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IT leaders are being squeezed from several directions at once: attacks are harder to contain, AI is moving into production, cloud bills are rising, legacy systems resist change, and teams must prove that technology spending improves the business. There is no single authoritative ranking, so the ten issues below are an evidence-backed synthesis of recurring concerns reported by different surveys. They are a practical answer to the question, “What keeps you up at night?”—not a claim that every organization faces them in the same order.
The evidence comes from the 2025 SIM IT Issues and Trends Study, the World Economic Forum’s Global Cybersecurity Outlook 2026, Info-Tech Research Group’s Infrastructure and Operations Priorities 2026, Flexera’s 2026 IT Priorities release, and the BCS 2025 technology-priorities survey. Their samples, dates and questions differ, so percentages should be read within their original populations.
At a glance: the recurring pressure points
| Issue | Evidence base | Typical consequence when neglected |
|---|---|---|
| Cybersecurity and resilience | SIM, WEF, BCS | Service disruption, data loss and regulatory exposure |
| AI integration, governance and value | SIM, Flexera, WEF, BCS | Uncontrolled use, weak returns and new attack paths |
| Cloud and SaaS cost management | Flexera | Budget overruns and underused subscriptions |
| Technical debt and legacy infrastructure | Info-Tech, WEF | Slower delivery and harder security maintenance |
| Skills shortages and workforce capacity | SIM, Info-Tech, BCS, WEF | Backlogs, burnout and dependence on contractors |
| IT-business alignment and value | SIM | Projects that do not support measurable outcomes |
| Ineffective processes and operational complexity | Info-Tech, Flexera | Manual work, inconsistent service and hidden risk |
| Interoperability and integration | Info-Tech | Duplicate data and brittle handoffs between systems |
| Third-party and supply-chain risk | WEF, Info-Tech | Incidents or outages inherited from suppliers |
| IT visibility, data use and governance | Flexera | Blind spots in assets, spending, data and accountability |
1. Cybersecurity and resilience
Security is no longer only a perimeter-defense problem. IT must keep critical services operating while threats, technology stacks and supplier dependencies change. SIM places cybersecurity among the leading IT-management issues, and BCS reports that 33% of surveyed technology leaders and professionals ranked it their top technology priority in 2025. Those figures describe the respective survey populations, not all IT departments.
The WEF’s Global Cybersecurity Outlook 2026 identifies the main resilience challenges reported by its respondents: 61% cited evolving threats and emerging technologies, 46% cited third-party and supply-chain vulnerabilities, and 45% cited cyber-skills shortages. WEF also reports legacy infrastructure as a challenge for 31% of respondents.
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What the issue requires
- Maintain tested recovery plans, offline or otherwise protected backups, and clear service-restoration priorities.
- Apply identity controls, multifactor authentication, segmentation, vulnerability management and logging according to the systems’ business criticality.
- Measure resilience as well as prevention: recovery time, recovery-point performance, exercise results and unresolved high-risk findings.
2. AI integration, governance and measurable value
AI has moved from experimentation into operating plans, but adoption creates work that ordinary software rollouts do not: data controls, model evaluation, human oversight, security testing and a credible way to measure benefits. In Flexera’s November 5, 2025 release, 33% of 834 surveyed global IT decision-makers named AI integration their leading priority for the coming year, while 19% prioritized demonstrating AI usage and effectiveness. Flexera CTO Brian Shannon said, “AI has moved beyond the hype phase and is now a critical component of IT strategy.” That is an executive characterization from a vendor-sponsored survey, not an independent benchmark.
BCS placed AI second among its 2025 technology priorities, at 24% of respondents. WEF expects AI to be a major driver of cybersecurity change while warning that adoption can introduce vulnerabilities, data exposure and governance demands.
Questions an IT leader should settle early
- Which business outcome is the system intended to improve, and what baseline will be used to measure it?
- What data may be entered, retained or used for training, and who is accountable for quality and privacy?
- Where is human approval mandatory, and how will errors, bias, abuse and model drift be detected?
- How will prompts, models, vendors and connected tools be inventoried and reviewed?
3. Cloud and SaaS cost management
Cloud consumption and SaaS subscriptions can expand faster than the controls around them. Flexera reported that 73% of surveyed IT leaders said their SaaS and cloud-infrastructure costs had risen, and 67% said cloud expenses weighed heavily on IT budgets. These are respondents’ reports from the 2026 IT Priorities release, not an audited measure of spending across every organization.
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- Idle compute, oversized databases, unattached storage and data-transfer charges.
- Licenses assigned to people who no longer need them or duplicated tools bought by separate teams.
- Architectures optimized for speed of deployment but not for predictable unit cost.
Effective cost management combines ownership tags, budgets and alerts with engineering changes such as rightsizing, scheduling, storage policies and workload-specific architecture. Finance, procurement and product teams need a shared view of cost per service or transaction rather than a single monthly cloud total.
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4. Technical debt and legacy infrastructure
Old platforms create a compounding tax: every change takes longer, specialized knowledge becomes scarce, and security fixes may be difficult or impossible to apply. Info-Tech reports reducing technical debt as a leading 2026 infrastructure priority. Its respondents also identify outdated infrastructure as an obstacle to cybersecurity objectives, consistent with WEF’s finding that legacy infrastructure challenges cyber resilience.
Choosing what to modernize
- Map applications and infrastructure to business services, dependencies, owners and recovery requirements.
- Rank debt by business impact, security exposure, operational fragility and cost of delay—not by age alone.
- Choose deliberately among replacement, re-platforming, refactoring, isolation or retirement.
- Reserve time for data migration, testing, rollback and staff training; a rushed migration can create a new form of debt.
