There are many MasterClass courses on AI but one in particular really got me thinking about the future of artificial intelligence in the workplace and how we can choose to implement it. It’s called, simply, AI Strategy at Work.
Amy Webb, who guides this MasterClass alongside AI strategist Conor Grennan and transformation expert Nichol Bradford, tells me that the course is a response to one theme: fear versus FOMO.
«This is a complicated technology,» Webb, CEO of the Future Today Strategy Group and professor of strategic foresight at NYU Stern School of Business, tells me. «That creates a sense of deep uncertainty, and when people are grappling with deep uncertainty, they are looking for leaders. They’re looking for experts. They’re looking for answers.»
Webb’s interest in AI began in college, when she became fascinated by using machines to rapidly simulate decisions as a way to understand what might come next.
She recalls realizing she was limited by what she calls the «squishy machine» in her head — the human brain — and wondering what would be possible with access to systems with greater computation ability.
But AI is still limited.
«If you put garbage into an AI system, you’re going to get garbage on the other end,» Webb says. «[The] same thing is true of your brain.»
Webb’s curiosity was reignited by advances in machine learning, prompting her to build early tools as generative AI emerged. Webb also began asking questions around power and control, like who was building the commercial tools, who was assembling the datasets and who was deciding what went into those databases.
Realizing that a largely homogeneous group was making foundational decisions about how AI systems recognize patterns and what they are trained on — namely, men — ultimately shaped how she thinks about AI, strategy and its impact on society.
Here’s what I learned from Webb’s AI MasterClass, and from speaking to her about it.
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How to get the most out of the AI Strategy at Work MasterClass
1. Don’t rush the tools
If you’re new to AI in the workplace, or a leader trying to learn the best way to amplify your toolkit, you may be tempted to rush the process of learning which AI tools to use and go all in on them.
But as this MasterClass stresses, strategy must come before execution. As Webb says, AI without critical thinking leads to either unrealistic optimism or paralysis.
Instead, focus on having your assumptions challenged, like your opinion on future work and your overall understanding of the tools being used.
2. Treat each lesson as a thinking exercise rather than a checklist
«You have to do the critical thinking first, and you are still the supreme orchestrator,» Webb says.
Her MasterClass is about reframing how you see your work and the role AI plays in it. Examine your current role, how it’s changing and what that means for a company or your team.
While it may feel overwhelming or like you need to play catch-up or overhaul your knowledge, you must think strategically about AI as something to enhance your job.
Anxiety about AI and the future of work is normal, but the point of this course is to learn where and how human judgment matters most.
3. Apply lessons to your role as you watch and learn
Since AI began seeping into our online lives, uncertainty has been a common response. This MasterClass is built to help you audit your role amid all the AI, instead of thinking about AI replacing you. As you progress through the course, identify where AI does and doesn’t fit in for you.
One way to do this is to use the course as an entry point for grounding it in your actual work, rather than hypothetical use cases. For example, for me as a writer, AI is helpful for highlighting and extracting verbatim quotes from interviews I conduct, and it can categorize them based on context. These quotes can be useful for either inspiring a section of writing or adding detail to support what’s stated.
AI isn’t writing the piece for me, nor is it replacing my thought process. But it is helping me choose quotes from my interview with Webb to include within my draft.
4. Revisit lessons, because the course becomes more useful as your understanding evolves
Clarity is necessary with AI. This MasterClass will become more useful as your understanding of AI tools evolves.
After you’ve finished the course and taken the time to think about it — like whether to use AI to help with decisions, try building new workflows or problem-solve for constraints at work — returning to it will be more helpful as you integrate and comprehend AI tools.
The goal? «AI becomes your assistive tool used in the middle of the work to help you go deeper and faster,» Webb says.
How should we be using AI at work?
This MasterClass offers a very clear, straightforward answer to this question and it differs from the more common «use these tools» advice that often accompanies AI education.
The biggest insight Webb and her colleagues offer is that AI amplifies human judgment.
At best, it’s a strategic collaborator, rather than a shortcut or replacement for thinking. Use AI as a tool for foresight rather than fantasy, and automate routine tasks to free up mental space that requires judgment, critical thinking, ethics and context.
«It’s not enough to understand what the basic technology is, or to screw around with prompts,» Webb says. «You also have to have tools to help you think critically about the future.»
This isn’t easy, particularly as AI becomes part of our daily toolkit — whether it’s suggestions from Gemini while writing in Gmail, Grammarly offering advice in a Word doc or AI search results when we Google something. AI generates immediate feedback, and it’s not absurd to become reliant on it as an all-knowing, perfect partner rather than something we can stay objective toward.
Preliminary research points to how we could become more reliant on AI than our own judgment in decision-making as a result of high AI use, stressing the importance of critical thinking.
For instance, following my conversation with Webb, I spent 10 minutes struggling to trust my own judgment around the framing of my thank-you email. At the 9-minute mark, I asked Claude, «Analyze this email and tell me if it sounds like ‘too much’ for a thank-you note.»
Using AI requires collaborating with it — something to think with, not something to think for you.
«More information is not necessarily better,» Webb says. «It’s just more.»
Who should watch AI Strategy at Work on MasterClass?
AI Strategy at Work is for anyone who wants to stay ahead as AI reshapes the workplace.
This class isn’t an introductory course to AI. Instead, it’s a framework for thinking critically about AI — pressure-testing ideas while protecting human judgment that machines can’t replicate.
AI is here, and the value of this course lies not in teaching tools or shortcuts, but in learning to anticipate change, not just react to it.
«You’re not going to be an expert in AI at the end of the class,» Webb says. You’re just going to have much more clarity than you did before.»
To access this class, MasterClass membership starts at $10/month (billed annually) and is currently running a 50% off promotion.
