CIOs’ Digital Agenda: Five Big “When”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 and depth of leadership competency to have in-depth understanding the "5W+1H" digital navigation. Here are Five big “When” in IT digital transformation.

           Five Big “When”s in IT Digital TransformationIT Transformation Debate: When Should IT Lead, When Should IT Follow? More often than not, technology is the catalyst for driving business change and digital transformation, however, in most of the companies, IT is still perceived as an order taker and support function, and most of IT organizations get stuck at the lower level of maturity for functional alignment or enabler. So IT is at a crossroad: Shall IT lead or follow? Should IT leadership rock the boat or just keep it afloat? And how to run digital IT with high speed and agility?  
When should the CIO take The Initiative to Promote Strategic Business Transformation? Either fast-growing businesses or well-established organizations have to continuously adapt to the numerous changes and well chart the path to significant business transformations such as digitalization or globalization, should CIOs take the initiative to promote such strategic business initiatives, if so, shall they promote at the front or lead from behind? Are they more as idea initiator or governance champion? And what’s the best scenario to take such transformational leadership?
Change Management at the Cross Road: When to Make a Big Jump, When to Take Small Steps? Due to the “VUCA” new normal of the digital age, either at the individual or organizational level, “Changeability” becomes an important measure to assess a person or a business’s potential, agility, and maturity. Unfortunately, change is not as easy as it sounds, more than two-thirds of business change initiatives fail to reach the expectation. Change Management in many organizations seems to be at the crossroad- Should you take an audacious approach of accelerating digital transformation, or take small steps for making incremental changes? What are the bottlenecks for changes, and how to avoid pitfalls in making a big leap?
The CIO’s Tough Choice: Be Proactive or Reactive, and When? Organizations large or small on the journey to digital transformation, IT plays a critical role as an enabler to drive changes. From IT leadership perspective, why are some CIOs reactive, rather than proactive in trying new technologies? Are they just reluctant to changing a working system, or are they not empowered enough?
When Shall you Go with Intuition, when shall you do Analytics? A business decision is both art and science, especially in the exponential change and business dynamic we face today, it is so difficult to make effective decisions without the right strategy and methodology. How do you decide whether you should go with your gut, or do a careful analysis? What questions do you ask?  What role does problem framing have in the choice balance between intuition and analytics or gut and reason? What factors do you consider? Do you have a rule of thumb??
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