Lately, I\u2019ve been asking CIOs, \u201cIf you had a chance to convene a roundtable of CIOs, from multiple industries, and ask them to discuss their approach to a particular challenge that you are facing, what would you ask them?\u201d\nThe questions these CIOs would ask their peers run the gamut from digital leadership to security to talent to technology. I chronicle many of their questions here, so that you might be able to benchmark your own challenges against theirs.\u00a0\n\u00a0Business Partners:\n\nHow have you changed the conversation about IT from one of cost to one of value?\nHow do you get your business partners to stop viewing projects as \u201ctechnology\u201d projects and get them to take accountability for making these projects a success?\nHow are you bringing business leaders together to develop a common business architecture?\nHow are you changing your culture so that your business partners are actually using the data that IT can now provide?\nWhat are the ingredients for successful IT governance?\n\n\u00a0Digital:\n\nHow are you driving digital change in an old, traditional company?\nI would love to hear about mainframe modernization exercises that other CIOs are doing.\u00a0 How are you leveraging state of the art technologies to improve your business?\nHow are CIOs considering their role in digital leadership?\u00a0 Supporting or leading?\n\n\u00a0Security:\n\nWhen it comes to cybersecurity, how do you reach a level of comfort to assure your Board of Directors that you are doing enough?\n\n\u00a0Cloud:\n\nWhat is the real impact of the SaaS trend that we are seeing in the industry? How will it impact staffing and service? What will the IT service delivery model look like in five years?\nHow have you derived value out of social media for your company?\nI would want to talk about the consumerization of enterprise IT.\u00a0 What are some elegant, simple solutions for mirroring what is happening in consumer technology for a corporate environment?\n\nTalent:\n\nHow have you taught better business acumen and project management skills to your staff?\nHow do you get your senior IT leaders to think more broadly and strategically about applying technology solutions to business problems?\n\n\u00a0Vendors:\n\nHow have you gotten your vendors to deliver the quality of work they promise when you are negotiating terms?\nHow have you gotten your vendors to behave like true partners?\n\nOf course, these questions beg many more questions.\u00a0 What questions would you ask your CIO peers? Please post a comment and let us know!