CIOs like to say there’s no better time to be in IT, highlighting the excitement and buzz around the opportunities that AI and evolving technologies bring to their role.
But IT leaders are also open about the challenges they currently face to ensure success for their organizations and themselves. Some of those obstacles are perennial problems; others are novel.
Here, tech execs share what they see as eight of the biggest issues confronting IT today.
Scaling AI for business value has become a nearly universal challenge, listed often by CIOs and other executives as the single biggest issue they face in 2026 — and the top CEO priority for most.
“As a CIO, as is the case with CIOs in my network, the biggest issue and the biggest priority is accelerating the speed and pace of AI adoption that leads to tangible business outcomes and value,” says Thomas Phelps, CIO and senior vice president of corporate strategy at Laserfiche and an advisory board member for the SIM Research Institute. He stresses that there’s pressure both to adopt AI faster and to get to value more quickly.
“We’re beyond being measured on proofs of concepts and pilots. [Executives] want product improvements and improvements in metrics like revenue per employee. They want to know how we’re using AI to generate top-line revenue growth, how we’re adopting AI tools for know-our-customer activities, for supporting customers post-acquisition, for improving service and customer support. They want to see we’re using AI to deliver results by transforming what we’re doing every day,” Phelps says.
Many CIOs are struggling to deliver on all this. The April 2026 CIO Report from research firm Gartner found that “72% of CEOs identify AI as their primary driver of growth, placing new pressure on CIOs to accelerate enterprisewide AI value realization.” However, “71% of CIOs struggle to prioritize the AI use cases that will deliver measurable business outcomes” and “59% of AI initiatives fail to make it into production.”
It’s no surprise that cybersecurity is a near universal issue for CIOs, as IT leaders have contended with hackers since the dawn of the internet age. But today CIOs say the stakes have gotten higher, the work has gotten harder, and the pressure more intense due to AI.
“Our ability to keep the company safe is getting harder and harder,” says Matt Ausman, senior vice president and CIO at Zebra Technologies. “I spend more and more of my time on cyber and on strategies to keep the company safe. It’s becoming a bigger monster in the room right now.”
CIOs also say they’re under the gun to defend against an onslaught of AI-enabled attacks as well as to implement AI to be more effective and efficient in their defense.
“Cybersecurity is not a new issue, but what is new is the scale and sophistication and depth of threats. We’re seeing a new level of sophistication as well as more profiling and coordination of activities with AI-driven attacks that is alarming and challenging,” says Greg Moore, vice president and CIO at KB Home.
Like other CIOs, Moore uses AI in his cybersecurity operations to improve defenses, detection, and response. And he also uses more conventional approaches, including employee awareness training, to help counteract the growing volume and velocity of attacks. Despite such efforts, however, Moore says cybersecurity remains a dominant concern and will likely remain a perennial top issue for CIOs for many years to come.
Executives and board members ranked cyber threats as the No. 1 global near-term risk they face, followed by third-party threats, according to the 2026 Executive Perspectives On Top Risks And Opportunities report from consulting firm Protiviti. They listed security and privacy as the No. 2 long-term challenge, and they put risks related to data required for AI use and cybersecurity exposure at the top of the list of priorities for AI use in the organization.
A 2026 survey of 2,000 workers conducted by security software maker BlackFog found that 49% used AI tools without their employer approval, with many using free versions in which they shared sensitive data.
The rise of shadow AI certainly has plenty of CIOs on edge, but they say the issue of shadow IT is more complicated today than in past years as organizations race to use AI to ensure they’re not left behind.
“Shadow IT has always been and will always be a problem,” says Ross Tisnovsky, a partner at Everest Group and leader of the firm’s CIO research and advisory practice, noting that shadow IT often adds complexity, cost, and risk.
So CIOs need to contain — if not outright eliminate — shadow IT, including shadow AI, to avoid those negative consequences, Tisnovsky says.
But they must also empower employees throughout the organization to embrace AI and use the technology to rework their own day-to-day jobs, he adds. Workers need to become citizen developers.
“The power of users should be harvested; we can’t tell them to stay out of it,” Tisnovsky says, noting that the speed of development that vibe coding enables can be a boon for organizations.
He says CIOs today must figure out how to enable employee use of AI tools and AI-enabled development, while putting in the right level of controls to limit negative consequences, such as unacceptable security risks, data leaks, and hallucinations. But they must not put in so many controls that workers try to go around IT and use unsanctioned technology.
Getting the right balance among those competing needs is no small task. “In fact,” Tisnovsky says, “finding the balance is probably the toughest part.”
Like cybersecurity and shadow IT, “legacy tech has been an issue forever,” Tisnovsky says. But like the other issues cited by CIOs for 2026, it has become more pressing today because it’s hindering successful AI adoption.
It’s not just legacy tech that is a hinderance, however. Tisnovsky says legacy data, processes, and skills are, too. All of these slow or block transformation.
