MIT Sloan Management Review
The smartest leaders aren’t necessarily the ones who know the most about AI, but those who know how to keep learning.
Four Habits of Tech-Savvy Leaders
Author: Melissa Swift
(AUTHOR’S BIO)
Melissa Swift is the founder and CEO of organizational consulting firm Anthrome Insight. She is also the author of Work Here Now: Think Like a Human and Build a Powerhouse Workplace (Wiley, 2023) and Effective: How to do Great Work in a Fast-Changing World (Wiley, 2026).
The new technology thundered onto the scene, generating fear and elation.
Financial markets gyrated. An army of workers trained up quickly, many occupying jobs that had never existed before. Infrastructure no one could have anticipated needing was built at a breakneck pace. All the while, people hotly debated the technology’s value, with some observers calling it an ignis fatuus — an elusive ghost — even as its inventors sang its world-changing praises.
Artificial intelligence?
Nope. The incandescent light bulb.
We love to say that we live in unprecedented times, but the reality is that technological disruption has spurred business disruption for a long time now. Light bulbs, internal combustion engines, printing presses: Business leaders have been continually challenged to adapt to world-changing technology.
But it’s not easy to be a technology-fluent leader — especially today, when the rate of change is once again at late-1800s levels. (Before you scoff, consider that during that era, the light bulb and the telephone were invented a mere three years apart. Take that, frontier AI models!) In a 2025 Gartner study, only 26% of top executives said they felt a high level of comfort with AI topics.
Technology changes so fast — and we leaders have so many other things to worry about — can we ever truly feel like we have our arms around the subject?
Yes, actually.
Across many years of working at the intersection of technology, business, and human nature, I’ve seen a repeated archetype for success: the calm, confident, tech-savvy leader. These folks don’t get swept up in every micro-trend; they don’t get flummoxed as new tech providers rise and fall. They’re up to the minute in the conversation but firmly anchored in what their company needs. They’re knowledgeable, but often not flashy about it. Like The Dude in the movie The Big Lebowski, they abide.
However, there’s nothing magical about their approach. I’ve found that these leaders follow a set of durable, replicable practices on several levels — ones that we’d all do well to emulate.
1. They take multiple, live paths to technology learning and guard time for it.
In workshops, when I ask executives how they learn about technology, the savviest folks give an array of answers: YouTube videos, vendor press releases, technical publications, and social media accounts, for example. There’s no dominant single answer. The common thread is that these folks use a multimodal learning approach. They’re balancing sources that might be more detailed but biased (like vendor information) with more high-level sources that have less of an axe to grind (like tech publication reporting).
While this group of leaders participates enthusiastically in company-sponsored training, they’re not reliant on such programs as their primary source of information. Indeed, they stay invested in current developments and proactively make time for technology learning on a day-to-day or week-to-week basis. Similar to motivated learners in any discipline, they find small increments of time to absorb knowledge: a podcast on the treadmill at the gym, or a quick article scan via social media on the train to work.
They also test and learn to find information sources that are not only readily consumable but also actually enjoyable. They’re able to sustain real-time learning over the long term because it’s a genuine source of pleasure.
2. They talk to many different people about technology.
Anyone familiar with adult learning theory will tell you that 20% of learning is accomplished with others, and being tech-savvy is no exception. Leaders who are truly immersed in the technological journey treat it as a team sport, enlisting the participation of like-minded people. I often hear these folks say that they engage IT professionals in casual chats about developments in AI, for instance. These aren’t goal-oriented exchanges — the chats don’t revolve around help desk issues or strategy conversations about implementation. Rather, they’re light but focused discussions around emerging topics (and probably something the IT departments of the world should be getting more credit for!).
Tech-savvy leaders also tend to seek out tech buddies: colleagues or friends they can compare notes with and share real-time experiences and tests. At times, these leaders even seek out reverse mentors — junior team members who can share what’s possible as leaders undertake next-level tasks, like building AI agents.
A quick but important note here: When I say “people” to talk to, I mean people: flesh-and-blood human beings. Talking to LLMs about developments in AI is a productive research strategy, but it doesn’t provide enough on its own. For a host of reasons, ranging from highly specific and tacit industry domain knowledge to visceral understanding of what it means to use a particular system, there is no substitute for human conversations about how we use technology. Tech-savvy leaders test their thinking and experience in the bright light of human experience, learning, and confusion: They don’t get stuck in echo chambers, even vast ones.
