The Playbooks AI
WEEKLY·ISSUE 009·July 15, 2026
Welcome

How to prompt AI.

Hey there! The question I keep getting lately, more than any other, is some version of: "How do I prompt this thing?" A lot of people are not sure how to talk to these tools, so this week I want to break it down and keep it simple. I will also show you exactly how I write my prompts.

Prompting is not just about the text you give the AI. It is about the context you give it: the files you attach, the examples you show it, the instructions you set, and the apps you connect.

I turned this into a full AI Basics page: How to prompt AI. That page has the full guide; this newsletter has the key points: what a prompt actually is, a five-line prompt template you can copy, and three techniques I use in my own prompts. No sponsorships here either: we read all three AI companies' prompting guides, tested them against my own prompts. These techniques work in whatever tool you already use.

What's in this issue
  • Beginner: a prompt is more than the words you type. Your message, your saved instructions, and the files and apps you give it access to are all part of the prompt. Two people can type the same sentence and get completely different results.
  • Intermediate: the five-line prompt template. Transform a vague prompt into a strong one, then copy the reusable template: what I want, what you need to see, what done looks like, what to avoid, and when to check with me.
  • Advanced: how I actually prompt AI agents. The three techniques from my real prompts: make the AI plan before it acts, point at context instead of pasting it, and dictate your request instead of typing it.
  • Also this week: big model and app news. GPT-5.6 launched and it is good, Codex moved inside the new ChatGPT desktop app, ChatGPT can now talk while it works, and included Fable 5 access runs through July 19.
AI Basics
BeginnerLevel 1

What a prompt actually is.

A prompt is how you point the AI at what you want. It is not just the sentence you type; three things shape what you get back:

  • Your message: the task you are asking for.
  • Your saved instructions: preferences you set once in settings, like "keep answers short" or "I run a small landscaping business."
  • What it can see: attached files, pasted screenshots, connected apps, and anything you tell it to go find.

That is why two people can type "review my budget" and get completely different results. One attached the spreadsheet, or said where to find it. The other attached nothing. Same words, completely different prompt.

Before you send a prompt, ask yourself: would a colleague reading this with no other context know what to do? If not, the AI will not either.

The takeaway: give the AI the context it needs, and treat it like a brilliant but new employee.

IntermediateLevel 2

Transform a vague prompt into a strong one.

Here is a task someone at a nonprofit might face. The vague version: "Write a thank-you email to the sponsor." The AI has to guess which sponsor, what they did, what you want next, and how your organization sounds. You get something generic, then spend three messages fixing it.

Now the strong version: "Write a thank-you email to the company that sponsored our fundraiser dinner last night. My notes from the event are attached. Thank them for the $5,000 sponsorship, mention that we hosted about 200 guests, and invite their team to visit one of our programs this fall. Keep it under 150 words, warm but professional. Don't ask about next year's sponsorship yet."

Same task, four changes: the situation is named, the AI can see the real notes, done is defined, and one boundary is explicit. That structure is repeatable. Here is the template:

The five-line prompt template
What I want: [the task and the outcome, in one or two sentences]

What you need to see: [attach the files, paste the notes, or name the source the AI should use]

What done looks like: [format, length, audience, and anything that must be included]

What to avoid: [anything off-limits, plus mistakes you have seen AI make on this before]

Before you act: [for big or risky tasks: "show me a plan first and wait for my go-ahead"]

The above is not a checklist, just the shape of a good prompt: skip any line that does not apply. Quick questions do not need prompts like this, but for bigger tasks, filling it out takes 30 seconds and should save you from correcting the AI many times later.

The takeaway: make sure to give the AI the complete story in terms of what you want.

AdvancedLevel 3

How I actually prompt AI agents.

For this issue we analyzed about 2,800 of my real prompts to Codex and Claude from the past ten months. Three techniques showed up constantly, and they matter most with agents: AI tools that open files, use apps, and keep working for minutes, even hours.

  • Make it plan before it touches anything. My most repeated line, by far: "Don't make any changes right now. I just want you to plan and think with me." The AI proposes a plan, I approve, then it acts. For you: if an AI can change real things you care about, make "show me the plan first" your default opener. The tools support it directly: Codex has a /plan command and Claude's agents have a plan mode.
  • Point, don't paste. I almost never retype context. I mention files on my computer, tell the agent to pull my notes through a connector (a connected app; ChatGPT calls them apps), or capture the window I am looking at. In the ChatGPT desktop app on Mac, where Codex now lives, tapping both Command keys sends the app in front of me as context (Appshots). For you: attach it, connect it, or name it in the prompt.
  • Dictate your request instead of typing it. I speak most prompts nowadays. On a Mac, press Command+D to dictate inside Claude. In Codex, press Ctrl+Shift+D. If your shortcut differs, click the microphone button. For every other app, I personally use Wispr Flow. My dictated prompts tend to ramble, but that is fine, because the rambling is context: what happened, what I already tried, what I am worried about. This tends to be far faster than if I were to type my prompt.

One big tip: when you catch yourself repeating the same setup in every prompt, save it as a custom instruction, a project, or a skill so it is already loaded next time. Step 5 of the full guide explains this further.

Note: none of these are about clever wording. They are about being intentional about what the AI sees and what we want it to do.

Also this week

Was this week's issue useful?

Got a sec? Tell me what to write more of.

See you next week,

Ky Tomita, The Playbooks AI