Future-Proofing IT: Building Skills for Tomorrow’s Challenges

Technology leaders are constantly working to stay ahead of the curve, but adopting new innovations isn’t just about having the latest tools—it requires the right talent to build, deploy, and manage them. With AI at the forefront of transformation and many organizations still in the early stages of their journey, the ability to upskill IT professionals has become a critical priority. However, before businesses can fully leverage AI and other emerging technologies, they must navigate challenges in identifying skill gaps, investing in workforce development, and determining the most effective learning strategies.  

Our 2025 Technology Executive Outlook Survey found that organizations primarily address skill gaps through internal development and upskilling. This reinforces the need for a well-structured upskilling strategy, ensuring employees can adapt to emerging technologies and organizational needs. By prioritizing continuous learning, companies can build resilient teams that keep pace with industry advancements while reducing reliance on external hiring.

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To better understand the current state of IT upskilling, we surveyed technology executives and practitioners in our communities, the Innovation Advisory Council and Technology Practitioner Council. The findings reveal key insights into how organizations approach skill development, the barriers they encounter, and their strategies to overcome them.

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Key Takeaways

1. Critical Need for Upskilling in IT: As AI and other emerging technologies continue to reshape industries, the demand for skilled IT professionals is more urgent than ever. Upskilling is not just a supplementary strategy but a foundational aspect of maintaining competitive advantage. Organizations are focusing on internal development programs to bridge skill gaps, emphasizing the importance of a strategic approach to workforce development.

2. Time and Investment in Learning: Developing proficiency in new technologies typically requires 4-6 months, with variations depending on the complexity of the technology and the prior experience of the employee. This timeframe underscores the necessity for efficient and well-structured training programs. Financially, investments vary significantly, with a substantial number of companies spending between $5,000 and $10,000 annually per employee on upskilling.

3. Challenges and Effective Strategies for Upskilling: The primary barriers to effective upskilling include limited time due to workload, insufficient hands-on training opportunities, and financial constraints. To overcome these challenges, organizations are increasingly turning to hands-on labs, workshops, and mentorship programs. These methods are preferred for their ability to provide practical experience and personalized learning, which are crucial for rapid skill acquisition and application.

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Understanding the Timeframe for IT Upskilling

One of organizations’ most pressing questions when planning skill development is how long it takes to get an IT employee proficient in a new technology.  

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According to our polling, most respondents (52%) indicated that it typically takes 4-6 months to develop proficiency in a new technology. This suggests that while learning new skills is a manageable investment of time, organizations must still be strategic in structuring training programs to maximize efficiency. A smaller portion of respondents (18%) noted that proficiency can be achieved in 1-3 months, indicating that specific skills—particularly those with substantial overlaps in existing knowledge—can be learned more quickly. On the other end of the spectrum, 17% of respondents indicated that it takes 10 months or longer, underscoring the complexity of advanced or highly specialized IT skills.

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Factors Influencing Skill Development Time

Several key factors affect the time required to upskill employees. When asked what most influences learning speed, respondents highlighted the following:

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The complexity of the new technology or skill (63%) was the most significant factor influencing learning speed. As technologies become more intricate, employees require more time and support to gain proficiency. Prior knowledge and experience (46%) also played a crucial role, as employees with foundational expertise can upskill faster. The availability of training resources (37%) and quality of training programs (31%) were also highlighted, indicating that organizations must provide high-quality learning materials and structured courses. Additionally, employee learning pace (38%) and support from colleagues and mentors (26%) were identified as key contributors, suggesting that organizations should foster a peer learning and mentorship culture.

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The True Cost of Upskilling: Is Your Budget Aligned with Reality?

Investing in skill development requires financial commitment, and organizations report a wide range of spending levels on upskilling initiatives:

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A significant portion of companies (31%) invest between $5,000 and $10,000 per employee annually for upskilling. This indicates that companies recognize upskilling as a strategic investment rather than an operational expense. The second most common spending range was $2,000-$5,000 (30%), showing that mid-sized investments are also prevalent. Meanwhile, 15% of organizations invest over $10,000 per employee, indicating that some businesses are making substantial commitments to training their workforce. These figures highlight the varying levels of investment, dependent on industry demands, company size, and specific job roles requiring upskilling.

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Overcoming the Barriers to Learning

Despite the availability of training programs, IT professionals still face significant obstacles when developing new skills. Organizations identified the following as the primary challenges:

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The most frequently cited barrier, lack of time due to daily tasks (76%), suggests that organizations must create dedicated learning opportunities rather than expecting employees to upskill on their own time. Limited hands-on opportunities (29%) were another notable challenge, indicating that while theoretical learning is available, employees struggle to apply knowledge in practical settings. Lack of financial support (19%) and unclear development direction from leadership (17%) also hindered upskilling efforts, showing that companies must actively support learning initiatives financially and strategically. Finally, staying motivated (10%) and access to quality training resources (5%) were additional challenges, emphasizing the need for engaging, high-quality learning experiences.

Upskilling That Works: What Do Practitioners Say?

Selecting the proper learning methods is crucial for organizations aiming to equip their workforce with the necessary skills to stay competitive. Technology practitioners identified the most effective approaches for IT upskilling:

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The most preferred method, hands-on labs and sandboxes (61%), allows employees to gain direct experience with new tools and technologies in a controlled environment, accelerating retention and comprehension. Workshops and boot camps (43%) offer structured, instructor-led training that helps employees quickly build expertise in focused areas. On-demand video content (43%) provides flexibility, enabling employees to learn at their own pace while balancing work responsibilities.

Additionally, mentorship and coaching programs (41%) create opportunities for employees to gain insights from experienced professionals, facilitating personalized skill development. Online courses and certifications (36%) provide structured learning paths with recognized credentials, making them a valuable tool for career progression. Lastly, in-house training programs (16%) allow organizations to tailor learning experiences to their specific technology stack and operational needs, ensuring greater alignment with business objectives.

By leveraging a mix of these approaches, organizations can create a well-rounded and sustainable upskilling strategy that meets the diverse learning needs of their workforce.

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Conclusion

The findings from our Innovation Advisory and Technology Practitioner Councils reinforce the importance of structured, well-funded, and time-efficient upskilling programs in IT organizations. While many organizations do not necessarily face a shortage of skilled talent, there is often a misalignment between existing skills and the demands of their strategic initiatives. To stay competitive, organizations must continuously assess the skills needed to support emerging technology initiatives, such as artificial intelligence, and leverage upskilling to ensure their workforce evolves accordingly. By addressing common barriers and investing in effective training methods, technology leaders can maintain an agile workforce capable of driving innovation and adapting to technological advancements.  

Are you looking for strategies to keep your team agile in the face of AI and other innovative technologies that are revolutionizing the industry? Our team of experts assists clients in creating and executing their digital transformation strategies. Explore how we can help here.  

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About Our Respondents

We consistently engage with our technology ecosystem to understand the current market needs. Our communities promote a collaborative and innovative atmosphere, allowing peers to share their experiences, priorities, challenges, and opportunities for transformation.

The Innovation Advisory Council is our exclusive global network of over 1,000 leading technology executives who meet to share insights and build partnerships while gaining exposure to and advising early-stage companies. The Technology Practitioner Council is an exclusive group focused on nurturing an ecosystem of knowledge sharing, innovation, and resource availability for IT professionals. Tailored for forward-thinking managers and directors in IT, this council is the driving force aligning with the rapidly evolving technology landscape.

Want to join our councils? Reach out today.  

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