Workshop 3 Intermediate 90 min

Your Department's Worst Day

Process the Monday-after-a-bank-holiday pile in minutes, not hours

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Workshop 3: Your Department's Worst Day illustration
1

Promise Check-In

Quick show of hands

2 min

Promise Check-In

2 min

Quick show of hands. Who ran their cross-system briefing from Workshop 2 on real data this week? What happened? Did you share it with your team?

Two sentences max per person. We are not troubleshooting here -- just surfacing the pattern. If something broke, note it. We will have time to fix things later.

The point of this ritual is not accountability. It is normalisation. Some of you ran it and it worked. Some of you ran it and the MCP connection had expired. Some of you did not get to it because Monday was chaos. All of that is expected. The habit forms through repetition, not perfition.

2

The Pile

Intro

The 10-minute claim applies to running the triage prompt and producing the report. Reviewing the out

3 min

The Pile

3 min
The 10-minute claim applies to running the triage prompt and producing the report. Reviewing the output, catching errors, and making final decisions still takes human time. Expect 10 minutes for generation + 15-20 minutes for review. That is still dramatically faster than the 2-3 hour manual process, but do not skip the review.

The facilitator opens an Excel file on the projector. Forty rows. Dense. Columns of IDs, descriptions, statuses, dates, amounts. The facilitator reads the first three items aloud.

"Alert ID 1042. Sanctions screening match. Similarity score 72%. Merchant registered in jurisdiction flagged for correspondent banking risk. Status: New."

"Ticket ID 8891. Merchant reports terminal not printing receipts. Priority: Medium. Last contact: 6 days ago. SLA: breached."

"Deal ID 3304. Value: 500,000 EUR. Stage: Uncontacted. Created: 14 days ago. Owner: unassigned."

Pause.

This is your Monday morning. Actually -- this is your Tuesday morning, because Monday was a bank holiday and nobody was here to process anything. Forty things need your attention. Some are urgent. Some are noise. Some are traps -- they look routine but they are not. And two of them contradict each other in ways that will cause problems if you do not catch it.

Manually, sorting through this pile takes 2-3 hours. Today we process it in 10 minutes. But processing fast is not the same as processing correctly. The speed is real. The accuracy is a draft. Your job is the judgment calls that Cowork cannot make.

3

Process Your Pile

Try It

Hands-on challenge

40 min
CHALLENGE
4

Chrome Automation

Step-by-Step

Not every system has an MCP connector

15 min

Chrome Automation

15 min

Not every system has an MCP connector. Chrome automation fills the gap for browser-based tools. It is slower than MCP, more fragile, and requires the browser to be open. But it works with anything you can see in a browser window.

5

The 5 Failure Modes

These were introduced briefly in Workshop 1

10 min

The 5 Failure Modes

10 min

These were introduced briefly in Workshop 1. Now you practise finding them in your own output. This is not theory — you are looking at the triage report you just produced and hunting for real errors.

6

Cross-Pollination

Exercise

Hands-on practice with role-specific prompts

10 min

Cross-Pollination

10 min

Pair up with someone from a different department. Swap triage outputs. Read with fresh eyes. Ask one question. Give feedback.

7

Monday Promise

Write down one specific commitment

5 min

Monday Promise

5 min

Write down one specific commitment. Not 'use Cowork more.' Specific: 'Monday at [time], I will run [skill] on [data source] and produce [deliverable].'

Steal This Prompt

Copy these prompts, customize the file paths to match your workspace, and use them in Cowork. Replace ~ with your actual home directory path if needed.

