By Ryan Sutton, Executive Director, Technology, Robert Half
Even the most meticulously planned digital transformation initiatives can lose momentum, or fail to deliver their intended business impact, without the support of skilled talent. As digital transformation evolves from a series of technology projects into a broader enterprise modernization journey, organizations need professionals who can help modernize systems, streamline processes, leverage data and AI, and drive change across the business. Yet, technology leaders continue to face persistent challenges in securing the specialized talent required to turn transformation goals into measurable outcomes.
According to Robert Half’s 2026 Tech Priorities and Opportunities report, 93% of technology leaders say their teams lack the staff and skills needed to achieve their priorities this year. The research also identifies the top 5 skills gaps in tech and IT departments—all of which are crucial to supporting enterprise digital transformation and modernization efforts:
AI and machine learningIT operations and infrastructure supportIT governance and complianceCloud architecture and operationsData engineering and analytics
Those gaps are especially consequential as many organizations pursue modernization across cloud, data, AI and cybersecurity. AI is a particular focus: 87% of small and midsize businesses (SMBs) and 97% of large enterprises are increasing their AI spending this year, with most AI initiatives already well beyond the pilot stage.
Organizations are also under increasing pressure to move faster to respond to shifting market demands, adapt to emerging technologies and deliver measurable results. These demands make enterprise digital transformation an ongoing effort rather than a series of one-time projects. Teams must be prepared not only to implement new technologies but also to operate, govern and improve them as they become embedded in the business.
As a technology leader, the stakes have never been higher to build a team that can help the business deliver on its digital transformation strategy. Meeting the challenge requires looking beyond immediate project staffing and technical skills alone. You also need to consider what expertise the business will need at each stage—and who will support the work once new technologies are in place.
Building future-ready technology teams
Digital transformation projects require more than technical abilities
Tech and IT leaders hiring for digital transformation initiatives should look for top performers who meet the technical requirements of a job but also bring sharp business instincts and soft skills that enable collaboration and real-time problem solving. These professionals can:
Turn business goals into smart, scalable tech solutions. Top contributors don’t just code and troubleshoot—they understand what the business is trying to achieve through technology modernization. They ask the right questions, challenge assumptions and map technical solutions to real-world outcomes. They also recognize when transformation requires rethinking a workflow or process rather than simply digitizing the way work has always been done.Lead change across teams and departments. Enterprise digital transformation doesn’t happen in a vacuum. Top performers know how to bring people together across locations, departments and disciplines. They can engage the employees who will use the technology and help keep teams aligned—even when priorities shift or unexpected issues arise. That ability is increasingly important: 48% of tech leaders surveyed for our 2026 Tech Priorities and Opportunities report cite collaborating with business units as a barrier to data and AI execution.Think big but deliver on time. Innovation doesn’t matter if customers never see it. High-performing tech pros know how to balance ambition with execution, turning bold and complex ideas into practical, well-outlined strategies and following through on delivery.Make calls based on hard data, not hunches. These professionals are comfortable with dashboards, metrics and analytics tools, but they’re also skilled at interpreting and communicating what the numbers mean for the business.Build security, data and governance into transformation from the start. Strong contributors understand that new systems and AI enablement can introduce risks involving access, privacy, compliance and data quality. They know when to involve security, data and governance specialists so appropriate controls and practices are part of the design—not added after implementation.Adapt quickly to changing tech and market demands. Resilience is key to digital transformation success. These professionals can stay focused when priorities change and help their team members navigate uncertainty without losing momentum.
Equally crucial, tech team members supporting digital transformation strategy must be able to:
Communicate clearly and persuasively. Star players can explain technical issues to nontechnical stakeholders and build buy-in for complex initiatives—without relying on jargon or overcomplicating the message.Stay curious and open to feedback. These pros see change as a chance to learn and grow. They’re coachable, proactive and always looking for smarter, more effective ways to deliver their best work—and help their colleagues do the same.Collaborate with empathy and respect. Digital transformation initiatives are a team sport. Strong performers know how to share credit and create a culture of mutual support, even (and especially) when under pressure.
