Analyst Answers: The CIO’s Biggest Digital Transformation Challenges

September 23, 2016

Contributor: Kasey Panetta

Gartner analysts share why culture, people, and technical debt will be some of the biggest challenges to CIOs on their digital journeys.

It's Gartner Symposium/ITxpo 2016 season and to help you get in the mindset for the breakthrough ideas and emerging technologies presented at each event, Smarter With Gartner reached out to some of our analysts to get their opinions on the CIO's digital transformation journey. Following this year’s theme of Lead 360: Drive Digital to the Core, their answers reflect the CIO leadership imperative across people, organization and technology platforms.

What’s the CIO’s biggest challenge in transforming the organization to a digital business?


The biggest challenge is reaching escape velocity. CIOs must apply energy to reduce technical debt while converting innovations into scalable capabilities, all of this while resisting the gravitational pull of the pretransformation organization. Top-performing CIOs use bimodal techniques and renewed influence to accomplish these goals.


People, no question -- their expertise, their profiles, their mindsets, their re-education. According to a recent Gartner survey, nearly 8 in 10 people believe that the skills and knowledge their organizations have in 10 years will bear little resemblance to the skills and knowledge they have today. Digital business will catapult CIOs and their organizations straight into 21st-century business models.

Nine areas of technology expertise — which savvy CIOs will be prepared to champion — will raise the competitive bar for companies and institutions, and will open opportunities for people who have the moxie and the interest to use digital business for career success. The people challenges of digital business are real, and CIOs must step off the sidelines and change the game. Papegaaij

The CIO’s biggest challenge in transforming the organization to a digital business is their organization’s culture.Your current culture contains the collective beliefs and deeply ingrained behaviors that got you to where you are now, but — when left unaddressed — will also get you stuck there.Changing the culture requires that you stop trying to push people in your direction; instead, inspire them to want to go in new directions. In other words, less push and more passion, less management and (much) more leadership.


Most CIO’s can be forgiven for leaping to the conclusion that the biggest challenge of creating a digital business is enabling the infrastructure and applications that actually support digital products. But there’s a growing line of reasoning that this may be the easy part. You, as CIO, have a staff of talented technologists who are probably chomping at the bit to make digital products a reality in your environment, if you’ll only give them the time and the money. And therein lies the challenge.

To get the money you need for tomorrow you have to make changes in how IT operates today. The digital transition for IT requires giving up a service mentality and instead adopting an investment mindset. Supporting the legacy systems of the past can’t be allowed to consume all of the money necessary to thrive in the future.

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