I’ve had several recent conversations with clients about the technology readiness of their workforce. A common theme keeps surfacing: many executives believed that as older workers retired and younger, more “tech-savvy” generations entered the workforce, the need for technology training would naturally decline.

The assumption was that people who grew up with game consoles, smartphones, and computers would easily adapt to modern healthcare systems and enterprise technology.

Looking across organizations, that hasn’t turned out to be true.

The Digital Native Myth

Being comfortable with an iPhone or social media platform doesn’t mean someone understands how to manage email and calendars in Outlook or Google Workspace. I’ve seen staff who don’t realize they need to accept a calendar invitation before it appears on their schedule. Others are unsure how to share a document, manage permissions, or find files stored in shared drives.

These are not intelligence or effort problems. They’re context problems. Enterprise systems require process understanding, data awareness, and collaboration across teams. Simply being comfortable with technology doesn’t automatically prepare someone to work effectively in a highly regulated, interconnected environment like healthcare.

Organizational Shortcomings

Even when employees are willing to learn, many organizations fail to provide the structure or resources they need. Tech onboarding is often skipped or abbreviated because leaders assume staff will “pick it up.” The result is inconsistent use of systems, reliance on workarounds, and unnecessary errors.

I’ve seen healthcare organizations where EHR calendars don’t sync with enterprise calendars like Outlook or Google. This leads to double-bookings, missed appointments, and frustration for staff who already feel overworked. Others face the same challenge in file storage, messaging tools, or task management systems.

And increasingly, the weakest link isn’t just training. It’s infrastructure.

Connectivity as a Clinical Dependency

As healthcare moves to cloud-based and SaaS tools, internet and voice connectivity have become critical parts of daily operations. Yet many small and midsize providers, especially those with multiple locations, still depend on a single broadband connection with no backup.

When that connection goes down, the EHR, VoIP phones, scheduling tools, and communication platforms all go down with it. Entire sites can be cut off from patient records, billing systems, and even internal messaging.

Common examples include:

No backup 4G or 5G internet connection for remote sites
VoIP phones that stop working when internet fails
No local or offline access to patient information
No monitoring system to alert IT or vendors when a site loses connectivity

This isn’t just inconvenient. It affects patient care, causes operational downtime, and creates compliance risk. In many cases, a simple backup line or cellular router could prevent these failures entirely.

Cultural and Leadership Gaps

There’s another challenge that often goes unaddressed: how organizations fill leadership roles. Many promote clinicians into management positions without giving them the technical or operational training they need to lead technology-driven teams.

Clinical experience is invaluable, but managing information systems, data governance, and technology strategy requires a different skill set. When those skills are missing, healthcare organizations end up with strong caregivers who are under-supported in technical decision-making.

This leads to gaps between clinical and IT teams, missed opportunities for automation, and an overreliance on outside vendors for decisions that should be made internally.

Building strong digital leadership means developing managers who understand both patient care and technology, not assuming one replaces the other.

Building True Technology Readiness

Technology readiness isn’t generational. It’s organizational.

To improve it, healthcare leaders should:

Map key processes against their technology stack instead of assuming alignment
Provide structured, role-based technology training and regular refreshers
Audit site connectivity and ensure every location has failover capabilities
Develop leaders with both operational and technical literacy
Treat technology enablement as part of culture, not a one-time project

Closing Thought

The healthcare workforce of today isn’t defined by age or digital upbringing. It’s defined by how well organizations equip, support, and connect their people.

Technology readiness isn’t inherited. It’s built. And in healthcare, that readiness directly affects efficiency, resilience, and patient safety.