AI Skill Series | 💡Your AI Operating System Starts Here: The 5 Moves Every Executive Must Make to Master AI
How to Go from AI-Curious to AI-Enhanced in 5 Steps.
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🎯 Goal: Train you to become an AI-Enhanced Executive.
🛠️ Note: This is the second in a series of practical posts to help you build your personal AI Operating System.
Do you want to get proficient at AI but don't know where to start?
If you’re confused by the flood of models, jargon, and hype, you’re not alone.
There seem to be two distinct “tribes” when it comes to AI today. One is made up of people using AI for everything, all day long. The other comprises folks who are understandably skeptical, believing that this is the latest technological mirage, and have so far limited their exposure, let alone exploration, of these tools.
If you’re in the second camp, I get it. But if you’ve been ignoring AI, hoping to run out the clock on your career before it makes a real impact, staying on the sidelines is no longer an option. It’s urgent to familiarize yourself with this technology now.
Even for those of us who are AI-curious, however, it’s bewildering to know where to begin and what first steps to take. That’s what this guide is for.
These five steps will help a total beginner get a fast start, but they will also enable more experienced users to be more systematic and strategic in their use of these tools.
Your AI Operating System starts here.
🚨 Your AI On-Ramp: The 5 First Steps to Becoming an AI-Enhanced Executive
1. Pick one model.
As of this writing, there are over 900 frontier models available. Even among the best-known, there are almost a dozen (ChatGPT, Claude, Gemini, Perplexity, Llama by Meta, GrokAI, DeepSeek, Mistral, and Manus), each with multiple sub-models (ChatGPT alone has 4.5, 4.1, 4.1-mini, 4o, o3, 04-mini, and o4 mini-high).
That much choice makes it daunting to know where to start. Sometimes clarity requires constraints. My recommendation: Pick just one to start.
Select from ChatGPT, Claude by Anthropic, or Gemini by Google. GPT is the market leader and an AI Swiss Army knife. Claude is the favorite of Silicon Valley power users. Gemini integrates seamlessly into your Google environment, whether you have an Android phone or use Google Workspace. Begin with one of those three.
Selecting just one model makes it easier to start using it daily. This is essential because I’ve discovered that the more I use AI, the more I think of ways to use AI.
But there’s another reason to stick with one model early on: It gets smarter the more it knows about you. Your outputs improve dramatically with the proper setup (see below).
Executive Move: Don’t pay for Plus (the level above free) until you reach the limits, but the $20/month fee serves as an excellent forcing function to build your daily AI habit.
2. Set it up right.
First, enable Memory. Here’s how and, more importantly, why:
With it on, ChatGPT can reference your past conversations and personal details—skills, projects, goals—making your planning deeply contextual and personalized. You stop repeating yourself. It also remembers your tone, preferences, and details.
The payoff: turning on Memory transforms AI into a strategic thought partner.
Even if you’re on the free plan, there is good news: OpenAI now includes a “light” memory version for non-paying users.
Second, create Projects. (That’s the name in ChatGPT and Claude; Google calls them Gems.)
Projects enable you to organize your AI workspace into themes, similar to folders. You can also set specific instructions per project. For example, I created a “Health and Fitness Folder” where I’ve instructed it to be an expert physiotherapist (to help me deal with all of my hockey and basketball injuries!) Here’s how to do that in ChatGPT.
Executive Move: When in doubt, ask your AI for guidance on optimizing the setup. It’s surprisingly good at helping you use it better.
3. Explore, then augment.
Start by fooling around. Ask it to plan a dinner with whatever’s in your fridge. Have it rewrite an invitation for your kid’s birthday party. Get a feel for how it works.
Getting proficient at AI is like learning to cook: You can follow recipes (or prompts), but true mastery only comes through hands-on experimentation.
Then, graduate quickly to real-world use. Use it to:
Summarize dense reports or industry white papers
Draft cold emails or meeting agendas
Improve your LinkedIn headline or team feedback
I’ve found that it helps to have AI one tap away. I’ve added ChatGPT to my iPhone’s home screen and saved it as a bookmark on my laptop; now I use it throughout the day across multiple workflows.
Crawl, walk, run, then fly.
Once you’ve got momentum, you’ll enter what I call the Explorer → Augmenter → Automator → Orchestrator progression.
Explorer: You're just trying it out.
Augmenter: You use it to improve thinking, writing, and workflows.
Automator: You start building basic automations and AI agents.
Orchestrator: You manage teams of agents and integrate AI into your decision architecture.
Executive Move: As you advance through this progression, it’s essential to be intentional about what you outsource to AI and what you preserve as human-only work. For more guidance on how to use AI strategically, check out this post I wrote a few months ago.
4. Go deep before going wide.
The temptation is to try every new model. Resist that urge at the start.
Jeremy Caplan of the Wonder Tools Substack offers a practical framework:
Pick: Choose a tool based on a real need.
Stick: Commit to it for a focused period.
Dig: Go beyond basics—push its boundaries.
Investing at first in mastering one model is how you’ll find real productivity breakthroughs.
Only after you have achieved fluency should you branch out. I use a 70/30 ratio: 70% of my time with my core model, 30% exploring new tools (like HeyGen for video or Gamma for presentations).
Executive Move: I set aside Friday afternoons to experiment with new AI models, while continuing to work with my core AI toolkit the rest of the week.
5. After trying AI monogamy, be polyamorous.
You should eventually get into the habit of working with multiple LLMs. Think of it as the cognitive equivalent of streaming services: No one just has Netflix, right? Most people have at least two or three.
Some tools produce better results for specific types of tasks. For example, Claude is generally viewed as more “emotionally intelligent” than the others, while Google NotebookLM is fantastic at making sense of reams of disparate documents. If you’re serious about augmenting yourself with AI, you should become fluent in multiple models.
There’s also a strategic reason for variety.
Beware of Model “lock-in”
John Herman of New York Magazine said the quiet part out loud in his recent article, “ChatGPT Does Not Want You Cheating on It With Claude.”
“Over the past few months, big AI firms have all made subtle pivots in the same direction. ChatGPT “can now reference all your past conversations” with an improved “memory.” Google announced Gemini with Personalization, which can “connect with your Google apps and services to provide responses that are uniquely insightful and directly address your needs. Together, though, they mark an attempt to realize a goal these companies have been talking about since the early days of ChatGPT: not just to get people to use their chatbots but to get them well and truly locked in.”
That’s why I’ve built a “second brain” in ChatGPT and a “third brain” in Claude. Don’t build your AI future on a single platform.
Executive Move: Think AIs, not AI.
🏆 The 60-Second Shift:
Pick one model. Choose between ChatGPT, Claude, or Gemini.
Set it up right. Enable Memory and start using Projects to organize your AI workspace.
Explore, then augment. Crawl, walk, run, and then fly.
Go deep before going wide. Pick, stick, and dig.
After trying AI monogamy, be polyamorous. Build your AI stack.
The AI bell can’t be unrung. This is not another falsely hyped technology, like NFTs or 3D printing. AI is already disrupting entire industries and will transform work and life as we know it.
You owe it to yourself to become an AI-Enhanced Executive.
🛠️ Your Move
💬 Still unsure where to start—or how to get to the next level?
I coach executives to build their personal AI operating systems. From tool fluency to workflow integration, I’ll help you go from overwhelmed to augmented. Let’s chat.
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IoNTELLIGENCE by Ion Valis. I'm an executive coach and personal AI strategist. To learn more about my work, please visit my website or connect with me on LinkedIn.