Module 5 Intermediate 45 minutes
4 objectives
  • Build one complete, role-specific automation end-to-end
  • Review someone else's output to sharpen your error detection
  • Document a reusable playbook with honest time estimates
  • Understand where your department's data fits Cowork's strengths — and where it doesn't
📁 8 files Start Workshop →

Building Workflows for Your Role — A complete automation sprint for your department

1Hook5 min
2Challenge20 min
3Learn10 min
4Setup7 min
5Learn3 min
1

Challenge Briefing

5 min

Challenge Briefing

5 min

Right. You've learnt the tools. You've spotted the mistakes. Now it's time to build something real.

Pick your department. Download your data pack. You have 20 minutes to build ONE automation that solves a task you genuinely hate doing every week. The kind of task where you think 'there must be a better way' every time you do it.

At the end, you'll swap outputs with a colleague and try to break each other's work. Peer review is not optional -- you will miss errors in your own output. Everyone does.

📋 2

The Sprint

⏱ 120020 min
CHALLENGE⏱ 20:00

The Task

Pick your department's challenge below. Use the corresponding data pack file. Build the full automation.

Each role variant includes known failure modes. Read them before you start — they'll help you know what to check.

Data pack file: Department-specific CSV files

Choose Your Prompt

Read chargebacks-weekly-export.csv from my workspace. For each open case, create an evidence preparation package: (1) Match each case to its Visa/Mastercard reason code category (fraud, consumer dispute, processing error, authorisation). (2) For each case, note the Card_Scheme (Visa/Mastercard/AMEX) and calculate the response deadline using public scheme rules: Visa 30 days from notification, Mastercard 45 days, AMEX 20 days. (3) Draft a rebuttal outline based on the reason code — what evidence is typically needed (transaction receipt, delivery proof, communication log, AVS match). (4) Flag cases approaching THEIR scheme's deadline within 3 days as URGENT — do not apply a single deadline to all schemes. (5) Create an Excel workbook: Sheet 1 — All cases with scheme, deadline, rebuttal outlines and evidence requirements. Sheet 2 — URGENT cases with a step-by-step action plan. Sheet 3 — Summary: cases by category and scheme, total amount at risk, win probability estimate based on reason code. Add a narrative summary recommending which 5 cases to prioritise this week and why.
Read hubspot-deals-export.csv from my workspace. For each unique Current_Provider (competitor) in the deals list: (1) Create a 1-page battle card in a single Word document. Each card should include: competitor name, number of your deals competing against them, typical deal size range, industries where you're competing, and 5 key talking points — what your company does better, what the competitor's known weaknesses are (based on industry patterns for payment providers), common objections merchants raise when switching, and a suggested opening line for the call. (2) Add an executive summary ranking competitors by total deal value at stake. (3) Flag any deals that have been in the same stage for more than 30 days as STALE — these need a different approach.
Read zendesk-tickets-48h.csv from my workspace (50 resolved tickets). Analyse the tickets and: (1) Identify the top 10 most common question patterns — group tickets by similar subject/issue type. (2) For each pattern, draft a knowledge base article: title, summary, step-by-step resolution, common variations, escalation triggers (specific conditions that mean the agent should stop troubleshooting and escalate to a specialist team), and when to escalate. (3) Flag any questions where different tickets got contradictory resolutions — these need a team decision on the correct answer. (4) Create a Word document with all 10 draft articles, ready to paste into your wiki. (5) Add an appendix: ticket volume per category, percentage of tickets each article would deflect, estimated time saved per week if these articles existed.
I have two files: screening-alerts.csv (30 alerts) and merchant-profiles.csv (20 merchant profiles). Simulate a weekly alert triage: (1) Match each alert to its merchant profile by Merchant_ID. (2) Pre-categorise each alert as FALSE POSITIVE (name match only, no other risk indicators, low-risk industry), NEEDS REVIEW (some risk factors present, medium-risk industry or elevated volume), or ESCALATE (multiple risk factors, high-risk industry, PEP/sanctions match, or merchant CDD review overdue >12 months). (3) For each alert, draft a 2-3 line investigation rationale explaining WHY you assigned that category — this is the part that takes the most time to write manually. (4) For each ESCALATE alert, add a recommended next step (e.g., request source of wealth documentation, refer to MLRO, trigger enhanced due diligence). (5) Create an Excel workbook: Sheet 1 — All alerts categorised with rationale. Sheet 2 — ESCALATE cases with summaries and next steps (for team lead review). Sheet 3 — Statistics: false positive rate, alerts by category, merchants with multiple alerts. Add a narrative memo summarising this week's risk landscape.
I have two settlement files: bank-settlements.csv and internal-settlements.csv (40 rows each). Reconcile them: match by Merchant_ID + Settlement_Date + Reference_Number. Create an Excel workbook with: Sheet 1 - Matched transactions (amounts equal). Sheet 2 - Variances (amounts differ) with Difference column, sorted by largest variance first, RED for >$500, YELLOW for $100-500. Sheet 3 - Missing from bank (in internal but not bank). Sheet 4 - Missing from internal (in bank but not internal). Sheet 5 - Summary with formulas: total matched, total variances, total missing, net discrepancy, largest single variance.
Read process-description-raw.txt from my workspace. This contains notes about our merchant onboarding process across multiple stages. Create TWO outputs: (1) A process analysis Word document that: maps each stage of the onboarding journey, identifies handoff points between teams, flags steps that are manual but could be automated, pays special attention to the CDD/due diligence stage (in most FinTech companies this is where onboarding gets stuck), estimates where the biggest time sinks are based on the process description, and recommends 3 specific bottleneck fixes. (2) A "New Starter Guide to Onboarding" — a 2-page plain-English document that someone joining the ops team could read on day 1 to understand: what the process is, who does what, where things get stuck, and who to ask when something goes wrong. Write it in a friendly tone, not corporate-speak.
Pick the department challenge that best matches your role. If none fit exactly, use the Support (knowledge base builder) or Finance (settlement reconciliation) challenge — these are the most universal.

