AI vs. Middle Managers: Evolving Leadership in the Digital Age.

I read a great article written by Aki Ito from Business Insider today about the trend of layoffs in middle management. It isn't new and it actually has a name - "The Great Flattening." The most troubling to me was this statement:

"those who lost their jobs in the Great Flattening are now facing a whole new horror: There aren't any positions left for them to take."

Many companies have tried numerous times to remove leaders in this middle layer and increase independent contributors. It doesn't seem to ever really yield the results companies are seeking, but companies keep trying. What I see now is the "double" or "triple" hat practice of adding responsibilities to leaders in a way to converge business units or centers of excellence.

As a seasoned HR and Talent professional with 25 years of experience, I’ve witnessed countless evolutions in workplace structures and the introduction of disruptive technologies. The insights from the recent Business Insider article about the changing role of middle management resonate deeply with today’s rapidly transforming organizational landscape—and let’s face it, middle managers might be the workplace’s most endangered species next to office donuts on a Monday morning. (BTW - those of you that cut half of the donut only to come back and take the other half...we know who you are!)

Middle managers/leaders have historically played an integral role in bridging the gap between executive leadership and front-line employees. They translate high-level strategies into actionable plans, nurture team dynamics, and ensure that organizational goals are met with human-centric oversight. Yet, with the rise of AI and advanced technologies, we’re seeing a paradigm shift. Tasks traditionally managed by people—such as performance evaluations, workflow optimization, and even operational decision-making—are increasingly being handled by machines. Somewhere, a spreadsheet is celebrating its promotion.

This shift brings undeniable efficiencies. AI offers precision, scalability, and data-driven insights that can streamline operations and eliminate redundancies. However, as we lean into these technologies, we must also reckon with what they lack. Machines can’t replicate the mentorship, empathy, and nuanced understanding of team dynamics that human managers provide. The potential erosion of these qualities raises critical questions about the future of organizational culture and leadership. After all, an algorithm can’t bring coffee to a team meeting or know when to give someone a pep talk after they’ve had a bad day.

There’s a clear risk associated with reducing or eliminating middle management/leadership roles without addressing the human needs they fulfill. Employees often look to their leaders not just for guidance, but for advocacy, support, and career development. If organizations fail to fill this void, they risk disengagement, confusion, and a loss of the very cohesion that drives success. Let’s be real—nobody’s venting to ChatGPT about their coworker’s loud chewing habits, but to be fair there is a GPT for that (check out Therapist ? Psychologist (non medical therapy) by By AIResearchPlus.com).

A balanced approach is key. By embracing AI to handle repetitive or administrative tasks, we can free managers/leaders to focus on strategic initiatives and the interpersonal aspects of leadership that AI cannot replace. Upskilling managers/leaders to work alongside these technologies is critical—they need to understand how to harness AI tools while maintaining their human touch. Because let’s be honest, the AI’s idea of “human touch” is a well-timed “Thank you for your feedback.”

This shift also demands transparency. Employees need to understand the role AI plays in their work and how it complements rather than replaces human oversight. Clear communication about the organization’s vision for integrating technology is vital to maintaining trust and morale. Nobody wants to wake up and find their annual review delivered by a bot named Karen or Chad.

In reflecting on these trends, I see a tremendous opportunity for organizations to redefine what leadership looks like in the digital age. Middle management/leadership doesn’t need to vanish; it needs to evolve. By combining the efficiencies of AI with the irreplaceable value of human connection, companies can create a hybrid model that not only drives performance but also sustains a culture of trust, development, and belonging. And hey, if we get this right, maybe we’ll have more time to tackle the real workplace issues—like why the ice cream machine is always broken.

The path forward isn’t just about adopting new tools; it’s about reimagining the workplace to amplify what humans do best while leveraging the strengths of technology. Done right, this evolution will lead to more resilient, adaptive, and human-centered organizations. And maybe, just maybe, it’ll finally give middle managers /leaders the recognition they’ve deserved all along. But the fear is real. Will the opportunities return or is it time to start something new? Is it time to truly evolve and not just embrace the bare minimum or learn the buzz words in order to appear informed?