TL;DR — The questions worth asking at 30, 60 and 90 days are different at each stage, and the answers tend to be more honest on video than in a written survey, where people default to safe, short answers. Below is a question set for each milestone and guidance on how to ask them.
- 30, 60 and 90 day check-ins should ask different questions, not a repeated template.
- A video response surfaces hesitation and tone a written survey answer hides.
- Keep it short — two or three questions per check-in, not a long form.
- Make clear the check-in is about improving onboarding, not evaluating the new hire.
On this page
Why the three milestones need different questions
At 30 days, a new hire is still working out whether basic things are clear — what their role actually covers, who to ask for what. At 60 days, the useful questions shift toward how the work itself is going and whether early impressions are holding up. By 90 days, the better questions are about fit and whether what was promised at hiring matches the reality of the role.
Questions by milestone
| Stage | Focus | Sample questions |
|---|---|---|
| 30 days | Clarity and basics | "What's still unclear about your role?" / "Who have you not met yet that you probably should have?" |
| 60 days | Workload and early fit | "What's taking longer than you expected to get comfortable with?" / "What's one thing that's gone better than you expected?" |
| 90 days | Overall fit and accuracy of expectations | "Does the role match what you expected when you accepted it?" / "What would have made your first three months easier?" |
Why video gets more honest answers than a form
A written survey at the 30 or 60 day mark tends to produce safe, short answers — new hires are naturally cautious about putting criticism in writing early in a job. A short video response, recorded privately and reviewed by one manager rather than circulated, tends to surface more — tone, hesitation, and the kind of detail that gets smoothed out of a typed sentence.
How to run the check-in without it feeling like an evaluation
Frame the request explicitly as feedback on the onboarding process, not a performance check — say so in the message that goes with the link. Ask two or three questions, not a long list, and make clear who will see the response. See Onboarding Video Checklist for where these check-ins fit alongside the rest of the onboarding timeline.
How to do this in Whoosh
Set up a short check-in campaign for each milestone with two or three questions, and send the link a few days ahead of the actual date so the new hire has time to think rather than answering on the spot. Responses land privately for the manager to review.
Start freeFrequently asked questions
Should the manager or HR send the check-in request?
Either works, but whoever sends it should also be the one reviewing the responses — new hires answer more openly when they know who will see it.
How long should each check-in take to complete?
Two to three minutes total across two or three short questions; longer than that and it starts to feel like a task rather than a quick check-in.
What should happen after the 90 day check-in?
Follow up on anything specific that was raised, even briefly — a check-in that produces no visible response trains people to stop answering honestly.
Can this replace a formal 90-day review?
No — treat it as a lighter-weight, more candid complement to a formal review, not a replacement for one.