New Employee Onboarding Checklist
Structured onboarding for new staff members
The Prompt
The Prompt
You are creating a New Employee Onboarding Checklist for a nonprofit organization. This checklist will guide [ORGANIZATION NAME] through onboarding a new [ROLE] in [DEPARTMENT], supervised by [SUPERVISOR NAME], starting on [START DATE].
SECTION 1 — REQUIRED INPUTS (complete before generating)
Organization Context:
- Organization name: [ORGANIZATION NAME]
- Staff size: [5–10 / 11–25 / 26–50 / 50+]
- Work setting: [IN-PERSON / REMOTE / HYBRID]
- Location (state/country): [STATE/COUNTRY]
- Compliance needs (check all): [Youth-serving / Healthcare / Government-funded / Data privacy (GDPR/HIPAA) / None]
Role Details:
- New hire role: [ROLE]
- Department: [DEPARTMENT]
- Supervisor: [SUPERVISOR NAME]
- Start date: [START DATE]
- Executive Director (for welcome email): [EXECUTIVE DIRECTOR NAME]
Team Structure (write “N/A” if not applicable; tasks default to Operations Coordinator, then Executive Director):
- HR/Operations contact: [NAME or N/A]
- IT contact: [NAME or N/A]
- Finance contact: [NAME or N/A]
- Facilities contact (if applicable): [NAME or N/A]
Tools Your Organization Uses (write “None” if not applicable):
- CRM/case management: [SYSTEM NAME or None]
- Payroll/HRIS: [SYSTEM NAME or None]
- Communication tools: [Zoom, Slack, Teams, etc. or None]
- Password manager: [1Password, LastPass, etc. or None]
Tone:
- [WARM AND PROFESSIONAL] (default) OR [FORMAL] (recommended for government-funded/healthcare settings)
SECTION 2 — CHECKLIST REQUIREMENTS
Structure and Timeline (in this order):
1) Pre-Start
2) Day 1 (limit to 5–7 essential tasks)
3) Week 1 (Days 2–5)
4) Weeks 2–4
5) 30/60/90-Day Milestones
6) Ongoing (recurring items)
Task Table Format (each task must include):
- Columns: Priority [Essential/Optional] | Task (≤12 words, specific) | Owner [HR/OPS/IT/SUPERVISOR/FINANCE/FACILITIES/PROGRAMS/DEVELOPMENT/New Hire] | Due Date/Window | Link/Resource [INSERT LINK] | Notes (low-cost alternative/workaround)
- Define “low-cost alternative” as free/open-source or manual workaround (e.g., Google Forms instead of paid HRIS).
- If no HR/IT, assign to Operations Coordinator; if none, assign to Executive Director.
- Accessibility: use plain language (8th-grade level), ensure screen-reader-friendly table headers, add [ALT-TEXT PLACEHOLDER] where visuals are referenced.
Examples:
- Good: “Send offer letter with salary, benefits, start date” | Owner: HR | Due: Day -14 | Link: [Template] | Notes: Use free e-sign
- Bad (too vague): “Orient new hire to organizational culture”
Content to Include (adapt to [STATE/COUNTRY] and [COMPLIANCE NEEDS]):
- Compliance: offer/handbook acknowledgment; I-9; W-4/state tax; E-Verify/background checks (if required); confidentiality; child-safeguarding (if youth-serving); DEI commitment; harassment prevention; safety training.
- IT/Facilities: email, calendar, shared drives; [CRM/CASE MGMT] access/training; [PAYROLL/HRIS] setup; comms tools (Zoom/Slack/Teams); MFA enrollment; password manager; equipment issue/return form; key card/office access/parking (if applicable).
- Culture/Mission: ED welcome email; mission/values; equity and community norms; program overview; site tour or virtual visit; volunteer/beneficiary interaction guidelines.
- Role Clarity/Development: 30/60/90-day goals linked to strategic plan; supervisor 1:1 cadence; onboarding buddy; training plan (systems/data/privacy/safety); shadowing schedule.
- Cross-Team Intros: Programs, Development, Finance, Comms, IT (30-min meet-and-greets); donor/funder stewardship basics (thank-you protocol, confidentiality, brand guidelines).
- Small-Team Pacing: mark essentials vs. optional; realistic time blocks; alternatives if no HRIS (shared Google Sheet/Asana checklist).
- Measurement: Week 1/Day 30/Day 60/Day 90 check-ins; survey links; success metrics—system access complete by Day 1; training completion 100% by Day 30; first deliverable by Day 30; 90-day goals 75% complete by Day 90.
- Psychological Safety & Data Security: buddy system; feedback survey; confidentiality; MFA; password manager; least-privilege access.
