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Worksheet: The Tool vs Teammate Map ·  © Cheek LLC 2026
Parade Week Packet  ·  Worksheets

Worksheet: The Tool vs Teammate Map

Every piece of work you might hand to an agent sits somewhere on a spectrum from Tool to Teammate.

Position 1 · Tool 2 3 4 · Teammate H · Human only
What it means Executes on command; zero discretion Drafts; a human reviews and sends every output Acts alone inside hard caps; humans review samples and exceptions Owns an outcome; plans multi-step work; uses judgment; escalates by rule Off the spectrum: the call stays human. Agents brief the decision; a named person makes it

At position 1 the human supplies all the judgment. At position 4 the agent supplies most of it, inside a boundary the humans designed. H is the honest fifth answer: some calls are never delegated, and knowing which ones is executive work.

Placement criteria

Score the work, not the technology. Four questions place any item:

Criterion The question
Discretion How much judgment does the work actually require, case by case?
Reversibility If it goes wrong once, can you undo it? At what cost?
Blast radius How much damage can one bad run do before anyone notices: dollars, customers, trust?
Oversight What review actually exists today: every output, samples, or nothing?

Low discretion, easy reversal, small blast radius, real oversight: the item can sit further right than it does today. High discretion or a wide blast radius does not mean never delegate. It means the move requires a boundary or a human gate, and you must be able to name it.

Place the Grand Inflation work

For each item, mark where it operates today (1 to 4, or H), where it could responsibly move, and exactly what boundary or human gate the move requires. The third column is the real work; the first two are just coordinates.

Work item Today Could move to The boundary or human gate the move requires
Answering a where-is-my-order ticket
Issuing a refund
Scheduling production batches
Drafting the AutoPlex uptime report
Posting from the official Breeze account
Monitoring social sentiment
Reading the fax queue
Deciding the parade wind call
Negotiating helium allocation tradeoffs
Maintaining the Gary Graph

Argue about these. The arguments are the exercise. A table filled in silence is a table filled in wrong.

Now your organization

Same map, your work. Pick eight real items from your own operation. Include at least one you suspect is a 1 that could be a 3, and at least one that everyone assumes is delegable but is actually an H.

Work item (yours) Today Could move to The boundary or human gate the move requires

The closing question

Of your eight, which single move returns the most hours or protects the most revenue? Circle it. That item, with its named gate, is the seed of your first agent at home.

Worksheet: The Agentic AI Opportunities AuditCheat Sheet: Connecting Your Agent