5 things IT managers get wrong about upskilling tech teams

Technology is changing faster than ever, and IT teams need to keep learning new skills to stay ahead. But many IT managers are going about training their people all wrong. They’re throwing money at the wrong things, frustrating their employees, and not achieving any real results for their businesses.

Here are five common mistakes that are sabotaging these training efforts before they even get off the ground.

Upskilling mistake #1: Training without application (the ‘learn-and-forget’ problem)

One of the most pervasive issues in IT upskilling is what Patrice Williams-Lindo, CEO at career coaching service Career Nomad, called the “training-and-forgetting” approach.

“Many managers send teams to training without any plan for application,” she said. “Employees return to overloaded sprints” with no guidance on how to incorporate what they’ve learned. Without application in their work, “new skills atrophy fast.”

This problem is rooted in basic learning science. Doug Stephen, president of enterprise learning at IT service provider Computer Generated Solutions and its subsidiary CGS Immersive, referenced the Ebbinghaus forgetting curve. “People forget 50% of new information within an hour, 70% in a day, and 90% within a month if there’s no reinforcement,” he said.

IT managers often spend their budgets training people to ensure they get well-versed in new technologies, Stephen said. “But in a lot of cases, they don’t carve out critical time to make sure their skills are being used in the right competency.”

Williams-Lindo stressed that effective follow-through means pairing training with mentorship, shadowing, and live projects within 30 to 60 days so skills stick.

“The 30- to 60-day window is crucial. Without immediate application, if you don’t use it, you lose it,” she said.

Raoul-Gabriel Urma, founder and group CEO at education technology company Cambridge Spark, noted that training only sticks if it’s directly and immediately applied to employees’ day-to-day work.

“The most sticky training involves project-based tasks that combine upskilling with day-to-day projects,” he said.

Tim Flower, VP of DEX Strategy at Nexthink, a digital employee experience platform vendor, said training should never be “one and done” — it should be continuous.

“Managers should create feedback loops where people can practice what they’ve learned and add prompts, reminders, and guides directly where the work gets done instead of siloed in a separate learning workstream,” he said.

Upskilling mistake #2: Chasing certifications over real competence

Another major pitfall is the overemphasis on certifications as proof of capability. Managers often assume that a certification is going to solve a problem without considering whether it fits the day-to-day job, said Tim Beerman, CTO at managed service provider Ensono.

What’s more, certification alone doesn’t equal real-world capability and doesn’t necessarily indicate that a person is competent, according to CGS’ Stephen. While a certification shows that someone has the capability to obtain learned knowledge, he said, it doesn’t guarantee practical application skills.

Williams-Lindo from Career Nomad agreed. “Chasing certs to tick HR boxes doesn’t guarantee someone can architect a cloud migration or secure a pipeline,” she said.

Stephen recommended building competency frameworks that combine certifications with hands-on skills testing. Using AI tools, IT managers can build rubrics that list all the competencies that are required for specific roles, so they can see exactly where employees are at and where they need to go to become experts, he said.

“In this case, blending certification in with practical competencies is going to help that person achieve what’s required in their job,” Stephen said.

Williams-Lindo suggested that managers should assess “whether certification paths align with actual job performance needs and workflows, not just brand prestige.”

Beerman emphasized the importance of ensuring that if employees get certifications, “they’re actually putting that to practice right away” rather than letting the knowledge “go stale pretty quickly.”

Upskilling mistake #3: Ignoring learning styles and individual differences

IT managers frequently apply a one-size-fits-all approach to training, failing to accommodate diverse learning styles and neurodiversity within their teams.

“Tech teams often include neurodivergent employees, and people learn differently,” Williams-Lindo pointed out. “A one-size-fits-all Coursera subscription or bootcamp might alienate some while overwhelming others.”

John Blythe, director of cyber psychology at Immersive, a cybersecurity training provider, identified this single-focus approach as a major training pitfall.

“All your employees are different. They all have individual differences,” he said. “So the best way to serve their needs as an organization is to ensure the training aligns to their learning preferences and their learning styles.”

People absorb information in different ways. Some are visual learners who need to see things, others prefer listening to explanations, and some need to get their hands dirty with actual practice and lab work, Blythe said.

