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CIOs: Ignore IT maturity and your upskilling will fail
CIOs face mounting IT talent shortages. Aligning upskilling with IT maturity helps build future-ready teams, optimize resources and sustain competitiveness.
Executive summary
- Upskilling without IT maturity leads to wasted investment, skill misalignment and employee burnout.
- Aligning upskilling with IT maturity ensures training is relevant, timely and supports business goals.
- CIOs should prioritize future-ready skills—AI fluency, cybersecurity, cloud management and data literacy—to maintain agility and competitiveness.
Persistent IT talent shortages make hiring top talent harder than ever. Eighty-seven percent of technology leaders are struggling to find skilled talent, according to a Robert Half survey, and 90% of organizations are expected to be negatively impacted by the IT skills shortage by 2026, according to IDC. The same study noted that the IT skills shortage could result in $5.5 trillion in losses due to product delays, business losses and diminished competitiveness.
The skills shortage has organizations scrambling to find talent that possesses future-ready skills to face the new era of digital transformation, such as automation, data analytics and AI literacy. The high demand for these skills makes them even more challenging to secure, especially for organizations that lack the resources to offer competitive salaries or attractive benefits.
These issues are manifesting in real-world consequences for CIOs and IT leaders, and simply "hiring better talent" is no longer feasible. Instead, companies are turning to upskilling to help their existing workforce develop the future-ready skills organizations need to stay competitive. However, in the race to stay ahead, many companies are missing a critical piece of the puzzle that can significantly hinder upskilling efforts -- IT maturity.
Why IT maturity matters for upskilling
IT maturity centers on how effectively a company uses its IT ecosystem to support organizational goals. Assessing IT maturity involves examining all facets of IT within an organization, including governance, processes, tool adoption and culture.
"As an IT organization grows in maturity, its skills need to evolve. If you upskill too early—before foundational maturity—you risk instability and wasted investment," said Brian Spanswick, CIO at Cohesity. He added that IT organizations in the early stages of their maturity require both tactical and technical skills to deliver and maintain IT services. "If an IT organization doesn't have a solid 'run' foundation, any additional maturity is wasted," he said.
The level of high IT maturity can vary depending on an organization's mission and objectives. IT maturity enables an organization to use its IT capabilities efficiently and cost-effectively while remaining flexible enough to adapt to changing business needs without disruption.
IT maturity also hinges on the organization's culture and readiness to adapt. "Any maturing process comes with a cultural mindset, both from a leader standpoint, like a CIO, who needs to create an environment where learning, failing and embracing change is encouraged," says Amit Modi, chief technology officer at Movius. "If you don't allow people to be comfortable in that environment, either the change process will be slow, they'll be resistant or that company is going to miss out."
An immature IT environment – one that is bogged down by inefficient processes, incongruent with the larger organizational culture and unable to adapt to changing needs or integrate with new tools – can be detrimental to upskilling efforts. "The risk of not reaching IT maturity before upskilling is that IT services won't meet and maintain the service levels that the enterprise requires to execute business operations," said Spanswick.
The consequences of upskilling in an immature environment can be far-reaching, including:
- Underused skills. Upskilling efforts may be misaligned with job roles or organizational goals, or the organization may lack the necessary supporting infrastructure to nurture these skills.
- Wasted time and resources. Inefficient or ineffective upskilling leads to wasted time and effort for the employee and wasted costs and resources for the organization
- Employee attrition. Disorganized and inefficient upskilling can lead to employees feeling stagnant and burned out, culminating in attrition and competitors poaching top talent.
To ensure that upskilling efforts are effective, initiatives should be aligned with maturity milestones, ensuring that upskilling is timely and relevant to the organization's current capabilities. For example, a low-maturity IT environment may train employees in foundational skills, such as digital literacy. When IT maturity is reached, an organization may introduce more high-level skills.
Skills CIOs should prioritize now
Effective upskilling hinges on identifying the essential skills that the organization currently needs, as well as future IT skills that will help maintain a competitive edge.
"CIOs should focus less on teaching teams specific programming languages or tools, and more on building system-level thinking and human oversight," said Agustín Huerta, senior vice president of digital innovation for enterprise core studio at Globant. "The future of IT will depend on whether IT teams can design scalable and secure systems that can use AI effectively, not based on whether someone codes in Python or JavaScript."
