The AI Surfer OSRecurring Work → Automate
Taylor’s 90-minute workshop01 / 10

A practical business-training workshop

Recurring Work → Automate

Turn one repetitive workflow into a clear, reviewable agreement your agent can execute—with the right context, boundaries, and human judgment.

90 minutesOne real workflowOne Automation ContractHuman-controlled autonomy

Spot the shift

Move from describing activity to naming the business outcome.

See the contract

Walk the Fathom intake case study from trigger to success check.

Build yours

Draft each contract piece directly with your agent in your own OS.

Set autonomy

Choose Read, Draft, Coordinate, or Act—and define approval.

Test + commit

Run one safe test, inspect the result, and choose the next repetition.

Presenter cue

Open with: “You do not need to automate your business today. You need one trustworthy contract for one recurring result.” Ask attendees to keep their OS and agent chat open beside this screen.

The whole process · Seven stages

From recurring work to a safe automation.

A dependable automation is built as a learning loop—not a single leap from idea to action.

01

Notice recurring work

02

Choose the business outcome

03

Write the Automation Contract

Detailed breakdown next
04

Start with the safest autonomy mode

05

Test and observe

06

Review what happened

07

Increase responsibility only with evidence

Contract = map

The Automation Contract makes the outcome, route, boundaries, checks, and recovery explicit. It guides the automation; it is not the automation itself.

Presenter cue

Trace the seven stages left to right. Pause at stage 3 and say: “This is the map we will learn to write. The automation comes later, after the map can survive a test.”

Next, we’ll sharpen the shift from recurring activity to an observable business outcome—then unpack every part of the contract.

01 · Reframe the work

Stop automating activity.
Contract for an outcome.

Activity language

“Check Fathom every day.”

Describes motion, not value. It leaves relevance, routing, and “done” undefined.

Outcome language

“Every qualified new call becomes an owned next action by 10 a.m.”

Defines a result the business can observe, inspect, and improve.

Automation is not “make it run.” It is “make the expected result, judgment, and recovery explicit.”

Observable

Someone can tell whether the result happened.

Bounded

The agent knows where its authority begins and ends.

Recoverable

When reality differs from the happy path, work lands safely.

Presenter cue

Ask for one recurring task from the room. Rewrite it aloud as “When X happens, Y is true by Z.” Point out that this is an operating promise, not a software feature.

02 · The Automation Contract · 1 of 2

Define the work.

1

Outcome

What it means

The business result that must be true—not the activity performed.

Question to ask

What becomes reliably true when this works?

Fathom example

By 10 a.m. each day, every new qualified call has a concise brief and a clearly owned next action.

Help me rewrite this recurring task as an observable business outcome. Use: “When [event] happens, [result] is true by [time].” Challenge vague activity words and ask only what you need to make success measurable.
2

Trigger

What it means

The event or schedule that starts the workflow.

Question to ask

Exactly when should the agent begin—and what counts as new?

Fathom example

At 8:30 a.m. each weekday, find calls created since the last successful run.

Define a precise trigger for my workflow. Identify the event or schedule, timezone, how to prevent duplicate runs, and what “new” means. Return one trigger statement plus any assumptions.
3

Context

What it means

The business rules and background needed to make sound judgments.

Question to ask

What would a capable teammate need to know before deciding?

Fathom example

Know our ideal client profile, active clients, offer names, team owners, and what “qualified” means.

Interview me for the minimum business context a capable teammate would need to run this workflow. Separate durable rules from case-specific facts, and flag anything ambiguous or sensitive.
4

Steps

What it means

The smallest dependable sequence from trigger to finished output.

Question to ask

What must happen, in order, and where is judgment required?

Fathom example

Collect → classify → extract decisions/actions → match owner → draft brief → route for review.

Turn my current process into the smallest dependable sequence. For each step, state the input, transformation, output, and judgment call. Remove steps that do not contribute to the outcome.
5

Tools & Sources

What it means

The approved systems and source-of-truth hierarchy the agent may use.

Question to ask

Where can the agent read, write, and resolve conflicting facts?

Fathom example

Read Fathom transcripts and CRM ownership; write a draft brief in The AI Surfer OS; do not edit the CRM.

Map the tools and sources for this workflow. Label each as read-only or writable, name the source of truth when data conflicts, and identify required access that has not been confirmed.
Presenter cue

Pause after each card. Taylor pastes the matching prompt into chat; participants answer there. The goal is a useful first draft, not perfect documentation.

03 · The Automation Contract · 2 of 2

Define the guardrails.

6

Output

What it means

The exact deliverable, destination, structure, and level of detail.

Question to ask

What should arrive, where, and in what format?

Fathom example

A six-line brief: call, category, summary, decisions, actions with owners/dates, and open questions.

Specify the output contract for this workflow: exact format, required fields, destination, naming, tone, and maximum length. Include one compact example that is easy to inspect.
7

Approval Rule

What it means

The boundary between what the agent may do and what a human must confirm.

Question to ask

Which consequences require a human decision?

Fathom example

Draft briefs automatically. Taylor approves before any client message, task assignment, or record change.

Design an approval rule for this workflow based on consequence, reversibility, confidence, and external visibility. State what the agent may do alone and what must pause for named human approval.
8

Success Check

What it means

The evidence that proves the outcome happened correctly.

Question to ask

How will we know this run is complete and trustworthy?

Fathom example

Every new call is accounted for; owner/date match the transcript; no unsupported claims; review queue delivered by 10.

Create a lightweight success check for every run. Include completeness, accuracy, timeliness, and one quality signal. Make each check observable without rereading the entire source.
9

Failure Path

What it means

What happens when data is missing, confidence is low, or a tool fails.

