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Digital transformation: 11 signs of a successful leader

Blog: The Enterprise Project - Digital Transformation

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:

7. They ask “why not” rather than “why”

The most effective digital transformation leaders bring the business with them. “[They] create solutions that answer business problems rather than operational or IT problems,” ISG’s Fisher says. “They know that IT is an enabler of transformation, [not the] transformation itself.”

8. They are mavericks

Speed? Conventions? Out the window. The best digital leaders know the old rules no longer apply and look for partners who can help them challenge the status quo. “The best way for IT leaders to improve and continuously keep up with the speed of IT is to establish a broad ecosystem of technology partners, which bring the latest in innovation and leading practices,” Bentham says.

9. They inspire others

Clear vision is critical. Even more important is the ability to move others. “Leaders need the ability to build focus, set a clear vision, explain it to their teams, and then inspire the teams to execute on the vision,” says Miglani of West Monroe. “The key here is to ensure that there is a well-defined vision that not just the technology team, but the entire organization can drive towards. The leader has to build a culture of collaboration and transparency.”

10. They prioritize customer experience

“All too often, technology leaders lead with providing the best or latest technology solutions without consideration for the actual customer experience,” says Miglani. “Successful tech leaders think of the customer first. A great way for leaders to build better appreciation for this is to get in front of customers, talk to them, and understand the pros and cons of their existing solutions.”

11. They serve as enterprise change agents

The most successful digital transformation leaders take on this role and gladly oversee customer experience transformation, reinventing the business model, elevating operational excellence, or ensuring trust and compliance. “The IT leader who has the ability to connect these transformation agendas to revenue, profit, and/or sustainability,” says Capgemini’s Bentham, “is ultimately the one who succeeds.”

[ Will your organization thrive in 2021? Learn the four priorities top CIOs are focusing on now. Download the HBR Analytic Services report: IT Leadership in the Next Normal. ]

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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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