In a small company, onboarding is mostly the founder or a manager talking. Asking the new person good questions at the right moment tells you what is confusing, what is missing from your documents and what they already know. Keep the list short: a new hire who gets a 50 question survey in week one will answer on autopilot.
Week one: what do you need to get started?
- What do you already know about how we work, from the interviews and from what you have seen?
- What has been unclear so far?
- Is there anything you have been waiting for, such as access, a person or a document?
- How do you prefer to get feedback and updates: written, a short call, or both?
- Whom have you asked for help, and did you get an answer?
Day 30: what is working and what is missing?
- What question did you have to ask more than once, and who answered it?
- Which document or answer was wrong, old or missing?
- Is your role what you expected when you accepted the job?
- What would have helped you in your first week?
- What is one thing we should stop doing or start doing for the next person?
Day 90: how is it going, and what next?
- What do you now know that you wish you had known on day one?
- Where do you still wait on one person for answers?
- What part of your work do you want to own more of?
- What should we write down so the next hire does not need to ask?
- What would make you want to stay and grow here?
Ask for the gaps, not for praise
The most useful answers are the specific ones: the question asked twice, the wrong document, the person who was never introduced. Ask open questions first, and add a rating scale only if you will act on the result. Timing matters: questions about career goals make little sense in week one, when someone is still finding the coffee machine.
Turn the answers into written answers
Every question a new hire asked more than once is a missing answer. Write each one down once, with an owner and a date, and send the next hire to the written version first. That is how onboarding gets lighter with every person you hire instead of staying a repeat of the same conversations.
Where an AI clone fits
An AI clone built on approved answers can take the new hire's routine questions, and pass the ones it cannot answer back to you. AskMyStartup is in private beta, and you can join the waitlist with your email below.
Related guides
A template to copy
Put this guide to work with New hire 30 60 90 day plan template for a small team: ten questions people ask, each with a blank for the approved answer.
Common questions
Five at each of three moments is enough: week one, day 30 and day 90. A short list gets honest answers, while a long survey gets rushed ones.
In the first week to remove blockers, around day 30 to find gaps in your documents and answers, and around day 90 to talk about growth and what the next hire needs.
Write down each missing or wrong answer once, with an owner and a date, and link new hires to it. Review the list after each hire.