‍

History has a way of repeating itself, just faster each time. The abacus gave way to the log table, then the calculator. Drafting tables and T-squares gave way to AutoCAD, and an entire profession, the draftsman, disappeared into a new one. AI is the latest version of this pattern, except this time the timeline has collapsed from a generation to a few years.

‍

Venture capitalist Navin Chaddha wrote about this in a LinkedIn newsletter, calling it the "readiness gap." More than 40% of core workplace skills are expected to change by 2030, and demand for AI literacy skills rose 70% in a single year. That's happening inside companies right now.

‍

The readiness gap doesn't look the same for everyone though. What you need to do about it depends on where you sit in your career. Someone starting out has a different playbook than someone running a company. Here's what it looks like at each stage.

‍

If You're Just Starting Out

‍

This is a genuinely great time to be entering the workforce, if you're willing to drop any bias you might have about working in tech or AI specifically. Learn AI fundamentals now, whether that's in school, through open courses, or through a bootcamp.

‍

As you learn to build with these tools, something changes. Your creative output gets bigger and better. That product you've always wanted to build to make your life easier? You can build it now, largely on your own. Or you can go join the company already building it. Either path puts you ahead of peers who are waiting for permission to start.

‍

If You're Mid-Career

‍

For the better part of two decades, the advice was consistent. Build your people management skills, learn to scale teams, improve team performance. That advice is now losing value.

‍

So what do you do? If you have core technical skills, go back to building. Become an individual contributor again, even if that feels like a step backward. It isn't. Roles like Program Manager will disappear, because the inefficiencies that cropped up with large projects go away with an agentic workforce.

‍

Workday's own CTO did exactly this. He left the role after less than a year to become an individual contributor at Anthropic, trading a C-suite title to build hands-on with frontier AI. If you want to read more about it, the link is here.

‍

If you don't have technical chops, this is your moment to go back to school, not necessarily for a new degree, but to get to the application layer that aligns with your domain. Think about the people who left physical retail for e-commerce a decade ago. The early movers did extremely well. The ones who waited didn't. The same window is open right now, and it won't stay open forever. Don't wait for the layoff to force the decision. Figure out which skills and which roles get you there, and start moving.

‍

If You're in the C-Suite

‍

Take a break... Just kidding! But seriously, your job has become the most challenging one.

‍

You're not being asked to adopt a new tool. You're being asked to rebuild your organization for a new era. That means genuinely understanding AI's capabilities by using it yourself, rethinking your business and workflows around it, and then getting your people to buy into a vision that didn't exist eighteen months ago.

‍

I expect a meaningful number of leaders will look at that scope of work and decide it's not for them. The ones who stay will need to be bold, creative, and entrepreneurial in a way traditional corporate tenure rarely demands. These are genuinely unprecedented times. They call for leaders who think differently and move with conviction, not committees who study the problem for another two quarters.

‍

The market is already pricing this in. Product executives who can build hands-on with modern AI tools and still operate at an executive level are starting to see pay detach from standard bands entirely, the same pattern we first saw with AI researchers. Lenny Rachitsky wrote about offers going out at ten million dollars a year for this kind of leader. Almost nobody gets that number, but it pulls the whole tier up. Staying hands-on isn't a demotion anymore. It's what's getting rewarded.

‍

If You Run a Small Business

‍

AI has created a new category. The solo operator who thinks big. As a single person or a small team, you can now scale in ways that were simply impossible five years ago.

‍

This is the same opening eBay, Amazon, and Shopify created for mom-and-pop retailers, who suddenly could reach buyers anywhere without opening a second location. That same opening is now available to white-collar service providers. You don't need to hire to grow. You don't need to open offices or add administrative headcount. You can test new offerings, draft contracts, bill clients, and collect payment, largely through AI agents doing the operational work.

‍

The Common Thread

‍

What doesn't change across any of these four stages is this. The winners are the ones who treat AI as something to actively work with, not something to wait out. The abacus users who resisted the calculator didn't get to keep using the abacus. They got replaced by people who could do the job faster.

‍

This is exactly what I see every day in executive search. The leaders who are thriving right now aren't the polished, off-the-shelf corporate stars with the cleanest resumes. They're the mavericks, the ones willing to rebuild the plane mid-flight, question their own playbook, and move before the data forces their hand. Finding those people, the diamonds in the rough who aren't actively job-hunting because they're too busy driving change where they already are, takes a different kind of search than the traditional, transactional approach most firms still use.

‍

Whether you're looking for your next leadership role, or your organization needs help finding the person to lead through this, we'd love to help. Contact us to find out more.

‍