Help me design a 30/60/90 day plan for someone I'm hiring. I want them to ramp fast, contribute by day 90, and not regret joining.
NEW HIRE'S ROLE: {title + level}
TEAM SIZE + COMPOSITION: {who}
CRITICAL PROBLEM they'll own: {real_problem}
WHAT 'SUCCESS BY DAY 90' looks like to me: {observable_outcome}
MANAGER ME: {hands-on / hands-off / process-light / structured}
REMOTE / HYBRID / IN-OFFICE: {policy}
WHAT WE'RE BAD AT as a team (be honest): {weakness}
MENTOR OR BUDDY?: {assigned or not}
WHAT THEIR FIRST PROJECT WILL BE: {concrete_first_deliverable}
WHAT THEY'LL HEAR (in week 1) that I want to pre-empt: {team_drama_or_history}
DELIVER for each phase (30 / 60 / 90):
1. **Outcomes** — what they'll have done.
2. **Inputs from me** — what I owe them (meetings, docs, intros, feedback).
3. **First 3 people they meet** + why each one.
4. **A single 'visible win'** they should ship in this phase.
5. **What to NOT push them on yet.**
6. **The honest check-in question** at the end of the phase: 'are you still glad you joined?'
7. **Red flag signals** that ramp isn't going well.
Also:
- A week-1 day-by-day plan (Mon-Fri).
- A doc I should write before they start (1 page: what success looks like, in writing).
- The 3 most-common 90-day failure modes for new hires + how to prevent each.
No 'introduce them to the team' generic stuff. Specific, opinionated.0 copies·0 saves·2 views
234 words·1,369 chars
Sample output
New hire: Senior PM. Team: 1 EM, 5 eng, 1 designer, 1 PM (them) — I'm the head of product. Critical problem: retention has been flat for 9 months; this PM owns the retention pod. 90-day success: has launched at least 1 retention initiative that affects metrics + has a written 6-month plan reviewed by leadership. Style: structured, hands-off after week 2. Remote. Team weakness: we ship without explicit hypotheses too often. No buddy assigned yet. First project: the dunning email overhaul that's been on the backlog for 4 months. Pre-empt: the previous PM left under tension with the EM; team is wary.
Pre-start: write this doc (1 page) before they start:
'Sasha — what success looks like in your first 90 days: By day 30, you've spent time with all 5 engineers + the designer 1:1, attended 8+ customer calls, and written a 1-page 'patterns I've noticed' doc. By day 60, you've shipped the dunning email overhaul, and you've published a written hypothesis-led plan for the next 2-3 retention bets. By day 90, the dunning project has shipped and is being measured, AND you've got an agreed-on 6-month plan with the EM and me. You should also feel like you have a real handle on which 3 customers we should be talking to most.'
Give this to them on day 1. They will refer to it 10 times.
Days 0-30 — Learn the system + ship one small thing
Parameters
Text generation parameters
FAQ
Write the 1-page success doc and SEND it before their first day. New hires read it on the weekend before they start. That doc shapes more of their first month than any 1:1. The prompt targets Claude Sonnet and lives in the Personal & Career category on mycopyprompt.
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Outcomes:
Inputs from me:
First 3 people they meet (besides their team):
Visible win in this phase:
Don't push them on:
Check-in at day 30: The honest question: 'are you still glad you joined?' Asked at end of a 1:1, with permission to be honest. The answer tells you 80% of what you need.
Red flags at 30 days:
Days 31-60 — Ship + start to lead
Outcomes:
Inputs from me:
Visible win:
Don't push them on:
Check-in at day 60: Ask: 'what's one thing that's working that you didn't expect, and one thing that's harder than you thought?'
Red flags at 60 days:
Days 61-90 — Own the path
Outcomes:
Inputs from me:
Visible win:
Don't push them on:
Check-in at day 90: 'In 5 minutes, walk me through what you'd do in the next quarter.' If they can do it cleanly, ramp went well. If they pivot to 'I need to understand more,' there's still real ramp left — that's OK to name.
Red flags at 90:
Week 1 day-by-day:
Mon: 60 min with me (welcome + success doc walkthrough). Tour of internal tools/docs. Setup access. End early. Tue: 1:1 with EM Maya (60 min). 1 hr customer call sit-in. Wed: 1:1 with each engineer (30 min × 5). Brain-melting but the highest-ROI day of the week. Thu: 1:1 with designer. Read 3 most-recent retention docs. Lunch with me. Fri: 1:1 with head of data + head of CS. End-of-week 30 min with me to debrief.
3 most common 90-day failure modes:
Manager goes silent after week 1. New hire thinks they're doing fine, isn't. Prevention: daily 15-min for first 5 days, weekly thereafter. Non-negotiable.
First project is too big. New hire flounders in scope. Prevention: pick a project that's 60% understood, 40% to-be-figured-out. Dunning email is right-sized.
'Just ramp up however feels right' onboarding. New hire spends 6 weeks in code/docs, hasn't talked to a customer, suddenly is expected to have strategy. Prevention: customer calls in week 1. Non-negotiable.