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[Podcast] S1 - E2: No More Onboarding Chaos – Smarter Playbooks with AI

  • Writer: Andrew A. Rosado Hartline
    Andrew A. Rosado Hartline
  • May 27
  • 5 min read



Here’s a quick, actionable checklist to turn today’s episode into real progress, plus reading links on the blog to dive deeper:


Starter Prompts


The prompts below follow the CO-START framework for clarity:

Element

Purpose

C — Context

Background the model needs

O — Objective

Desired business outcome

S — Specifics

Key facts, tools, placeholders

T — Tone

Formality and style

A — Audience

End-user of the output

R — Requirements

Structural / quantitative rules

T — Type

Output format (table, CSV, outline)

How to Use

  1. Copy the full prompt block.

  2. Replace each ALL-CAPS placeholder—e.g., [ROLE_TITLE], [DEPARTMENT_NAME].

  3. Paste into GenAI Chatbot of choice and run the prompt.

  4. Review the draft, then use Find / Replace in Word, Google Docs, or another editor to change any remaining placeholders to internal terms.

  5. Iterate as necessary (e.g., “Add a risk column” or “Limit bullets to 10 words”).


Prompt 1: 30-60-90 Framework

You are an onboarding consultant.

CO-START
- CONTEXT: A new [ROLE_TITLE] joins the [DEPARTMENT_NAME] team in a [INDUSTRY] organisation.
- OBJECTIVE: Deliver a comprehensive 30-60-90-day onboarding plan that accelerates performance.
- SPECIFICS: Primary tools are [PRIMARY_TOOL_1], [PRIMARY_TOOL_2], [MESSAGING_PLATFORM].  
  Integrate placeholders—e.g., [SAMPLE_PROJECT], [KEY_STAKEHOLDER], [SECURITY_TRAINING_URL].
- TONE: Formal, concise, action-oriented.
- AUDIENCE: Hiring manager and new employee.
- REQUIREMENTS: Provide objectives, week-by-week tasks, quantitative success metrics, and knowledge checkpoints.
- TYPE: Markdown table with three sections (Days 1–30, 31–60, 61–90).

Return only the table.

Prompt 2: FAQ Document

You are an HR knowledge-base writer.

CO-START
- CONTEXT: Frequently asked questions from a new [ROLE_TITLE] in [DEPARTMENT_NAME].
- OBJECTIVE: Reduce repetitive inquiries during the first month.
- SPECIFICS: Supply 20 questions organised under [TOPIC_CATEGORY_1], [TOPIC_CATEGORY_2], [TOPIC_CATEGORY_3]; use placeholders such as [INTERNAL_WIKI_LINK].
- TONE: Professional yet approachable.
- AUDIENCE: Non-technical new hires.
- REQUIREMENTS: Bullet-point Q&A; limit each answer to 40 words.
- TYPE: Plain-text outline with Heading 2 sub-sections.

Provide the outline only.

Prompt 3: Living Glossary

You are compiling a departmental glossary.

CO-START
- CONTEXT: New personnel in [DEPARTMENT_NAME] must understand domain-specific terminology.
- OBJECTIVE: Produce a concise reference of 30 acronyms and jargon items.
- SPECIFICS: For each term, include a one-sentence definition and a placeholder link [DOC_LINK].
- TONE: Clear, explanatory, non-jargon.
- AUDIENCE: Employees unfamiliar with the terminology.
- REQUIREMENTS: Alphabetical order.
- TYPE: Two-column csv Term,Definition & Link.

Return only the table.

Prompt 4: Role-Specific Functions Matrix

You are a process analyst.

CO-START
- CONTEXT: Clarifying responsibilities for [ROLE_TITLE] within [DEPARTMENT_NAME].
- OBJECTIVE: Create a “Core Functions” matrix outlining key responsibilities.
- SPECIFICS: Provide at least eight functions (e.g., Backlog Grooming, Risk Escalation, Vendor Handoff, Sprint Demo).  
  Columns: Function, Primary Tool, Key Stakeholders, Success Metric, Placeholder Document.  
  Use ALL-CAPS placeholders such as [KPI_BUG_FIX_RATE], [SYSTEM_OF_RECORD].
- TONE: Formal and structured.
- AUDIENCE: Project managers who rely on Excel for tracking.
- REQUIREMENTS: Comma-separated values (CSV) format with header row.
- TYPE: CSV block.

Return only the CSV.

Practical Guidance for Replacing Placeholders

Most office suites provide a Find and Replace function that lets you update every placeholder in seconds. The steps below use Microsoft Word; Google Docs, LibreOffice, and other editors have equivalent commands.


  1. Paste the AI-generated draft into Word (or another editor).

  2. Press Ctrl + H (or select Home → Replace) to open Find and Replace.

  3. In Find, enter the exact placeholder—for example, [DEPARTMENT_NAME].

  4. In Replace, enter the real value—for example, Product Engineering.

  5. Select Replace All—Word updates every occurrence.

  6. Repeat for each placeholder, such as [ROLE_TITLE], [PRIMARY_TOOL_1], and so on.

This approach maintains consistency and reduces manual editing to a few seconds per field.