Scoring

6/6 = Gold. 4-5 = Silver. 1-3 = Bronze.

Verification Checklist

0/6 verified
3

Pair Review

10 min

Pair Review

10 min

Find a partner -- ideally someone from a different department. Now swap laptops (or files). Your job: try to find something wrong with their output. Check 3 numbers. Look for dodgy classifications. Count the rows.

Here's the thing: catching errors in someone else's work is much easier than catching your own. That's not a character flaw -- it's how human brains work. Which is exactly why peer review isn't optional.

Review checklist:

  1. Check 3 numbers against the source data
  2. Look for classification errors
  3. Verify completeness (row counts match?)
  4. Note anything that looks overconfident or unsupported

What to discuss: What did Cowork get right? What did it get wrong? What would you change in the prompt?

🔧 4

Playbook Documentation

7 min

Playbook Documentation

7 min
1

Name your automation (e.g., 'Weekly Chargeback Case Review', 'Sales Call Prep Briefs')

2

Record: your role, frequency (daily/weekly/as-needed), estimated time saved

3

Paste the EXACT prompt you used (the one that worked, not the first draft)

4

Write your verification checklist — the specific checks for YOUR output

5

Note known failure modes — what did Cowork get wrong, or what should you always double-check?

6

Save to your workspace. If your time-saved estimate is uncertain, write 'TBD — tracking for 2 weeks' instead of guessing.

5

What You Have

3 min

What You Have

3 min

At this point you have three things:

  1. A working automation for your specific role — tested on realistic data
  2. A peer-reviewed output — someone else checked your work and found things you missed
  3. A documented playbook with the prompt, verification steps, and known failure modes

Whether this is worth adopting depends on your actual workflow. Run it next week with real data. If it saves time after accounting for review, keep iterating. If it doesn't, you've lost 45 minutes and learned something about where Cowork falls short for your role. Both outcomes are useful.

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.

"The Evidence Assembler"

Chargebacks
Read my chargeback export CSV. For each open case, match to reason code category and draft a rebuttal outline with requi...
Show full prompt
Read my chargeback export CSV. For each open case, match to reason code category and draft a rebuttal outline with required evidence types. Flag URGENT deadlines. Create Excel with cases, outlines, and priority recommendations.

"The Knowledge Base Builder"

Customer RelationsSupport
Read 50 resolved helpdesk tickets. Identify the top 10 recurring questions. Draft a knowledge base article for each with...
Show full prompt
Read 50 resolved helpdesk tickets. Identify the top 10 recurring questions. Draft a knowledge base article for each with title, steps, and when to escalate. Flag contradictory resolutions. Estimate ticket deflection per article.

