Digital transformation: Who should lead? 8 questions to ask

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

237 readers like this

4. What is the person’s appetite for risk?

“Rather than a digital strategist, organizations should look for leaders that are flexible risk takers, who understand that digital will require a certain amount of failures and experiments to get projects right,” Lyke-Ho-Gland says.

5. Has the person ever launched a disruptive initiative in the company?

Shaking up the status quo challenges even experienced leaders. “Most digital transformations require changes to some elements of the business model,” says Edwards of Everest Group. “Knowing that the model was responsible for past success, one can expect some organizational resistance to change. Having a leader who is experienced in handling this resistance is valuable.”

[ Read our related article: Does your change management plan cut it in the digital age? ]

6. Does the person have clarity of vision?

As we noted earlier, digital transformation can be confusing to people on the front lines of the organization. “The right person should have a clear point of view on what digital transformation is, and what it is not,” says Ankur Laroia, Managing Director of BDO’s Houston office and leader of its Digital Transformation Services practice. They should be able to explain the reasons behind it, the business strategies it supports, and the organizational changes required.

7. Can this person work in an agile manner?

Things change quickly in digital transformation, and leaders have to keep up. “Falling in love with last week’s solution could lead to failure. Success is keeping an eye out for changing business needs, customer perspectives and technology and developing plans quickly on how to respond,” Edwards says.

8. Does the person play well with others?

Digital transformation is a team sport, so collaboration is key. “This person will not have the authority to make everything happen,” says Edwards. “He or she must work with the other leaders in the organization.” The leader will also need to be able to synthesize input from multiple sources. “A good digital transformation leader will be able to listen to multiple perspectives and not make trade-offs to please everyone that will invariably lead to failure,” Edwards says. “Instead, the leader will work to understand the implications of the perspectives and ensure that decision remain aligned with the achievement of business outcomes.”

[ How can open source principles help with your transformation? Get the ebook: Digital transformation, the open source way. ]


7 New CIO Rules of Road

CIOs: We welcome you to join the conversation

Related Topics

Submitted By Victoria Roos Olsson
November 27, 2020

Many of us will continue to work at home, simultaneously juggling multiple roles, for some time to come during the pandemic. Consider these tips to stay healthy and productive

Submitted By Carla Rudder
November 26, 2020

Remote work will be the reality for many of us for the forseeable future. Let's be thankful for the lessons we've learned on how to stay productive, beat burnout, and lead effectively

Submitted By Carlos M. Meléndez
November 25, 2020

Organizational buy-in is a key part of successful digital transformation. Here's how to tap the talent and perspective of some key roles as you build your strategy.


Email Capture

Keep up with the latest thoughts, strategies, and insights from CIOs & IT leaders.