Delegate the task. Not the judgment. Yet.
Phase 5 gave Claude hands. This unit teaches you to take your hands off the steering wheel — not all the way, just enough that Claude can drive a full routine while you watch.
By Phase 5 you have Skills that read, draft, confirm, and act. Each one does one task end-to-end. But your real work is multi-task. Your Monday morning is six things in sequence. Your customer renewal cycle is a chain that spans days. Your campaign launch is a tree of small decisions that all have to happen in the right order.
Phase 6 is where you hand off the whole chain. You write the objective, name the rules, define when Claude should pause — and let Claude design the sequence. You stop being the conductor and start being the reviewer.
What you'll walk out with
A workable model of trust — when to delegate, what to delegate, and how to keep the leash long without losing the dog. A specific framework for designing multi-step workflows. Two worked examples of professionals handing off entire routines. And two hands-on builds — your first multi-step workflow and your first checkpoint-and-escalation rulebook.
What Unit 6 covers
- The Phase 5 ceiling — single-task orchestration and the cost of conducting.
- The mindset shift — from operator to delegator.
- The three-step trust model — Show me, Tell me, Trust me. Graduated autonomy.
- The objective brief — how to spec multi-step work without micromanaging.
- Checkpoints and escalation — where Claude pauses and where Claude stops.
- Two worked examples — Priya's Monday morning routine; a customer renewal cycle that spans days.
- Three Phase 6 mistakes — delegating without observing, no checkpoints, no escalation rules.
- Two hands-on builds — your first multi-step workflow and your escalation rulebook.
- The Phase 6 ceiling — you're still initiating, and the hook into Unit 7.
You're still conducting.
Phase 5 made every single task end-to-end. Phase 5 didn't make the sequence end-to-end. You can feel the difference once you watch yourself work for a week.
Marcus's Friday looks like this now: trigger the pipeline recap Skill. Approve. Trigger the renewal forecast Skill. Approve. Trigger the leadership Slack summary Skill. Approve. Three Skills, three triggers, three approvals, three moments of attention. The carrying is gone. The orchestration isn't.
Esteban's Monday morning is similar: run the recap, then the location flag, then the calendar invite. Each one separately, each one needing him to remember what's next.
Three signs you're hitting the Phase 5 ceiling
1. You have a checklist you mentally run through.
It's not written down anywhere, but you know it. Step 1, do this Skill. Step 2, do that Skill. Step 3, file this. The checklist lives in your head. It's also the source of every "I forgot to do X" moment in your week.
2. Triggering Skills back-to-back feels like work.
Each Skill takes seconds. The clicking between them takes more. By the third or fourth trigger, you're tired of being the dispatcher. That tiredness is the signal.
3. Skills depend on each other and you're managing the dependencies.
Skill A's output is Skill B's input. You're copying between them. The whole routine is a graph of dependencies you're walking by hand.
The Phase 6 promise
You write the objective once: "Run the Monday morning routine. Pull the weekend numbers, flag the worst location, draft the manager email, propose a Tuesday call with the flagged location, file the recap." Claude designs the sequence. Pauses where you said to pause. Reports when done. You become the reviewer, not the conductor.
Stop assigning steps. Start assigning outcomes.
The shift is from "here's what to do, in this order" to "here's what done looks like — and here's how to know when to pause for me."
For five units, you've been describing work to Claude — first the task, then the brief, then the procedure, then the Skill. Each one made you more precise about the work. Phase 6 asks for less precision, not more. You give Claude the objective and the rules. Claude designs the path.
The slogan that does the work
Delegate the task. Not the judgment. Until you've seen the judgment.
This sentence is the entire Phase 6 governance model. Delegate the procedural work freely. Reserve the judgment until Claude has shown you it knows how to use it. Then, slowly, let go of the judgment too.
The graduated autonomy pattern
Trust isn't a switch. It's a dial. The cleanest way to turn it: Show me, Tell me, Trust me.
- Show me. The first time you run a new workflow, Claude pauses at every step and shows you what it's about to do. You approve each one. Slow, careful, instructive.
- Tell me. The second and third times, Claude doesn't pause — but narrates as it goes. You watch. You can interrupt. Trust is forming.
- Trust me. The fourth time forward, Claude runs the whole thing without narration. It pauses only at the checkpoints you defined and reports when done. You review the result, not the steps.