“The more you provide that opportunity for people to engage in training a way that they learn best from, the more likely they’ll take it on board and transfer it back to the job,” he added.

Nexthink’s Flower agreed, sharing his own personal experience with learning.

“I’m a visual learner. If you put a ton of text in front of me, I zone out and don’t retain much of anything. So I need visual aids for greater impact, and couple it with hands-on exercises so the concepts stick.”

The solution involves creating varied learning experiences. Williams-Lindo recommended blending microlearning, project-based labs, and peer-led learning to create more inclusive upskilling.

Cambridge Spark’s Urma suggested seeking out upskilling courses that use varied teaching methods, including workshops, e-learning, video and imagery, project-based modules, written exercises, coaching, and presentation.

Upskilling mistake #4: Focusing on hype skills without business alignment

Many IT managers fall into the trap of pursuing trendy technologies without connecting them to actual business needs.

Williams-Lindo warned that focusing on hype skills without business alignment backfires. While AI, cloud, and blockchain sound strategic, she said, if they aren’t tied to current or near-future business objectives, teams will spend time learning irrelevant tools while core needs are ignored.

“Upskilling should map directly to pain points and revenue opportunities,” she said.

George Fironov, co-founder and CEO at developer hiring platform Talmatic, identified this as the most common mistake tech leaders make.

“IT managers spend too much time on flavor-of-the-month skills without linking them to real business needs,” he said. “It’s simple to pursue the latest technology fad, but if the skills don’t map to real projects or strategic initiatives, the training is a check-the-box activity and not a value proposition.”

Kevin Surace, CEO and CTO at Appvance, which makes autonomous software testing tools, emphasized the importance of starting with business problems.

“Ask: What do we need to solve in the next 6 to 12 months? Then reverse-engineer the skills needed to address it,” he said. “Upskilling should be a strategic investment, not a blanket initiative.”

Flower reinforced this approach, explaining that the first step always must be a problem statement that’s well-defined.

“What are we trying to solve, and why?” he said. “Then ask ‘why’ again — as many times as it takes to get to the real problem. Anything else is just training on hype.”

Upskilling mistake #5: Treating conferences as magic bullets

IT managers love sending their teams to conferences, thinking it’s going to solve all their training problems. They’ll see some big tech event getting buzz, buy tickets for everyone, and sit back waiting for their people to return as coding wizards or cloud experts.

But that’s not how it works. Instead, employees end up in sessions that have nothing to do with their actual jobs, listening to stuff they really can’t use, and then they go back to the same old routine with zero plan for what to do with all that information floating around in their heads.

Nhi Nguyen, founder and partner at business consultancy Agilify, sees this pattern repeatedly. “IT managers tend to just send everyone to different IT conferences. Sometimes the team isn’t a fit for a particular conference,” she said.

The problem starts with poor selection. IT managers often choose conferences based on hype rather than relevance to their teams’ actual needs and skill levels. Then they compound the mistake by providing zero follow-up or accountability.

Nguyen said her team takes a completely different approach. They carefully match conference selection to each employee’s set of skills and career track. When people return, there are clear expectations, such as presenting key takeaways in a lunch-and-learn session to share knowledge with the team or launching an internal project where they can use what they learned.

“Sometimes just watching it and doing it are two different things,” Nguyen noted. “We want some way to have some application of the work.”

How to make training work

To be successful, IT managers need to stop throwing training at the wall and hoping something sticks. Real upskilling means taking the time to understand what your business needs are and where your people want to go in their careers, then creating a plan that brings those two together.

The goal isn’t just better-trained employees. As Williams-Lindo explained, it’s about transforming “training from a cost center into a growth and retention engine, ensuring tech talent evolves alongside business needs.”

This means managers can’t just set up training and walk away. They need to stick around, ensure people can actually use what they’re learning in their real work, and face the fact that helping their teams keep up with new skills isn’t optional anymore — it’s how their companies stay in business.

The organizations that get this right aren’t just going to hang onto their top talent longer. They’re setting themselves up to win when AI takes over all the boring, repetitive work and human skills become incredibly valuable — as long as they’re the right skills, learned the right way.

More on upskilling:

How — and why — to upskill your employees

How to discover hidden tech talent in your organization

Balancing hard and soft skills: the key to high-performing IT teams