DevOps Institute

3 Global Upskilling Challenges and 9 Tips to Overcome Them

DevOps Basics, Humans of DevOps, Upskilling

By Eveline Oehrlich, CRO, DevOps Institute

IT leaders have squared off against challenge after challenge in the past few years. From a global perspective, the biggest challenge for IT organizations today is human talent. An extensive new Korn Ferry report finds that by 2030, more than 85 million jobs could go unfilled because there aren’t enough skilled people to take them.

In addition to identifying must-have IT skill capabilities in the modern DevOps landscape, the Upskilling IT 2022 Report highlighted practitioners’ self-identified obstacles to career progression. We found that IT organizations globally face similar challenges. Here are a three of the biggest challenges at play: 

    1. Insufficient resources and skill gaps are the top global challenge.
      From a global perspective, forty percent of our respondents said that the resource and skill shortage is one of their top three challenges today. According to McKinsey, 9 out of 10 global executives and leaders say that their organizations face a skill gap or expect to develop additional skill gaps in the next three to five years. During the past few years, IT organizations have already faced skill gaps. The desire to accelerate technical innovations and digital transformation makes it harder to identify and narrow current and future skill gaps.

    3. Most skill gaps are around cognitive, technical and process and framework skills.
      To identify skill gaps, we leveraged eight skill capabilities that we have used for the past four years in our research. Our survey explored the position that business leaders and individuals had toward each skill capability relative to the gaps they are seeing. The cognitive skill capability includes analytical capabilities, quantitative and statistical knowledge, statistics, data modeling, and knowledge of Artificial Intelligence and Machine Learning which are essential skills for digital transformation and business growth.

    5. Upskilling initiatives have grown, but evidence suggests a lack of time, content, and leadership support.
      The top barriers to skill development within the organizations are lack of time, lack of budget, and lack of offerings in content, topic, or depth, and that upskilling is not a priority for leadership. While fifty-two percent of survey respondents confirmed that they had an upskilling program in place, IT organizations must prepare for what skills are necessary, how to manage their talent supply, and look at the underlying skills of people that must support this digital journey.


Tips For Adding, Building, and Fostering Continuous Learning in IT Organizations

Most individuals (66%) across the globe are happy with their work. In general, they master the skills they need for the job (67%), have learned a new skill in the past 12 months (95%) and use the newly learned skill often (60%). A study conducted by Salesforce in April 2021 found that 72% of workers claim they’d be more engaged with work if their company increased investments in training, and 69% believe they would be happier with their work. But there is more to an upskilling imperative beyond keeping employees happy about the amount of training they receive. When asked which factors would improve career satisfaction, the global order was:

  1. Financial factors
  2. Personal factors
  3. Technological factors and social-psychological factors
  4. Physical factors

Upskilling is A Professional and Organizational Imperative. Leadership and individuals are both responsible for jointly owning upskilling IT. The development of skills and talents cannot be without strategy and planning. We recommend the following to make every day at work an upskilling experience:

  1. Make your upskilling journey intentional.
    Individuals often think about upskilling narrowly to enhance or expand their technical skills. Individuals should think more broadly and intentionally about the breadth and depth of skills beyond technical skills.

  3. Getting on the shortlist means having a good chance of getting the job.
    Survey respondents indicated that their number one hiring criteria are technical skills, but in many instances, those are just ‘table stakes’ – they might get individuals to a second interview or on a shortlist. Still, they don’t get you the job. In many instances, human skills determine the selection of a candidate for the job.

  5. Don’t just think about now; think beyond now.
    From your current employee perspective, upskilling is imperative to keep your current job or receive additional compensation and prepare and position yourself for the next job you want to have.

  7. Be more thoughtful and holistic about the training you receive via your jobs.
    Formal instructional training is not the only form of training. In many instances, it’s less effective because students rarely return to their jobs and immediately employ all the knowledge/skills they’ve just received.

  9. Growing your leadership and business knowledge might enable your future.
    Individuals who extend their business and leadership accomplishments might have a better ability to progress in their careers. While people may want technical skills today, business knowledge and leadership experiences may be more important for the job you seek 5 years from now.

  11. Invite feedback on your job performance to target development needs.
    Don’t wait for your supervisor, team member, and business customer to provide feedback on how you are doing. Invite others to give you feedback. Once others know that you welcome feedback, you will receive more of it. Feedback is a key mechanism for measuring skill development and targeting development needs.

  13. Leaders must adopt a continuous learning frame of mind and not just allocate a budget for training activities.
    While there is importance in establishing a budget to ensure key training is happening, continuous learning should be part of an individual’s job. On-the-job work experience is one of the best forms of training. This on-the-job work experience requires that work assignments are presented to employees as learning opportunities. For example, being asked to lead a distributed project is a tremendous opportunity to up-level an individual leadership skill if presented and perceived as a great upskilling opportunity.

  15. Leaders must provide powerful learning experiences through continuous feedback.
    If management can identify, monitor, and provide feedback on the developmental opportunities connected to a particular assignment or activity, then that assignment can be a powerful learning experience. Continuous feedback should be provided – not just during the annual performance review.

  17. Today, leaders need to remove roadblocks to success.
    Leaders must keep projects on track by supporting team members and individuals and removing roadblocks to their success. That requires diplomacy, trust-building, empowerment, influencing people and culture and vision.


An upskilling strategy and making continuous learning part of the job help organizations have the skills they need. In addition, an upskilling approach encourages individuals to grow and learn and enables organizations to leverage existing staff by reskilling to move into future-facing roles.

Interested in more insight? Download the Upskilling IT 2022 Report.

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