5. Skills shortages and workforce capacity
Demand for security, cloud, data and AI capability is growing faster than many organizations can hire or develop it. Info-Tech reports lack of skilled personnel as an infrastructure and operations challenge, with 43% of its respondents citing it. WEF reports cyber-skills shortages as a resilience challenge for 45% of its respondents. BCS describes AI as a substantial skills gap among its surveyed leaders and professionals. These measures cover different roles and populations and should not be combined into one labor-market percentage.
SIM’s 2025 study, published in 2026, found that 54.2% of organizations reported increasing IT headcount—the lowest share since 2020. That combination of rising capability requirements and constrained staffing makes prioritization as important as recruitment.
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Practical responses
- Define the few capabilities that are mission-critical and build them internally where continuity and context matter.
- Use structured learning, mentoring and rotations to turn existing staff into practitioners rather than relying only on courses.
- Document runbooks and architectural decisions so expertise is not trapped in one person or supplier.
- Use partners for bounded capacity, while retaining ownership of risk, design and operational knowledge.
6. IT-business alignment and proving value
Technology teams are expected to contribute to growth, efficiency, customer experience and risk reduction—not simply deliver projects. SIM lists alignment between IT and the business among the most important management issues and treats value and strategic contribution as CIO performance criteria.
Make the connection explicit
- Translate each major technology initiative into a business outcome, such as faster claims handling, fewer outages or lower cost per order.
- Assign an outcome owner outside IT as well as a technical owner.
- Set a baseline, target and review date before delivery begins.
- Stop or redesign work when evidence shows that the expected outcome is not materializing.
This approach prevents activity measures—tickets closed, servers migrated or models deployed—from being mistaken for business value.
7. Ineffective processes and operational complexity
Even well-designed platforms underperform when the processes around them are inconsistent. In Info-Tech’s infrastructure and operations survey, 46% cited ineffective core processes as a challenge. Flexera also highlights visibility gaps and unsanctioned SaaS use, which can create duplicated work, unmanaged data and unclear accountability.
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Where to simplify first
- Standardize request, change, incident and access workflows, with an exception path for genuinely urgent work.
- Remove approval steps that add delay without reducing risk, and automate repeatable checks.
- Publish service ownership, escalation routes and operating-level expectations.
- Review the tool estate for overlapping monitoring, ticketing, collaboration and security functions.
8. Interoperability and integration
Systems that cannot exchange reliable data force staff into spreadsheets, re-keying and manual reconciliation. Info-Tech reports interoperability issues among infrastructure and operations challenges, cited by 35% of its respondents. The source does not break that result down by technology or sector, so the remedy must be tailored to the organization’s architecture.
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A durable integration approach
- Start with the business data and process that must flow, then define ownership, quality rules and timing.
- Prefer documented APIs, event interfaces or managed data products over fragile point-to-point scripts where the scale justifies them.
- Version interfaces, monitor failures and make replay or reconciliation possible.
- Include identity, authorization, privacy and retention requirements in the interface design.
9. Third-party, supply-chain and critical-vendor risk
Outsourcing does not outsource accountability. WEF identifies third-party and supply-chain vulnerabilities as a leading cyber-resilience challenge, with 46% of its respondents citing them and particularly acute concern among large companies. Info-Tech reports that 44% of its respondents prioritized mitigating risks involving critical infrastructure vendors.
Control the dependency
- Classify suppliers by the services, data and recovery consequences they could affect.
- Review security practices, subcontractors, incident-notification terms, access controls and recovery evidence before renewal.
- Maintain an accurate dependency register and a tested exit or substitution plan for critical services.
- Monitor material changes in ownership, architecture, hosting location and concentration risk.
10. IT visibility, data use and governance
Leaders cannot manage what they cannot see. Flexera reports concerns about visibility gaps, unsanctioned SaaS and the need for further investment to extract value from data. In practice, this issue spans asset and license records, cloud usage, data lineage, access rights, service health and the quality of management reporting.
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- Keep authoritative inventories for hardware, software, cloud resources, SaaS subscriptions, data stores and service owners.
- Define common terms and data owners so finance, security and operations reports do not contradict one another.
- Log access and material changes, retain evidence for the applicable regulatory period, and review exceptions.
- Expose uncertainty: a dashboard should show stale, missing or estimated data instead of presenting false precision.
How to decide what comes first
The surveys show why a universal ranking would be misleading. SIM’s 2025 study included 704 IT executives, including 211 CIOs, across 344 organizations and was published in MIS Quarterly Executive in 2026. Flexera’s release describes 834 global IT decision-makers and is dated November 5, 2025. Info-Tech’s priority interviews took place from August to October 2025, with diagnostic measures covering August 1, 2024 through July 31, 2025. The BCS overview reports leaders’ and professionals’ views but does not state a sample size on the overview page. WEF’s percentages come from its Global Cybersecurity Outlook 2026 survey population.
Use those findings as signals, then rank your own backlog against seven questions:
- Business impact and continuity: Which failure would stop a critical service or materially harm customers?
- Security and resilience: Which exposure could become an incident, and how quickly could you detect and recover?
- Time to contain: Can a control reduce risk this quarter, or does the work require a multiyear transformation?
- Total cost and measurable value: What will the change cost to build, run, migrate and support, and what outcome will it improve?
- Workforce capability: Do you have the skills to operate the proposed solution safely?
- Dependencies: Which vendors, data flows and legacy systems could delay or undermine delivery?
- Organizational context: How do size, sector, geography and regulatory obligations change the trade-offs?
A small regulated organization may put recovery testing and supplier controls ahead of an ambitious AI rollout. A fast-growing software company may first need cost visibility and integration discipline. The right sequence is the one that reduces the most consequential exposure while building the capability needed for the next decision.
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