Last week I was on a park bench, watching my kids tear around a splash pad, when my phone rang. A friend who is smart and runs his own business had questions about AI. Not the kind I usually get asked. Simple ones. “Do I need to hire someone for this?” That kind.

Halfway through my answer, something landed. I’ve spent years answering enterprise-level AI questions about governance, strategy and rollout plans, for people who already speak the language. And here was a friend asking the honest version of the same questions, half-apologizing for it, as if “where do I start?” were an embarrassing thing to want to know.

It isn’t. It’s the right question. It’s just not the one that gets answered in public.

That’s the gap this series is for. Most of what’s written about AI assumes you’ve already read everything else written about AI. The words pile up. Agents, models, tokens, pipelines. Somewhere under that pile, a perfectly capable business owner concludes this stuff must be for other people. Same technology, two very different experiences: some people get leverage, most people get vocabulary.

What I’m doing about it

For the next 21 days, I’m answering one plain-language question about AI every day. One question, one answer, no jargon.

The rules I’m holding myself to:

  • One question a day. The kind a friend asks on a phone call, not the kind a panel debates on stage.
  • Plain words only. If a technical term sneaks in, it gets explained in one sentence or cut.
  • Real tasks, not hype. Every answer connects to something you actually do: emails, quotes, invoices, customers.
  • Short. Each piece reads in a few minutes, and each stands on its own.

Who this is for

If you run a business or a team and quietly suspect that everyone else has AI figured out, this is for you. In my experience, they don’t. Most people are exactly where you are: curious, a little skeptical, and short on time.

You don’t need a technical background. You don’t need to have touched a single AI tool. You just need the questions you already have, including the ones you’ve been embarrassed to ask out loud. Those are usually the best ones.

My friend got his answer on that phone call. Over the next three weeks, you’ll get twenty-one of them.

Tomorrow, Day 1: the most useful question you can ask about AI in your business, and it starts with noticing what you do over and over again.