Example Placeholder Key

Placeholder

Example Replacement

Notes

[ROLE_TITLE]

Project Manager

Use the exact job title from HR records.

[DEPARTMENT_NAME]

Product Engineering

Match the department label in the org chart.

[INDUSTRY]

SaaS

Keep broad unless a narrower descriptor is necessary.

[PRIMARY_TOOL_1]

Jira

Use names employees will recognise.

[PRIMARY_TOOL_2]

Confluence

List additional core systems in daily-use order.

[MESSAGING_PLATFORM]

Microsoft Teams

Replace with Slack, Google Chat, etc.

[SAMPLE_PROJECT]

Alpha Release Q4

Choose a low-risk or illustrative project.

[KEY_STAKEHOLDER]

Jane Smith — VP Product

Include role/title so new hires see reporting lines.

[SECURITY_TRAINING_URL]

https://intranet.company.com/training/security

Confirm the link is accessible on Day 1.

[KPI_BUG_FIX_RATE]

Resolve 90 % of P1 bugs within SLA

Translate numeric targets into clear, measurable statements.

Store the key (e.g., Placeholder_Key.xlsx). After generating the AI draft, open Word, run Ctrl + H for each entry in the key, and save a company-specific version for distribution.


Documentation Library

Document

Why It Matters

Role-specific 30-60-90

Aligns expectations Day 1

Interactive FAQ

Reduces repeated questions

Glossary Flashcards

Demystifies jargon

Stakeholder Map

Makes politics visible

Escalation Matrix

Prevents ping chaos

Wiki Article Template

Captures fixes in real time

Mermaid → Iteration Walk-through


Check out From Stuck to Strategy: A Project Manager’s Guide to Visual Thinking with AI to see how even a non-coder can use Mermaid code with GenAI and generate mind maps in seconds! (With examples and tools 😀)


Conversion Prompt


“Convert the 30-60-90 plan into a Mermaid flowchart with swimlanes for IT, HR, MANAGER, BUDDY, NEW_HIRE. Use diamond nodes for decision points and include placeholder metric [TIME_TO_FIRST_COMMIT].”


Iteration Logic

  1. Iteration 0 — Capture linear steps only.

  2. Iteration 1 — Insert decision diamonds where failures may occur.

  3. Iteration 2 — Add swimlanes and a KPI node.

  4. Feedback Loop — Ask GenAI chatbot: “Identify missing compliance steps for a [REGULATED_INDUSTRY] firm.” Integrate its nodes, export PNG, publish to wiki.


Code Samples


Iteration 0

mermaid
flowchart TD
	Start[Day 0 - New Hire]
    	Start --> IT[Equipment & Access]
    	Start --> HR[Payroll Setup]
    	Start --> ManagerKickoff[Manager 1:1]
    	ManagerKickoff --> BuddyIntro[Peer Buddy Assigned]
    	BuddyIntro --> QuickWin[First Low-Risk Ticket]

Iteration 1 – Failure paths

mermaid
flowchart TD
	Start --> A{Laptop Delivered?}
	A -- No --> ITFix[Escalate to IT]
	A -- Yes --> B{Accounts Active?}
	B -- No --> ITFix
	B -- Yes --> ManagerKickoff[Manager 1:1 + Sprint Shadow]
	ManagerKickoff --> Retro15[Day 15 Retro]

Iteration 2 – Owners + KPI

mermaid
flowchart TD
    subgraph HR
        HR1[Verify I-9] --> HR2[Benefits Brief]
    end
    subgraph IT
        IT1[Ship Device] --> IT2[Provision SSO]
    end
    subgraph PM
        PM1[30-day Goals] --> PM2[Shadow Stand-ups]
        PM2 --> PM3[Close First Ticket]
    end
    HR2 --> PM1
    IT2 --> PM1
    PM3 --> KPI[Time-to-First Ticket ≤ 14 days]

Example AI-Generated 30-60-90 (Excerpt)

Day 1–30

Day 31–60

Day 61–90

• Complete IT & HR onboarding

• Shadow two stand-ups

• Close ≥ 1 low-risk ticket

• Co-lead sprint planning

• Publish first Wiki article

• Present project-charter draft

• Own sprint demo

• Hit 80 % story-point accuracy

• Mentor next hire during tool setup

(Generated with Prompt 1; placeholders converted.)


Quick-Win Automations

Task

Tool

Benefit

Auto-post Day-1 checklist in Slack

Zapier

Eliminates “Where do I start?” DMs

Daily FAQ-views digest to channel

Slack bot

Exposes unclear steps in real time

Auto-hold “Ask Me Anything” block

Reclaim.ai or internal scheduling tool



Share Your Results


  1. Run the prompts (placeholders in ALL CAPS).

  2. Use Word/Docs Find / Replace to inject proprietary data.

  3. Iterate your Mermaid diagram until every path and owner is confirmed.


Call to action: 

Post on LinkedIn with #PMLifeHacksAI and tag me to discuss!


Resources


 
 
 

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