How I Became an Expert at Prompting—and How You Can Too

If you’ve ever tried using AI tools like ChatGPT or Microsoft’s Copilot, you know that the results can be hit or miss. Some days, it feels like AI can read your mind. Other days? Not so much. The difference lies in the art of prompting—how you ask, guide, and structure your queries to get the outcomes you want.

Prompting isn’t just typing words into a box; it’s about thinking systematically and creatively. Once mastered, it’s a skill that can save you hours of frustration and elevate your results. And yes, it’s a skill anyone can learn, even if you don’t think you’re a “tech person.”

As an early adopter of AI tools like Microsoft Copilot, I’ve had the privilege of training over 16,000 Microsoft employees, helping them unlock their potential to improve their workflows and daily work.

Every day, I receive requests from professionals across the globe seeking guidance on refining their prompts or crafting them for specific use cases—proof that prompting is a skill many are eager to master. Along the way, I’ve led prompting hackathons, spoken on podcasts, served as an interview panelist, and shared insights as a global speaker on generative AI. These experiences have shaped my belief that anyone can master prompting with the right mindset and tools.

The Foundations of Great Prompting

Prompting is part science, part art. It combines structured thinking with curiosity and experimentation. Based on my own experiences, I believe prompting requires four essential skills:

1. Structured Writing Skills

Think of a good prompt like an essay outline. It needs structure and clarity. AI thrives on context, so the more organized and specific you are, the better. For instance, asking, “Write a professional email to a client about a delayed delivery,” provides a clear framework.

I learned this lesson early in my career while managing technical projects as a DoD contractor for NASA. Back then, writing concise, precise communication was a survival skill. One poorly worded email could derail a schedule. This same discipline applies to prompts. AI is your assistant, not a mind reader. If you want clarity, you have to provide it first.

2. Principles and Systems Thinking

Prompting isn’t just about asking for what you want—it’s about understanding the “why” and “how” behind your request. When you grasp core principles (like asking for step-by-step instructions or specific formats), you unlock AI’s true potential. This is known as chain-of-thought prompting, and we see advanced models embed this methodology into prompting.

Systems thinking, in particular, is a game changer. It’s about seeing the connections between inputs and outputs. For example, if I need AI to help with a project plan, I don’t just ask for a “plan.” I break it into components: objectives, milestones, risks, and resources. By guiding the AI through a system of connected parts, I get a more thought-out and tailored result.

3. Curiosity

Let’s be honest—prompting is as much about play as it is precision. You must be willing to try different approaches, ask questions, and explore what the AI can do.

As someone who’s coached over 16,000 people on AI tools, I’ve seen how curiosity transforms outcomes. One client, a marketing executive, started with the basics: “Write a tagline for my product.” But with some curiosity, she pushed further, asking for taglines in the style of Hemingway, Shakespeare, and even a TikTok influencer. Each iteration brought fresh ideas, sparking creativity she didn’t know she had.

4. Experimentation

Prompting is a sandbox. There’s no perfect formula, and that’s what makes it fun. Every time you tweak a prompt, you’re running a micro-experiment.

During a workshop I ran at Microsoft, we experimented with prompts like “Explain AI to a 5-year-old” versus “Explain AI to a room of Fortune 500 CEOs.” The results were night and day. This showed the group how small changes in framing can unlock entirely different insights.

How to Build Your Prompting Muscles

Like any skill, prompting gets better with practice. Here’s how to sharpen yours:

1. Start Small but Specific

Don’t overwhelm yourself with complex prompts at first. Instead, try simple, specific tasks. For example, instead of saying, “Summarize this report,” say, “Summarize this report in three bullet points for a C-suite audience.”

Over time, you’ll naturally build a sense of what works. The important part is consistency. Practice chatting with AI daily until you establish a habit. Studies show it takes roughly 10 hours to become proficient at prompting.

2. Think Iteratively

A great prompt often evolves. If the first attempt isn’t perfect, don’t get discouraged. Adjust and refine. AI tools improve the more context and feedback you give.

Here’s an example from my work: While drafting a strategy deck, I asked Copilot for a slide on “key business risks.” The result was okay but generic. By tweaking the prompt to “Identify three risks for a global tech company entering a new market, focusing on regulatory, cultural, and competitive challenges,” the output became laser-focused.

3. Learn from the Results

If an output isn’t quite right, reverse-engineer it. What part of your prompt might have led to the mismatch? Was it too vague? Did it lack context? Treat each response as a lesson. Additionally, be voracious about learning from other prompt examples and what worked best.

4. Embrace Playfulness

Some of the best prompting happens when you stop taking it so seriously. Ask the AI to write a poem, create a “Shark Tank” pitch, or draft a mock press release. These playful exercises spark creativity and reveal new ways to use the tool.

One of my favorite moments was when I asked an AI to rewrite a business case “as if Morgan Freeman narrated it.” Not only was the result hilarious, but it also helped me see the potential for storytelling in otherwise dry content.

Another prompting event I led involved leading 500 people through an imagined space exploration adventure. It wasn’t until the end that I revealed we used advanced prompting techniques that could easily be translated into business scenarios. I’ll never forget the surprise and elation people felt when they realized how much fun they had learning advanced prompting techniques without even knowing it.

Why Prompting is the Future of Work

Prompting isn’t just a skill—it’s a mindset. It forces you to think critically about your goals and how to communicate them effectively. In an AI-driven workplace, this will be invaluable.

Reflecting on my career, I see prompting as a natural extension of systems thinking and strategic problem-solving. From satellite module training to content brainstorming, the same principles applied: clarity, curiosity, and iteration.

Now, as AI becomes a part of everyday work, these skills aren’t just nice-to-have—they’re essential. Prompting empowers you to reclaim your time, reduce busy work, and focus on what matters most.

Wrapping It Up: The Prompting Mindset

Prompting isn’t magic; it’s a skill you develop with practice. By combining structure, curiosity, systems thinking, and experimentation, you can unlock the full potential of AI tools in your work and life.

And remember, it’s okay to start small. Every great prompter was once a beginner typing, “Write me an email.” With time and practice, you’ll go from that to building prompts that help you tackle complex strategies, uncover fresh ideas, and maybe even narrate your business case like Morgan Freeman.

So, roll up your sleeves and start experimenting. You might surprise yourself with the results. Prompt smarter, work better, and never stop exploring.

Happy prompting,

Yen Anderson