Here are some of the skills that CIOs should prioritize now to stay agile in a changing world:
- AI and automation fluency. Skills related to AI and automation – including AI for IT operations, prompt engineering, and workflow automation – are becoming increasingly important as AI adoption continues to impact work operations, particularly within the IT sector. Fifty-one percent of IT leaders report suffering from an AI skills shortage, according to a report from Harvey Nash.
- Cybersecurity resilience. Security measures, such as cloud security, identity and access management and threat intelligence, have always been essential but are increasingly important as cyberattacks and hacking become more common and sophisticated.
- Cloud and hybrid infrastructure. Understanding cloud and hybrid environments is essential as IT moves away from traditional infrastructure toward a more agile and scalable model. Employees must be able to navigate this change by developing skills such as multi-cloud management, including microservices and serverless computing, as well as cloud-native architecture and financial operations.
- Data and analytics literacy. Data and analytics literacy enable IT teams to make informed, strategic decisions, keeping the organization agile and future-ready. Knowing how to use skills like visualization, data governance, and how to provide decision-making support are all core parts of data literacy that IT teams must keep top of mind.
- Soft skills for transformation. Soft skills are just as important as technical skills – but are sometimes overlooked in upskilling. Learning essential soft skills, such as change management, cross-functional collaboration and leadership agility, can help employees adapt to changing needs when the time comes. IT organizations should place an emphasis on soft skills, such as critical thinking, according to Spanswick. "The ability to formulate a hypothesis, test it against real-world scenarios, assess the findings and update the hypothesis is critical to mature the IT services effectively and efficiently," said Spanswick.
How to build a resilient upskilling strategy
Upskilling can be an integral part of a CIO workforce strategy, but without a solid plan in place, companies can risk derailing their upskilling efforts. Planning upskilling efforts ensures that the process is deliberate and that the most relevant skills are prioritized.
Employees may initially resist new technologies or training. However, employees are also more likely to buy into an upskilling initiative when it's clear that the strategy has been thought through and tailored to the organization's needs.
Here are five steps to build a resilient, future-proof upskilling strategy:
- Assess IT maturity. Obtaining an honest pulse check on the organization's current IT maturity, through tools such as the IT maturity model, is essential for building a successful strategy. CIOs should look beyond tech stacks to gain a holistic view of the IT environment. Being honest about where gaps and challenges lie ensures that the upskilling strategy can properly address these issues.
- Tie training to future-forward IT roadmaps. Once IT maturity has been assessed and current gaps identified, tech leaders should look ahead to anticipate the skills that may be needed in the future. "CIOs need to be explicit about the future skills the organization needs, by when, and set clear expectations, while also giving teams the space to personalize learning based on role relevance," said Kian Katanforoosh, CEO and founder of Workera.
- Align with HR and business units. When all business units are aligned with the upskilling strategy, it ensures expectations are aligned with all business needs. Gaining buy-in from necessary stakeholders before implementing the strategy ensures that concerns can be addressed.
- Measure outcomes. Measuring outcomes such as adoption rates, project acceleration and completion, and reliance on external hiring can all signal the success of upskilling. "Companies should focus on measuring the real impact their solutions create, not just how efficiently teams operate," says Huerta. "Outcomes are reflected in how the products, services, or strategies they build influence customer behavior, business performance, or the organization's overall capacity to generate value."
- Refine the strategy. Once the successes and challenges of upskilling have been identified, those insights should be used to optimize and refine it. Organizations should "continuously refine their strategy to double down on what creates measurable impact and evolve as quickly as the market and technology do," according to Huerta. The upskilling strategy should be regularly assessed to ensure it continues to meet the business's needs.
Executive takeaway
When upskilling is conducted without considering IT maturity, resources, time, and effort are spent on upskilling that won't stick. That means leaders must invest money and resources in reskilling, or risk being overtaken by competitors that possess stronger skill sets and greater adaptability.
Linking phases of maturity with training needs ensures the workforce stays aligned with the organization's current needs and can accurately predict what it may need in the future to handle the next wave of digital transformation or disruption.
In an era where hiring is limited and optimizing resources is more crucial than ever, an upskilling strategy that prioritizes IT maturity can be the competitive advantage organizations need to achieve—and maintain—a competitive edge.
Alison Roller is a freelance writer with experience in tech, HR and marketing.