"The Battle Card Generator"

Sales
Read CRM deals export. For each competitor, create a 1-page battle card: strengths, weaknesses, common objections, sugge...
Show full prompt
Read CRM deals export. For each competitor, create a 1-page battle card: strengths, weaknesses, common objections, suggested opening lines. Rank competitors by total deal value at stake.

"The Retention Save-Call Brief"

SalesRetention
I'm about to call a merchant who wants to cancel (or reduce their plan). Here's what I know: - Monthly transaction volum...
Show full prompt
I'm about to call a merchant who wants to cancel (or reduce their plan). Here's what I know:
- Monthly transaction volume: [amount]
- Current pricing: [rate]
- How long they've been a customer: [months]
- Reason for cancellation request: [stated reason]
- Competitor they're considering: [if known]

Create a 1-page save-call brief with: (1) 3 retention talking points based on their usage and tenure, (2) what pricing flexibility I might have (based on their volume tier), (3) competitor comparison points (publicly known differences), (4) suggested opening line that acknowledges their frustration without being defensive. Keep it practical — I'm reading this 2 minutes before the call.

"The Alert Triage"

Compliance
Cross-reference AML alerts with merchant profiles. Pre-categorise as FALSE POSITIVE, NEEDS REVIEW, or ESCALATE. Draft es...
Show full prompt
Cross-reference AML alerts with merchant profiles. Pre-categorise as FALSE POSITIVE, NEEDS REVIEW, or ESCALATE. Draft escalation summaries. Calculate false positive rate and risk statistics.

"Customer Feedback Theme Finder"

ProductLeadershipSupport
I have a file with customer feedback (survey responses, NPS comments, or support feedback). Read all entries. Identify: ...
Show full prompt
I have a file with customer feedback (survey responses, NPS comments, or support feedback). Read all entries. Identify: (1) the top 5 most common themes — what are people actually talking about? (2) the top 3 things customers love — direct quotes where possible, (3) the top 3 complaints or frustrations — with frequency count, (4) any emerging issues mentioned by 3+ people that weren't in previous reports, (5) a 1-page executive summary with recommended actions. Create a Word document. Include a "quotable quotes" appendix with the most vivid customer comments (anonymised).

"The Subscription Audit"

FinanceLeadershipOperations
I'm pasting our team's list of software subscriptions and tools (name, cost per month, number of users, what it's used f...
Show full prompt
I'm pasting our team's list of software subscriptions and tools (name, cost per month, number of users, what it's used for). Analyse the list and identify: (1) tools with overlapping functionality (e.g., two project management tools), (2) tools with very few active users relative to licences paid for, (3) tools that could potentially be replaced by features in other tools we already have, (4) estimated annual savings if we consolidated or cancelled the flagged items. Create an Excel workbook: Sheet 1 — full audit with recommendations per tool (keep/review/cancel), Sheet 2 — savings summary. Be specific about which tools overlap with which.

[Paste or attach your subscription list]

"The Incident Post-Mortem Drafter"

OperationsLeadershipEveryone
I'm pasting the Slack thread (or incident log) from a recent incident. Create a structured post-mortem document with: (...
Show full prompt
I'm pasting the Slack thread (or incident log) from a recent incident. Create a structured post-mortem document with:

(1) **Timeline** — what happened, when, in chronological order.
(2) **Root cause** — what actually broke (be specific, not "human error").
(3) **Impact** — who was affected, for how long, what was the business impact.
(4) **What went well** — response actions that worked.
(5) **What didn't go well** — where the response was slow, confusing, or wrong.
(6) **Action items** — specific fixes to prevent recurrence, with suggested owners.

Keep it factual, not blame-y. Format as a Word document ready for team review.

[Paste the incident thread here]

"The Call Prep Brief"

Sales
I have a sales call in 30 minutes. Here's what I know about the prospect: - Company: [name] - Industry: [sector] - Size:...
Show full prompt
I have a sales call in 30 minutes. Here's what I know about the prospect:
- Company: [name]
- Industry: [sector]
- Size: [employees or revenue range]
- Current provider: [competitor, if known]
- Deal stage: [where we are in the pipeline]
- Notes from previous contact: [any context]

Create a 1-page call prep brief with: (1) company context — what they likely care about based on their industry and size, (2) 3 qualifying questions I should ask (tailored to their situation, not generic), (3) likely objections and how to handle them, (4) competitive positioning vs. their current provider (based on publicly known differences), (5) suggested call agenda (keep it to 3 items max). Write it so I can scan it in 2 minutes.

