Whenever digital transformation comes up in a group of CIOs, there\u2019s often debate on what constitutes a transformation program. Is a cloud migration transformational? When IT organizations adopt agile practices to deliver new applications, is that transformational? If the CIO sponsors a citizen data science program and deploys new self-service data visualization tools, is that transformational? What about devops, investing in artificial intelligence, or experimenting with blockchain?\nI remind CIOs that everything I just listed, and many other technology and practice investments are just that \u2013 they are investments. More often they are helping organization transition from a legacy capability to a modernized one or may be establishing an entirely new capability. But to be transformational, the investment must do a lot more than just deliver new capabilities.\nDriving digital transformation requires a portfolio of ongoing investment\nA digital transformation program and its underlying investments needs to significantly change how a business delivers experiences to its customers. It should enable the business to deliver new types of products and services and possibly help shift sales into more lucrative markets. It must demonstrate both top line and bottom line changes that often requires the organization to be more competitive and data driven. To do this, it\u2019s going to radically change how the organization is structured and operates, and it\u2019s definitely going to require a new set of digital and data skills.\nAny one investment is likely going to be a step in a multi-step journey. A review of real-word digital transformation success stories will show you CIOs that took on multiple initiatives that delivered business impact. For example, for the Town of Cary it included application rationalization, new mobile and voice user experiences, a new SaaS development platform, agile practices, new workspaces, and hackathons.\nTo pull this off, CIO must develop, communicate, and manage a portfolio of investments. It will require CIO to capture the benefits and returns of digital investments and market to the organization the quick wins and the larger successes. They must continually sell the benefits, because transformation isn\u2019t a onetime program and almost always required people in the organization to develop new skills, change their practices, and adopt new mindsets.\nManaging and marketing a digital portfolio\nFor many CIO that are in year two or more into their digital transformation programs, it\u2019s critical to reenergize business partners on the goals and remind colleagues progress on the journey. To do this, CIO should be leveraging their PMOs to demonstrate the transformation across multiple axes.\nMost portfolio reporting start with business strategy followed by their programs and initiatives. A digital portfolio should add additional views such as\n\nA customer view starting with target markets and illustrating programs aimed to grow reach, revenue and other KPIs for each targeted segment.\nAn analytics view should articulate the initiatives aimed to deliver new data driven insights along with ones looking to enable new data sources or mature governance and data management practices.\nA workforce portfolio should highlight programs to drive culture change, enable learning, change the working environment, and improve fundamental practices.\nA technology view should highlight programs around new platforms and programs to improve practices like agile and devops that underpin the transformation.\n\nThis communication is essential especially when CIO often start with small digital transformation investments to gain support and demonstrate wins. As the program grows, it\u2019s easy for executives and colleagues to lose interest or even burn out with the changes being driven. CIO need to take a proactive approach on communicating their progress, marketing their wins, and disclosing their challenges to ensure everyone is engaged through the journey.