change factor to foster different outcomes. But, at 54 I do understand the 4 quadrants of my pyramid, that sits upon my inner core. I have found that #10 is a critical key to me.

    10> The single most important thing I found in my life, is that my personal life is the gas and stp that hums my engine. For me, the two most important ingredients to my success, is have someone that truly lights up my life. I would spend more time trying to find that “friend”. Rumi used to say, when you are looking for your friend, the friend is looking for you. What an important key to my happiness.

    Well Dr. Marla, you have once again probed my mind. Great thoughts to ponder. GREAT READ and articulation of critical points.


  7. Great questions for self-refelction too 🙂 my friends & I always talk about how we ended up in our careers or what we’d do to change them. I think it’s because we are now reaching the 5 year milestone after graduating university and thinking if it was all worth it in the end (questions my parents would never have asked, they’d just be working hard to advance their lives). Our views overlap in that we’d love jobs with people we get along with, good standard of life and of course, the ability to holiday a lot! haha

    Thanks for the food for thought 🙂




  8. I originally entered the field of IT but lately I find myself being drawn towards business/marketing in particular. Middle ground being online media for marketing [best of both worlds right?].
    I’m the type of person that loves making big moves so who knows, maybe there’s a career switch in my near future.

    Thanks for posting Marla!


  9. Brian – thanks for reading. We have all had a challenging manager at one time or another – that experience can be very trying and certainly can get in the way of our desired career purpose for a period of time. I’m glad to know you still feel strongly about your career choice. Thanks so much you for sharing your answers.


  10. Why did you choose your line of work (be completely honest)? Because I feel that it is a noble profession and i can contribute to the education of those who undertake the work.
    Would you make that same choice today? Absolutely!
    When you think about work, do you feel energized? Yes
    If you could create your dream role, what would that be? Director of Education
    Who was your most challenging boss? My last one who believed and stated that the only opinion I am allowed to have is his.
    Who was your most aggravating co-worker? My previous manager
    Are you most creative alone or on a team? Alone, I need time and space to create
    What kind of work spaces motivate you? Future thinking and one’s not afraid to let go of the past
    What is your most memorable failure? My last position, I let emotion cloud my judgement.
    What single thing would you change (if you could) to improve your work life? Work out how to be taken seriously without having to “yell” to be heard.


  11. David – thanks so much for taking the time to offer your feedback. It is appreciated. You’ve included some great options here. Maybe we should have a second installment.


  12. Hi Marla,
    my response to these is “mostly wrong questions”. Its like we are on slightly different planets. Don’t get me wrong, your questions are very familiar, and remind me of cocktail parties and 1:1’s with managers. I am 3 months away from retiring, so perspective is not the same as someone just starting or midway through a career.

    The reason these are not the right questions is that most of them do not develop a connection to me or what motivates me. I could answer all of them, and you would be a long way from understanding my career goals and life goals.

    Here is an alternative set of questions that would come a lot closer to being the kind of questions that would get a meaningful response from me:
    1. how well balanced is your job with the rest of your life?
    2. how challenging is your job?
    3. does your job align well with your capabilities?
    4. how rewarding is your job?
    5. does your job get your creative juices flowing?
    6. do you perform better with more or less supervision than you have in your current job?
    7. do you like problems to solve that are open ended or closed ended?
    8. do you get enough interaction and teamwork in your current job?
    9. which metrics should your performance be measured by?
    10 describe your ideal job in terms of balance with your life, fit to your capabilities, creative opportunities, interaction with team and managers, type of problems you will solve, and the rewards you will earn.


  13. Great thought-provoking questions, Marla! In addition to these, I would ask if your work provides you with a sense of purpose AND if it is the kind of work that you would never want to retire from.


  14. Matha,

    I am a trainer and HR consultant. I love my work and feel energized by
    the thought of work.

    But what I would like to change ; Not having to sacrifice time spend with my young children for a challenging assignment. I should not be forced to choose one for another. I want both!


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