Yet getting the resources needed to modernize these areas is a challenge, because for so long executive leadership teams did not see an obvious ROI for the work, he says. “Yes, it would enable future products, but they often couldn’t quantify that. But we’ve reached the point that that future ROI is here.”
CIOs are finding ways to get the support and resources they need to modernize, says Kim Bozzella, global head of technology consulting and CIO C-suite solution at Protiviti.
“CIOs are reframing tech modernization as an AI enablement investment rather than pure maintenance, a positioning shift that helps unlock business case funding. Some are leveraging AI itself — code generation, automated testing — to accelerate debt remediation,” she explains.
Whether enabled by AI or another force, many CIOs are tasked with leading transformation. “You have to move the business forward,” says Marco Bill, senior vice president and CIO at Red Hat.
Transformation, however, remains a tough task by nearly all accounts.
For example, Bill says his company has an upcoming ERP transformation which — as experienced CIOs know — requires buy-in from multiple stakeholders, employee engagement, careful planning, and great execution to reengineer all the components that go into such an undertaking. The AI tools that now come standard with such transformation up the amount of change, the challenges, and the expectations. “These programs are big, and they need a lot of change management, because you’re changing how people do stuff,” Bill says. “It’s like performing like heart surgery while you’re doing a sprint.”
CIOs say it’s not just transformation that’s taxing them, their IT teams, and their organizations. It’s the volume and velocity of change.
“Change management can’t keep up with the evolution of technology now,” Ausman says.
Ausman has found that 5% to 10% of his organizations want to live on the bleeding edge and are energized by all the change happening. “But the rest aren’t keeping up with the pace,” he says. “So what do we do about that? Sometimes I have to rein in the top 10%, and other times I have to push the rest of the organization.”
To help, he formed an AI transformation council that reports to him but is led by someone from the business side. The council has been able to bubble up challenges and identify what leadership can do to address those. It uses a federated approach to engage the various business units, and it uses training and other tools to help everyone in the organization meet adoption standards.
Such efforts, Ausman adds, have helped the organization speed up its ability to change.
AI is changing how work gets done, and workers — including those in IT — need to adjust. That, along with longstanding issues around talent shortages and upskilling needs, has put a lot of pressure on CIOs.
“AI agents are beginning to perform tasks previously owned by humans, creating urgent questions about role design, headcount, and the skills needed to work alongside AI. At the same time, IT organizations already face a shortage of AI talent that the market hasn’t yet seen scale,” Bozzella says. “The shift to a blended workforce — humans and AI agents operating in shared workflows — requires new op models, org structures, joiner/mover/leaver processes, and metrics. IT must simultaneously upskill its own teams, build the platforms that enable AI-human collaboration, and support business units through their own workforce transitions.”
To help tackle all that, Bozzella sees CIOs partnering with CHROs to define AI-augmented job architecture, understand agent identity and access needs, and identify reskilling and training programs that give teams the skills to redefine work.
Longtime IT leader Greg Taffet is one such CIO contending with tomorrow’s workforce issues today.
He says employee retention remains a big issue for CIOs, because with so much disruption and AI-related work happening, “everybody wants to grow their careers and is jumping jobs faster than they can get experienced in the jobs they have.”
Taffet, managing partner and CIO at strategic technology consultancy Taffet Associates, says technologists are typically looking for AI-related work and, in particular, jobs with big tech companies, making it harder for CIOs to attract talent.
“I’ve been trying to solve for this by making myself the person people want to work for, by making myself someone in the marketplace who has a good reputation,” he says, noting it has helped.
Taffet is also working with HR teams to ensure that automated systems don’t preclude promising candidates who can be trained to fill open positions. That, too, has helped with — although not fully solved for — the ongoing challenge of building and retaining the right team with the right skills, Taffet adds.
One of the biggest challenges facing IT leaders today, Bozzella says, is transforming themselves into the CIOs that will be needed in the future.
“The CIO role is expanding well beyond IT as AI and tech broadly are now embedded across all aspects of the business (finance, HR, ops, CX, etc.),” she says. “Technology is now the engine of business transformation, and boards expect CIOs to lead enterprisewide AI and technology strategy, not just execute it.”
As Bozzella sees it, “CIOs now carry accountability that historically sat with business leaders. This requires deeper business strategy/organizational change acumen while still managing in increasingly complex tech estate,” she explains.
To meet the future, forward-looking CIOs are building tighter relationships and partnerships with their C-suite peers to co-lead and own transformation agendas.
“This represents a redefinition of the role,” she says, “from tech steward to enterprise transformation leader.”
The majority of CIOs are moving toward that future version of the role. According to CIO.com’s 2026 State of the CIO survey, 83% of CIOs say they’re becoming a changemaker, increasingly leading business and technology initiatives.