The CEO's Guide to Getting Started with AI

I was speaking to a room full of CEOs recently, and at the end one of them asked the question everyone was thinking: "This all sounds great. But I don't know where to start."

It is the most honest thing a leader can say about AI right now, and it is not a knowledge gap. It is a starting-line problem. You are waiting for a strategy, a plan, the right tool, the right moment. Here is the part nobody tells you: that clarity does not arrive before you start. It comes from starting. The honest answer to where to start with AI is smaller and less glamorous than you expect. You do not need an AI strategy. You need reps.

The short version: start with yourself, not your company. Pick one AI tool, bring it one real problem this week, and use it every day for two weeks. Skip the strategy deck and the committee. Build reps first.

The one shift: start with yourself, not the company

Stop trying to roll out AI to your company. Start using it yourself.

That sounds too simple to matter. It is the whole game. Your team calibrates its effort to yours, and if you have never opened the tool, your people read that as permission to wait. They will. You also cannot set direction on something you have never touched. Every confident, useful decision you will make about AI in your business is downstream of you having used it on your own work for a few weeks. Leaders go first. Not as a slogan, as the actual first move.

Your first week with AI: a five-step checklist

You can do all of this in the next seven days. None of it needs a budget approval or a committee. This is how to get started with AI without overthinking it.

1. Pick one tool and pay for the business plan. The serious options are Claude, ChatGPT, Google Gemini, and Microsoft Copilot. Pay for a business or team plan rather than the free tier, because the paid business plans commit to not training their models on your company data. The free ones often make no such promise. If you cannot decide, start with the one your company already pays for, or pick Claude or ChatGPT and move on. The choice matters far less than starting. One warning: go to the official site directly. Type the address yourself or use the links above, and do not click the first sponsored result in a Google search. I have watched two different CEOs pay a monthly fee for a knock-off "GPT" app they found at the top of their search, convinced they had bought the real thing. The impersonators buy the top ad slot precisely because it works. The real tools live at claude.ai, chatgpt.com, gemini.google.com, and copilot.microsoft.com.
2. Bring it one real problem today. Not a toy example. Take something you would normally hand to someone else, a board summary, a tough email, a first cut of a plan, and do it with the tool instead.
3. Use it daily for two weeks. Fluency comes from reps on real work, not from a demo. Keep it open, and reach for it before you reach for the person you would normally ask. If you want the handful of basics that move the needle most, our free AI training walkthrough, the reference guide, and the Leading in the Age of AI working session cover prompting, giving the tool context, and setting custom instructions.
4. Write your guardrails on one page. Which data never goes in, which tool is approved, who to ask. One page, not fifty. That is enough to start safely.
5. Name one painful workflow to pilot next. Something frequent, annoying, and easy to check. That becomes your first team project once you have the personal reps behind you.

What not to do

Just as important is what to skip, because the most common first moves are the ones that feel like progress but are really avoidance.

• Don't form a committee. A committee that deliberates for a year while your people quietly use consumer AI on their phones is the worst of both worlds.
• Don't buy a big platform. You do not know what you need yet. Buying enterprise software before you have used a chatbot is buying a gym membership to learn how to walk.
• Don't wait for a strategy. The strategy is the output of starting, not the prerequisite.
• Don't delegate the learning. Handing this to someone junior so you can stay above it is the one shortcut that guarantees you stay stuck. When you are ready to bring your team along, that is what our AI training is built for, but it starts with you.

Where this leads: the next 90 days

Week one is personal. The next ninety days are organizational, and they have a shape: set your foundation, build fluency across your team, automate a first workflow, scale what works, and earn the right to let AI agents do delegated work. That is the full arc, and I have written it up stage by stage in The Leader's Guide to Implementing AI. Read that when you are ready for the map. If you want to see where your organization stands today, the AI-Ready Leader Assessment takes a few minutes. For now, the only job is to get your own reps in.

Start smaller than you think

One tool, one real problem, this week. The CEOs who get this right are almost never the ones with the best technology. They are the ones who stopped waiting and started using.

Common questions

How should a CEO start with AI? Start with yourself, not the company. Pick one tool, pay for the business plan, and use it on your own real work every day for two weeks before you think about a company-wide rollout.

Do I need an AI strategy first? No. The strategy is the output of starting, not the prerequisite. Build personal reps, automate one painful workflow, and let the strategy take shape from what you learn.

Which AI tool should a CEO use? Any of the serious ones will do to start: Claude, ChatGPT, Google Gemini, or Microsoft Copilot. Pay for a business plan so your data is not used for training, and pick the one your company already has if you cannot decide.