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Generate a personalised first-week checklist for a new joiner

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Generate a personalised first-week checklist for a new joiner

A new joiner starts Monday. HR sends them a generic 40-item checklist that scares everyone. Claude reads the job description, the team's standard onboarding doc, and the new joiner's CV — then produces a tailored 12-item week-one plan they can actually finish. Audience: beginner · ~20 min · 7 steps

You'll end up with

A markdown checklist with three sections (Day 1 · Days 2–3 · Days 4–5), each item including who to talk to and why it matters. Personalised to the joiner's role and prior experience.

Before you start, you need
  • Nothing — Claude will invent a realistic job description, generic team onboarding doc, and joiner CV for you to practise on. (Once you trust the loop, swap in your real JD + onboarding doc + the joiner's CV — handle the CV as personal data per GDPR.)
  • Claude Code installed and a terminal open (see Day 1)

Generic onboarding checklists are how new joiners learn that nobody really thought about their first week. Forty items, half of them only relevant to people in the office on Tuesdays, no order, no explanation of why anything is on the list.

This use case is a small fix with disproportionate impact: a checklist that looks like it was made for this person.

Compliance check before you start. Job descriptions and team onboarding docs are usually internal but non-sensitive. A new joiner’s CV is personal data under GDPR — handle it with the same posture as any other personal data. For your first run, use your own CV or a sanitised sample, not a candidate’s. Once you trust the loop, talk to your line manager about how real CVs should flow.

Step 01

Build the workspace

Open the .

Press ⌘+Space, type “Terminal”, and press Enter.

Open the Start menu (press the Windows key), type “Ubuntu”, and press Enter. If you don’t see Ubuntu listed, install WSL first.

In Ubuntu, ~/Desktop is a folder inside ’s Linux home (/home/<your-Linux-username>/Desktop) — not the Windows desktop you see in File Explorer at C:\Users\...\Desktop. That’s fine: the files are real and Claude can read and write them. Anywhere this use case says “open in Finder / File Explorer”, run explorer.exe . from your Ubuntu terminal — Windows opens that exact WSL folder in Explorer.

Type each line:

mkdir -p ~/Desktop/claude-lab/onboarding-anna
cd ~/Desktop/claude-lab/onboarding-anna
claude --dangerously-skip-permissions
  • mkdir -p ~/Desktop/claude-lab/onboarding-anna — make a folder named after the joiner, inside claude-lab on your Desktop (-p creates claude-lab too if it’s not there yet — it’s the one home for all hub use cases).
  • cd ~/Desktop/claude-lab/onboarding-anna — move into it.
  • claude --dangerously-skip-permissions — start . The flag stops Claude you for permission on every file write — safe in a fresh, dedicated folder like this one. (If you’d rather see every prompt for your first run, just type claude — same thing, more interruptions.)
Step 02

Ask Claude to invent the three input documents

You don’t have a real JD, team onboarding doc, or CV to hand — and you don’t need them. Tell Claude:

Create three files in this folder:

File 1: job-description.md — a realistic JD (~1 page) for “SME Credit Analyst” at NBG retail bank, Athens HQ. Include: responsibilities (credit underwriting for SME loans up to €500k, portfolio monitoring, contributing to risk committee submissions), required (2+ years credit analysis, comfortable with financial-statement analysis, knowledge of Greek SME sector, Greek + English fluency), reporting line (Head of SME Credit), what success looks like at 6 / 12 months.

File 2: team-onboarding.md — a deliberately generic 40-item bank-wide onboarding checklist (~2 pages of ) that HR sends every new joiner. Mix relevant items (laptop pickup, badge, mandatory KYC training, data-protection module, code-of-conduct sign-off, SAP-CRM access request, intranet account, internal phone number) with items that only apply to specific roles (cash-handling training, -front-line uniform fitting, ATM-vault access request, trade-desk system permissions, customer-call-recording authorisation). Order them haphazardly — that’s how real generic checklists look.

File 3: anna-cv.md — a realistic CV for “Anna Papas” (~1 page). Background: 2 years as a junior credit analyst at a competitor Greek bank; before that an Athens University economics degree (2:1 equivalent); strong on financial-statement analysis and Excel; some SQL exposure from a fintech internship; KYC-certified at her current bank; native Greek, C1 English. Add a “Personal” line: lives in Kifissia, 27 years old, joined cycling club.

Make all three feel like real corporate documents — not bulletted summaries. The team-onboarding one in particular should have a 1990s-HR-document tone: long sentences, “the colleague shall”, lots of capitalisation.

Claude writes all three files straight away.

Two minutes of synthesis from Claude that would have taken you twenty to write by hand — and the files now feel realistic enough to do the actual exercise on.

Step 03

Let Claude create the context file

The checklist quality is set by the context you give Claude. The more specific the context, the more useful the checklist.

Tell Claude:

Create a file called context.md in this folder. Put these 6 lines inside it (with my values):

Joiner name: Anna Papas
Role: SME Credit Analyst, NBG retail bank, Athens HQ
Joining team: SME Credit team (8 people)
Manager: M. Vassilas (Head of SME Credit)
Working pattern: 3 days on-site (Mon/Tue/Thu), 2 remote
Banking experience: 2 years junior analyst at a competitor — knows the basics, new to NBG-specific systems and policies

Claude writes the file straight away.

Two minutes of thought here is what separates “useful checklist” from “another bureaucratic document”.

Step 04

Ask for the personalised checklist

Send this to Claude:

Read context.md, job-description.md, team-onboarding.md, and anna-cv.md.

