ONE-ON-ONE QUESTIONS · 15 QUESTIONS

One-on-one questions for new employees (first 90 days)

In the first 90 days a new hire is quietly deciding whether they made the right choice. Weekly one-on-ones with the right questions help them settle faster and tell you early if something is going wrong.

Week one to two

  • How has your first week compared with what you expected?
  • Do you have everything you need: access, equipment, information?
  • Who have you met so far, and who else should you meet?
  • What has been confusing that nobody has explained yet?

Month one

  • What is clearer now than it was on day one?
  • What would have made your first month easier?
  • Do you know what success looks like for you at three months?
  • Is the job what you thought it would be?
  • Who has been most helpful so far?

Month two to three

  • What do you feel confident doing on your own now?
  • What are you still unsure about?
  • With fresh eyes, what do we do that seems strange or slow?
  • What would you change about how we onboard people?
  • How are you finding working with the team?
  • What would you like to take on next?

How to run it

  • Meet weekly for the first three months, even if it is short.
  • Write down their "fresh eyes" observations. They disappear after month three.
  • Agree a 30-60-90 day plan in the first week so both of you know what good looks like.

What to avoid

  • Overloading them with information in week one.
  • Asking "any questions?" and moving on. Ask specific ones.
  • Waiting until the probation review to give feedback.

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