30-60-90 day plan prompt: free ChatGPT template
Updated · By Robert Breen
Use this when someone new starts and you want both of you to agree on what "doing well" means by day 90. Without a plan, the first three months drift and the first real feedback comes too late. This prompt lays out three phases (learn, contribute, own) with a few goals each, how you'll both know each goal is done, the people to meet and the check-in dates. It uses only the targets you give it, so it won't invent a quota.
It works for the manager writing the plan or for a new hire drafting their own to bring to the first one-on-one.
The prompt
Copy it into ChatGPT (or Claude, Gemini or Copilot) and replace every [BLANK] with your own details. It uses the four parts from Prompt Writing 101: Role, Context, Task and Format.
Role: You are a manager at [BUSINESS], writing a 30-60-90 day plan for a new hire. Context: The new hire is [NEW HIRE AND ROLE], starting [START DATE]. By day 90 they should [DAY 90 OUTCOME]. Resources and people they'll work with: [RESOURCES AND PEOPLE]. Use only the targets and numbers I've given. Don't invent quotas, metrics or deadlines; if a goal needs a number I haven't given, write TO SET. Task: Write the plan in three phases: days 1 to 30 (learn), 31 to 60 (contribute) and 61 to 90 (own). Give each phase three or four goals, and for each goal say how we'll know it's done. List who to meet in the first two weeks and suggest a check-in at the end of each phase. Format: One table per phase with the columns Goal, Done when, Support. Then a short Who to meet list and the three check-in dates counted from the start date. Under 400 words.
Fill in the blanks
[BUSINESS]- Your business name and what you do.
[NEW HIRE AND ROLE]- First name and job title.
[START DATE]- The first day, so the check-in dates are real.
[DAY 90 OUTCOME]- The one or two things they should be doing on their own by day 90, with numbers if you have them.
[RESOURCES AND PEOPLE]- Playbooks, SOPs, tools and the people they'll learn from.
Example, filled in
A made-up example from the free lesson Build a Custom GPT That Writes Sales Follow-Up Emails. Northwind Scheduling Software is the made-up software company in the sales follow-up Custom GPT lesson, which loads a sales playbook into a GPT. A new account executive starts in November.
Role: You are a manager at Northwind Scheduling Software, a scheduling app for service businesses, writing a 30-60-90 day plan for a new hire. Context: The new hire is Ava, account executive, starting Monday, November 2. By day 90 they should run their own demos and follow-ups for inbound leads and hold a pipeline of at least 15 qualified deals. Resources and people they'll work with: our sales playbook and follow-up rules, the CRM, call recordings of past demos, Ben (senior account executive) for shadowing, and me for weekly one-on-ones. Use only the targets and numbers I've given. Don't invent quotas, metrics or deadlines; if a goal needs a number I haven't given, write TO SET. Task: Write the plan in three phases: days 1 to 30 (learn), 31 to 60 (contribute) and 61 to 90 (own). Give each phase three or four goals, and for each goal say how we'll know it's done. List who to meet in the first two weeks and suggest a check-in at the end of each phase. Format: One table per phase with the columns Goal, Done when, Support. Then a short Who to meet list and the three check-in dates counted from the start date. Under 400 words.
What a good answer looks like
- A learn phase built on your playbook, call recordings and shadowing Ben, not generic "get to know the culture."
- "Done when" lines you could check, such as "ran two demos with Ben observing and used the follow-up rules afterward."
- The 15-deal pipeline in days 61 to 90, and TO SET wherever a number would have been made up.
- Check-in dates counted from November 2 (early December, early January, end of January), with none on New Year's Day.
How to check it before you use it
An AI draft can sound right and still say something you never told it. Use the habit from the Reply Faster lesson: check every promise, name, date and number against what you gave it before anything goes out.
- Check every number in the plan. If it isn't one you gave, it's invented; replace it with your number or TO SET.
- Count the check-in dates from the start date yourself, and move any that land on a weekend or holiday.
- Ask whether each phase is realistic for someone new. Owning deals in month one usually isn't.
- Share it on day one and change it together at the first check-in; a plan the new hire helped shape is one they'll use.
Why this prompt works
TO SET does for a plan what "Not stated" does in a meeting summary: it marks a gap instead of filling it with a guess. The Done when column makes each goal checkable, a simple output format choice that changes how useful the plan is at day 30.
Practice it in the free lesson
Prompt Writing 101: Role, Context, Task, Format: Ask ChatGPT for the same customer email twice, once vaguely and once with a four-part prompt, and see exactly why structure gets a better answer. You do every step yourself in a practice copy of ChatGPT, and nothing touches your real accounts.
Also useful: Build a Custom GPT That Writes Sales Follow-Up Emails
Terms used here
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