In today’s fast-moving digital world, upskilling your tech team is no longer an option, it’s a requirement. Today, companies need technical staff that are flexible and adaptable in their learning, development, and application of skills to deal with agile delivery practices, cloud computing, cybersecurity threats, and unique positions that call for AI.
But here’s the problem: many IT managers are upskilling all wrong.
Even if the intent behind training is right, their approach is often such that there is little impact, wasted time and resources as well as frustrated groups of workers. So that you do not merely tick the training checkbox, let’s look at what most go wrong in providing training to your employees – and how to develop a strategy that works.
Treating Upskilling as To-Do, not a Plan
A common mistake is to look at upskilling as a periodic task-a budget line item or a one-off course-also known as a strategic investment in upskilling people.
When the training is not business-driven, the training becomes out of sync. Meanwhile, important gaps in cloud architecture, security, or automation are left unfilled while development resources are spent on learning technologies that developers will never use.
A smarter approach:
- Aligning training to actual project needs and product roadmaps;
- Use a skills matrix to map current capabilities against future needs.
- Focus on results – how are things going to be better after the training?
According to a McKinsey report, organizations where learning programs are linked to business value are over 2x more likely to experience productivity gains.
Risk of Muddling Certifications for Competence
Certifications are a good starting point but do not qualify for actual ability. Too often, IT managers are using certifications as the primary measure of success for learning, because a badge or credential represents preparedness.
In fact, certifications only indicate exposure, not expertise. They don’t show them how someone handles a production outage at midnight, creates scalable systems, or works cross-functionally under pressure.
Instead, focus on:
- Integrating formal qualifications and project-based learning.
- Giving team members opportunities to apply what they’ve learned in real systems.
- Using code reviews, architecture walkthroughs, and retrospectives as feedback mechanisms.
Remember: the aim is to develop job-relevant capability and not merely check times off an examination.
Certifications are strongly correlated with job performance for only 38% of employers according to CompTIA.
One-Size-Fits All Training doesn’t work
Technical teams are heterogeneous – skills, roles, experience levels and learning styles are enormously varied. However, many training course providers take a one-size-fits-all approach and present a single website or bootcamp to all.
This leads to disengagement. Some engineers find that they are under-challenged, while others find themselves overwhelmed. More importantly, it is a waste of time by not meeting the learners where they are.
What works better:
- Personalize learning paths by job role, skill gap, and learning preference.
- Offer a mix of modalities: video, hands-on labs, peer programming, instructor-led sessions, and documentation.
- Allow team members to choose tracks aligned with their career goals (e.g., moving from backend development to DevOps or security engineering).
By understanding people’s preferences when it comes to learning, you can ensure higher levels of engagement and retention – not just of knowledge but also of your talent.
Teams with customized learning path are 4x more likely to feel motivated to advance their skills (source: LinkedIn Learning 2024 Workplace Report).
Neglecting Reinforcement and Application
The big problem with most upskilling programmers is that there isn’t any follow through.
Engineers go through a workshop or course – but weeks later the knowledge is lost because it’s not applied. The best training is rendered useless if not put into practice.
Avoid the ‘learn and forget’ cycle by:
- Embedding time in the sprint for applying new skills immediately.
- Assigning real-world projects that align with the training.
- Creating internal “tech talks” where team members present what they’ve learned.
- Encouraging mentorship and code pairing between junior and senior engineers.
When learning is reinforced as practice it can be part of the team’s daily workflow-not a forgotten event.
Without reinforcement, 70% of knowledge is lost within 24 hours, according to Harvard Business Review.
Jumping on Trends and Ignoring Real Problems
It’s easy to get caught up in a hype cycle. While AI, quantum computing, blockchain and other buzzwords get news coverage, not all tech teams should jump into the fray head first.
Too many IT managers invest in trend-based training without assessing whether the skills are actually needed for current business challenges. Meanwhile, such foundational skills as secure coding, cost optimization for the cloud or reliability for data pipelines are ignored.
A better method:
- Train on short-term business priorities and pain points;
- Create what we’re calling “exploration labs” for any emerging technologies but don’t train everyone on it until proven.
- Note that this is the summary of the skills roadmap I present in my course.
A Gartner study showed that 64% of CIOs who jumped into emerging technology training without having a business use case didn’t see much, if any, ROI:
How to Create Effective Upskilling Strategy
To avoid these kinds of common mistakes, IT managers should instead adopt a more holistic approach to learning with an agile twist for their teams. Here’s a strategic framework for your upskilling efforts:
- Assess
- Conduct skills audits
- Identify gaps based on upcoming initiatives
- Prioritize mission-critical areas (security, reliability, performance)
- Plan
- Create personalized development plans
- Set clear, measurable goals (e.g. reduce bug rate, increase deployment speed)
- Allocate time during sprints for learning (10–15%)
- Deliver
- Blend training formats: online learning, mentoring, labs, workshops
- Partner with reputable platforms (e.g. Pluralsight, Coursera, or internal academies)
- Use internal experts to deliver company-specific content
- Reinforce
- Assign tasks or projects based on the new skills
- Offer peer reviews, feedback sessions, and retrospectives
- Encourage internal knowledge sharing across teams
- Measure
- Track metrics like deployment frequency, incident resolution time, team velocity
- Run post-training surveys and retention assessments
- Adjust based on what’s working (or not)
The best upskilling programs are not revolutionary but evolutionary. These evolve in step with your technology and your people.
Why Getting Upskilling Right Is a Competitive Advantage
Upskilling isn’t only about keeping up with tech – it’s about creating a culture of adaptability and excellence. When done right, it leads to:
- Improved retention: Talented engineers want growth.
- Better performance: Teams become faster, more reliable, and more innovative.
- Reduced risk: Strong foundational skills lower the chance of critical errors.
- Increased ROI: Projects ship faster, downtime decreases, quality improves.
The organizations that value constant learning – and that is done on an ongoing basis, not just once a year, but as a core function of the way the organization operates – will win the war for talent, customer loyalty and digital agility.
Final Takeaway
Upskilling isn’t a “nice to have” anymore. But when talking about the type of goal, the difference lies in the approach you take.
Don’t be duped by empty certifications, sexy technology or generic learning routes. Build a strategy that empowers your engineers, supports your business goals and can evolve with your technology stack.
In technology, the early adopters never keep up, they lead.