
Published in Winter 2026
Think about how you learned to drive a car and think about how you learned to use a smartphone. Completely different, right?
We teach people how to drive cars and require them to display that knowledge before we hand over a license. Smartphones, on the other hand, are a fully DIY exercise. Nobody walked you through the overall functionality or any of the apps. You just picked it up and used it.
Integrating new workplace technology today is a funny mix of the “car” model and the “smartphone” model. But at today’s pace, this combination of approaches isn’t working. The number of technologies the average worker touches in a day has increased dramatically in recent years. Organizations are now challenged to train on more technologies, faster.
Moreover, sophisticated emerging technologies are no longer neatly categorizable. Is generative artificial intelligence (AI) a “car” — complex and a bit dangerous? Or is it a “smartphone” — easy peasy intuitive? It doesn’t help that the underlying technology itself changes week to week, a seminal issue of the cloud era in general. The costly, time consuming and often confusing journeys organizations go through to try to train employees how to use generative AI won’t be the last such scramble.
Scrambles are unsustainable. It’s time to completely reset our approach to technology training.
Good With Technology
What would a good reset look like? This is an issue that I’ve been working on for the better part of a decade, helping large, complex organizations take their people on the digital transformation journey. I’ve also explored the issue of how we can best use technology at work across research and interviews for two books. For my upcoming book “Effective: How to Do Great Work in a Fast-Changing World,” I pressed some top-notch chief information officers and other C-suite figures on a very specific question: What does it mean to be good with technology at work?
This research combined with years of observation and experimentation on “what works in the wild” led me to a surprising conclusion: We have to go back to the basics. It’s something that in more than 50 years of the Information Age, we’ve never done.
We need to help people learn how to be good with technology — ANY technology.
What organizations currently lack, and what the most technologically adept workplaces possess on an informal or even accidental basis, is a reliable methodology for keeping folks digitally fluent. Concretely, this translates to a backbone of learning about the core skills of technological adeptness.
A common skill set helps all employees, in all roles, succeed at working fluidly with an array of technologies. Moreover, establishing a common language and toolkit around core technological skills speeds the development of all subsequent tactical tech trainings around specific technologies, removing uptake time, cost and content creation pressures.
Foundational training about technology may sound amorphous, but it actually points to a very specific set of skills and should be governed by a set of execution principles fairly different from how tech training operates today.
The “What”: Skills Foundational Tech Training Should Underscore
Ask technologically adept folks what it means to be “good with technology” and observe how technological capability plays out in practice, and you will hear and see a pretty consistent set of skills that training can then be built off of. These skills can be summarized as:
- Data, logic and the fundamentals of code. Do we all need to learn how to code? Absolutely not, especially in an era where coding is more and more automated. But understanding the very basics of how code is built, where information comes from and what software does with it dramatically enhances our ability to work with technology. A little understanding goes a long way. It’s fascinating to see how executives who had two hours of training on Visual Basic 20 years ago are more astute users of generative AI today. Know a little bit about how all software works, and you can use any software better.
- Experimentation and debugging. Most of today’s tech training walks users through a linear path of the technology working perfectly. This is a mistake. Really adept users of technology can both play around with the system to ensure they’re getting full value from their use, and they can fix it (to some degree) when things go wrong. Experimentation and debugging aren’t loosey-goosey processes; there are overarching strategies to each that can be applied over and over.
- Understanding technology’s possibilities and limitations (including how technologies work together). Much of what reads as reticence in technology adoption is in fact users’ natural reactions to not knowing either the potential or the limitations of technology. And oftentimes, problems erupt because users are genuinely not conscious about how technologies do or don’t work together. (“Wait, those systems don’t talk to each other?”) These are issues that can be addressed head-on by giving technology a real “job description,” as you would for any human on your team.
- Safety and security. New cyber scams erupt every day, and new technologies surface new safety issues constantly. But once again — there’s a concrete backbone of ideas about everything from protecting identifying information to ensuring information quality to basic well-being in a technology-rich environment that can, and should, be taught.
The “How”: Creating Foundational Tech Training That Truly Works
To get employees more adept with technology at a core level, form must follow function. Training should mirror how tech is utilized in modern organizations. This training should be:
- “Sandbox” based. The training should allow users to test and learn with technology in a protected environment.
- Always-on and iterative. The training should be framed as an accessible resource rather than a one-time event.
- Engaging and fun. People who genuinely work well with technology today are those who enjoy it. This is a sentiment that can be driven in a broader population by treating tech-based activities more as play, less as drudgery.
- Contextualized, in the flow of work, role-and-level appropriate and milestone-driven. The better connected fundamental understanding of technology is to an employee’s current work tasks and career stages, the better it will resonate. This is particularly true at higher leadership levels, where organizations often do a poor job of articulating the (actually very relevant) role of technology in leaders’ jobs.
- Structurally aligned to subsequent tactical training. For example, every training on a new technology should include a section on debugging specific to that technology.
It may feel strange to go “back to basics” and talk about things like the basic principles of software or data. But giving employees this foundational understanding truly accelerates the velocity of every technology-specific effort — and helps ease the stress of a working world where tech plays a greater and greater role.
Fix this missing link, and people and technology will work together elegantly.