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remains front and center for CIOs, with multiple surveys and reports indicating that DX is a top priority for IT leaders even now, after a decade or so of transformation initiatives. That continuing priority for DX reflects the ever-increasing importance of transformation for business success, as the technology landscape itself evolves increasingly faster. Findings from speak to this point, with 88% of surveyed CIOs saying that their role is becoming more digital- and innovation-focused.
Meanwhile, TEKsystems’ found that 84% of its respondents consider digital transformation as a core pillar of business strategy. Yet, organizations still struggle with getting transformation right. Some still see transformation as a project with a start and end date.
Others view it as a technology initiative, . Regardless of the particular challenges to DX success, those who are may have missed signs indicating the need to tack and set a new course. But the signs are there, for those who take the time to look.
To that end, CIO.com asked longtime IT leaders — current and former CIOs as well as consultants and executive advisers — to share the questions they think CIOs should ask themselves to determine whether they’re sailing to success or about to dash onto the rocks. 1.
Is this initiative about optimization or about growth and disruption? Moving more workloads to the cloud, adopting cloud-native development, adopting agile development principles, and implementing automation are not inherently transformational, particularly if they’re only optimizing existing products, services, and processes, says Anant Adya, executive vice president and head of Americas delivery for Infosys. “Digital transformation is when you’re helping the company grow and disrupt,” he says, explaining that true transformation grows the company’s revenue or improves its customer and worker experiences. To that end, DX experts say CIOs need to be clear on the business outcomes their initiatives will deliver and articulate outcomes in top- and/or bottom-line figures.
2. Am I using data to drive my transformation strategy? Or put another way: “Do I have a for identifying and prioritizing digital transformation programs?” Adya asks. Adya says many executives answer no.
“Data is essential for making informed decisions and measuring the success of transformation efforts,” Adya says. “Organizations should leverage data analytics to identify trends, gain insights, and optimize their transformation initiatives based on data-driven evidence.” 3.
Is the organization’s data ready to drive transformation? The , released in early 2024 by Dun & Bradstreet, found that 81% of the surveyed 1,000-plus senior decision-makers agreed that the primary role of data in their organizations is to help grow the business. Yet only 57% believe their data can help them achieve that goal. Atif Zaim, national managing principal for advisory at professional services firm KPMG US, says CIOs must ask if the state of enterprise data and data infrastructure is ready to support transformation.
If it’s not, they’ll need to turn that around or otherwise miss out on the ability to seize on opportunities presented by emerging technologies such as generative AI. 4. Is my strategy organized around problems to solve, or technologies? CIOs who organize transformation workstreams around problems to solve are on the right track, says David Rogers, a faculty member at Columbia Business School and author of .
“Every successful digital transformation I’ve seen is organized around a strategy problem to solve or a growth opportunity,” he adds. Rogers says successful organizations have standing teams that work on specific areas. An omnichannel retailer, for example, would have a team organized around order fulfilment, an area where retailers are constantly challenged to do better to meet customer expectations and best their competitors at doing so.
The team can then work on whatever it takes to solve the problems in its particular area, Rogers says, “whether it’s coming up with new processes, people, training, robotics, anything that can improve it.” That gives the team a business outcome to reach, not merely IT functionalities to deliver. 5.
What enterprise capability gaps will this transformation initiative close? Brandon Germer, a senior director analyst with research firm Gartner, advises CIOs to ask and answer specifically what enterprise capability gaps a particular transformation initiative will close before pursuing that initiative. “This helps avoid the fascination with a technology for technology’s sake, or pursuing things that add value but maybe not the most value for the investment,” he says. Kamales Lardi, author of (2022) and CEO of Lardi & Partner Consulting, recommends the same approach, although phrases the CIO question differently.
She says CIOs should ask, “Where do we fall short?” CIOs can look at various areas such as revenue, customer experience, and risk to find shortcomings where transformation is needed. 6. Will my AI strategy solve a problem or address a gap? Greg Taffet, managing partner of Taffet Associates and a provider of fractional CIO services, recommends a similar strategy when assessing AI plans.
“The newest question we have to ask is about AI,” he says. “While AI provides tremendous improvements for many problems, we have to properly vet the use of AI to make sure we are getting the right outcomes.” 7.
Who leads transformation with me? Krishna Prasad, chief strategy officer and CIO at UST, a digital transformation solutions company, says CIOs should not go it alone on transformation initiatives. “Initiatives tend to hit brick walls if you don’t have commitment from other leadership,” he says. Research backs that up, says Germer.
Gartner has identified three types of transformation activity, which have varying levels of success. The first group consists of business unit executives who pursue transformation initiatives without IT’s involvement; this group succeeds in meeting target outcomes for their investments 37% of the time. The second group consists of executives who collaborate with IT to achieve transformation, with IT using a traditional delivery model where a business leader serves as an executive sponsor; this group succeeds in hitting their targets about 45% of the time.
The third cohort consists of executives who co-lead transformation with CIOs; their success rate is 71%. Germer says the figures clearly show that “the way forward is to co-lead digital delivery.” Gerner says in this group the CIO and the business unit execs co-own delivery and accountability, they use multidisciplinary product teams to own and manage a product or service, and those fusion teams are measured on whether they achieve or exceed the desired business outcomes.
8. Am I engaging people on the front lines to formulate DX plans? According to Rogers, the answer should be yes. “You need people on the front lines, because it is the business units who have people out there talking to customers every day,” he says, adding that while C-suite support for transformation is crucial, the front-line perspectives offered by lower-tier employees are those that can identify where change is needed and can truly impact the business.
“Your transformation should not be planned entirely from the top by the leadership team,” he explains. “You need to organize your transformation to both surface and support ideas for new digital initiatives that are coming from business units, from customer-facing teams, and from functions like HR.” 9.
Am I identifying and using the right business metrics to measure progress? Most CIOs have like uptime and application availability to determine whether a tech-driven initiative is successful. Still, there’s no guarantee that CIOs use the most appropriate metrics for measuring progress on a DX program, says Venu Lambu, CEO of Randstad Digital, a digital enablement partner. “It’s important to have the technology KPIs linked to business outcomes,” he explains.
If your business wants to have faster time to market, improved customer engagement, or increased customer retention, those are what CIOs should measure to determine success. 10. Do I have a DX budget and/or completion timeline? An affirmative answer to this question indicates a problem, as experts stress that transformation isn’t a task to undertake and complete but an operational and strategic imperative that should be woven into all the organization does.
Rogers acknowledges the challenges of that, saying “the constancy of transformation is the hardest thing for companies.” That’s particularly true for established organizations, which aren’t good at change due to their size and complexity. This is not an insurmountable situation.
Rogers in his latest book profiled established companies that are DX leaders and identified elements they have in common. “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: , 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 at a much faster pace than in the past, he says, adding that tech leaders must also confirm that their to ensure all vendors supporting the company are equally capable of keeping pace. Germer says is just the start, however. To truly be successful, CIOs need to evolve the IT operating model, too.
For example, . They should use performance metrics based on business outcomes rather than tech metrics to measures success. And they should have .
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.” More on digital transformation:.
