Free AI 30-60-90 Day Plan Generator
Describe the role in a sentence. Get a 30-60-90 day plan the new hire and their manager can work through together: goals and tasks for each stage, a check-in at the end of each 30 days with the outcome recorded, and due dates counted from the start date.
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The CheckFlow AI 30-60-90 day plan generator turns a one or two sentence description of a role into a 30-60-90 day onboarding plan, free and without an account. It writes the plan as a checklist template, with three stages, tasks with due dates counted from the start date, and check-ins that record progress and the next goals. Start a free trial to assign it and run it.
From a sentence to three months with a plan.
1. Describe the role
Say who is joining and what success looks like, such as “a new customer success manager, with a manager check-in at the end of each 30 days”. Up to 500 characters.
2. Watch the plan being built
The generator checks the template library first. If nothing fits, or you ask for a new one, it builds the plan step by step in a preview of the template designer, usually in 15 to 30 seconds.
3. Run it with the new hire
Start a free trial and the plan becomes a template in your workspace. Start one for each new hire and every task falls due on the right day.
The basics
What a 30-60-90 day plan is
A 30-60-90 day plan sets out what a new hire should learn, take on and deliver in their first three months, in three stages. The first 30 days are usually about learning and meeting people, days 31 to 60 about taking on real work, and days 61 to 90 about working independently. A review at the end of each stage checks progress and sets the next goals.
It is written by the hiring manager with the new hire. It is not the plan a candidate brings to an interview. A good plan has these parts.
- 01
Goals for each stage
Measurable, and agreed with the new hire.
- 02
Tasks with dates
Counted from the start date, so the plan moves if the start date does.
- 03
The people to meet
Who they should get to know, and by when.
- 04
A check-in at 30, 60 and 90 days
With the outcome written down, not just held.
- 05
Support when it is off track
Extra steps for someone who needs more help.
- 06
An owner
Usually the hiring manager, with HR able to see progress.
For goals and examples at each stage, read our 90-day onboarding plan guide. For the tasks before and on day one, use the AI onboarding checklist generator.
A real example
What the generator built from one sentence
We gave the generator “Create a 30-60-90 day onboarding plan for a new customer success manager, with goals and a manager check-in at the end of each 30 days” on 26 October 2026. The library had a ready-made 30-60-90 Day Onboarding Plan, so the generator showed that first. We chose Generate a New One with AI Instead, and it wrote Customer success manager: 30-60-90 day onboarding.
It came back with 12 steps in 3 sections, “Days 1–30: Learn and align”, “Days 31–60: Build ownership” and “Days 61–90: Operate independently”, with 15 fields and 12 due dates. Every step is due a set number of days after the checklist starts: the first goals after 3 days, the three manager check-ins after 30, 60 and 90 days, and the work in between spread across each stage. A date that falls on a weekend moves to the next business day.
Each check-in records the progress and support needed, then the agreed goals for the next stage. It added no conditions or halts this time. To get extra steps for a check-in that goes badly, say so in the description. The same description within 30 days gives the same plan back.
- Three stages of 30 days
- A due date on every task
- Check-ins with the outcome recorded
- Goals agreed for each next stage
- One template for every new hire in the role
Draft and finish
What the generator drafts, and what you add
The free generator gives you a first draft from a description. The parts that depend on your team and the person joining are finished in CheckFlow.
| Part of the plan | Free generator | In CheckFlow |
|---|---|---|
| Stages and goals | Three stages, with goal-setting tasks | Edit the goals for the role, or add a stage before day one |
| Tasks and dates | Due dates counted from the checklist start | Start the checklist on the first day, or count from a start-date field instead |
| Check-ins | A check-in at the end of each stage, with fields for the outcome | Make the fields required, and add an outcome drop-down |
| Support when off track | Only when the description asks for it | Add steps that appear only for a “needs support” outcome |
| Who does each task | Not assigned | Assign tasks to the manager, the new hire, HR or a buddy |
| Overdue tasks | Not set | Overdue alerts go to the task’s assignees, or to Administrators when nobody is assigned |
| Every new hire | One template | A checklist per new hire, each one visible in the Reports Grid |
See onboarding software for how teams run onboarding in CheckFlow, and HR checklist software for the rest of the employee lifecycle.