Triage the Pile

Read the Excel file in my workspace. This is my department's backlog. Categorize every item by urgency. Flag anything th...
Show full prompt▼ 
Read the Excel file in my workspace. This is my department's backlog.
Categorize every item by urgency. Flag anything that needs immediate attention.
Produce a triage report as a Word document (.docx) with:
- Executive summary (3 bullets)
- Prioritized action list (urgent first)
- Items that need more information before acting
- Patterns you notice across the pile
5 min with Cowork · 30 min manually

Triage 40 Screening Alerts

Read the alert pile Excel file. These are screening alerts requiring review. For each alert, categorize as: FALSE POSITI...
Show full prompt▼ 
Read the alert pile Excel file. These are screening alerts requiring review.
For each alert, categorize as: FALSE POSITIVE, NEEDS REVIEW, or ESCALATE.
Draft a one-sentence rationale for each categorization.
Produce a triage report as a Word document (.docx) with:
- Executive summary: counts by category
- ESCALATE items first with full rationale
- NEEDS REVIEW items with suggested next steps
- FALSE POSITIVE items grouped by dismissal reason
- Any cross-alert patterns (same merchant, same geography, same alert type)
10 min with Cowork · 2 hrs manually

Triage Weekend Support Queue

Read the ticket pile Excel file. This is the weekend support backlog. Categorize each ticket by urgency: URGENT (SLA bre...
Show full prompt▼ 
Read the ticket pile Excel file. This is the weekend support backlog.
Categorize each ticket by urgency: URGENT (SLA breach risk), TODAY, THIS WEEK, NEEDS INFO.
For URGENT tickets, draft a one-sentence next step.
Produce a triage report as a Word document (.docx) with:
- Executive summary
- URGENT tickets with next steps
- Tickets grouped by category
- Repeat-issue patterns (3+ tickets for same root cause)
- Recommended FAQ articles to reduce future volume
8 min with Cowork · 45 min manually

Triage Stale Pipeline Deals

Read the deal pile Excel file. This is the pipeline backlog. Categorize each deal: HOT (ready to close), WARM (needs fol...
Show full prompt▼ 
Read the deal pile Excel file. This is the pipeline backlog.
Categorize each deal: HOT (ready to close), WARM (needs follow-up), STALE (no contact > 14 days), DATA ERROR (suspicious values).
For HOT deals, draft a call prep brief.
Produce a triage report as a Word document (.docx) with:
- Executive summary with total pipeline value by category
- HOT deals with call prep briefs
- STALE deals with recommended re-engagement approach
- DATA ERROR items for CRM cleanup
8 min with Cowork · 30 min manually

Triage Operations Request Backlog

Read the request pile Excel file. This is the operations request backlog. Categorize each request: URGENT, ROUTINE, BLOC...
Show full prompt▼ 
Read the request pile Excel file. This is the operations request backlog.
Categorize each request: URGENT, ROUTINE, BLOCKED, DUPLICATE.
Flag any requests that appear to be related (same merchant, same issue type).
Produce a triage report as a Word document (.docx) with:
- Executive summary
- URGENT items with recommended actions
- BLOCKED items with what's needed to unblock
- DUPLICATE clusters for consolidation
- Automation failure patterns (bot failures followed by manual requests)
8 min with Cowork · 45 min manually

Triage Contract Review Queue

Read the review pile Excel file. This is the contract review backlog. Categorize each review: URGENT (deadline < 7 days)...
Show full prompt▼ 
Read the review pile Excel file. This is the contract review backlog.
Categorize each review: URGENT (deadline < 7 days), STANDARD, LOW RISK (template-based), NEEDS ESCALATION (non-standard terms).
For URGENT items, flag the specific clauses requiring attention.
Produce a triage report as a Word document (.docx) with:
- Executive summary
- URGENT reviews with clause-level flags
- NEEDS ESCALATION items with risk description
- Suggested prioritisation for this week
8 min with Cowork · 30 min manually

Key Takeaways

  1. Triage a high-volume department backlog (30-50 items) into actionable priority categories using a single universal prompt

  2. Use Chrome automation to extract data from browser-based tools that lack MCP connectors

  3. Apply the 5 Failure Modes framework to catch classification errors, hallucinated references, and overconfident language in your own output

Materials

Download these files to use with the exercises above. Previews load automatically.

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