Job Descriptions Are Dead. How To Upskill?

Your company's ability to truly benefit from AI isn't just a tech problem—it's a people and learning challenge that requires a complete cultural and mindset reboot.

October in San Francisco is always a whirlwind, and the SF Tech Week of 2025 was the decentralized brain of the tech world, drawing in the biggest names, from top investors to pioneering founders. The central question wasn't about the next gadget, but the next generation of workers.

upGrad Education —a recognized leader in enterprise upskilling—convened a phenomenal panel to tackle the most critical issue facing leaders today: Talent Readiness for the AI Era.

upGrad Education released the The Workforce Wishlist 2025: United States of America - the CEO Srikanth Iyengar summarized the 3 biggest take aways. Wait for it.

The Heavy Hitters: Who Was on the Field? (A Panel with Punch)

Our session, expertly moderated by Michele Griffin (Founder, PremierGTM, and former a16z veteran), featured a dream team:

• James Young (Sr MD, Slalom)
• Saurabh Sharma (Chief Product Officer, You.com)
• Dharma Rajagopalan (SVP, Growth, Automation Anywhere)
• Yours truly! You can follow me on Linkedin

The conversation was electric, focusing on how roles and talent strategies are evolving, what’s broken in traditional learning, and how companies can partner on talent readiness.

Mindset is Your Most Valuable AI ‘App’ (Behavioral Insight)

AI threatens the very core of our professional identity. In my segment, I shared my take on AI adoption through the lens of Behavioral Science, noting that AI can trigger the "threat response" in David Rock’s SCARF Model (Status, Certainty, Autonomy, Relatedness, and Fairness).

As an employee, if AI makes you feel less important (Status) or unsure about your future (Certainty), you’re going to resist. That’s just human nature! We slow ourselves down without addressing those fears.

Neha Prasad Mullick of upGrad hit the nail on the head:

"Psychological safety drives adoption and sustainability — fostering an environment where employees feel safe to experiment, fail, and learn with AI accelerates personal growth and directly contributes to long-term business sustainability."

This requires reframing the employee's identity. Roles are shifting from Fixed Jobs to a portfolio of fluid capabilities. Our job is to help people move up the three levels of AI skills: learning about AI, learning with AI, and using AI in reimagining work.

Broken Models: Why Your Training is a Dinosaur (Data Analysis)

We looked at the challenges in enterprise AI adoption. According to insights stemming from the UpGrad initiative, two key issues keep emerging:

1. AI Transformation is often Tactical, Not Strategic: As Neha explained, "leaders need to integrate AI initiatives into their mid- to long-term strategic plans rather than treating them purely as short-term efficiency exercises." If it’s just a quick fix, it won’t stick.
2. The Content Gap: The traditional learning model is broken because it offers generic content. Users today are used to Hollywood-level content and storytelling. You can’t just offer a PDF and expect engagement. We must build confidence, not just skills, by fostering a culture where making mistakes is the path to fixing them.

James Young Senior Managing Director from Slalom Marketing Consulting reinforced this, saying that AI has unlocked “a new dimension for just-in-time, personalized experiences at a scale previously not possible.” If we’re still doing generic, once-a-year training, we’re missing the point.

Learning's Not a Lecture, It's a Lifestyle (Action Steps)

So, how do we fix the learning model? The best advice came from the audience and the panelists—a clear signal of what leaders should start, stop, and prioritize now.

Dharmendra Sethi, CVP of GlobalLogic, summarized his takeaways perfectly:

“Make learning a habit, not an event… Build a culture of continuous learning using nudge theory.”

The path to talent readiness is simple, but not easy:

• START by curating customized, role-specific learning pathways.
• STOP just rolling out tools. Instead, redesign workflows entirely. Dharmendra noted, "Tie learning to live projects and evolving roles so people reinvent how they work, not just what they click."
• PRIORITIZE cross-functional collaboration. Measuring the true ROI of AI investments is complex and "demands coordinated effort across all business functions," as Neha observed.

This strategic shift is what unlocks growth. As Dharma Rajagopalan of Automation Anywhere put it, what’s exciting is that agentic automation is moving beyond cost savings:

"We're entering a new era where automation becomes a revenue driver — fueling growth, accelerating innovation, and helping teams deliver real, measurable impact."

The key to harnessing this potential? Collaboration—across enterprises, system integrators, and startups, ensuring the workforce is as adaptable as the technology itself.

The future is collaboration between humans and with AI

The future of talent is not about competing with AI; it's about collaborating with it, which starts by prioritizing cultural and mindset change. Leaders must pivot from viewing training as a cost-center event to fostering a continuous learning habit built on psychological safety and personalized, context-driven content.

I write about the intersection of leadership, learning, and future-of-work trends in my weekly newsletter. Don't miss the next issue! Subscribe here.

What is the one thing your company should stop doing today to truly prepare for the AI era? Share your thoughts in the comments below!

The Workforce Wishlist 2025

Imagine if your adventure meant a broken spine, would you repeat the adventure?

Abhilash Tomy is a two time circumnavigator of the globe. He spent more than 500 days at sea in a boat that just had power for a battery to power the satellite in case of a mishap. What happened then is unbelievable. Listen to this man on 15th Oct at 5pm India Time. Go to linkedin.com/in/abhijitbhaduri and find the top post and click "Join"

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