Tips
How to describe a role for a better first draft
- 01
Name the role and the team
“A customer success manager joining a team of six” gives a closer plan than “new hire plan”.
- 02
Say when the check-ins happen
At 30, 60 and 90 days, weekly, or with someone other than the manager.
- 03
Say what success looks like at 90 days
A first release, a full customer portfolio, a store run without help: the plan works back from it.
- 04
Leave out personal details
Describe the role, not the person. The new hire is chosen when the checklist starts.
Free AI generators
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Already have a plan in a document?
The free generator works from one description. Inside CheckFlow there are two more ways to build a 30-60-90 day plan with AI.
Import the plan you already have
Generate with AI reads Word, PDF, Excel and CSV files, web pages and photos of paper checklists, and builds the template in the designer, assigning tasks to your existing groups.
AI in CheckFlowBuild it in conversation
Claude, ChatGPT, Gemini, Grok, Copilot or any other AI assistant can connect to the CheckFlow MCP server, talk the role through with you and build the template in your workspace.
Read the MCP guideThe first-day checklist too
For the paperwork, equipment and accounts before day one, use the onboarding checklist generator.
AI onboarding checklist generator
Assign the check-ins in our 30-60-90 plan to the hiring managers, and the rest to the new hire.
read: "members, groups, tags, templates"
Your workspace has a Managers group, so I will assign the three check-ins to it and leave the other tasks to be assigned to the new hire when each plan starts. I will show you the change before publishing.
Onboarding templates with a live demo
Prefer to start from one written by people? Each opens as a live checklist.
Related pages
AI 30-60-90 day plan generator questions
Is the AI 30-60-90 day plan generator free?
Yes. You can generate and preview 30-60-90 day plans without an account or a credit card. To keep it free for everyone there is a limit on how many templates can be generated in an hour, and a template found in our library does not count towards it. To edit it and run it with your team, start a free trial.
What does the generated plan include?
A name and a short description, the tasks grouped into stages, short instructions where they help, fields to record goals and check-in outcomes, and due dates counted from the start of the checklist. When the description asks for them, it also adds steps that only appear for certain answers and halts on steps that must be done first.
Is this the same as a 30-60-90 day plan for a job interview?
No. Candidates write those to show how they would approach a role. This generator builds the onboarding plan a manager runs with someone who has already joined, so the tasks have owners and due dates and the check-ins have a record.
How are the due dates worked out?
In our example every task was due a set number of days after the checklist started, from 3 days to 90, moved to the next business day when it fell on a weekend. Start the checklist on the new hire’s first day, or change the rules in the template designer to count from a start-date field instead.
How is it different from the AI onboarding checklist generator?
The onboarding checklist generator covers the tasks before and around the first day: paperwork, equipment, accounts and introductions. A 30-60-90 day plan covers the goals and check-ins over the first three months. Many teams run both, one after the other.
Can I use one plan for every new hire?
Yes. Keep one template per role and start a checklist from it for each new hire. Each one has its own due dates, assignees and record, and the Reports Grid shows where every new hire is in their plan.
Why did I get a template from your library instead?
Before generating anything, the generator compares your description with the ready-made templates in our template library. When one is a close match you see it straight away, written by our team rather than by AI. If it is not what you wanted, choose Generate a New One with AI Instead.
What happens to what I type?
Your description is compared with our template library and, if nothing fits, sent to an AI model. Both run on Microsoft Azure for CheckFlow, and your description is not used to train AI models. The description and the template are kept for up to 30 days, so the same request gets the same answer and the template is still there when you sign up. Please leave personal details out. See our privacy policy.
Give the next new hire a plan they can follow.
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