Run three observational evals, then review and send

What you do: read the steps of one check. What you get: you know what you're watching in Rounds 2 and 3.

Each time your Chief of Staff checks your inbox is called a wake: the Chief wakes up, looks at your new email, and goes quiet again. For now, a wake only happens when you ask for one by saying "Check my email". In the next lesson, you plan a schedule so the Chief waking up happens on your defined schedule.

On Outlook (Microsoft 365) in Codex, step 1 works differently: Outlook's search gives the team the text of each email along with the list. Part 3 says what else changes on Outlook.

You only pick when you start a check yourself, like in these test rounds. Once the team checks on a schedule, it takes all your new email, and your Chief still sorts every one into a pile.

Nothing is deleted, archived or marked as read along the way. Between your two yeses the team stops only for five things: money, sending anything outside, deleting, posting publicly, and account authority. Each one waits on your Needs-you list with the work saved up to that point; everything else keeps going.

Everything the team does is written down in the record: the files under runs/, one folder per email. Gigawatt reads the record with you after each round.

Attachments come to you. The team doesn't open them. Open them yourself in your mail app.

When the team sorts something wrong, tell your Chief. Your Chief shows you the exact change to your categories so it sorts that kind of email right next time, and saves it only when you say yes. Read the suggested change closely before you do.

More: a wake, step by step, and your categories.

What you do: give your Chief three practice emails, look at what the team made, then run an observational eval with Gigawatt. What you get: your first observational eval notes, with nothing touching your mailbox.

The practice emails are for a made-up restaurant, Hattie B's Hot Chicken (a practice example, not affiliated with Hattie B's). A practice email can never be sent. You'll find them in your workbench folder, in course/workforce/week3/support-pack/sample-emails/. Open them in your file manager or your editor.

Do this now

1. Write what you expect. Open each email. Before you hand any over, write one or two sentences for each: what should the team do with it? This is the first step of every observational eval: you write what you expect before you see what happened. You give these sentences to Gigawatt later.

2. Hand each one to your Chief. Open 01-email.md. Copy only the From, Subject and Date lines and the body. Leave out the first comment line and the Case, Send, Frozen-At and Attachment lines.

In a new thread with your Chief of Staff, say this, with the email pasted under it:

The plan should say this is a practice email, how careful the team will be, and that nothing will be sent. Do the same for 05-email.md and 07-email.md, each in its own new thread. All three can run at once.

3. Look at what the team made. Each run gets its own folder under runs/. Your Chief's plan names it. Open these four files in it, in your file manager or editor:

1. case/case-plan.md: the Support Lead (Holler)'s plan
2. drafts/draft-v1.md: the reply the Communications Writer (You've Got Mail) wrote
3. review/review.md: Kansa's twelve questions and its mark
4. flow-receipt.md: every step that ran, and what each agent said it was missing

For 07-email.md there's no draft. Open decision.md and find the line that says why.

As you read, ask: could the next agent act on this without asking a question back? More: all twelve files in a job folder, and what to look for.

4. Run the observational eval with Gigawatt. In a new thread with the Operator (Gigawatt), say:

Give it your sentences exactly as you wrote them. Gigawatt saves them word for word and writes one line for each agent. It also gives you a "not yours yet" list: each thing an agent said it was missing, like your prices, a policy, or how you sign off, quoted from that agent's own files. That list is what you work through in Make the team yours, later this week. Finally, Gigawatt names the one change that would help most.

What you should see: for the first email, a calm, plain draft with one question left open. For the second, a draft that's mostly blanks, never marked ready. For the third, no draft, a plain reason, and a line under Needs you.

5. Stick one change back in. If Gigawatt's one change is small, like a sorting rule, make it with the agent Gigawatt names (your Chief, for a sorting rule) and say yes, so it goes in before Round 2. Bigger changes, like your voice, wait for Make the team yours.

What you do: ask your Chief to check your email, pick three to five different kinds, read the drafts, then run an observational eval with Gigawatt. What you get: your first drafts in your own mailbox, and notes on how they compare with what you expected. Nothing is sent.

This first check covers email that arrived after you set up the team. The team answers only from the places you approved in Set up your email department. Where it has no source, it leaves a blank for you.

Pick a mix of emails, not just the first few on the list. This round shows you how the team handles different situations. So pick three to five emails, including at least:

• one easy one, like a simple question the team should be able to answer
• one that needs something only you know, like a price or a date
• one the team should leave alone, like a newsletter or something personal

If your inbox doesn't have one of these right now, say so when you pick. Gigawatt notes it, and you look for that kind in Round 3.

