Why Digital Natives Are Struggling For The Digital Skills They Need

We’ve all heard the phrase ‘digital native’ right? It’s usually said with a mix of envy and relief, or even a slight eye roll sometimes.

I mean, if younger generations grew up surrounded by smartphones, social media and always-on connectivity… surely, they’re instinctively equipped for the digital workplace. Right?

Except… a lot of the time… they’re just not.

Despite spending more time online than any previous generation, many digital natives are struggling with the basic digital skills organisations today rely on. Be it data literacy and workflow automation to secure information management and cross-platform collaboration.

The problem isn’t capability though; it’s assumption.

A lot of the organisations I speak to tend to mistake familiarity with fluency, which almost always leaves genuine training needs unaddressed and widens the very skills gap leaders thought had closed.

If a digital transformation is to succeed within a business, leaders have to question the myth at its heart…the idea that digital confidence is something we’re born with, rather than something we build.

The Real Digital Skills Gap

I’ve been finding more and more that the assumption digital skills are an age-based advantage is starting to unravel.

Across multiple studies, the pattern is consistent: younger workers may be more comfortable with technology, but that doesn’t mean they’re competent in how organisations actually use it. The gap isn’t generational anymore… it’s contextual. And it’s widening as technology such as AI moves faster than learning cultures can adapt.

What The Data’s Showing

Recent research from Microsoft’s Work Trend Index found that nearly 60% of Gen Z workers feel anxious about not having the digital skills their jobs require, the highest of any generation surveyed.

Meanwhile, LinkedIn Learning’s Global Workplace Learning Report highlighted that confidence in data literacy, digital collaboration and analytical problem-solving actually declines amongst younger employees compared to older peers once they enter enterprise environments.

The explanation is simple: what most younger workers excel at is consumption, not creation.

They’re fluent in social platforms, short-form communication and app-based workflows… but these don’t translate easily into enterprise systems like Dynamics 365, Power BI or Copilot.

Navigating data models, understanding security boundaries or automating a process through the Power Platform requires structured thinking and context awareness that consumer tech rarely teaches.

This is createing a silent mismatch.

Managers assume new hires will “pick it up” because they’re digital natives, but without clear onboarding or mentorship, they end up struggling in silence.

The result: lower productivity, rising frustration and missed opportunities to embed innovation across the workforce.

Age Isn’t The Divider… Opportunity Is

What really defines digital capability isn’t when you were born.  It’s how you’ve been supported to learn.

Access to training, time to experiment and role models who normalise curiosity make far more difference than generational labels ever could.

Older employees, for example, often outperform their younger colleagues in areas like compliance, data governance and workflow consistency… not because they’re more “technical”, but because they apply structured problem-solving and follow process. They’ve learned how systems connect, how data flows and why accuracy matters. These are precisely the habits digital transformation depends on.

Younger staff, on the other hand, tend to thrive when they’re invited into active learning environments: reverse mentoring, peer-to-peer experimentation and visible leadership support for “try, test, and learn” initiatives. The organisations closing their digital skills gap aren’t dividing by generation, they’re building cultures where curiosity is rewarded and training isn’t treated as remediation but as momentum.

The truth is that digital skills are learned behaviours, not inherited traits. And the sooner leaders start designing learning strategies that reflect that, the faster transformation efforts begin to stick.

The Cultural Cost Of The Myth

The belief that younger employees will simply “get it” has a hidden price… one that affects learning culture, morale and ultimately, digital transformation outcomes.

When leaders assume capability instead of building for it, they create two tiers of disadvantage: younger workers who are undertrained, and experienced employees who are underestimated. Both outcomes weaken the organisation’s collective confidence in technology and slow down transformation projects that rely on genuine adoption.

Undertraining The Young, Overlooking The Experienced

Many organisations unintentionally design learning programmes that reinforce stereotypes.

Younger recruits are often given lighter or shorter digital onboarding because they’re assumed to already be proficient. They’re handed systems credentials rather than context, exposed to dashboards rather than decision-making and expected to “figure it out” along the way.

The result?

They become quick at clicking, but slow at connecting… missing the why behind data flows, compliance rules and automation logic. Without structured learning, the gap between using digital tools and leveraging them effectively only grows wider.

At the same time, older employees are too often sidelined from transformation initiatives because of perceived resistance. Labels like “technologically cautious” or “change-averse” become shorthand for not worth the investment. Yet, in many cases, these workers bring precisely the traits transformation needs most: process awareness, risk management and an ability to document, share and standardise new ways of working.

When both groups are misjudged, one undertrained, the other underutilised, organisations create a self-fulfilling prophecy. Transformation fatigue sets in, and the belief that “people just don’t get it” becomes an easy excuse for deeper cultural failures around learning, leadership and inclusion.

When Assumptions Block Transformation

The “digital native” myth doesn’t just shape training budgets though. It also shapes how leaders approach entire transformation programmes.

Far too often, I’ve seen technology investments made on the assumption that end users will naturally adapt. Systems like Dynamics 365, the Power Platform or Copilot are deployed with minimal change management, because teams are assumed to be digitally fluent.