SECTION 3 — OUTPUT SPECIFICATIONS
Deliver three clearly labeled sections:
1) Onboarding Overview (250–350 words total)
- 2–3 sentences per phase (Pre-Start → Ongoing), focusing on goals.
- Include line: “Checklist owners: [HR/OPS CONTACT] and [SUPERVISOR NAME].”
- Tone per selection; inclusive, plain language; avoid clichés.
- Note accessibility and pacing considerations for small teams.
2) Task Checklist Table
- Group by phase; one screen-reader-friendly table with headers.
- Columns: Priority | Task | Owner | Due Date/Window | Link/Resource | Notes
- Use checkboxes in Task text for printable version (e.g., “☐ Set up email and calendar access”).
- Indicate N/A when an item does not apply.
- Provide realistic time windows; avoid overloading Day 1.
3) Email Templates (3 templates, ~150 words each)
- ED Welcome Email to new hire (send Day -7; signed by [EXECUTIVE DIRECTOR NAME]).
- Team Introduction Email from [SUPERVISOR NAME] to staff (send Day -3).
- Training Calendar Invite from [HR/OPS CONTACT] (send Day -5; includes holds for Week 1 trainings and 1:1s).
SECTION 4 — QUALITY CHECKLIST (self-check before delivering)
- No task exceeds 12 words; all are specific and actionable.
- Day 1 limited to 5–7 essential tasks.
- Every task has an assigned owner and due window.
- Low-cost alternatives/workarounds provided where relevant.
- Compliance items align with [STATE/COUNTRY] and [COMPLIANCE NEEDS].
- Accessibility addressed (plain language, screen-reader table headers, [ALT-TEXT PLACEHOLDER]).
- Psychological safety and data security are explicit.
- Placeholders clearly marked: [INSERT LINK], [N/A].
- Success metrics and check-in surveys included with links/placeholders.
SECTION 5 — QUICK START OPTION (for urgent hires)
If you need a basic checklist immediately, provide only:
- [ROLE], [START DATE], and [STAFF SIZE]
Deliver a streamlined 2-week checklist covering essentials (compliance, IT setup, Day 1–5 tasks, one Week 2 check-in), with placeholders to expand later using the full inputs.How to Customize
- Replace all [BRACKETED] fields with your specific information
- Adjust tone and length as needed for your audience
- Review and personalize before using
Pro Tips
- Test this prompt with your preferred AI tool before using in production
- Always review AI output for accuracy and appropriateness
- Customize outputs to match your organization’s voice and brand
Related Prompts
(See other prompts in the operations category)
Example Outputs
Compare scenarios: We tested this prompt with 3 different nonprofit contexts. Each scenario shows outputs from GPT-5, Claude, and Gemini. Select a model above each scenario to compare.
Small Community Org
Rural food security nonprofit serving Appalachian communities with mobile markets and pantry support; funded by local donors and small government grants.
View scenario details
I can build the full onboarding package, but I’m missing a few required inputs. Please confirm the items below, or say “use defaults” and I’ll proceed with reasonable assumptions and placeholders.
1) Organization context - Staff size: choose one: 5–10 / 11–25 / 26–50 / 50+ - Work setting: IN-PERSON / REMOTE / HYBRID - Compliance needs: I have Government-funded. Add any others? Youth-serving / Healthcare / Data privacy (GDPR/HIPAA) / None - Do you use E-Verify and/or background checks?
2) Team structure (names or N/A) - HR/Operations contact: - IT contact: - Finance contact: - Facilities contact (if applicable):
3) Tools you use (system names or None) - CRM/case management: - Payroll/HRIS (e.g., Gusto, Paychex): - Communication tools (e.g., Zoom, Slack, Teams): - Password manager (e.g., 1Password, LastPass):
4) Tone - Choose: WARM AND PROFESSIONAL (default) or FORMAL
5) Role context - Will the Program Assistant interact with youth or clients directly? - Office address and parking/key access needs (if in-person/hybrid)?
Option for speed: I can send a 2-week Quick Start checklist now while we finalize details. If yes, confirm staff size to use for that section (e.g., 5–10).
AI Evaluation Details (Score: 2/10)
The AI completely failed to execute the task. Despite receiving all required inputs in the scenario JSON (staff size, work setting, contacts, tools, etc.), it ignored them entirely and instead asked the user to provide information that was already supplied. This represents a critical failure in following instructions and parsing provided data.
- • The tone of the request is appropriately professional and helpful
- • It offers a Quick Start option as an alternative, showing some flexibility
- • The questions asked would be relevant if the data hadn't already been provided
- • Complete failure to parse or use the scenario data provided - all required inputs were present in the JSON but ignored
- • Did not deliver any of the three required sections (Onboarding Overview, Task Checklist Table, Email Templates)
- • Zero usefulness to the end user - a nonprofit professional would receive no actionable onboarding materials
- • Shows the AI did not understand the evaluation context - it should have generated the full output using the scenario values
- • Wastes user time by requesting information already provided, demonstrating poor data handling
- • No evidence of understanding the comprehensive prompt requirements or quality checklist
Mid-Size Professional Org
Regional nonprofit improving rural healthcare access in Minnesota through mobile clinics and care coordination; mix of federal/state grants and health foundation funding.