Do this now

1. Write what you expect. Look at your inbox in your mail app, without replying to anything. For each email you'll pick, write a sentence: what should the reply say, and how should it sound? Write one too for anything the team should leave alone.

2. Start the check. In a new thread with your Chief of Staff, say:

You'll see a numbered list: time, sender, subject, and "attachment" or "older mail" where they apply. On Outlook the listing may already include message text. In the same thread, pick three to five messages from different real conversations and say why, for example:

If your email is Outlook (Microsoft 365) in Codex. A few things work differently:

• Outlook's search gives the team the text of each email along with the list. So on Outlook, the team has seen your emails before you pick. It still only works on the ones you pick.
• The team can't see drafts you started yourself in Outlook. Leave any email you've already started a reply to out of your picks.
• Outlook doesn't give the team a conversation ID, so each selected message becomes its own job. Pick only one message per real conversation, including across rounds. If the team already has a draft or an unresolved job for that conversation, ask your Chief to settle that existing work instead of selecting a later message and making another reply.
• It's drafts only. The team saves and checks one reply draft for the selected message. You inspect it in Outlook; only an eligible draft may be sent manually. A held or practice draft must not be sent. No browser fallback changes that.

Synthetic example for your pick. Items 1 and 2 are two replies in the same catering conversation; item 3 is a separate newsletter. Picking item 2 leaves item 1 out, so the team cannot create two replies to the same conversation. For your own picks, check the conversations in Outlook and explain your choice with the numbers. If you cannot tell whether two items belong together, leave one out and ask your Chief to hold it. Your existing three-to-five selection is the action to inspect.

3. Watch the sort. Check that anything about money, a password or a payment change is under Needs you, with no draft. Check that each skipped email has a reason and a way to undo it. When the drafts are ready, your Chief briefs you: Needs you first, then each draft by number, with Kansa's mark.

The team must leave your own drafts alone. Outlook's connector cannot reliably list unrelated drafts you started yourself, so leave any conversation with your own unfinished reply out of your picks. Do not mistake a missing warning for a check of all your Drafts.

The team drafts first, then asks. Anything only you know shows as a clearly marked blank in the draft. Nobody stops to ask you in the middle. At the end, your Chief lists every blank in one place, draft by draft, with a suggested answer where the team has one. Answer them all in one message, in the same thread where you started the check, for example:

Your Chief fills them in, Kansa checks the new version, and then it can be sent. Kansa never marks a draft ready to send while a blank is open. Your sign-off name comes from your profile, and each reply greets the sender by the name they signed with, so neither is a question.

4. Look at the review page. Your Chief also makes a review page that shows everything from this check in one place. It starts with one sentence on what happened to your email, then shows what needs you, the drafts ready to send, and what the team filed. In Claude Code, your Chief opens it beside this chat, on this computer only. The first time, it may ask for your yes to have Gigawatt add the page to your workbench. In Codex, open the file it names. Nothing on the page sends. On routes where the Chief can send, its buttons can copy a message such as "Send #2". Outlook drafts-only items have no Send button. Practice and Held items must never invite a manual send. More: what the review page shows.

5. Run the observational eval with Gigawatt. In a new thread with Gigawatt, say:

Give it your sentences. If the team skipped something you would have answered, go back to your Chief's thread for this check and say: "You should not have skipped that one." Your Chief records it, and the sorting rule for that kind of email gets fixed with you.

What you should see: sorts you agree with, or a question where your Chief wasn't sure. Calm, plain drafts, probably not fully in your voice yet. Blanks for facts only you have, all listed together at the end. Nothing sent.

6. Stick one change back in. As in Round 1, say yes to Gigawatt's one small change before Round 3.

What you do: run one more check, read every draft from Rounds 2 and 3, and decide which are usable. What you get: reviewed replies and Gigawatt's account of the three rounds. On Codex Outlook, any sending is your manual action; the team does not report it as a confirmed send.

How sending works on routes where the Chief can send. The next four steps apply only where the Chief can send. They do not unlock sending on Codex Outlook Email. There, use the manual-review branch below; telling the Chief "send" never changes the drafts-only limit.

What happens when you say "send":

1. Your Chief runs its safety checks (below). If any one fails, nothing is sent, and your Chief tells you why.
2. Your Chief shows you one line: who it's going to, the subject, and the first line of the reply. Check all three.
3. Your app asks you once more, if it has its own ask. Claude Code does. Say yes only if that line shows the person and the email you meant. Saying no sends nothing. Where there's no second ask, like in Codex, your yes to that one line is the go-ahead, so check it closely.
4. Your Chief tells you what happened: sent; held, with the reason; or not sent, because you said no.

