The 30/60/90 plan for the person you just hired

The problem. You just hired someone, you’re relieved, and you have no real onboarding plan — just a vague intention to “get them up to speed.” A generic 30/60/90 template you find online won’t reflect what your specific, small, early-stage company actually needs from them.

The play. Draft a specific plan grounded in the actual JD you wrote and your actual goals — what they should be doing, learning, and shipping at each milestone — rather than a generic management-consulting template.

Setup (5 min). Have the JD you hired against and GOALS.md handy — see the job-description playbook if you don’t have one written down.

The prompt:

We just hired someone for this role: [paste the JD]. Here's GOALS.md for
what we're prioritizing right now.

Draft a 30/60/90 day plan:
- Day 30: what they should understand about the business and be doing
  independently, concretely — not "get ramped up"
- Day 60: what they should own with real autonomy
- Day 90: what "clearly a good hire" looks like, specifically, so we're not
  relying on a vague gut feeling at the 90-day mark

Be honest about our stage — don't assume resources, team size, or process
we don't actually have. Flag anything that depends on something we haven't
built yet (a tool, a process, another hire).

What you get. A specific plan tied to what this hire needs to actually do at your company, plus an honest, concrete definition of success at day 90 — so that conversation isn’t a vibe check.

What to watch for.

• If the draft assumes onboarding infrastructure you don’t have (a buddy system, existing docs), that’s a real gap to notice now, not a plan detail to gloss over.
• Share the plan with the new hire directly — a 30/60/90 they’ve seen and can ask about is far more useful than one that lives only in your own notes.

Make it repeatable. Reuse this for every hire in a similar function, updating it based on what actually happened last time — the gap between the plan and reality is the most useful thing to fix before the next one.