How and Why IT Executives Must Upskill Themselves in 2020

by Pranav Ramesh
June 17, 2020
Importance of upskilling for IT executives

“I believe companies are going to start valuing training… and if your company doesn’t, it behooves you to figure out a way to gain those skills”

– Eric Lannert, CTO at Cloudbakers

Employer training was once a fundamental component of most human resources departments at large organizations. In recent years, however, companies across the world have drastically reduced their spending in nearly all aspects of learning and development.

The future of work puts the responsibility of learning both technical and leadership skills in the hands of the employee. Fortunately, the number of resources one has to learn new skills has grown exponentially both in terms of quality and quantity. The ability to upskill oneself is now more than accessible provided the candidate or employee is willing to look for it.

The decline in employer training

“The program at Continental bank resulted in… some 40 CIOs. It focused on business solutions not necessarily technical solutions. Unfortunately, it’s not around anymore.”

– John Fisher, former CIO and current Founder of RethinkingIT

Since 1998, employer-funded training has steadily declined worldwide by over 20% (1). The pace is quickening in the United States as the total expenditure on workplace training dropped from $93.6 billion in 2017 to $83 billion in 2019 (2). This $10.6 billion decline in on-the-job training comes despite research showing the benefits that properly trained, engaged, and growing employees bring the company. 

Many current c-suite IT executives credit learning and development (L&D) programs from early in their careers with paving their way to their success. Unfortunately, as John mentioned above, many of them no longer exist. 

What has replaced the previous investment in employee training in the current corporate environment? Technology has changed and evolved but employee learning has shifted course. It is as important as ever but the onus of responsibility is no longer on the employer.


Learning new tools.

Obtaining new certifications. 

The responsibility for these professional skills growth has shifted to the employee’s hands. 

The shift in ownership over skills

“Find out what’s really important, and find out what you’re good at, and then you capitalize on it.”

– Mark Griesbaum, Former CIO/COO and Managing Director at Affinity4U


The tech stacks used by IT companies change as quickly and frequently as the tools themselves. Each feature update, bug fix, and code optimization results in a new version and, quite often, comes with a new skill to be learned. While employer demands for specialization increase it becomes impossible for any single team, or individual, to know it all regardless of their knowledge or experience.

“The new world of work is about skills, not necessarily degrees.” says Jaime Dimon, CEO of JP Morgan Chase (4). Chase recently invested $350 million into “Future of Work” programs designed to teach deeply technical and highly specialized skills to their employees. They, however, are the anomaly. <