"The 1:1 Prep Sheet"

Leadership
I have a 1:1 with a team member in 30 minutes. Here's what I know about their recent work: [Paste: their completed tick...
Show full prompt
I have a 1:1 with a team member in 30 minutes. Here's what I know about their recent work:

[Paste: their completed tickets/tasks this week, any blockers mentioned, feedback from others, upcoming deadlines]

Create a 1:1 prep sheet with: (1) **Wins to acknowledge** — specific things they did well (be concrete, not generic), (2) **Check-ins** — things to ask about based on their current workload, (3) **Growth areas** — one development topic to raise based on patterns in their work, (4) **Blockers to unblock** — anything I can help clear, (5) **One question to ask** — something that shows I'm paying attention.

Keep it to half a page. I'll read this walking to the meeting room.

"The Interview Question Generator"

LeadershipHR
I'm interviewing for this role: [title, team, level]. The key competencies we need are: [list 3-5 skills or traits, e.g....
Show full prompt
I'm interviewing for this role: [title, team, level]. The key competencies we need are: [list 3-5 skills or traits, e.g., "cross-team collaboration, attention to detail under pressure, experience with regulated environments, clear written communication"].

Generate 10 behavioral interview questions that: (1) target these specific competencies (2-3 questions per competency), (2) use the "Tell me about a time when..." format, (3) include a follow-up probe for each question to go deeper, (4) avoid generic questions that any candidate could answer with a rehearsed story. Include a scoring rubric: what a strong answer looks like vs. a weak one for each question.

"The Process Audit"

OperationsLeadershipEveryone
I'm describing how my team currently handles [process name]. Here's how it works today: [Describe the process: who does...
Show full prompt
I'm describing how my team currently handles [process name]. Here's how it works today:

[Describe the process: who does what, in what order, using which tools, how long each step takes, where things get stuck]

Audit this process and identify: (1) **Manual steps** that could be automated or eliminated, (2) **Bottlenecks** — steps where work piles up or waits, (3) **Redundancies** — places where the same information is entered/checked twice, (4) **Handoff risks** — where work passes between people/teams and context gets lost, (5) **Quick wins** — 3 things that could be improved this week with minimal effort. For each finding, explain WHY it's a problem and suggest a specific fix.

"The Announcement Drafter"

LeadershipHR
I need to announce the following to my team / department / company: [Describe: what's changing, why, who's affected, wh...
Show full prompt
I need to announce the following to my team / department / company:

[Describe: what's changing, why, who's affected, when it takes effect, what people need to do]

Draft an internal announcement that: (1) leads with what's changing and why (not background/history), (2) clearly states what people need to DO (if anything), (3) acknowledges concerns people might have, (4) provides a contact point for questions, (5) keeps a [professional / warm / direct / reassuring] tone. Keep it under 300 words. People will skim this — make the first sentence count.

Key Takeaways

  1. You built a role-specific automation and tested it against sample data — the next test is real data

  2. Pair review catches errors you'd miss in your own output — build it into your process

  3. A documented playbook is only as good as its honesty — track real numbers, not estimates

  4. Your department's data has unique patterns — generic prompts produce generic (often wrong) results

Safety Note:

When using real work data (not course sample data), always check for PII before dropping files into Cowork. Redact card numbers, remove personal identifiers, and anonymize where possible. Check with your compliance team about what data is approved for use with AI tools -- policies vary by organisation and jurisdiction.

Materials

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

📊
chargebacks/chargeback-weekly-report.xlsx40 chargeback cases with deadline highlighting (Chargebacks team)
Download
📊
sales/hubspot-pipeline-export.xlsx10 deals with company details (Sales team)
Download
📊
support/support-tickets-48h.xlsx50 tickets with priority highlighting (Support team)
Download
📊
compliance/compliance-screening-data.xlsx30 alerts + 20 merchant profiles (2 sheets, Compliance team)
Download
📊
finance/settlement-data.xlsxBank vs internal settlements (2 sheets, Finance team)
Download
📄
operations/meeting-notes-raw.docxRaw onboarding process notes — Word doc (Operations team)
Download
📕
visa-dispute-guidelines.pdfVisa reason codes and VAMP thresholds (PDF reference)
Download
📝
playbook-template.mdPlaybook documentation template (Everyone)
Download