Technology has never been easier to use—but somewhere along the way, we lost the basics.

Remember when 'The files are in the computer' was just a joke in Zoolander? Well, working with my colleague Gabby, a 23-year-old master's student, made me realize it’s not that far from the truth—and it got me thinking about how much technology has changed.

I’m not trying to date myself here, but growing up in the 90s and early 2000s gave me a front-row seat to the evolution of computers. I remember as a young kid thinking it was so cool to go to my dad’s big, adult office where he had a computer at his desk—it felt like a whole new world to me. My earliest memories of technology include the whirring hum of dial-up internet, the tactile click of inserting a 3.5-inch floppy disk, and the triumphant feeling of successfully finishing a round of Oregon Trail in the elementary school computer lab.

Fast forward to college, where my trusty Nikon and Apple PowerBook G4 helped me build my first blog, uploading photos and sharing stories long before Instagram made it effortless. Then there was my experience in the Marine Corps, where I encountered an outdated computer system with floppy disk drives—a strange contrast to my personal experience with Gmail and torrenting sites that required nuanced knowledge of file sharing, P2P networks, and maintaining an online reputation.

Now, in 2025, I’m leading Compass Coffee, a company that thrives on innovation, where we use tools like AI to enhance our systems and Bitcoin to pay farmers half a world away. Yet, every so often, I encounter moments that leave me scratching my head. Take my recent experience with Gabby, a young professional from a generation that grew up with technology but missed the fundamentals, now navigating the early stages of her career with determination and enthusiasm. Her earlier standout memories with technology include blowing on a Nintendo game cartridge to get it working with her DS Lite, binge-watching Fred videos on YouTube, and playing Flappy Bird at the lunch table when she got her first iPhone in 7th grade.

Gabby needed help organizing some project files. When I suggested moving them to a new shared folder, she stared at me, completely puzzled. It was my Zoolander moment: “The files are in the computer!” Lucky for me, Gabby didn’t smash her laptop like Hansel. Instead, she leaned in, asked questions, and together, we started working through the basics. I began by teaching her about file structures and hierarchies—how to organize files logically so they’re easy to find and use. We talked about file extensions, like the difference between a JPG and a PNG, and why those distinctions matter depending on what you’re working on. It’s been a process, and we’re still working through it, tackling one concept at a time. Each step builds on the last, and it’s clear that with a little guidance and practice, these fundamentals are starting to click for her.

This moment wasn’t about Gabby alone—it’s indicative of a generational shift in how we engage with technology.

The Evolution of Technology

I grew up in a time when you needed to understand the fundamentals of how computers worked because nothing was intuitive. If you wanted to listen to music, you dealt with Napster (and the risks that came with it). If you wanted directions, you printed them off MapQuest, wrestled with GPS units, and—heaven forbid—had to read a map.

But today’s technology is designed to be frictionless. iPhones and Chromebooks abstract away the complexity. Why learn about file systems when iCloud syncs everything automatically? Why understand aperture and shutter speed when your phone’s camera optimizes it all with a tap?

This simplicity is incredible. It saves time, removes barriers, and makes technology accessible to millions. But it’s also a double-edged sword.

A Missing Foundation

Gen Z grew up with these incredible tools but missed out on learning the underlying skills that make them work. I’ve seen this firsthand when trying to train employees on business systems like NetSuite, database software, or even basic file management. These aren’t complex tasks, but they require foundational knowledge about how data is organized and moved—a skillset many younger employees haven’t been exposed to.

Gabby and I discussed this generational gap, and her perspective opened my eyes. For her, school didn’t teach these skills because it was assumed her generation would pick them up naturally. “No one ever actually taught us how to use computers beyond the basics—or even that we needed to. Most families I grew up with had a computer at home, but us kids used them for things like homework or entertainment—not to learn the fundamentals of how they worked.”

This makes sense when you consider the tech landscape of the last 20 years. As teachers believed the younger generation were “digital natives,” fewer resources were dedicated to teaching digital literacy. Meanwhile, industries evolved toward interfaces that prioritized user experience over user education.

Why It Matters

For businesses like Compass Coffee, this gap can pose challenges. We collaborate across cities and time zones, working with freelance designers in Chicago, a graphic designer in Texas, and a video editor in the Philippines. Sharing and organizing files isn’t optional—it’s the backbone of how we operate efficiently.

Understanding foundational tech concepts also empowers people to adapt to the ever-changing digital landscape. The tools will evolve—what won’t change is the need to understand how data flows, whether it’s through a cloud server, a blockchain, or something we haven’t imagined yet.

A Message to Leaders

To my fellow business leaders: This is not a rant about “kids these days.” Gen Z brings incredible strengths to the workplace. They’re also a generation that has endured a lot—pandemics, remote learning, and a rapidly changing world. But what I see is resilience, curiosity, and a willingness to grow. With the right tools and guidance, they’ll take the skills we teach them and do things that will leave us in awe.

Gen Z is incredibly proficient at using modern tools to get things done quickly, but they often lack the foundational skills to adapt when systems or tools change. Addressing this gap requires a mix of patience, mentorship, and a focus on foundational tech education—something that businesses, educators, and leaders can work together to solve.

As leaders, fostering a growth mindset in our teams is critical. Carol Dweck’s book Mindset: The New Psychology of Success is a powerful resource for helping individuals and teams understand that abilities and skills can be developed through effort and learning. Recommending it to your employees and embracing its principles can encourage them to see challenges as opportunities for growth. By cultivating this mindset, you’ll create an environment where curiosity thrives and skill gaps are approached with confidence and enthusiasm.

Invest in teaching foundational skills. Create environments where asking questions is encouraged, and make training part of the onboarding process. It’s a chance to empower a generation eager to learn and prepare them for the challenges of tomorrow.

A Message to Gen Z

Here’s the good news: These gaps aren’t permanent. They’re opportunities.

To those entering the workforce: No one expects you to be an expert at everything. But understanding the basics of how technology works beneath the surface will set you apart. Seek out resources—YouTube tutorials, online courses, books—and don’t hesitate to ask for help.

Take this as your chance to sharpen your tools, as Seth Godin—renowned marketing expert and author—would say. The more you understand now, the more capable and confident you’ll be in navigating your career.

Bridging The Gap Together 

The future of work isn’t just about the tools we use—it’s about the people who wield them. By equipping this generation with foundational skills and a growth mindset, we’re empowering them to turn challenges into opportunities and possibilities into realities. The best is yet to come.

As leaders, we have a unique chance to shape the future workforce. But this is a conversation, not a one-size-fits-all solution. I’d love to hear from business leaders and Gen Z professionals alike—what challenges have you faced, and how have you addressed them? Let’s open the forum to share ideas, insights, and experiences so we can bridge this gap together.

Because when we invest in this dialogue and give the next generation the tools—and the time—they need, they’ll accomplish things we can’t even dream of yet. And maybe, just maybe, we’ll finally stop searching for the files “in” the computer.