CIOs’ Digital Agenda: Five Big “Which”s in IT Digital Transformation Nov. 2016

Due to the changing nature of technology, IT leadership role also continues to involve & shift the focus, to move up the maturity level. More and more CIOs are requested to take more responsibility and many CIOs present the breadth of leadership competency. Here are Five big “Which” in IT digital transformation.           Five Big “Which”s in IT Digital TransformationWhich Lessons Shall you Learn to Harness IT and Business Relationship ? Digital is about breaking down silo thinking and harness cross-functional communication and collaboration. Although, many say, the gaps between business and IT are actually enlarged because the different function of the business takes the pace with varying speed in digital transformation. The laggard would drag down the speed of change in the business as a whole. Hence, it’s important to build up a trust relationship between functions, between functional leaders, and between leaders and employees.?  Windshield or Rear Mirror: Which is more Important to Leaders?Every leader is unique,and they may also have different leadership style: the pivotal leaders are the pathfinder to look forward, and discover the new trail to let others follow through; the seasoned leaders have plenty of experience, look back with rich and invaluable leadership lessons to learn from. Forward-looking or with an eye on the history and culture - both could be essential.What kind of leader do you prefer? Which leadership style do you have.
Which Color is CIO’s Parachute ? Based on the feedback from CIO forums, it seems that it is not only the CIO who is being asked to simultaneously be proficient as a strategic leader to a tactical manager, and even a technician being able to sing Kumbaya with every level in her/his company. It seems that other technical specialists may also be getting asked to perform similar functions. If this type of talent is really out there, it seems that the term associated with the above condition is described via the Purple Squirrel Syndrome?
Which is the best way to demonstrate Multidimensional IT value?  IT is at the cross road, some high-performing IT organizations have built solid value proposition, and moved up its maturity to become the game changer and business catalyst for their companies. However, the majority of IT organizations get stuck in the lower-level of maturity and struggle to prove their unique value, for helping the business gain competitive advantage.  So what are the best ways to demonstrate IT value, through analytics or metrics up front; through business cases or portfolios; through governance discipline; through agile practice or just through business-IT mutual understanding?
Which IT Best Practices Do You Take at the Time of Uncertainty?  IT is huge investment and costly in most of organizations, whether it is "planning" or "performance";  "process" or "people" issues - the CIOs shouldn't have been “overwhelmed” by complexity of IT and uncertainty of business dynamic, besides setting up practical IT Principles to follow, what are those IT practices can be shared?
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