Tech's middle-management layer is shrinking, and something quietly disappearing along with it is the long-term career conversation.
As AI reshapes engineering organizations, companies are flattening their hierarchies — fewer managers, bigger teams, and leaders who are expected to keep writing code themselves. Paddy Lambros, who runs the AI-driven engineering marketplace Dex, put it bluntly: the era of "purely pastoral" managers overseeing small teams of five or six is over. What's replaced it is a much more transactional dynamic, one focused on shipping work rather than developing people — "sink or swim," as he described it.
Mitchell Kosowski lives this daily. As an engineering manager at a startup with roughly 20 direct reports, he splits his day between coding and back-to-back meetings, joking that he spends "90% of his time" on each — a bit that's stopped feeling funny. Coaching still matters to him, but as AI accelerates the pressure to ship features, deeper career discussions are often the first casualty.
This is part of a larger reassessment of what managers are even for. Companies used to promote their best individual contributors into leadership as a way to multiply their impact — regardless of whether those people actually wanted to manage others, or had any aptitude for it. Now AI is giving senior talent an off-ramp: Lambros' own company staffs former founders and engineering leads as senior individual contributors instead of forcing them into people-management roles, on the theory that it's better to let strong performers keep doing what they're good at.
Other firms are recalibrating too. Deel has pushed its manager-to-employee ratio from roughly 8-10 up to 12-15, according to cofounder and CEO Alex Bouaziz, since AI now absorbs much of the administrative overhead that used to cap team size. Deel also pushes its managers toward a "player-coach" model, staying hands-on with the product and customers rather than drifting into pure oversight — part of a broader effort to eliminate layers of middle management that Bouaziz believes AI is helping render obsolete.
Still, he warns there's a limit: hand a manager 20-30 direct reports, and you've essentially signaled that you don't want any real interaction between managers and their teams — just execution. Bouaziz argues that investing in people's growth now pays off later, since the leaders of tomorrow are shaped by whoever mentored them today.
Scott Stevenson, CEO of the contract-AI startup Spellbook, sees career development becoming less of a formal ritual and more of an improvised, in-the-moment thing, woven into daily work rather than scheduled for a quarterly sit-down. One-on-ones, he says, are often the first meetings people cancel when the week gets overloaded — not because they don't matter, but because they're the easiest thing to sacrifice to keep up with the pace. He hears from people across the industry who feel genuinely adrift, unsure where their careers are heading amid the constant churn.
To keep that thread from disappearing entirely, Spellbook leans on formal midyear and annual reviews as a backstop for the deeper conversations that daily work no longer makes room for. And Kosowski's advice to workers is simple: don't wait for career development to be offered — ask for it, and be willing to fight for the time.