DevOps Institute

Seven Steps To Successful IT Upskilling in 2023

Culture and Human Skills, Upskilling

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By Eveline Oehrlich, Chief Research Officer, DevOps Institute 

The need for upskilling IT people has become increasingly important, given the pace at which technology is changing and the resulting impact on business operations. The rise of automation, artificial intelligence, and machine learning has transformed the IT industry, with new software, hardware, and platforms emerging every day. The goals to improve customer and employee experience and the desire to improve the way software is developed and services are offered are supported through different process frameworks. While there are differences among process frameworks and the lifecycle of a product or service goes through many stages, and many stakeholders are involved, each one with different expectations, all of which are supported through automation. And finally, the different stakeholders must work together to achieve their different expectations, while at the same time collaborating and working together to achieve the ultimate goal for their business. 

I am excited to share that we have published our 5th annual Upskilling IT 2023 Report which shares the different skill gaps, upskilling priorities, and must-have upskilling capabilities. While some individuals are somewhat satisfied with the existing upskilling capabilities they are given, there is plenty of room for improvement. Now more than ever, it is imperative that IT professionals continuously upgrade their skills to keep up with changes and ensure their relevance in the job market. Upskilling and reskilling IT professionals will not only help individuals to remain competitive in the job market but will also enable organizations to stay ahead of the competition by leveraging the latest technology. 

Here are some reasons why upskilling IT individuals and teams is critical in 2023:

  • Digital transformation starts with human transformation: With the advent of digital transformation, businesses across all sectors are looking to leverage technology to improve operations, increase efficiency, and drive growth. Upskilling IT professionals enables them to embrace digital transformation initiatives and lead the charge in implementing innovative solutions that can help businesses succeed in the digital age.
  • Meeting changing job requirements: The rapid pace of technological change means that the skills required for jobs are evolving quickly. Upskilling IT professionals ensures that they have the skills necessary to meet the changing job requirements of the future. TOP MAJOR SKILL CATEGORIES FOR MODERN IT ENTERPRISE ORGANIZATIONS INTHE FUTURE
  • Improving productivity and efficiency: Upskilling IT professionals can help organizations improve their productivity and efficiency by leveraging the latest technologies and process frameworks and automation tools. This means that they can work faster, smarter, and more effectively, leading to better outcomes for the organization.  
  • Reducing the skills gap to support modern IT requirements: The skills gap is a growing concern for many organizations. It is becoming increasingly difficult to find IT professionals with the skills needed to support modern IT. Closing the skills gap via upskilling and reskilling enables organizations to leverage the latest technology, process frameworks and automation effectively.   
  • Enabling innovation and staying ahead of the competition: Enabling teams to innovate and experiment with new technology, applying new process frameworks and adopting modern leadership styles means that they can develop new products and services, streamline operations, and create new revenue streams. 

Seven Steps to Successful Upskilling IT in 2023 

As technology, working models, and the demographics of IT teams continue to change, upskilling needs to be ongoing to stay ahead, and upskilling programs must be continually updated and made attractive. In summary, upskilling engages and improves retention, enables employee growth in terms of personal and professional development, and helps an organization achieve its goals. Upskilling is owned by both the management team and the employee. 

Here are several steps to improve your upskilling in IT:  

  • Create a strategic upskilling plan: Creating an upskilling program involves the steps of aligning, assessing, mapping existing skills and understanding skills gaps. The long-term needs of an organization should drive the skill requirements, compare these requirements with current skills and determine the best way to fill the gaps. From our 2023 research, we know that process, technical, human, leadership, and automation skills are the top five must-have skill domains to focus on when creating an upskilling plan.  
  • Continuously update the upskilling and learning programs: There is a huge opportunity to improve upskilling programs: 19% of our survey respondents admit to being dissatisfied with their company’s upskilling program, 25% are neither satisfied nor dissatisfied, 33% are satisfied and 22% are very satisfied. Additionally, 30% said that upskilling is not a top priority for management, and 29% said that a lack of content, breadth, or depth is a barrier to upskilling in their organization. It is essential to find out what exact improvements should be made to meet your employees’ upskilling needs.  
  • Make continuous learning a key priority for everyone at all levels: While it is important to establish a budget to ensure that key training takes place, continuous learning should be part of an individual’s job. While 40% of our survey respondents cite a lack of budget as the second biggest challenge to upskilling, the lack of time is the bigger issue. Introduce on-the-job work experience which requires that work tasks are presented to employees as learning opportunities. For example, being asked to lead a distributed project is a great opportunity to develop an individual’s leadership skills if it is presented and perceived as a great opportunity to develop. 
  • Empower your leaders to provide powerful learning experiences through continuous feedback: If management can identify, monitor, and provide feedback on the development opportunities associated with a particular assignment or activity, then that assignment can be a powerful learning experience. It’s largely a matter of how a manager or leader frames and presents the task and the employee’s attitude toward receiving it. NOTE: Feedback should be ongoing, and not just one-off communication each year during the annual performance review.
  • Make skills training part of the job and introduce learning by doing: We have heard from our community that acknowledging a need for training can reveal performance issues. As a result, people may not choose training even if it would be helpful. One way to work around this is to make skills training the default, with the option to opt-out if the employees’ skills are sufficiently advanced. Peer learning, buddying, workflow shadowing, pair programming, job rotation and shadowing are attractive upskilling methods for 40% of our survey respondents.
  • Make the connection to career progression clear: While 67% of IT professionals are satisfied with their careers, we also found that they would like to see changes in personal or financial factors to further improve their satisfaction. Moving to a different role with a higher salary will incentivize employees to upskill.
  • Make sure your leaders model upskilling: 30% of our survey respondents say that upskilling is not a priority for the management. It is essential that leaders and managers act as role models and motivate their team members to take advantage of different upskilling opportunities. If budgets are not available, alternative upskilling frameworks such as mentoring or coaching can be a successful way of learning. 

In conclusion, upskilling IT professionals in 2023 is essential for businesses looking to stay competitive in the digital age. By continuously upgrading skills and knowledge, IT professionals can help organizations embrace digital transformation, meet changing job requirements, improve productivity and efficiency, reduce skills gaps, and enable innovation. 

Ultimately, upskilling IT people is a win-win for individuals and organizations, enabling them to succeed in an ever-changing technological landscape. But leaders and individuals must take ownership of their upskilling journey. Many people think of upskilling too narrowly, as simply improving or developing their technical skills. The breadth and depth of skills go beyond technical skills. Individuals should think more broadly and intentionally about the different skill sets and focus on the top must-have skills that are interesting and exciting. Combine your own upskilling development plan with the team’s gaps or needs.

Next Steps

Not sure where to start? The DevOps Institute Business Solutions team can help you map out the best plan to support your IT organization to accelerate change, upskill and reskill, attract, engage and retain talent, as well as gain industry insights. Our Business Solutions can be customized to suit your organization with any combination of the following to support and drive your organizational digital or transformational journey. Contact us today.

Upskilling IT 2023 Report Download graphic IT Skills


Eveline is an independent research director at the DevOps Institute. She held the position of VP and Research Director at Forrester Research, where she led and conducted research on a variety of topics including DevOps, Digital Operational Excellence, IT and Enterprise Service Management, Cognitive Intelligence, and Application Performance Management for 13 years. She has advised executives and teams around the world on challenges and potential changes in people, processes, and technology. She is the author of many research papers and thought leadership pieces and is a moderator and speaker. She has more than 25 years of experience in the IT industry.


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