A 30-60-90 day plan that works at a 20-person company

Thirty days is long enough to know whether someone understands the work, sixty to know whether they can do it without supervision, and ninety to know whether they can improve it. Splitting the first quarter this way gives you two chances to correct course before the conversation gets hard.

Write the plan before the offer is signed. If you cannot describe what "good" looks like at day 30, the role is not defined well enough to hire for yet.

The goal is context, not output. The hire should finish this stretch able to explain what the company does, who the customer is, and how their work reaches that customer.

• Required reading — Handbook, security basics, product overview, and how your team writes things down.
• Meet the map — Six to eight short intros with the people they will actually depend on, each with a stated purpose.
• First real task — Something small and shippable in week one, reviewed by their manager, so they learn your process by using it.
• Checkpoint at 30 days — One question: can they describe the customer's problem in their own words and name the part they own?

Now shift from supervised to accountable. Hand over a recurring responsibility with a real name, not a vague area.

• A named responsibility — One recurring deliverable, process, or account that is now theirs by default.
• Measurable target — A simple count for the period: tickets resolved, calls made, features shipped, shifts closed.
• Feedback in both directions — Ask what's slower than it should be. A 45-day hire sees your friction more clearly than you do.
• Checkpoint at 60 days — Can they run their responsibility for a week with no one checking in?

By day 90, a good hire is changing something, not just executing. Ask for one concrete improvement to the work they inherited.

• One improvement shipped — A process cleaned up, a doc written, a step automated, a metric moved.
• Goals for the next quarter — Set them together so expectations are shared rather than announced.
• Onboarding retro — Ten minutes on what was missing from their plan. Fold the answer back into the template for the next hire.

The reason onboarding erodes at fast-growing companies is that the plan lives in one person's notes. Keeping it as a role template means the fifth hire gets the same start as the first, with each checkpoint visible to the hire instead of hidden in a manager's head.