Hey there! This week I want to answer a question people ask all the time: "Which AI should I use?"
That sounds like one question, but it is really a few stacked together: the app, the model inside it, the workspace it runs in, and what your plan actually gives you access to.
The better starting point is the job. I recorded a full walkthrough and turned it into an AI Basics page: How to choose the right AI tool. That page is the full guide; this issue is the highlights. In one line: name the job first, then pick the tool that can see the right context, do the right kind of work, and fit your cost, privacy, and access constraints.

When someone asks, "Which AI is best?", they may be asking four different things at once.
That distinction matters because the same tool name can hide different capabilities. A free ChatGPT user and a company Copilot user are both using AI, but the work each tool can do is very different.
The full AI Basics page gives the current decision map: How to choose the right AI tool. Start there if the tool landscape feels messy.
This is the frame I use. Before I pick the AI, I answer three quick questions: what am I trying to produce, what does the AI need to see, and does it need to give me advice or actually do work somewhere?
Those routes cover the first question. A real job answers the other two. Your manager asks you to compare three project-management tools. The job is a one-page recommendation, the inputs are current vendor pricing (what the AI needs to see), and nothing in your files needs to change, so it is advice, not action. My route: Google AI Mode or Perplexity for the current facts, then Claude to turn the notes into a clean one-pager. One job, two tools.
If you cannot say the job clearly, switching from one chatbot to another will not magically fix the output. The tool matters, but the job comes first.
I need help choosing an AI tool. My job: [what I am trying to accomplish] What the AI needs to see: [files, data, notes, browser, project files, app, or source material] The output I want: [draft, answer, plan, spreadsheet, code change, research summary, etc.] My constraints: [free plan, usage limits, privacy, work data, connected apps, team sharing, deadline] Recommend the kind of AI tool that fits this job and explain the tradeoff in plain English.
Tool choice is not just about which model is smartest. Once the job is clear, the constraints can change the answer. Instead of a checklist, here is how I actually handle each one:
Notice the same tool can win one bullet and lose another: Google AI Mode is great for source-backed research and a bad place for sensitive data. That is why I do not want readers memorizing one static ranking of AI tools. The useful skill is learning how to route the work. As models, plans, and access change, I will keep the more current version on the site.
See you next week,

Ky Tomita, The Playbooks AI