If AI Eats the Entry-Level Job, Where Do Leaders Come From?

I sat down recently with Chris Berta, an executive search partner, to talk about a question he has been chewing on for two and a half years: if AI takes away entry-level jobs, where do people learn their craft, and how do they ever become leaders? It is the kind of question that sounds abstract until you realize nobody has a good answer. Chris has been asking people leaders for years. No one does. His starting point is the old 70-20-10 rule of thumb: roughly 70% of what you learn comes from doing the work, not reading about it. If the doing gets automated, the learning has nowhere to happen. His proposal is a more deliberate apprenticeship model. Map out a project, define the expected outcome, do the work, then run a real post-mortem where everyone talks honestly about what went wrong and what they learned. Not the glossed-over kind. The real kind. I love the line of thought, and my first reaction was to wonder whether companies will actually pay for it. It reminded me of living in Switzerland, where apprenticeship is a deep part of the culture. I asked my barber there how it worked, and she told me the government pays the apprentice while she trains them. Free labor, basically. I asked why she was not doing it. “It just slows me down,” she said. That is the whole problem in one sentence. Training an apprentice slows you down, and in a market where everyone is racing to ship faster with AI, nobody wants to be the one who slows down. You would expect the associate product management and rotational PM programs to be growing and getting more intentional right now. They are not. Chris is honest that he does not know the solution either, but he named the deeper incentive problem. It reminded me of healthcare: private insurers do not invest much in preventative care because the average person stays on a policy for about three years, so the payoff lands on the next insurer. Companies face the same math with training. Why invest two years in someone who will take the skills to a competitor? The Swiss answer is that the government decided it is in the country’s interest to train the next generation and subsidized it accordingly. Whether the U.S. is in a policy-making mood right now is, shall we say, an open question. We also talked about what the hiring market looks like from Chris’s seat. The pendulum has swung to employers. Internal recruiters are drowning in volume, and since every resume is now ChatGPT-polished to the same job description, candidates all look identical. A friend at Amazon told Chris he does not even look at careers-page applicants anymore. He works his network and asks the referrer real questions. That is where Chris thinks executive search gets more valuable, not less: judgment about who fits, not keyword matching. He told me about a placement at Bloom Energy where the candidate’s title did not fit the role at all, but the projects she had run were exactly what the role needed. “It wasn’t a keyword match,” she told him afterward. “It was a goal match.” On org design, Chris is seeing real compression. Middle management layers are being knocked out. At Microsoft and Oracle the cuts skewed senior, partly because it is a bigger cost save. The role I am hiring for right now would have been a people manager a few years ago. Today it is a very senior IC. Chris is seeing the same pattern, plus new shapes emerging: CROs combining sales and marketing, and someone senior owning AI implementation at more and more companies. His phrase for the current moment is “people plus AI.” You cannot hand the whole thing to the model. You need the human in the loop with oversight and editorial vision, or, as he put it, everything just looks like everyone else’s slop. We are planning to reconnect in six to twelve months and see how it is shaking out. My bet is we are still mid-sort, and the companies that figure out the talent pipeline question first will have a real edge. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit firesidepm.substack.com