Which A.I. tool should I use?
By Chris Castleman · Updated October 17, 2026 · 5 min read
People ask me this more than anything else. The honest answer: the big ones are all good now, and the best tool is usually the one you'll actually open. But they do have personalities, and some fit certain jobs better.
The four general assistants
These are the ones you chat with. All of them have a free version and a paid plan that's around $20 a month per person.
| Tool | Made by | Good fit if… |
|---|---|---|
| ChatGPT | OpenAI | You want the one most people know, with lots of extras like images and voice. |
| Claude | Anthropic | You do a lot of writing, or work with long documents, and want a careful, natural tone. |
| Gemini | You live in Gmail, Google Docs and Google Drive. | |
| Copilot | Microsoft | You live in Outlook, Word and Excel. |
My advice: try two of them on the same real task, side by side, and keep the one whose answers you like better. Don't overthink it. You can switch any time.
The tools you already pay for
Before you sign up for anything new, look at the software you already use. A lot of it has A.I. built in now:
- Your email and documents. Google Workspace and Microsoft 365 both have assistants that can draft replies and summarize long threads.
- Your design tool. Canva can write captions and resize one design into every format you need.
- Your point-of-sale, scheduling or accounting software. Many now offer A.I. features for things like menus, reminders or reports. Check the settings or the "what's new" page.
Using what you already have means no new password, no new bill and nothing new to learn.
When the free version is enough, and when it isn't
The free versions are great for trying things out. I'd pay for a plan when:
- You use it most days. Free plans run out of messages or use a less capable model when they're busy.
- You're putting business information into it. Business and team plans come with stronger privacy terms. See Keeping your data private with A.I.
- You want it to remember your business. Paid plans let you save instructions and documents, so you don't have to explain who you are every time.
Beyond chat
Some of the most useful setups don't involve a chat window at all: a form on your website that drafts a quote, an inbox that sorts itself, or a weekly report that writes itself from your sales numbers. Those are built by connecting an A.I. model to your other tools. They take a bit of setup, but once they're running, you don't have to think about them.
My short answer
If you want one recommendation: start with whichever assistant matches the email you already use (Gemini for Gmail, Copilot for Outlook), or Claude or ChatGPT if you're not sure. Use it for a week on real work. Then decide.
If you want help choosing the right tools for your situation, I'll go through it with you in an hour. Book a time, or ask me a question first.