In the context of digital transformation and business automation, the need for upskilling and reskilling is highlighted to ensure workforce success and competitiveness. With nearly one-third of business tasks currently automated, the World Economic Forum’s Future of Jobs Report 2023 predicts a rise to 42 percent by 2025, indicating that six out of 10 employees will need reskilling by 2027. While the COVID-19 pandemic expedited digital skills adoption, effective upskilling tactics remain essential. There are four primary ways chief information officers (CIOs) can enhance digital upskilling efforts. First, make digital upskilling non-negotiable. C-level leadership must prioritize digital upskilling, emphasizing its value to employees and the business. Showcasing its direct impact on work and clarifying the business benefits are crucial. Next, extend upskilling across all functions. Digital upskilling should encompass the entire organization, with essential digital skill sets applicable across roles and customized skill-building exercises catering to specific job functions. It’s also important to facilitate and incentivize continuous learning. Encourage continuous learning through intrinsic motivation, rewards, tuition reimbursements, and partnerships with training providers. Employee upskilling benefits both the organization and the individual. Finally, track, analyze, and highlight benefits. Measure upskilling effectiveness through metrics tied to productivity, innovation, cost reduction, and customer service. Continuous data analysis ensures the program’s alignment with digital transformation goals. Upskilling initiatives can address talent shortages, improve employee retention, and optimize hiring processes, but they must align with broader digital transformation objectives for optimal outcomes.