Have you ever found yourself tongue-tied for words on social media?

Well, here are 100 questions below in the question-of-the-day format that can be asked to initiate a conversation.

Some of these questions can also be used in conducting an interview or an informational interview or even when meeting someone new at a public career conference.

At any rate, even one question can be the start of a beautiful career story, discussion, or blog post waiting to be unleashed.

So, use your creativity and imagination!

Asking even one question could even be the start of forming a new brainstorming / discussion / mentoring session about career trends or the changing labour market in 2024 and beyond!

So whether you are interviewing a career expert or someone you want to find more about their career in case you are making a career transition, your kid is graduating high school and wants to explore career options or you are working on a project, asking the right person the right questions is the key to finding out the information you need and want.

Perhaps you are seeking to find your "ikigai" - your reason for being. Some of these questions would be a great place to start exploring your options and finding out what makes you or others tick.

1.          What was your first job?

2.          What was your best job?

3.          What was your worst job?

4.          How did you get your current job?

5.          What field/industry do you work in?

6.          What one piece of advice do you wish you had known before you took your current job?

7.          How old were you when you got your first “real” job?

8.          How much money did you make at your first job?

9.          What’s a “good day” at work for you?

10.       What is your dream job?

11.       What is the best job search advice you ever received?

12.       Should you “friend” your boss on Facebook?

13.       Have you ever been fired from a job? Why?

14.       Have you ever been stumped by a question in a job interview? What was the question?

15.       What’s the weirdest job interview question you’ve ever been asked?

16.       How many interviews did you go on before your most recent job offer?

17.       How far is your commute to your current job?

18.       What question do you dread being asked in an interview?

19.       What do you want to be “when you grow up”?

20.       If you were fired from your job tomorrow, would you be ready to start looking for another job right away?

21.       If you made a career change, what would it be? (And what do you do now?)

22.       Does your spouse make more money than you do?

23.       What do you love about your job? [Valentine’s Day]

24.       How many days of vacation do you get each year? [Memorial Day]

25.       Where are you headed on vacation this summer? [Memorial Day]

26.       Do you have a job interview horror story? [Halloween]

27.       What is your New Year’s Resolution [December/January]

28.       Have you ever won any awards at work? What for? [Emmy or Oscar nominations or ceremony]

29.       If you won the lottery, how much money would you have to win before you quit your job? [big lottery drawing]

30.       If you won the lottery tomorrow, would you quit your job? [big lottery drawing]

31.       If you could change one thing about your current job, what would it be?

32.       Who do you most admire in your profession — and why?

33.       When you were little, what did you want to be when you grew up? What do you do now?

34.       Do you have a “side hustle” (part-time job or self-employment)? What is it?

35.       Who would your dream boss be?

36.       What company is your “dream” employer? (What company have you always wanted to work for?)

37.       If you could be instantly fluent in another language that would help you in your current job, which language would it be?

38.       What’s your favorite job-related movie?

39.       If you could come up with a hashtag to describe your current job/career, what would it be?

40.       Does your employer have a social media policy for employees? What do you think of it?

41.       If you have a college degree — does it relate to the job you’re doing now?

42.       If you could do one thing differently in your career, what would it be?

43.       If you could do it all over again, would you choose the same career path?

44.       If you weren’t doing your current job, what do you think you would be doing?

45.       Growing up, who had the most influence on your career path?

46.       What class, training, or workshop has had the biggest impact on your career?

47.       Work isn’t everything. What do you enjoy doing in your spare time?

48.       Have you ever considered turning a hobby into a business?

49.       Do you volunteer? If so, where, and what do you do?

50.       What advice would you give someone just starting out in your field?

51.       What one thing do you wish you had known about your current job/company before you started here?

52.       Do you hang out with your co-workers outside of work?

53.       How do you keep your work-related skills up to date?

54.       What one word would you use to describe your company’s dress code?

55.       If a movie was made about your life, who would play you? Who would play your boss?

56.       What book has most influenced you? Why?

57.       What is your biggest work-related accomplishment?

58.       What do you most want to be remembered for?

59.       If your co-workers had to describe you in one word, what word would they choose?

60.       If your current employer asked you to relocate anywhere in the world, where would you agree to go?

61.       If you could do over one thing in your job/career, what would it be?

62.       What is the most difficult challenge you’ve ever faced at work?

63.       If you became famous for doing something that you don’t currently do, what would it be?

64.       If you had to work in one job for the rest of your life, would it be your current job, or would you want a different job?

65.       What would the title of the biography of you be called?

66.       Where is the coolest place you’ve ever traveled for work?

67.       Do you prefer working alone, with a team, or both?

68.       What song best describes a typical day at work for you?

69.       What is the most incredible thing you’ve ever done at work?

70.       Have you ever met someone famous while doing your job?

71.       What one thing would make your current job better?

72.       What is the most memorable thing a boss/supervisor has said to you?

73.       What is the worst thing that has ever happened to you at work?

74.       If you could work for any person in the world, who would it be, and what job would you want?

75.       If you could adopt one personality trait from one of your co-workers, what would you take?

76.       Which character from “The Office” are you most like?

77.       If you could have one person from history work for you as your personal assistant, who would it be — and why?

78.       If you went back to school right now, what would you study?

79.       What did you get your degree in — and are you using that knowledge right now in your current job?

80.       If you could work with anyone in the world (dead or alive), who would it be?

81.       You just ended up on the front page of the local newspaper because of your job. What does the headline say?

82.       Do you belong to a trade association or organization in your industry? What’s the biggest benefit you get from being a member?

83.       What is your biggest regret about your career?

84.       Have you ever turned down a job offer? Why?

85.       Have you ever quit a job in the first 30 days?

86.       Where do you see yourself (professionally) five years from now?

87.       What is the best part of your job?

88.       If you could do any job in the world for one day, what would it be?

89.       If you could change one thing about your job, what would it be?

90.       What’s the best compliment you’ve ever received from a customer?

91.       What’s the best compliment you’ve ever received from your boss?

92.       What is your favorite item in your office?

93.       Which would you choose: Come in late, or leave early?

94.       Which would you choose: More money, or more flexibility in your job?

95.       Which would you choose: A raise, or more vacation time?

96.       If you were featured on the cover of a magazine for your work, which magazine would it be?

97.       In your opinion, what is the worst job in the world?

98.       In your opinion, what is the best job in the world?

99.       What job would you be willing to do if it paid $1 million a year?

100.    What age do you want to retire?

Are you seeking a career transition or need career support? Call Creative Horizons Communications today or visit www.creativeresumestrategist.com.

Think creatively and visualize a new career horizon!