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101 CIO Interview Questions

        posted by , January 13, 2013

Chief Information Officer (CIO) is a challenging executive role. The ideal candidate is a business and technology visionary with a proven track record of managing IT delivery and driving IT-business alignment.

CIOs should be interviewed by core members of the executive team and senior technology leaders in your organization. A few sample questions to get you started:

Executive Management

1. What do you look for in new talent?

2. What shortcomings have you experienced with your management style?

3. How do you adapt your management style during an economic downturn?

4. Can you give me an example of a time where you had a significant disagreement with another executive? How did you resolve the situation?

5. What non-monetary incentives do you use to retain key performers?

6. Can you give me an example of a project that you sponsored which failed? What did you learn from the experience?

7. Can you give me an example of a time you influenced corporate strategy? What was the result?

8. How do you deal with staff who are more interested in office politics than the interests of the company?

9. What criteria do you use to terminate staff for cause?

IT Management

10. How do you use metrics to manage IT? What are some common metrics pitfalls?

11. Do you view business as a customer or a partner of IT?

12. How do you deliver IT cost transparency?

13. Can you describe a time when executives made unreasonable requests to IT? How did you manage it?

14. How do you balance tactical business demands with the need to stick to a long term strategy?

15. What project are you most proud of? Can you give me a example of a project you were involved in that failed?

16. Who do you most admire for their management style?

17. When do you require a RFP as part of the procurement process? When is a RFP too much?

18. How do you ensure a fair and competitive procurement process?

19. How do you manage sudden increases and decreases in budget driven by economic conditions and company results?

20. How do you ensure that IT line managers are involved in strategic IT planning?

21. How do you create a IT strategy for a organization with weak finances? How about a company with deep pockets?

22. How will you market IT to your peers on the executive team and to the CEO?

23. Can you give me an example of a long term IT strategy you successfully implemented?

24. How do you stay abreast of what your competitors are doing in the IT space?

25. How do you scale IT projects for faster delivery?

Projects and Delivery

26. What percentage of IT projects meet time/cost/quality targets?

27. Why do IT projects fail?

28. What do you look for in a project manager?

29. What are the benefits of having a PMO?

30. What project management methodologies are you familiar with?

31. Can you describe the software development lifecycle (SDLC)?

32. What information is contained within a requirements document?

33. What types of projects are best delivered by the agile project management methodology?

Technology and Architecture

34. What is Enterprise Architecture?

35. How do you stay current with emerging business and technology trends?

36. How do you align IT with business strategy?

37. What are the top 5 challenges facing IT organizations this year? What are the top 5 opportunities?

38. Are you familiar with the concept of the technology hype cycle?

39. Do you feel that any recent technology trends are all hype?

40. Do you see any trade-off between innovation and standardization? Can you give me an example?

41. How do you approach the buy vs build decision?

42. What area interests you most — applications, data or infrastructure?

43. If you could have a executive dashboard that displayed any 5 IT metrics — what metrics would you choose?

44. How do you ensure that networking, computing and storage resources can be quickly and cheaply scaled to meet business demands?

45. What do you look for in a chief architect?

46. How do you balance time to market with quality?

47. What are the principles of master data management?

48. What makes a good / bad user interface?

49. What are some typical gaps in business processes? How do you fix these gaps?

50. How do you get the business to buy in to a long term IT strategy?

51. What is the importance of open technology standards?

IT Service Management

52. How is high availability measured?

53. What is the difference between incident and problem management?

54. What metrics best measure quality of service?

55. How do you ensure help desk service excellence?

56. What does continual service improvement mean to you?


57. How do you sell security initiatives to the business?

58. What do you think about security convergence?

59. What are the biggest security threats to an organization like ours?

60. How do you strike a balance between information sharing and information security?

61. Does the business need to involved in security? How?

62. What kind of information is contained in a security incident response plan?

63. What is the relationship between information security and change management?

64. What are the key laws governing information security?

65. Can you give me an example of a security incident that occurred in your organization? How did you manage it?

66. What are the most important standards related to information security?

67. How does security governance relate to corporate governance?

68. Are you familiar with the security concept known as defence in depth?


69. What is your approach to interviewing?

70. How do you ensure that procurement is highly competitive and fair?

71. How do you strike a balance between economies of scale and vendor lock-in with outsourcing partnerships?

72. Do you have experience negotiating with outsourcing partners?

73. How do you think IT sourcing will change in the next 10 years?

74. Can you give me an example of a time that one of your vendors did not meet their commitments? How did you resolve the situation?

75. Have you ever initiated legal action against a vendor or partner? Has a partner ever initiated legal action against you?

76. Do you have experience with process outsourcing? What processes did you outsource? How did it go?

77. What are the risks of outsourcing? How do you mitigate these risks?


78. Give me an example in which you developed untapped potential in your staff.

79. How do you ensure that business partners with IT — for example: ensuring that business provides diligent requirements?


80. What is the role of the CIO?

81. Who reports to the CIO?

82. What are some of the key challenges for the CIO?

83. As CIO who are your top five stakeholders?

84. Do you think CIOs make good CEOs? Why / why not?


85. What is the primary focus of IT governance?

86. What is the CIO's role with respect to corporate governance?

87. Who is typically involved in IT governance activities?

88. Do you have an IT governance program in your current organization?

89. What metrics and measures of IT are of interest to the board of directors and shareholders?


90. From what you know about our company — what percentage of our revenue do you estimate can be directly attributed to IT?

91. From what you know about our company — what do you think the budget of our IT department might be?


92. Can you think of a mission statement for me now — that embodies what your approach would be in this role?


93. How does technology empower employees to do their jobs ?

94. Can you give me an example of a time that you applied out-of-the-box thinking to solve a business problem?

95. What technologies will transform the business world in the next 5 to 10 years?


96. What should a organization such as ours do to protect our intellectual property?

97. How has the legal landscape changed in the past 5 years (from an IT and information security perspective)?

98. How do privacy laws affect a company like ours?


99. Are you a risk taker?

100. What is the worst business mistake you have ever made? What did you learn from the experience?

101. What are your long term career goals?

These questions should be tailored for your organization. Your questions should validate the CIO's understanding of your business and industry — which is not covered here.

This article is part of the ongoing series: how to win your next job.

More interview questions can be found here.

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