3. They find hands-on ways to practice and have a blast doing so.
It stands to reason that tech-savvy executives move pretty quickly from learning and talking to getting their hands dirty — experimenting with new technologies and iterations almost as soon as tools appear. While many of us have recently “learned by doing” through dialogue with LLMs, this group has been doing the same thing for years with far more banal, less-user-friendly technologies. They dive right in, even when the tech seems boring and incremental.
For the secret to their advantage, listen to the verbs they use to describe engagement with a particular piece of tech. “I played around with the new model for a few minutes this morning.” “That new system? Yeah, messed around with it last week.” “I toyed with the app a bit and figured some things out.” They have a spirit of play, of looseness. They’re engaging with technology in low-consequence, unstructured ways. As I’m fond of saying, they’re approaching technology like crows do — having more fun doing something with tech than without it. (Crows are happier using a stick to do a task than accomplishing the same thing without the stick.)
4. They seek balance and avoid false urgency and shortcut-driven thinking.
Despite the heated tone in public discourse about AI these days, I’ve found that the most tech-savvy executives aren’t thoughtless sycophants, mindless boosters, or fearmongers. When someone is haranguing you about how afraid you should be or how you’re going to fall behind, they’re often not actually speaking from a position of true awareness and understanding. Leaders who understand technology are energized but, on some level, quite relaxed; they’re confident in their ability to direct a thoughtful journey at the right pace.
Truly tech-savvy executives are pretty balanced voices in the AI conversation. They’re excited about the potential of AI but aware of its limitations — much as you might admire a human coworker while knowing what they’re bad at.
This is an incredibly helpful set of behaviors as organizations make AI implementation decisions. You don’t want a mindless cheerleader signing off on what you build, buy, or implement — you want someone who can see both the potential and the limitations of different tech choices.
Balanced voices on AI can also cut through some of the hot air and sneaky business currently circulating. I smile every time I think about a conversation I had with a good friend who is super savvy in this realm (OK, it was fellow MIT SMR author Vipin Gupta), where I asked him if I was losing my mind or whether a piece of technology being described to me as agentic AI simply … wasn’t. With a warm laugh, he rephrased the definition of agentic AI into incredibly simple terms and confirmed to me that I was in fact potentially being bamboozled. Organizations need that voice in the room — the person espousing critical thinking born of deep technological understanding. AI bamboozlers are, unfortunately, everywhere.
Start With One Habit
For executives, becoming more tech-savvy can be an intimidating journey — which is why real understanding levels remain relatively low among leaders. The intimidation is an entirely fair feeling: Technology is complex and ever-changing. And AI in particular relies on computational and mathematical concepts that far outdistance what many of us studied at school or worked on directly in our professional lives.
You don’t have to go from zero to Altman or Amodei all at once, though — nor do most of us need to. Instead, you can pick one element of one strategy and start there. Is there a single source of technology information you could add? Maybe a wry podcast? Could you talk to one more person about how you use technology at work, perhaps a peer you’re already close to? Is there a place you can start testing out AI in tiny increments, even building an agent to tackle an annoying task in your personal life? And finally, is there a small way you can create more balance in your view of fast-changing technology, by either becoming more optimistic or more skeptical, depending on your current mindset?
Two threads connect all of the behaviors of technology-savvy executives: curiosity and agency. You have to want to know more, and you have to actively go after that knowledge. That is not easy in a world where we’re inundated with loud voices telling us what to think and do, from mainstream sources to social media to the missives of tech CEOs themselves. But it’s vital that we resist being told and instead seek out real knowledge and experience, especially as AI evolves.
Which brings us full circle back to the incandescent light bulb.
There’s a beautiful and moving scene in the TV show The Gilded Age lightly fictionalizing an early large-scale demonstration of electric lights in New York City. The gas lamps are dimmed; everyone counts down in the darkness; and then Thomas Edison flips the breaker switch, lighting up the night to the oohs and aahs of the assembled crowd. The scene truly brings to life Arthur C. Clarke’s famous statement that “any sufficiently advanced technology is indistinguishable from magic.”
This is the best and most dangerous thing about technology, from light bulbs to AI: It can seem like magic. But by knowing it better — by seeking true understanding — we as leaders position ourselves to still experience much of the joy and the gain while minimizing pain, loss, and bamboozlement.
It’s time to start better habits. You’ve got this.
Credits: TCA, LLC.