Produce week-one-checklist.md with these three sections, in this order:

Day 1 (Monday) — max 4 items. Things that must happen before lunch on day 1: laptop pickup, the access requests that take longest to land, manager 1:1, team intro. Each item: who they need to see, where (room or Teams), why it matters in one sentence.

Days 2–3 — max 5 items. The core systems-and-policies block: which internal systems they need access to, which mandatory training modules apply to a credit analyst, the 2–3 meetings they should attend as observers. Each item: same format.

Days 4–5 — max 4 items. Their first piece of real work, paired with a buddy. Should be a small, finishable task that lets them feel useful by Friday afternoon. Each item: same format.

Hard rules:

  • Skip items from team-onboarding.md that don’t apply to a credit analyst (e.g. front-line cash-handling training).
  • Skip anything Anna already knows from her CV (don’t put “Introduction to credit risk fundamentals” on the list if she has 2 years of credit analysis behind her).
  • Add an introduction to one specific NBG policy or system that her prior bank wouldn’t have used.
  • Every item needs a why. “Mandatory KYC training (Day 2)” is incomplete; “Mandatory KYC training (Day 2) — required by Bank of Greece for anyone handling client files, takes 90 minutes” is the right shape.

Press Enter. Claude reads the files and writes the checklist in 30–90 seconds.

Step 05

Sanity-check before sending

Ask Claude:

Show me week-one-checklist.md.

Read it twice — once as you, once as Anna. Questions to ask yourself:

  • Is day 1 too crowded? Four items is the cap. If Claude wrote six, push back: “Day 1 has too many items — Anna’s manager will only have 30 minutes on Monday morning. Cut to four.”
  • Is anything on the list that her CV makes redundant? “Introduction to corporate banking” for a 2-year banker is condescending.
  • Is the Friday task real? “Read the team’s risk policy” is not a task. “Draft a one-page memo on borrower XYZ’s covenant compliance for the credit committee — paired with M. Costa” is.

Iterate. Three of these revisions usually produce a checklist that lands well.

Make Claude prove it followed its own rules

The judgment calls above are yours; the rule-compliance is Claude’s to demonstrate. Paste:

Verify your own checklist. (1) Count the items per section and show me the counts — the caps are 4 / 5 / 4. (2) Go through team-onboarding.md item by item and produce three lists: kept, skipped-as-irrelevant-to-the-role, skipped-as-redundant-with-the-CV — and for every “redundant” skip, quote the CV line that justifies it. (3) Confirm every checklist item has all three parts: who, where, why. Fix anything that fails and re-run.

List 2 is the one worth reading: it shows you exactly what Claude decided not to include and why — which is where personalisation either happened or didn’t. A wrongly-skipped mandatory training is the failure mode that matters here, and this check surfaces it.

Step 06

How you'd actually deliver it

In real life, the two delivery options that land best with new joiners: (1) paste the into Teams as a direct message — checkboxes, bold, headings render natively — with a one-liner like “Looking forward to Monday — this is your first week, designed for you. We’ll go through Day 1 together at 10am.” (2) Print it — people who get a printed checklist on day 1 keep it on their desk, people who get a PDF lose it in their inbox. We’re pretending here — the file on your Desktop is the deliverable.

Save the folder. The next joiner’s checklist reuses the and the team onboarding doc — only context.md and the CV change. Twenty minutes becomes five.

The deeper win: the joiner spends their first week doing instead of waiting for someone to tell them what they should be doing. That’s worth a lot more than the time you saved.

Make the next joiner’s checklist faster with CLAUDE.md

The rules you established this time are stable — they apply to every SME Credit joiner. The joiner’s name and CV change; the rules don’t. Tell Claude:

Create a CLAUDE.md in this folder. Put in it the stable rules for week-one checklists in the SME Credit team:

  • Three sections: Day 1 (max 4 items), Days 2–3 (max 5 items), Days 4–5 (max 4 items)
  • Each item: who they see, where (room or Teams), why it matters in one sentence
  • Skip items from the bank-wide onboarding doc that don’t apply to a credit analyst (cash handling, uniform, ATM-vault access, customer-call-recording authorisation, trade-desk modules)
  • Skip anything redundant with the joiner’s prior experience (don’t put “Introduction to credit risk fundamentals” on the list for someone who already has 2 years of it)
  • Add at least one NBG-specific intro (e.g. the RatingPro scoring ) that a competitor bank wouldn’t have used
  • Day-4/5 task must be small, finishable, and pair the joiner with a buddy
  • Every item needs a why

CLAUDE.md is the magic filename reads automatically every time you start claude in a folder containing it. Next joiner: copy the and the team-onboarding doc into a new folder, drop in the new joiner’s CV, write a one-line context.md with name and prior experience, run claude --dangerously-skip-permissions. Five minutes.

Step 07

Level up — a checklist the joiner actually ticks off

Optional, and the version that changes who the document is for: not a list the manager sends, but a page the joiner uses all week. One :

Read week-one-checklist.md. Build a single self-contained file anna-week-one.html that I can open by double-clicking — no server, no internet, no external libraries. The three sections (Day 1 · Days 2–3 · Days 4–5) with a real checkbox per item that remembers its state when the page is closed and reopened (use the browser’s local storage). A progress bar at the top (“5 of 13 done — nice pace”). Each item shows the who / where / why. Tone friendly, not corporate. Accent colour #007a8a.

Email the file to Anna before Monday. She double-clicks it, ticks things off through the week, and the progress bar does the encouragement. The state lives in her browser — nothing is sent anywhere, no account, no app.

The pattern to remember — any output Claude can produce as text, it can also produce as a small interactive page. The upgrade prompt is always the same shape: “turn this into a single self-contained interactive HTML file I can open by double-clicking.” It works on every use case in this hub.

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