In short, a future-ready tech workforce should be technically proficient but also emotionally intelligent.
Find out why soft skills are also critical for achieving AI readiness and building and maintaining a strong data foundation for AI.
Why a flexible talent strategy is essential to digital transformation success
Bringing together the right mix of tech talent to support a transformation initiative starts with understanding what work needs to happen at each stage, what expertise it requires and who will own and support it after implementation. From there, you can determine which skills should be retained and strengthened internally, which can be developed among existing employees, and where contract talent or specialized outside expertise will add the most value.
A flexible staffing approach can help you assemble the team you need to execute your digital transformation strategy. Depending on the scope and scale of the work, options may include:
Core, full-time teams for work that requires deep collaboration, strategic alignment and institutional knowledgeNearshore or offshore teams to handle tasks like coding, testing or system maintenance at scaleSpecialized contract talent to deliver targeted technical skills for specific implementations or bridge short-term skills gapsConsulting partners who can provide high-level guidance on complex system integrations, technology strategy, architecture planning and moreCross-functional delivery and adoption roles, including project management offices (PMOs), project managers and business analysts, to help move digital transformation initiatives from planning through implementation and into sustained use
Blending these staffing resources strategically helps you to stay agile, access specialized expertise when needed and keep transformation initiatives moving forward. A blended model also requires clear ownership, shared working practices, strong documentation and deliberate knowledge transfer so critical expertise remains in the organization after a contract or consulting engagement ends.
Building your talent pipeline for the future
Digital transformation and technology modernization are ongoing—and technology leaders must balance hiring, upskilling and evolving their teams as priorities and skills needs change.
Creating pathways for your employees to engage in continuous learning can help build future-ready capabilities within your own organization and reduce dependence on a small number of specialists.
Two strategies to accomplish this are:
1. Strategic cross-training
Provide structured opportunities to promote cross-functional learning. Set up regular peer-led sessions where, for example, infrastructure teams can explain cloud architecture to application developers, or security specialists can share best practices with engineering teams. These knowledge exchanges can also help your team members understand how their contributions fit into the company’s broader digital transformation strategy.
Use these exchanges to document critical processes and system knowledge as well. Our 2026 Tech Priorities and Opportunities report identifies transferring legacy system knowledge to new team members as one of the top 5 challenges affecting modernization project execution. Stronger documentation and knowledge-sharing practices can make collaboration easier and reduce the risk that essential knowledge leaves with one employee or outside specialist.
2. Targeted skills-building
Focus on the high-demand skills your digital transformation efforts need most—think AI and machine learning, cloud architecture and operations, IT governance and compliance, and data engineering and analytics. Then, provide pathways for employees to earn relevant certifications or take part in practical workshops or online courses focused on high-demand skills. Also, be sure to give your team the breathing room—the actual time and resources—to dive in and really absorb new knowledge.
Where possible, pair formal learning with assignments that allow team members to apply new skills to real business challenges. This helps employees put new skills into practice while giving tech leaders a clearer view of where the team is ready to take on greater responsibility.
Learn more about how organizations can strengthen their tech and IT skills bench to close gaps and deliver on 2026 priorities.
Moving forward with confidence
Get the report now
As companies continue to evolve, technology alone isn’t enough to keep transformation on track. Many organizations are expanding their focus from digital transformation to a broader enterprise transformation strategy, considering the technology, data, operations, organizational structure, talent strategies and more that can help their business compete and grow as the market changes. Technology teams play a critical role in enabling these new strategies by developing the systems that support them.
Whether the focus is on a digital transformation strategy or a larger enterprise transformation, having a clear plan across the organization, aligning technology talent with each stage of the road map and establishing who will own, support and improve new capabilities once they’re in use can make the difference between sustained progress and a stalled initiative.
With smart workforce planning, opportunities for growth, deliberate knowledge transfer and clear accountability for the adoption and governance of technologies like AI, you can build tech teams that turn goals into real results and sustain them over time.
For more data on tech skills gaps and the challenges teams of all sizes face in executing critical projects this year, download and explore Robert Half’s 2026 Tech Priorities and Opportunities report.