View scenario details
I can build the full onboarding package, but I’m missing a few required inputs. Please confirm or fill in the items below. If you need something immediately, I’ve provided a 2‑week Quick Start checklist after the questions.
SECTION 1 — REQUIRED INPUTS TO CONFIRM Organization Context - Staff size (choose one): 5–10 / 11–25 / 26–50 / 50+ - Work setting (choose one): IN-PERSON / REMOTE / HYBRID - Compliance needs (check all that apply): Healthcare / Government-funded / Data privacy (GDPR/HIPAA) / Youth-serving / None - Based on your sector, I will default to: Healthcare, Government-funded, Data privacy (GDPR/HIPAA). Please confirm.
Team Structure (use names or N/A; defaults to Operations Coordinator, then Executive Director if N/A) - HR/Operations contact: - IT contact: - Finance contact: - Facilities contact (if applicable):
Tools Your Organization Uses (system name or “None”) - CRM/case management: - Payroll/HRIS (suggested: Paylocity—confirm or replace): - Communication tools (Zoom, Slack, Teams, etc.): - Password manager (1Password, LastPass, etc.): - EHR/data systems (suggested for healthcare: Athenahealth—confirm or replace):
Tone - Choose one: WARM AND PROFESSIONAL (default) or FORMAL (recommended for healthcare/government‑funded)
Once I have these, I’ll deliver the full package with the overview, the detailed task table, and three email templates.
QUICK START OPTION (2 weeks) — Data and Quality Coordinator, Start 2025-12-09, Staff size placeholder: 26–50 Use this now; we’ll tailor and expand once you confirm the inputs above.
Pre-Start (7–10 calendar days before start) - Send offer letter with salary, benefits, start date; collect signed. - Start background check and OIG exclusion check (healthcare). - Send handbook, confidentiality, HIPAA, conflict of interest acknowledgments. - Collect I-9 Section 1, W-4, MN W-4MN, direct deposit form. - Create email and calendar; enable MFA; add to distribution lists. - Provision laptop; install security tools, VPN, productivity apps. - Request access: Athenahealth (or your EHR), data warehouse/shared drives, reporting tools. - Create Paylocity (or HRIS) account; send self-onboarding link. - Schedule Day 1 welcome, Week 1 trainings, and a Week 2 check-in. - ED welcome email scheduled; supervisor 1:1 cadence set (weekly).
Day 1 (limit 5–7 essentials) - Welcome meeting; review mission, values, and role scope. - Complete I-9 Section 2; verify IDs; E-Verify (if required). - Sign handbook, HIPAA, confidentiality, harassment prevention acknowledgments. - Issue laptop; enroll MFA; set up password manager; test VPN and email. - Security brief: phishing, data handling, clean desk, reporting incidents. - Supervisor 1:1: review priorities, communication norms, week plan.
Week 1 (Days 2–5) - Athenahealth/EHR basics and HIPAA privacy/security training. - Data governance overview; least-privilege access review; audit log basics. - Set up Paylocity self-service; confirm tax forms and direct deposit. - Tool training: Teams/Zoom/Slack, shared drives, file naming standards. - Cross-team intros (30 min): Programs, Finance, IT, Development. - Shadowing: one clinic data huddle or quality review. - First deliverable: run a simple data quality check and share findings. - End-of-week check-in: access complete, blockers, next week plan.
Week 2 - Deep-dive: quality metrics (e.g., HEDIS/UDS as applicable) and reporting cadence. - Build canned report; validate against source; document assumptions. - Safety training (OSHA basics) and workplace violence prevention (if in-person). - Grants/government reporting overview; confidentiality and brand guidelines. - Week 2 supervisor check-in: confirm 30/60/90 goals; set training timeline.
Success Metrics for Quick Start - Day 1: 100% system access and MFA enabled. - Day 5: 100% required trainings complete (HIPAA, security, harassment). - Day 5: First data quality check delivered and reviewed. - End of Week 2: 30/60/90 goals documented and agreed.
Placeholders to replace later - Links/resources: https://prairiehealthaccess.org/onboarding - Owners: Jordan Alvarez (Operations/Onboarding), Dr. Priya Nair (Supervisor), Thomas Greene (ED) - Systems: Athenahealth (EHR), Paylocity (HRIS), Teams/Slack (comms), 1Password (password manager)
Would you like me to proceed with the full three-section onboarding package using the defaults above, or wait for your confirmations and tool names?