But when the rollout does begin, adoption stalls.

Teams start to rely on legacy processes, automation tools go unused, and dashboards stay unopened. It’s only at that point, months later, that the realisation lands: the barrier wasn’t the technology, it was the missing skills and confidence to use it meaningfully.

I’ve seen organisations across multiple sectors experience this and the lesson is clear.

Transformation fails when it’s treated as a generational inevitability rather than a cultural responsibility. The most successful digital programmes are those that assume nobody’s born ready, and invest equally in creating the confidence, context and curiosity needed to make technology work for everyone.

What Digital Readiness Really Looks Like

To my mind, digital readiness isn’t about age, confidence or how many apps someone can juggle… it’s about mindset and adaptability.

True digital maturity is built when people understand why technology matters, not just how to use it. It’s the shift from seeing digital tools as tasks to complete, to seeing them as enablers of better outcomes.

Organisations that thrive in digital transformation share one thing in common: they don’t assume readiness; they cultivate it.

From Exposure To Empowerment

Most employees, regardless of their generation, will have exposure to technology.

They’ll know how to navigate interfaces, search online, share files or use apps. But empowerment needs to go further: it’s about applying technology to solve problems, create value and make better decisions.

True digital fluency, means being able to move between tools, adapt to new systems, and critically assess data. It’s the ability to connect a workflow in D365 or build a quick Power Automate flow, without needing to be a developer. It’s understanding how automation and AI can free up time for higher-value work, and having the confidence to experiment safely within organisational guardrails.

Empowerment also means reframing failure.

In digitally mature cultures, trial and error isn’t seen as waste… it’s part of the process. Employees are encouraged to test, iterate and improve. That’s how curiosity becomes capability.

Building A Continuous Learning Culture

Digital readiness isn’t a one-off milestone, it’s an ongoing state of learning.

The technologies organisations depend on today will evolve again within months, so capability must evolve with them. That demands a learning culture where development is continuous, accessible and psychologically safe.

Successful organisations are embedding this mindset in practical ways:

• Micro-learning and in-flow training through tools like Viva Learning, LinkedIn Learning, and Microsoft Learn, making skills development part of everyday work rather than an annual event.
• Reverse mentoring, where younger employees share platform familiarity whilst older colleagues share business logic and governance experience, levelling the field in both directions.
• Cross-team collaboration, encouraging finance, operations and marketing staff to co-build solutions using GPT’s or Copilot Studio, breaking down silos through shared experimentation.



• Recognition and visibility, where leaders celebrate small wins… an automated report, a smarter data dashboard, a reimagined workflow… reinforcing that progress is collective.

In these environments, “digital native” becomes a cultural identity rather than a generational label.

Everyone is empowered to learn, test, and grow.

How Leaders Can Quickly Close The Gap

Bridging the digital skills divide has to start at the top.

Culture follows what leaders model and measure. If leaders treat technology as an operational bolt-on, the workforce will too.

But when they make digital curiosity visible, normalise learning and provide structured pathways for growth, they turn readiness from rhetoric into reality.

Audit Your Organisation’s Real Skills Baseline

Most organisations assume they know where their teams stand… until they look closely.

A proper digital skills audit exposes the gap between perceived and actual capability. It identifies not just who can use the tools, but who truly understands them, who’s confident to experiment and where support is lacking.

Simple assessments can surface powerful insights. For instance, reviewing how many people actively build reports in Power BI, automate tasks or engage with learning tools like Viva or LinkedIn Learning reveals far more than a training survey ever could.

FormusPro’s own readiness assessments often highlight a pattern: the technology is in place, but the people haven’t been given time, context or confidence to use it.

Once leaders see that gap clearly, they can focus investment where it matters…not on new systems, but on enabling the ones they already have.

Use Technology To Democratise Learning

Digital transformation doesn’t work when training is confined to one-off workshops or static e-learning.

The pace of change is too fast. Learning has to happen continuously, in the flow of work, using the same platforms people already rely on.

Modern tools make this easier than ever.

By embedding these, organisations stop treating digital skills as something to be “taught” and start making them part of everyday practice.

Learning becomes ambient… not an event but an environment.

Model Digital Curiosity At The Top

Leaders who want their people to experiment must be seen doing it themselves.

When executives use Copilot in meetings, share dashboards from Dynamics, or openly discuss their own learning curves, it sends a powerful message: exploration isn’t a risk; it’s an expectation.

Visibility also builds trust.

Employees are far more likely to engage with new tools when they see leadership engaging too…not delegating transformation, but participating in it. It turns digital adoption from compliance into culture.

Closing Thoughts On Why Digital Natives Are Struggling

Digital transformation doesn’t fail because of technology; it falters because people are left out of the journey.

The idea of a digital native has made it easy to believe readiness comes preinstalled, that some generations will simply adapt while others will struggle. But the evidence tells a different story: capability grows where culture allows it.

When organisations stop segmenting learning by age and start investing in inclusive digital development, they unlock something far more powerful than proficiency… they build confidence. And confident teams don’t just adopt technology; they amplify it.