Digital transformation: 11 signs of a successful leader

The competencies of a successful digital transformation leader can be markedly different from those of the traditional IT boss. For aspiring digital transformation leaders – or CIOs looking to fill digital leadership roles - these traits and skills matter
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As IT organizations are charged with creating their organizations’ digital futures, the direction at the top is critical. However, the competencies of a successful digital transformation leader can be markedly different than those of the traditional IT boss.

“Traditional IT leadership revolved around meeting delivering systems, connectivity, and updates on time, on budget, and to scope. This may have involved agile practices, but it was clearly around efficiency,” says Iain Fisher, an ISG director within the Northern European digital strategy and solutions practice. “Successful digital transformation seeks to go outside the IT silo and understand what the end customer actually wants, which is then questioned and innovated upon.”

[ How does your team stack up? Read also: Digital transformation teams in 2021: 9 key roles. ]

Digital transformation leaders are accountable for delivering business results. “Past traditional IT leaders had the luxury of dictating the budget required to deliver a project, but had no obligation to commit to the outcome of the business,” says Greg Bentham, vice president of cloud infrastructure services at Capgemini North America. “Today’s IT leaders are required to put skin in the game.”

For those newly ascendant or aspiring digital transformation leaders – or CIOs charged with or looking to fill digital leadership roles – here are eleven of the most important hallmarks of effective transformation heads.

[ Get answers to key digital transformation questions and lessons from top CIOs: Download our digital transformation cheat sheet. ]

1. Digital transformation leaders connect the dots

Effective digital transformation leaders understand what outcomes drive a successful business (i.e., they connect top-line measures to their initiatives). But they also know how to connect those measures to the people, process, and technology required to achieve them, says Bentham of Capgemini.

2. Digital transformation leaders democratize tech understanding

The best digital transformation leaders avoid speaking in acronyms and never try to flout their tech lexicon. Instead, they keep it as simple as possible. “Technology is complex,” says Rahul Miglani, senior manager at business and technology consultancy West Monroe, “and a successful leader will work to remove the complexities and simplify it.”

3. Digital transformation leaders empower their teams

Rather than operating in a top-down fashion, pushing decisions and delivery, they pave the way for their IT organizations to create innovative solutions, says Fisher. The most effective digital transformation leaders have created teams that themselves remove roadblocks to creativity and innovation.

4. Digital transformation leaders are masters of the market

“In any business, a successful leader has vision and can effectively communicate this vision and the associated strategy in an effective way,” says Miglani. ”Most technology leaders can demonstrate mastery of technology trends; however, a successful [digital transformation] leader will listen to the voice of the customer and associated market trends and build innovative technology solutions that solve real problems that their customers are facing.”

[ Culture change is the hardest part of digital transformation. Get the digital transformation eBook: Teaching an elephant to dance. ]

5. Digital transformation leaders focus on flow

Batches are a thing of the past for the best digital transformation leaders. They deliver what is needed and “continually improve creating a flow of value to their customer,” says Fisher. Think value creation versus value delivery.

6. Digital transformation leaders practice pragmatism

While understanding emerging technologies and leading-edge practices is important, realism reigns. “It’s equally important to ensure that trends translate to the culture of the people and the goals of the organization,” Miglani says. “It’s important for the leader to have an open mind and be willing to listen and adapt.”

Let’s explore five more crucial traits for digital transformation leaders:

Stephanie Overby is an award-winning reporter and editor with more than twenty years of professional journalism experience. For the last decade, her work has focused on the intersection of business and technology. She lives in Boston, Mass.