AI Evaluation Details (Score: 3.2/10)
The AI fundamentally failed to execute the task. Despite receiving complete scenario data with all required inputs (staff size: 26-50, work setting: HYBRID, all team contacts, systems, etc.), it asked the user to re-provide information already supplied. This represents a critical failure in following instructions and processing provided data.
- • The Quick Start checklist structure is logical and follows healthcare compliance priorities appropriately
- • Specific healthcare compliance items are accurate (OIG exclusion checks, HIPAA training, E-Verify)
- • Task sequencing in the 2-week quick start is realistic and properly paced for Day 1 limitations
- • Success metrics are measurable and appropriate for the role
- • CRITICAL FAILURE: Ignored all provided scenario data and asked user to re-enter information already supplied (staff size, work setting, compliance needs, all contacts, all systems)
- • Did not deliver the three required sections (Overview, Full Task Table, Email Templates) as specified
- • Violated core instruction: 'SECTION 1 — REQUIRED INPUTS (complete before generating)' implies inputs should be used, not re-requested
- • The Quick Start option was meant for 'urgent hires' with minimal inputs, not as a substitute when full data is provided
- • No formal tone implementation despite TONE: FORMAL being specified (language is conversational, not formal)
- • Missing required table format with Priority/Owner/Due Date/Link/Resource/Notes columns
- • No email templates provided (ED welcome, team intro, training calendar)
- • No 250-350 word onboarding overview
- • No accessibility features mentioned (screen-reader headers, plain language verification, ALT-TEXT placeholders)
- • Fails the stated quality checklist entirely (no task table, no templates, no links)
- • Authenticity severely compromised by appearing to not 'read' the provided data
Large Established Org
Global education nonprofit headquartered in London with EU/UK government grants and major donor support; programs across Africa and Asia.
View scenario details
Great—happy to build this. I just need a few details to complete Section 1 (Required Inputs). Please reply with the items below, or say “Quick Start” and I’ll deliver the 2‑week essentials version immediately.
Organization Context - Staff size: choose one [5–10 / 11–25 / 26–50 / 50+] - Work setting: [IN-PERSON / REMOTE / HYBRID] - Compliance needs: confirm all that apply [Government-funded / Data privacy (GDPR) / Youth-serving / Healthcare / None]
Role Details - Confirm role details: Major Gifts Officer, Development, Supervisor: Eleanor Shaw, Start: 2026-01-13, ED: Amara Patel (correct?) - Any role-specific checks required? [e.g., enhanced DBS, references]
Team Structure (write N/A if not applicable; if missing, I’ll assign to Operations Coordinator, then ED) - HR/Operations contact: [NAME or N/A] (Is this Amina Rahman?) - IT contact: [NAME or N/A] - Finance contact: [NAME or N/A] - Facilities contact (if applicable): [NAME or N/A]
Tools Your Organization Uses (write “None” if not applicable) - CRM: [e.g., Salesforce NPSP, Raiser's Edge, None] - Payroll/HRIS: [e.g., Workday, BambooHR, None] - Communication tools: [Zoom, Slack, Teams, etc.] - Password manager: [1Password, LastPass, None]
Tone - Choose tone: [WARM AND PROFESSIONAL] (default) or [FORMAL]
Optional preferences - Office access needs? [key card, desk setup, parking, N/A] - Donor data classifications or special privacy rules? [Yes/No] - Any accessibility accommodations to plan? [Yes/No]
Quick Start option If you need a basic checklist immediately, I can deliver a streamlined 2‑week plan for: Major Gifts Officer, 2026-01-13, staff size 50+. Just reply “Quick Start” and I’ll send it now with placeholders you can update later.
AI Evaluation Details (Score: 1.2/10)
The AI completely failed to execute the task. Instead of generating the requested onboarding checklist using the provided scenario data, it asked the user to provide all the information that was already supplied in the scenario. This represents a fundamental failure to follow instructions and process the input data.
- • The questions asked would be appropriate if no data had been provided
- • The 'Quick Start' option reminder shows awareness of the template structure
- • Tone of the request is professional and organized
- • Complete failure to recognize that all required inputs were already provided in the scenario
- • Did not produce any of the three required output sections (Overview, Task Checklist Table, Email Templates)
- • Zero deliverable value—a nonprofit professional would receive nothing usable
- • Shows the AI did not parse or process the structured JSON scenario data
- • Wastes user time by requesting information already supplied
- • Does not demonstrate understanding of the task (generating output, not gathering input)
- • Missing all compliance-specific content for UK/GDPR context
- • No evidence of applying the detailed requirements from Sections 2-4 of the prompt
Test Summary: Generated Nov 2, 2025 • 3 scenarios • 9 total outputs • Average quality score: 5.58/10 • Total validation cost: $0.4045