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Oct 09 2026
Management

How Leaders Overcome IT Staffing Shortages Through Retention and Upskilling

Amid constrained hiring, higher education IT leaders are rethinking roles and building new capabilities within the teams they already have.

The talent tension in higher ed has many dimensions. Attracting IT talent has been a long-standing challenge for a variety of reasons, including compensation, burnout due to workload demand and limited or unclear advancement pathways. 

As if those challenges weren’t enough, policy changes and enrollment trends have created a cascading effect. Research funding, declining international student enrollment and overall uncertainty are piled on to the difficulty IT leaders are already grappling with in hiring and keeping an adequate number of staff to meet the needs of their campus. Layoffs and hiring freezes have become commonplace at institutions of all types, and teams have shrunk around the work rather than grown into it, leaving the remaining team members with expanded responsibilities and fewer colleagues to rely on. 

Still, the academic calendar marches on, and the business of creating an exceptional student experience means that all business units (including IT) are maintaining or modernizing with the people they already have. Future-proofing the organization therefore requires a deliberate approach to identifying the skills of their current staff and capitalizing on that talent. 

DISCOVER: CDW’s Talent Orchestration services help institutions cultivate a thriving workforce.

Equally, creating a development pathway for gaining near future skills and certifications for every role sends the message that IT leaders value their team. Higher ed IT leaders need to signal that they are intentionally investing in their team in any way possible, not simply planning on replacing roles as technology changes. 

Preserving Legacy IT Expertise While Looking to the Future

Despite pressure to modernize and improve business practices, higher education institutions often cannot retire legacy platforms as quickly as they would like. The IT staff members who understand those systems hold valuable knowledge about integrations, workflows, data and campus operations. But preserving that expertise requires knowledge transfer, especially when they may not be able to backfill employees who retire or leave. 

Documentation is a tried-and-true way to preserve knowledge, and pairing it with job shadowing reduces the potential for disruption. Longstanding IT talent should not be confined to legacy work. Pairing employees with different skill sets to cross-train is one way to preserve legacy knowledge and upskill segments of the team. It also creates opportunities for experienced staff to develop coaching skills and participate in the modernization of the systems they know best.

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Build New Technological Capabilities Within Your Current Team

Waving the “do more with less” banner is a reality for many IT leaders. An important exercise, therefore, is to audit the existing skills of your team. Accurately identifying your team's collective skills is the starting point for mapping emerging skills to the team you already have in place. With funding scarcities, IT leaders have an advantage when making a case for specific professional development that advances the entire unit. 

READ MORE: A better-trained staff leads to stronger security in higher education.

This is also a lens through which new roles can be identified. Predicting job titles that may disappear or emerge is less important than identifying the capabilities the institution will require. 

Consider how many roles are already folding in data literacy as an essential component of the job. A systems administrator, for example, may increasingly be expected to evaluate utilization, communicate costs, manage vendor performance or advise leaders on the value of cloud investments. The important point is not that every systems administrator must become a cloud ROI analyst, but that institutions should regularly update job descriptions to reflect the work employees are already being asked to do and provide the preparation needed to do that work well.

Turn the Org Chart Into a Professional Development Map for IT Leaders

Higher education IT leaders facing restructuring have an unexpected advantage: the chance to intentionally redesign job roles and responsibilities. Acknowledge and prioritize the evolving competencies your unit needs into an existing role rather than removing a role entirely. A redesigned organizational chart should reflect these new skill requirements explicitly.

Budget constraints are real, and relief isn't on the horizon. But that doesn't mean accepting stagnation. Instead, it creates the window to make strategic choices about where limited resources go. Prioritize training and development for the competencies most critical to your redesigned structure and make that training nonnegotiable in your budget allocation.

Three practical approaches can upskill and reskill your existing tech team without breaking an already-strained budget. 

First, tie training and certifications directly to implementation projects. Rather than generic professional development, negotiate learning into the rollout of new systems. This way the training becomes immediately relevant and embedded in the implementation timeline. 

Second, when you contract for platform or system implementations, build job shadowing into the vendor agreement. Pair your existing IT staff with the implementation expert; that continuity transfer is far more valuable than the contracted system expert handing off documentation after launch. 

Finally, staff augmentation through contracting can itself be a development strategy when structured intentionally. Your people learn alongside the external expert sourced as part of the contract agreement rather than being sidelined during the transition.

UP NEXT: The 2027 EDUCAUSE Top 10 highlights an era of change.

What separates institutions that stagnate from those that adapt won't be the size of their IT budget, instead it will be whether leaders chose to invest in the people already on their team. That investment doesn't have to wait for a strategic planning cycle or a line-item approval. It can start this week, with a conversation about which systems administrator wants to learn cloud cost analysis, or which vendor contract could include a shadowing clause instead of a handoff document. 

Institutions that come out ahead over the next five years probably won't have solved the hiring shortage; most won't, budgets being what they are. They'll simply have gotten better at recognizing the capacity within the teams they already have and building toward it intentionally instead of waiting for headcount that is unlikely to happen any time soon.

This article is part of EdTech: Focus on Higher Education’s UniversITy blog series featuring analysis and recommendations from CDW experts.

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