Onboarding is where new hires decide if they made the right call. Do it well and they’re productive in weeks. Do it poorly and they’re confused for months, or gone in six.
The problem is most managers wing it. You’re busy, the new hire starts Monday, and suddenly you’re scrambling to figure out what they should actually be doing in week one.
These ChatGPT prompts for onboarding new hires fix that. Five prompts that cover the first 90 days, from the day after you finish the interviews to their first 1-on-1.
Table of Contents
Prompt 1: 30/60/90 Day Plan
The scenario: You’ve got a new hire starting soon and need a structured ramp-up plan. You know what you want them doing eventually, but haven’t mapped out how they get there.
The prompt:
Create a 30/60/90 day onboarding plan for a new [job title] joining my team.
Context:
- Team size: [X people]
- Their main responsibilities: [list 2-3 core duties]
- Key tools/systems they'll need to learn: [list them]
- First project they'll own: [describe it]
For each phase, include:
- Learning goals
- Key relationships to build
- Deliverables or milestones
- How I'll know they're on track
Keep it realistic. Don't overload the first 30 days.Why this works: New hires want to know what success looks like. A 30/60/90 plan gives them a roadmap and gives you something concrete to check progress against. It also forces you to think through what’s actually realistic in the first month versus what can wait.
Tip: Share the plan with your new hire on day one. It signals that you’ve prepared for their arrival and sets clear expectations from the start.
Prompt 2: Pre-Arrival Checklist
The scenario: Your new hire starts Monday. You’re pretty sure you’ve got everything covered, but you’ve been burned before. Laptop wasn’t ready. Access wasn’t provisioned. Nobody told the team they were coming.
The prompt:
Create a pre-arrival checklist for a manager onboarding a new [job title].
Include:
- Equipment and workspace setup
- System access and accounts they'll need
- Meetings to schedule for their first week
- People they should meet (and why)
- Documents or resources to have ready
- Anything I should communicate to the team before they arrive
Assume I have [X days] before their start date.Why this works: The first day sets the tone. When everything’s ready, your new hire feels expected and valued. When it’s not, they spend day one watching you scramble, wondering what they signed up for.
Tip: Send this checklist to yourself a week before every new hire. It takes five minutes and saves you from the “we’re still waiting on your laptop” conversation.
Prompt 3: First Week Schedule
The scenario: You want your new hire’s first week to feel structured, not chaotic. But you also don’t want to overload them with back-to-back meetings while they’re still figuring out where the bathroom is.
The prompt:
Create a first week schedule for a new [job title] joining my team.
Context:
- They're starting on [day of week]
- Key people they need to meet: [list roles, not names]
- Systems they need to learn: [list them]
- Their first project or focus area: [describe briefly]
Balance their week between:
- Orientation and setup
- Introductions and relationship building
- Learning time (reading docs, exploring systems)
- Actual work to get a small early win
Don't stack meetings all day. Leave buffer time for questions and absorbing information.Why this works: New hires often feel like their first week happens to them rather than for them. A structured schedule shows intention. It also protects their time from people who want to “grab 30 minutes” before they’ve even logged in.
Tip: Block an hour on Friday afternoon for a casual check-in. Ask what made sense, what didn’t, and what they need for week two.
Prompt 4: Role-Specific Training Checklist
The scenario: Every role has stuff to learn. Systems, processes, tribal knowledge that lives in someone’s head. You want to capture all of it so your new hire isn’t pinging you with questions for the next three months.
The prompt:
Create a training checklist for a new [job title] on my team.
They need to learn:
- Tools/systems: [list them]
- Key processes: [list recurring tasks or workflows]
- Team norms: [how we communicate, meet, make decisions]
- Domain knowledge: [industry or company-specific context]
For each item, include:
- What they need to know
- How they'll learn it (documentation, shadowing, hands-on)
- Who can help if they get stuck
- How to tell when they've got it
Start with the essentials for week one, then build out from there.Why this works: Most onboarding fails because it’s all in the manager’s head. This prompt forces you to externalize it. Once you have the checklist, you can reuse it for every new hire in the same role.
Tip: Have your new hire add to the checklist as they go. They’ll catch gaps you forgot about, and the next person benefits.
Prompt 5: First 1-on-1 Agenda
The scenario: Your new hire has been here a week or two. You’ve had hallway chats but nothing structured. You want to check in properly and catch any issues before they become problems.
The prompt:
Create an agenda for my first 1-on-1 with a new [job title] who started [X weeks ago].
Include questions that cover:
- How they're feeling about the role so far
- What's clicking and what's confusing
- Whether they have what they need (access, resources, clarity)
- Relationships - who have they connected with, who do they still need to meet
- Anything that's surprised them (good or bad)
- What I can do to help in the next two weeks
Tone: Supportive, not evaluative. This is about them, not their performance yet.Why this works: New hires often won’t tell you what’s wrong unless you ask directly. This agenda gives them permission to be honest. It also signals that you care about their experience, not just their output. If you need more structure for ongoing 1-on-1 meetings, we’ve got prompts for that too.
Tip: Don’t skip this meeting. The first few weeks are when small frustrations are still fixable. Wait too long and they become “just how things are.”
Making These Prompts Work
A few things that make these ChatGPT prompts for onboarding new hires more effective:
Front-load the context. The more specific you are about the role, team, and tools, the better the output. Generic inputs get generic onboarding plans.
Reuse and refine. Once you’ve got a solid 30/60/90 plan or training checklist for a role, save it. Update it each time you hire, but don’t start from scratch.
Share the outputs. These aren’t just for you. Give your new hire the plan, the checklist, the first week schedule. Transparency builds trust.
Check in early. Onboarding isn’t a document you hand someone and walk away. Use the first 1-on-1 to find out what’s actually landing and what’s not. Eventually, you’ll be writing their first performance review – a solid onboarding makes that conversation much easier.
Frequently Asked Questions
How soon should I start preparing for a new hire?
At least a week before their start date. Equipment, access, and meeting invites take longer than you think. Use the pre-arrival checklist and give yourself buffer time.
What if I’m onboarding someone into a role I’ve never hired for before?
Start with the training checklist prompt. It forces you to map out what they need to know even if you’ve never documented it. Then adjust as you learn what’s missing.
Should I share the 30/60/90 plan with the new hire?
Yes. On day one if possible. It sets expectations, gives them a roadmap, and shows you’ve actually thought about their success.
How do I know if onboarding is working?
Ask. The first 1-on-1 is your checkpoint. If they’re confused, overwhelmed, or missing key information two weeks in, you’ll hear it – but only if you create space for honesty.