15 digital transformation questions every CIO must answer

15 digital transformation questions every CIO must answer

“They have a defined vision of where they’re going and why, and why they in particular should pursue that path. They have the discipline of picking the problems that matter most, and they’re good at validating ventures iteratively,” he says.

Other distinguishing points: DX is not treated as a project with its own budget, or even an IT program led by the CIO.

“Where I’ve seen [transformation] work is where it’s really led by the business and IT is a critical supporting function or where it’s the two in close partnership,” Rogers says.

11. Is transformation companywide?

CIOs should similarly examine whether transformation is happening across the organization or if it is occurring only in pockets.

“Too often operational dysfunction or functional siloes get in the way of successful, enterprise-wide transformation. We often see firms invest in digital transformation for some functions but not others as quickly, which results in a capability and experience gap that can be evident to customers, stakeholders, and internally as well,” Zaim says.

“CIOs must take a holistic approach to understanding where roadblocks or challenges might exist in an organization. A transformation might start with their IT team, but they must engage teams from across the business to promote new ideas, provide funding, and celebrate success,” he adds. “CIOs also can ask themselves about their role in enhancing the digital acumen of non-IT leaders. When digital proficiency extends beyond IT-focused roles at the leadership level, the benefits from digital transformation are more pronounced.”

12. Is all my talent ready — and am I making the right moves on IT talent?

CIOs should first ask themselves whether they’re hiring people with the mindset and background to drive change or just hiring for tech skills.

Rogers says CIOs need people who are comfortable collaborating with those different than themselves, making decisions on data, and working with ambiguity.

“Those aren’t technical skills, so if you’re just focused on acquiring the right tech skills, you’ll be limited in your ability to deliver impact,” he adds.

At the same time, Lambu says CIOs still need their workers to have the tech skills required for current and future DX initiatives and must recognize that the need to upskill is as constant as transformation itself.

Moreover, CIOs must enable that continuous training at a much faster pace than in the past, he says, adding that tech leaders must also confirm that their partners are taking a similar approach to ensure all vendors supporting the company are equally capable of keeping pace.

Germer says upskilling IT talent is just the start, however. To truly be successful, CIOs need to evolve the IT operating model, too. For example, they should have product teams. They should use performance metrics based on business outcomes rather than tech metrics to measures success. And they should have product-based rather than project-based funding.

13. Is our workforce primed for digital success, and am I doing what’s needed to ensure that?

Workers throughout the organization also need skills to enable successful transformation, Landi says, noting that “CIOs have a key role to play here.”

She adds: “The question CIOs should be asking is: How do we get a workforce that’s highly skilled and engaged in working aside technology?”

CIOs cannot push this off to human resources, and they can’t see this as only a change management exercise, Lardi explains. Rather, CIOs should be part of the team communicating “everything to everyone around the digital journey and why it is important and making sure everyone in the organization has the necessary understanding of the technology.”

14. How much time do I have to be successful?

Laserfiche CIO Thomas Phelps puts it this way: “The question I’d ask is, ‘How much runway do I have for this initiative, and what are the competitive pressures?’ Because that question leads to the budget question and the resource questions. If I need to get there in six months versus two years, that impacts the budgets and resources I need to allocate and culturally whether the organization can change fast enough to get there as well. The worst thing to do in a transformation effort is to underestimate the level of resources needed. That’s why there are situations where there are starts and stops or initiatives that don’t pay off or fail.”

He notes that many organizations don’t allot a realistic enough time to achieve transformation, saying, “It’s important to understand the why, the context around the timeframe and the objectives of the initiative and to propose what’s realistic for the organization. Then as CIO you can give the executive sponsor and stakeholders options.”

He also advises CIOs to identify discreet milestones that can be used to measure progress and success along the longer, overall transformation journey.

15. Am I adequately addressing cybersecurity risk?

Cybersecurity threats are continuing to evolve, as are regulatory requirements and risks to data integrity.

“So the question should be: Are you keeping your cybersecurity frameworks up to date with the risks that are continuously evolving?” says Marc Lijour, an entrepreneur, researcher, educator and member of the professional association IEEE. “You don’t want to protect against the world of yesterday. You have to keep up to date with what the new threats are; you have to try to keep ahead of that cat-and-mouse game [with cyber adversaries].”

The CIOs who are successful in that attempt, Lijour says, are those who address security and risk early in their transformation journeys and those who have embraced a secure-by-design approach.

Adya offers similar advice: “Organizations implementing DX face potential risks and challenges, such as data privacy breaches, security vulnerabilities, and resistance to change. Organizations should establish strong data privacy policies to mitigate these risks, invest in cybersecurity measures, and foster a culture of change through effective communication and training.”

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