The safety checks. Before anything goes out, your Chief runs seven checks. It checks that:

• it hasn't already been sent
• nothing has stopped it: no hold on it, no stop, and your off switch isn't there
• no earlier attempt to save or send it is still unclear
• it goes only to the person who wrote to you, with no one added and no hidden copy
• the Quality Reviewer (Kansa) marked it ready to send, with no blanks left
• it's the exact version you saw
• it isn't a practice email

Other routes. Claude Code with Gmail keeps its own supervised sending path. A route qualified for that app/provider proves no other route. The Codex Outlook drafts-only limit is not removed by your yes, a browser, computer control or a saved send-route skill.

Outlook Email in Codex: review, then decide yourself. Your Chief never sends these drafts. Before a manual send, check that the item is not Practice or Held, no full stop or off switch is active, Kansa approved this exact version with no blanks, and no placement or earlier send is unclear. Open the draft in Outlook: To is the original sender only, Cc and Bcc are empty, the subject and quoted original belong to the selected message, and the reply keeps its reviewed words and line breaks. If Bcc was not reported by the connector, inspect it yourself in Outlook. If you edit any words, ask for a fresh version and review before sending. If anything is uncertain, keep it unsent and ask your Chief what would settle it. Never send a held or practice draft manually. Only after these checks may you choose to press Send yourself in Outlook. Tell the Chief what you actually did; that report alone is not mailbox confirmation or a measured edit outcome.

When something goes wrong

If an email is "held", do not send it manually or ask for it to be sent again. "Held" means your Chief has paused that email because it can't tell whether it already went out. Asking again could send it twice. Ask your Chief what would clear it up, and wait.

If you edit a draft yourself, it needs your yes again. Changing a draft in your mail app makes it a new version. Kansa checks it again and your Chief shows it to you again before it can go.

Some problems stop all sending, for every email. For example:

• a draft addressed to the wrong person
• a send you didn't approve
• the same reply sent twice
• an agent following instructions found inside an email (prompt injection)
• one customer's details showing up in another customer's draft
• a draft that touches a password or a payment

The team keeps reading and sorting your email, but sends nothing until you've looked and told your Chief to carry on.

Your off switch. You can stop all sending yourself, any time. Do both:

1. In any thread with your Chief of Staff, say "Stop all sending".
2. In your workbench folder, open work-orders/standing/ in your file manager and make a new, empty file named autonomy-off. (If your computer adds .txt to the end, that still works.)

While that file is there, the team places no drafts and makes no sends. It cannot disable Outlook's own Send button. Leave held or practice drafts unsent yourself too. On Codex Outlook, removing the file and clearing the stop can resume eligible drafting; it never gives the Chief permission or a tool to send. Other routes where the Chief can send keep their two-step restart.

More: all the safety checks, and after a send · everything that stops all sending.

Do this now

1. Write what you expect, then run the second check. As in Round 2, write a sentence for each email before you look. Then, in a new thread with your Chief of Staff, say:

In the same thread, pick a mix of three to five emails again, say why, and wait for the drafts. As in Round 2, the team drafts first, and your Chief lists every blank at the end for you to answer at once, in that same thread.

2. Read every draft from Rounds 2 and 3. For each one, decide: send it as it is, ask for changes, skip it, or edit it yourself first. For Codex Outlook, use the manual-review branch above and choose in Outlook yourself. For a route where the Chief can send, tell your Chief which to send in the same thread. For example:

For a draft you want changed, say what to change in your own words, in that same thread:

A changed draft keeps its number. Kansa reviews the new version, your Chief shows it to you, and it needs your yes again.

3. Run the observational eval with Gigawatt. In a new thread with Gigawatt, say:

Then, in the same thread:

The schedule in the next lesson is built on Gigawatt's answer. A round that went well means: a mix of three to five emails, and no problem left that nobody explained. If Gigawatt finds a problem, that isn't a failure. Fix it before anything runs on a schedule.

If you get stuck

More answers: when you get stuck.

What you'll keep

Three observational evals in the record: your expectations in your own words, Gigawatt's notes, every job folder, and the drafts you used, with what you changed. The schedule in the next lesson is built on this record.

Before you finish

You can also name the safety checks your Chief runs before it sends, and one item on your "not yours yet" list. Self-assessed. No gate.

Words you now own

• Observational eval: writing down what happened against what you expected, before anyone grades it. Each round is one.
• TOAST: Take the output, Observe it, Analyze why, Stick one change back in the oven, Test again.
• Wake: one check of your inbox.
• "Not yours yet" list: what the agents said they were missing. You work through it in Make the team yours.
• Held: waiting until your Chief has settled it. Never ask for a held email to be sent again.

Next: Plan your email team's schedule, and how you can entrust your team to do more without you.