The dial moves at your pace. Some workflows graduate to Trust me in a week. Some never do — the stakes are too high, or the variance is too wide. That's a feature, not a failure.
The objective brief.
A Phase 6 workflow is specified differently than a Phase 4 Skill. You write an objective brief — what "done" looks like, what the rules are, where Claude should pause. Claude designs the steps.
Objective
The outcome, not the procedure. "By 8am Monday, the leadership channel has a recap, the flagged location's manager has a meeting request on her calendar, and the recap is filed."
Notice what's not in there: how to do any of it. The objective specifies the destination, not the route.
Rules
The constraints Claude has to respect. "The recap goes to #operations-leadership only. The meeting request is a hold, not a confirmed invite. Email goes from my account. Anything that flags worse than 15% below plan needs my approval before sending."
Checkpoints
Scheduled pauses where Claude shows you a draft, a decision, or a proposed action and waits for input. Checkpoints are the steering wheel — without them, you've given the trip away.
Good checkpoints are placed at irreversible moments: before any external send, before any external schedule, before any spending decision. Skip the checkpoint, run the risk.
Escalation
Conditions where Claude doesn't just pause — it stops and surfaces. "If pipeline is down more than 10%, do not run the recap; instead, send me a heads-up." "If a customer reply is hostile, stop the renewal sequence and notify me."
Escalation rules are the safety net. They're what makes a long leash safe to extend.
The brief format — four parts
Objective · Rules · Checkpoints · Escalation. Use this shape for every Phase 6 workflow. The brief stays short — usually under 300 words — because you're specifying intent, not procedure.
Priya's Monday morning workflow.
Priya is operations manager at a 60-person digital agency. Her Monday morning has been the same routine for years: project margin check, account-at-risk flag, team standup prep, client-facing emails, calendar housekeeping. 90 minutes every week. She wants it back.
She has Phase 5 Skills for each piece. She has not yet chained them. Here's how she writes the objective brief:
By 8:30am Monday: I have a 5-minute review packet covering last week's project margins, accounts at risk, the standup agenda, and any client emails that need my attention. Recap is filed. Standup deck is ready. Time-sensitive client emails are drafted, awaiting my approval.
- Drafts only — no external send without my approval.
- Standup deck uses last week's template; no design changes.
- Account-at-risk threshold: margin under 18% OR projects past deadline by >1 week.
- Recap goes to
/operations/monday-recaps/in Drive. - Don't include anything from board-prep folders.
- After pulling margin and risk data: pause and show the at-risk list before generating outreach drafts.
- Before drafting any client email: confirm with me which clients to draft for.
- Final review: present the full packet — recap, deck, drafts, calendar items — and wait for "looks good" or per-item edits.
- If more than 3 projects are in the at-risk band, stop the routine and message me — we're not running automatically that week.
- If any client emailed about contract termination in the last week, stop and surface immediately.
- If any project's margin dropped more than 5 points from prior week, flag the cause in the recap and pause for review.
What's different from her Phase 5 Skills
The brief specifies the outcome — "I have a 5-minute review packet" — and the rules. It doesn't say "run Skill A, then Skill B, then Skill C." Claude figures out which Skills are needed and what order to run them. The checkpoints are where Priya stays in the loop. The escalation rules are her safety net.
The first three Mondays, Priya runs in Show me mode — Claude pauses at every step. By week four, she's at Tell me — Claude runs, narrating, she watches. By week six, she's at Trust me — Claude runs the whole thing and she reviews the packet at 8:25am. 90 minutes became 8 minutes.
A customer renewal cycle on a long leash.
Not every Phase 6 workflow runs in 15 minutes. Some run for days, spanning email replies, internal coordination, and time-sensitive decisions. The same brief format works.
Sasha is head of customer success at a 40-person SaaS company. Renewal cycles run 90 days out. The standard sequence: outreach, response, value review, pricing discussion, decision. Each one used to be a separate Phase 5 Skill she ran by hand. The whole cycle for one customer used to take her about 3 hours, spread over weeks, with three forgotten follow-ups per month. Here's her Phase 6 brief:
Customer reaches their renewal decision date with: outreach completed at T-90, T-45, T-15; a value-review document delivered if they engaged; a pricing conversation scheduled if requested; me involved at any pause point. Renewal is signed, churned, or escalated — never silently expired.