Question to ask

How does the workflow stop safely and make recovery easy?

Fathom example

Do not guess. Label the issue, preserve the transcript link, add it to the exception queue, and notify Taylor.

Write the failure path for this workflow. Cover missing input, conflicting facts, low confidence, duplicate data, and tool failure. For each, define safe-stop behavior, notification, and recovery information.
10

Starting Mode

What it means

The lowest autonomy level that creates value while earning trust.

Question to ask

What is the safest useful first version?

Fathom example

Start in Draft: prepare the daily brief and exception list; Taylor reviews and acts.

Recommend a starting autonomy mode—Read, Draft, Coordinate, or Act—for this workflow. Explain the choice using risk and reversibility, then define what evidence would justify moving up one level.
Presenter cue

Emphasize that Approval Rule, Failure Path, and Starting Mode are not red tape. They are what let a useful automation survive real-world ambiguity.

04 · Case study

From new call to owned action.

01 · NOTICE

New calls

Find recordings since the last successful run.

02 · READ

Transcripts

Extract intent, decisions, commitments, and uncertainty.

03 · REASON

Qualify + route

Apply ICP, client, offer, and ownership rules.

04 · DRAFT

Daily brief

Create review-ready actions with source links.

05 · CHECK

Human review

Taylor approves consequences; exceptions stay visible.

Example daily output

3 new calls · 2 qualified · 1 exception

Northstar discovery — Qualified. Proposal requested. Taylor owns draft by Thu. Source attached.

Acme client sync — Decision: move launch to Oct 12. Morgan owns timeline update. Approval required before client confirmation.

Untitled recording — No participant identity. Held in exception queue; no action created.

Why it is trustworthy
  • Every call accounted for
  • Claims trace to transcripts
  • Ownership rules are explicit
  • External actions pause
  • Exceptions remain visible
Using the Automation Contract we drafted, simulate one run on a representative example. Show the output, the checks you performed, any assumptions, and anything that would pause for approval. Do not take external action.
Presenter cue

Trace one call across the arrows. Ask: “Where could this quietly go wrong?” Convert answers into context, approval, success, or failure rules.

05 · Set the agency level

Earn autonomy one rung at a time.

ReadObserve, retrieve, summarize, and surface patterns. No changes.Lowest consequence
DraftPrepare an artifact or recommendation for human review.Easy to reverse
CoordinateRoute work, request inputs, and schedule approved next steps.Visible impact
ActExecute bounded decisions without per-item approval.Earned trust

Move up when…

Outputs are consistently accurate, exceptions are caught, the action is reversible, and the owner understands the failure modes.

Move down when…

Rules change, source quality drops, consequences grow, errors repeat, or nobody can explain why the agent chose an action.

Presenter cue

Starting low is not timid; it shortens the learning loop. For Fathom, begin at Draft. “Act” is a promotion based on evidence, not enthusiasm.

06 · Use judgment

When not to automate yet.

The process is unstable

The steps change every time because the team has not chosen a standard.

The volume is trivial

Automation costs more to build and monitor than the repetition costs to do.

The signal is unreliable

Inputs are incomplete, inaccessible, or too inconsistent to support decisions.

The stakes are too high

A mistake is harmful, public, legally sensitive, or difficult to reverse.

Judgment is tacit

The expert cannot yet explain how good decisions differ from bad ones.

No owner exists

Nobody will inspect quality, handle exceptions, or update rules.

First simplify. Then standardize. Then document. Then automate.

Stress-test whether this workflow is ready to automate. Evaluate stability, frequency, input quality, consequence, reversibility, explainability, and ownership. Recommend: automate now, run manually with a checklist, or redesign first—and explain why.
Presenter cue

Invite one “not yet” example. This is a win: identifying a bad automation candidate prevents expensive confusion and reveals the operational work needed first.

07 · Participant build sprint

Build one contract live.

Choose the repetition
Frequent, annoying, observable, and low-to-moderate consequence.
4 min
Name the outcome + trigger
Paste prompts 1–2. Make “done” and “start” precise.
6 min
Supply context, steps, and sources
Paste prompts 3–5. Separate facts from judgment.
9 min
Set output + guardrails
Paste prompts 6–10. Choose the starting autonomy mode.
8 min
Simulate one real case
No external actions. Inspect the output and exceptions.
5 min
Revise one weak rule
Fix the ambiguity most likely to cause a bad run.
3 min
Act as my Automation Contract editor. Review the full contract for ambiguity, missing ownership, hidden assumptions, unsafe authority, and weak success checks. Ask at most three high-value questions, then return a revised contract and a safe first test.
Presenter cue

Run a visible timer. Announce each transition and circulate. At minute 27 say: “Simulation, not activation.” At minute 32 ask everyone to improve exactly one rule.

08 · Close the loop

Your next repetition is the real test.

Before you switch it on

  • The outcome is observable and time-bound.
  • The trigger cannot silently duplicate work.
  • Sources and write permissions are explicit.
  • Approval matches consequence and reversibility.
  • Success can be checked without redoing the work.
  • Failure stops safely and reaches an owner.
  • The starting mode is the lowest useful autonomy.

Next steps

  1. Run one representative case in simulation.
  2. Compare it with a strong human result.
  3. Revise the weakest contract rule.
  4. Run three supervised repetitions.
  5. Review evidence before raising autonomy.

Start with one outcome. Make the contract clear. Let trust compound.

Turn my final Automation Contract into a three-run pilot plan. For each run, define the test case, human review point, evidence to capture, and go/no-go criterion. Keep all external actions behind approval until the pilot is complete.
Presenter cue

Close by asking each person to say: workflow, starting mode, and when they will run the first test. Remind them the contract is a living operating document.

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