Digital transformation: Who should lead? 8 questions to ask

Should that outside hotshot lead your digital transformation work – or an insider who knows more about the culture and customers? Ask these questions to decide this contentious issue
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In a recent article, two INSEAD management professors argued against putting digital experts in charge of digital transformation. A hotshot fresh off a stint at Amazon or Google might seem the ideal choice, they wrote, but a business insider may be better suited to oversee the significant organizational change required in the typical enterprise setting.

There is no one right answer to the question of who should lead a digital initiative. “It’s important to highlight that digital transformation can take multiple forms with varying degrees of transparency to the customer or end user,” says Brian Caplan, director with management consultancy Pace Harmon.

The organization may be extending existing capabilities to mobile platforms. It may be pursuing game-changing capabilities like IoT-based process innovation. The company may want to build new digital products and services – or entirely new business models. The project could simply involve changes to underlying applications or infrastructure in pursuit of a cloud strategy.

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

As we’ve noted recently, the very term “digital transformation” means different things to different people - to the point of making some leaders cringe. It’s important to define your own meaning and vision and communicate that clearly and repeatedly.

How to examine a leader’s fit for your digital transformation

A stall may prompt pressure to reevaluate who’s leading.

The leadership question doesn’t just come up at the start of digital transformation work. For example, a stall in your team’s digital transformation efforts, or a new expansion project, may prompt pressure to reevaluate who’s leading. Here are eight key questions to ask to help determine the best choice to lead a digital transformation initiative:

1. How well does the person understand the current business strategy?

Ask this first, because it’s absolutely fundamental. “Since there is no universal set of right answers for digital, it is important to understand what the business is trying to achieve,” says Cecilia Edwards, partner at management consultancy and research firm Everest Group. “This will reduce the likelihood of implementing initiatives that have no or the wrong business impact.”

It’s also important that the person be tech savvy enough to translate between business needs and technology solutions. “While the leader doesn’t need to implement, there will be a team of technologists that the leader will engage with,” Edwards says. “He or she will have the responsibility to ensure the technology solutions proposed align with the business objectives and customer perspectives identified.”

2. Will this person be trusted?

If business leaders won’t work with the transformation leader, the effort is likely doomed.

“In addition to understanding the organization and culture, someone with credibility in the organization is a big help, especially when it comes to ‘selling’ the digital vision to rank-and-file employees,” says Holly Lyke-Ho-Gland, Principal Research Lead, Process and Performance Management Research at APQC.

“If the leader is from outside, it helps to pair them with an organizational insider with a good reputation.” If business leaders won’t work with the transformation leader, the effort is likely doomed, Edwards says.

3. Does the person know the customer?

Many digital efforts focus on customer experience, both internal and external. “Being able to view things from the customer’s perspective and understanding their specific journey with the company ensures the transformation has enough of a positive impact and is aligned with customer needs and expectations,” says Edwards of Everest Group.

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.