We Tested Masterclass's New AI Coach: The Surprising Results

IMHO Reviews Podcast

In a world where professional development often means another Zoom seminar or a static online course, the idea of a personal, on-demand coach sounds like a luxury reserved for the corner office. We've become accustomed to learning by watching, but what about learning by doing—especially when the stakes are high? Masterclass, the brand synonymous with slickly produced lessons from the world's most famous experts, has just thrown a curveball into this landscape with its new AI-powered app, "Masterclass On Call." It promises to give you a direct line to AI versions of figures like negotiator Chris Voss, entrepreneur Mark Cuban, and even chef Gordon Ramsay to practice your most critical conversations. The concept is futuristic and bold, but does it work? We put it to the test, and the results were genuinely surprising.

This comes at a time when research is challenging our assumptions about AI's limitations. A recent April 2025 study in Frontiers in Psychology found that users can build a 'working alliance' with an AI coach that is surprisingly similar to one built with a human coach.

Our investigation went beyond a simple feature tour. We subscribed, dove in, and engaged the AI coaches in a series of challenging role-play scenarios. We tried to negotiate a raise with Chris Voss's AI, pitched a business idea to Mark Cuban's persona, and even navigated a difficult feedback session. We weren't just looking for clever chatbots; we were testing for genuine value. Can an AI provide nuanced feedback? Can it adapt to different conversational styles? Most importantly, can it actually help you build confidence for the real world? We asked the same strategic question to multiple AI coaches to see if we'd get diverse, valuable perspectives, and we meticulously analyzed the "instant, actionable feedback" provided after each interaction.

The first surprise was the uncanny human-like quality of the interaction. While not perfect, the AI, trained on proprietary data from the instructors themselves, often responded with a level of intuition that defied our expectations of a simple script. It felt less like talking to a machine and more like a guided, reflective exercise. The second surprise was the practicality of the advice. The feedback wasn't generic fluff; the AI would pinpoint specific word choices or suggest alternative phrasing to improve clarity and impact.

This aligns with extensive research on learning. A Boston Consulting Group report highlights that when psychological safety is high, employees feel 3.3 times more enabled to reach their full potential and are four times less likely to consider quitting.

But perhaps the most significant surprise was the psychological power of its "stress-free sandbox." There is a unique freedom in practicing a high-stakes conversation with zero fear of embarrassment. The ability to stumble, try a radical approach, and fail without real-world consequences is a profoundly effective learning tool that traditional coaching can struggle to replicate. Of course, the experience isn't without its limitations. The AI can't read true human emotion, and it’s not a replacement for a human mentor for deep-seated career challenges. We also noted the absence of downloadable materials that are common on the main Masterclass platform. This review breaks down our complete experience—the moments of genuine insight, the technical shortcomings, and our final verdict on who this app is truly for, and whether it's worth the investment.