- All outreach sent from my email; my voice; never templated.
- Value review document uses our standard template, pre-populated with the customer's usage data.
- Pricing discussions are scheduled with our standard pricing window (90-day notice respected).
- Any reply with negative sentiment, legal language, or executive-level escalation: stop and route to me.
- Before each outreach send (T-90, T-45, T-15): show me the draft and the customer's current usage context.
- If the customer replies asking for pricing: pause and confirm the discount band I'd like to authorize, if any.
- Before any meeting is scheduled with their executive sponsor: confirm timing with me.
- Any reply containing "considering alternatives," "evaluating other vendors," "RFP," or legal language: stop and surface immediately.
- If the customer doesn't respond to outreach by T-30 days, stop and surface — escalation may need to come from our CEO.
- If the customer asks for discount >20%, do not propose; stop and route to me with the customer's argument.
What this Phase 6 workflow actually looks like over 90 days
Sasha kicks it off in one chat. Claude runs the T-90 outreach (after Confirm), waits for a reply, processes the reply (running the right Skill from her Project), checks against the escalation rules, and if everything is normal, proceeds to T-45 prep on the right date. Two-week rhythm. Sasha gets a heads-up when the next checkpoint is coming. She approves the next move. The workflow continues.
When she goes on PTO, she trusts the workflow because the escalation rules will halt it on anything weird. When she comes back, the work is exactly where she would have left it. Long leash, real safety net.
Reflection · 3 minutes
Pick a multi-step routine in your work. Sketch the objective in one sentence. What are 2–3 rules that have to be respected, and 1–2 things that should make Claude stop and surface?
Three mistakes that turn long leashes into runaways.
Phase 6 is the first phase where the cost of getting it wrong shows up days later, not seconds later. These three patterns cause most of those costs.
Mistake 1 — Delegating without observing first.
You write the brief. You skip Show me. You skip Tell me. You go straight to Trust me. Run one runs fine — you weren't watching. Run two has a bad call that compounds. By run three, you're discovering the problem from a customer's reply to an email Claude sent without you knowing.
Mistake 2 — No checkpoints.
The brief specifies the objective. It doesn't specify where Claude pauses. The workflow runs end-to-end and you discover after the fact that an external email went out with a tone you wouldn't have used. Once a Phase 6 workflow is in Trust me, your only insertion points are the checkpoints. None defined means no insertion points.
Mistake 3 — No escalation criteria.
The workflow has objectives, rules, even checkpoints — but no explicit conditions for stopping. So Claude doesn't stop. It runs into edge cases and resolves them itself, often incorrectly. You discover an angry customer reply was answered with a standard response three days ago. The escalation rule that would have stopped that didn't exist.
The Phase 6 debugging move
When a workflow misbehaves, ask which of the four brief parts failed. Objective unclear? Rules incomplete? Checkpoint missing? Escalation criteria too narrow? The fix lives in the brief, not the next conversation.
Your turn.
Two hands-on builds. First a full multi-step workflow brief — the kind you could run starting next Monday. Then your escalation rulebook — the standing rules that protect every workflow you build.
Design your first multi-step workflow.
Pick a recurring multi-step routine in your work — Monday morning, weekly customer cycle, monthly close, campaign launch. Spec it as an objective brief. Objective, Rules, Checkpoints, Escalation.
One way to write a "monthly close" workflow
Objective: By the 5th of each month, all close-related deliverables are complete: month-end revenue summary filed, variance commentary drafted, board package starter posted to the leadership Drive folder, my list of items needing live review is queued.
Rules: (1) Use our standard close template — no format changes. (2) Revenue figures from our accounting system, not estimated. (3) Variance commentary written in our voice — direct, no hedging. (4) Anything tagged "draft pending" stays draft until I approve. (5) No outbound communication to anyone outside Finance.
Checkpoints: (1) After revenue summary is generated: pause and show me the headline numbers before drafting commentary. (2) Before posting anything to the leadership Drive folder: show me the final package for review.
Escalation: (1) If revenue is more than 5% off forecast in either direction: stop, do not draft commentary, surface to me. (2) If the accounting system shows any failed transactions or reconciliation errors: stop, do not file. (3) If any prior-period entries were modified between last month and now: stop, surface immediately.
