The 5 Levels of Claude: Ask, Think, Teach, Delegate, Automate (Every Prompt)

Most people never get past asking Claude questions, and that's a fine place to start. You type a question, it answers, you leave. That's level one. This guide is every prompt from the video, what good output looks like, and what to do when it goes wrong, so you can climb all five levels this week.

The five-level framework is from Sabrina Ramonov's newsletter (sabrina.dev); the examples, prompts and tips here are ours.

Your running example is a personal morning briefing: your meetings, the emails that need a reply, and anything that moves a deadline. Every level builds a piece of it.

• 1. Ask. Claude's job: Answers. What you hand it: Your question plus your situation. Plan: Free.
• 2. Think. Claude's job: Pushes back. What you hand it: A plan to poke holes in before it helps. Plan: Free.
• 3. Teach. Claude's job: Saves your way. What you hand it: A job, taught once and saved as a skill. Plan: Free.
• 4. Delegate. Claude's job: Does the whole job. What you hand it: Your apps, through connectors. Plan: Paid (Cowork); the Gmail and Calendar connectors also work on Free.
• 5. Automate. Claude's job: Does it on its own. What you hand it: A schedule. Plan: Paid (scheduling).

Terms, once:

• Skill. A page of instructions Claude keeps, so it can do one job your way every time.
• Cowork. Anthropic's name for Claude doing a whole job for you, step by step, with your files and apps, and no terminal. On newer accounts it's built right into the normal chat.
• Connector. A link between Claude and an app you already use, like Gmail or Google Calendar.
• Scheduled task. A job Claude runs for you at a set time, like every weekday at 7.

• Levels 1 to 3 work on the free plan. Skills need code execution turned on in your Claude settings, and you switch them on under Customize > Skills.
• Levels 4 and 5: doing the whole job (Cowork) and putting it on a schedule need a paid plan. Claude Pro is $20 a month (US, billed monthly). The Gmail, Google Calendar and Google Drive connectors themselves also work on the free plan, so you can try reading your calendar and inbox in a normal chat first.
• Cowork is in the Claude app on paid plans. On newer accounts there's no Cowork option to pick: you describe the task in any conversation, and every step below works the same way.
• Everything below saves to a Google Doc or stays inside the task, so nothing depends on files on your computer.

What it is. You ask, Claude answers. The one upgrade: give it your situation, not just your question.

You're on this level if every chat starts with a question and ends with an answer. You're ready to move up when:

• Your answers are useful but sound like they'd fit anyone.
• You catch yourself typing the same background into every chat.
• Claude goes along with everything you say.

Prompts (copy and paste):

The vague version, so you can see the gap:

The version with your situation:

What good output looks like. It uses your details. It tells you to do something specific with your free hour, and it skips the generic advice. If you could paste the same answer under someone else's name, it didn't use your situation.

Example result (example): it tells you to block the free hour for the proposal and to prep each call in the gaps between them.

What it is. Before Claude helps, you ask it to push back on your plan. You get the weak spots while they're still cheap to fix.

You're on this level if Claude tells you something you didn't want to hear. You're ready to move up when:

• You know what you want but haven't checked whether it's a good idea.
• Your plans keep growing because everything sounds worth doing.
• You're about to build something and haven't asked what could go wrong.

Prompts:

Morning brief version (paste your plan first, then the question):

For comparison, run this one in a separate chat:

What good output looks like. Three numbered weak spots, each tied to something you actually wrote.

Example result (example): Claude says the things you act on would get buried, like an email that needs a reply under a pile of newsletters.

What it is. You teach Claude your way of doing a job once, then save it as a skill. Three moves: show, fix, save.

You're on this level if you've stopped explaining the same thing twice. You're ready to move up when:

• You've explained the same job to Claude three times.
• You know what you want the output to look like.
• You want it to come back in the same format every time.

The three moves:

1. 1Show. Paste something you like: a briefing you wrote by hand, a past calendar, a meal plan that worked.
2. 2Fix. Let it draft, then correct it out loud. In the video I said to make it shorter and put my first meeting at the top.
3. 3Save. Turn it into a skill, and name the rules you just fixed so they're in it.

Prompts:

Show:

Fix:

Save:

What good output looks like. Claude writes the skill and shows it as a card with a save control. Click it and it's saved. Open it under Customize > Skills: it's a page of plain English, and you can change any line yourself. From now on, "run my morning brief" in any chat should come back in the same format.

What it is. You hand over a whole job. Claude makes a plan, goes and gets what it needs from your apps, and saves the result as a Google Doc.

Anthropic calls this Cowork, and it needs a paid plan.

You're on this level if you hand Claude a whole job and it goes and gets what it needs. You're ready to move up when:

• You're still pasting your calendar and inbox into chats by hand.
• You have a skill that works and you trust its format.
• The job has clear steps: read these, check that, write this.