Notice the safety in the brief. The objective is precise. The rules are concrete (not "be careful" — "no outbound communication to anyone outside Finance"). The checkpoints land at the irreversible moments. The escalations halt the workflow on the conditions that should never resolve themselves automatically.
Write your escalation rulebook.
A standing set of rules that apply to every workflow you ever build. Think of it as the safety net under all your Phase 6 work — the things that should always make Claude stop and ask.
Your escalation rulebook.
Walk through your work mentally and list the things that should ALWAYS stop a workflow. Legal language. Threshold breaches. Sentiment changes. New stakeholders. Anything that doesn't deserve an automatic answer.
One way to write your escalation rulebook
Sentiment: Stop any workflow on hostile language, mention of attorneys/legal counsel, "considering alternatives," "evaluating other vendors," "speaking with your competitor," or any threat (implicit or explicit).
Numbers: Stop on any variance >15% from forecast or plan. Stop on margin drops >5 points week-over-week. Stop on any data inconsistency (missing values, conflicting sources). Stop if revenue or cost numbers are categorically new (a customer billed twice; a new line item).
Stakeholders: Stop if any communication involves my CEO, board members, regulators, auditors, legal counsel, or anyone above my management chain. Stop if a new contact appears that isn't already in the customer's account record.
Decisions: Stop on anything involving a discount >10%. Stop on anything contractual. Stop on hiring, firing, or compensation. Stop on anything that costs money outside the standard budget. Stop on anything legally binding.
The rulebook is the safety net. Reference it from every workflow brief you write. The same escalation rules apply across all of them — and seeing the list reminds you which workflows are missing the rules they should have.
You're still initiating.
Phase 6 is genuinely transformative. Multi-step routines run themselves. You review, not conduct. Then one Monday you'll realize: every workflow still starts because you opened Claude.
The Monday morning routine ran. You triggered it. Marcus's pipeline recap ran. He triggered it. Sasha's renewal cycle ran. She triggered it. Even when Claude works for hours autonomously, the first step is always you, deciding it's time.
That's the Phase 6 ceiling. Claude executes. You still decide when.
What Phase 7 fixes
Phase 7 — Partner — inverts that. Claude runs on a schedule. Claude watches the things you said to watch. Claude surfaces things that need your attention before you'd have thought to look. You stop opening Claude to ask "what's going on?" Claude opens to tell you.
For the first time in the framework, the relationship genuinely flips. You become the one being briefed.
The signal you're ready for Phase 7
You're running multiple Phase 6 workflows confidently. You trust the escalation rules. You've stopped re-checking what they did. And — most importantly — you've started to wish Claude would tell you about things instead of waiting for you to ask. That wish is the entire setup for Unit 7.
Reflection · 2 minutes
What's one piece of your business or work you wish Claude would just tell you about — without you having to ask?
Are you ready to move to Partner?
Three questions to diagnose your readiness for Phase 7 — the inversion where Claude initiates.
1. How many multi-step workflows are you running today with checkpoints and escalation rules?
2. How often have your escalation rules saved you from a bad outcome?
3. How often do you wish Claude would tell you about something before you asked?
Your readiness
Answer all three questions above to see your readiness for Phase 7.
Seven questions.
One per major idea in this unit. Click for instant feedback.
0 of 7 answered · 0 correct so far
1. The Phase 5 ceiling — the limit even great operator Skills can't push through — is:
2. The three-step trust model is:
3. An objective brief specifies:
4. Checkpoints and escalation rules together do what?
5. The most common Phase 6 mistake — and the most expensive — is:
6. Why are escalation rules non-negotiable for any Phase 6 workflow?
7. The Phase 6 ceiling — the limit even great workflows can't push through — is:
Finish the knowledge check to see your score.
Your workflow brief and your escalation rulebook are saved.
The new thought process.
Delegate the task. Not the judgment. Yet.
Trust earned slowly is trust kept. Show me, Tell me, Trust me — graduated autonomy is the whole game.
The objective brief replaces the procedure.
Specify what "done" looks like. Specify the rules. Claude designs the steps.
Checkpoints + escalation = a safe long leash.
Pauses where you want to weigh in. Halts on the conditions that should never auto-resolve.
Initiation is what's left.
You're still the one starting every workflow. Unit 7 inverts that — Claude opens the conversation.