Setup, once:

1. 1Open the Claude app on a paid plan. If you see Cowork, start a new task there. If you don't, open any conversation.
2. 2Go to Customize > Connectors and connect Gmail, Google Calendar and Google Docs. Google Docs is a separate connector from Google Drive, and it's the one that creates a new Google Doc. (Drive is for searching, uploading and sharing files; this job doesn't need it.)
3. 3Keep code execution on from level 3, so your morning brief skill still works. By default, Claude asks for your OK before each action it takes for you, so expect a few approval clicks the first time.

One tip: say Google Doc by name. If you just ask for a doc, Claude makes a regular file instead of a Google Doc.

Prompts:

Morning brief version:

Client follow-ups version:

What good output looks like. Claude makes a plan, reads the calendar, reads the inbox, then saves the doc and shows it as a Google Doc card with your real meetings, the emails that need a reply, and your deadlines.

What it is. The same job, on a schedule. The brief shows up on its own every weekday.

You're on this level if the job shows up without you asking. You know it's working when:

• You'd be annoyed if the brief didn't show up tomorrow.
• You've stopped changing anything in it.

The one sentence:

How to set it up yourself:

1. 1Once the level 4 doc has been right two mornings in a row, say the one sentence.
2. 2In the same task or conversation, type the sentence. Claude may ask a question or two about the schedule.
3. 3Claude proposes the task's name, schedule and instructions. Read them, then click Schedule.
4. 4Check how the task asks for approval. Manual, the default, asks before each action, so a 7 a.m. run can sit and wait for your click. If you'd rather it finish on its own, create the task from Scheduled > New task > Set up manually, paste the level 4 prompt, pick Weekdays, and pick the approval mode that lets it run without asking (read the option names in the modal). None of these prompts send email.
5. 5Open Scheduled in the left sidebar. Your task is there with its upcoming runs.

Scheduled tasks are on paid plans only. They run remotely, so they run on their schedule even when your computer is asleep, and from October 6, 2026 new Cowork tasks on Pro and Max run in the cloud. A scheduled task can't use a folder on your computer, which is why every prompt in this guide reads your Google apps and writes a Google Doc.

What good output looks like. At 7 the next morning, Scheduled shows a finished run, and the new brief is in your Google Docs.

The whole climb, in order.

1. 1Level 1. You ask what to focus on today, with your three calls and your Friday proposal. You get a useful answer, and you notice you'd want it every day.
2. 2Level 2. You say you want a briefing with all the news, your whole inbox and your calendar. Claude names the three weakest parts. One is that the email you actually need to answer would get buried.
3. 3What goes first. Your meetings, the emails that need a reply, anything that moves a deadline. Those three lead the briefing.
4. 4Level 3. You paste a briefing you wrote by hand, ask Claude to match it, correct the draft (shorter, first meeting on top), and save it as a skill called morning brief.
5. 5Level 4. With Gmail, Google Calendar and Google Docs connected, you tell it to use your morning brief skill, read today's calendar and unread email, and save a Google Doc. You open the doc and check it against your real day.
6. 6Level 5. You type one sentence: run my morning brief every weekday at seven in the morning. You read what Claude proposes, click Schedule, check the next run under Scheduled, and go to bed.
7. 7Day after. The brief is waiting. One line is off, so you open the skill and change that line.

Level five took one sentence. Levels two to four took the thinking.

1. Ask for a number, not an opinion. Ask Claude "any thoughts on my plan?" and you'll usually get "looks great." Ask for the three weakest parts, and it has to go find three. The number is what forces it to look.

2. The skill is a page you can edit. When the brief is off, don't argue with Claude in the chat every morning. Open the skill under Customize > Skills and change the line that's wrong. It's plain English, so the fix takes ten seconds, and every future run picks it up.

Two rules for when Claude touches your email and calendar:

• Claude asks before it sends. Gmail can send, reply and forward, and by default Claude asks your approval before each.
• Nothing in this guide sends email. Every prompt reads your calendar and inbox and writes to a Google Doc. Drafts go in the doc, and you send them yourself.

1. 1Day 1 (Ask). Pick one real job from tomorrow. Run the vague prompt, then the version with your situation, and compare.
2. 2Day 2 (Think). Write your plan for the job in 2 or 3 sentences. Ask for the three weakest parts. Then ask "any thoughts?" in a new chat and compare.
3. 3Day 3 (Teach). Paste an example you like, fix the draft out loud, and save it as a skill. Open the skill and change one line yourself.
4. 4Day 4 (Delegate). Connect Gmail, Google Calendar and Google Docs, and run the level 4 prompt. Check the doc against your real day.
5. 5Day 5 (Automate). If the last run was right with no edits, say the one sentence. Click Schedule, find it under Scheduled, and read the brief tomorrow.

Pick the one job you'd least like to do tomorrow, and run the level 1 prompt on it today.