First one-on-one questions to ask a new direct report

Getting to know them

• What do you enjoy most about your work?Copy
• What are you proudest of from the last year?Copy
• What is something about you that would surprise the team?Copy
• What do you want to be doing in two or three years?Copy

How they like to work

• How do you like to receive feedback: in the moment, in writing, or saved for our one-on-ones?Copy
• When are you most focused during the day, and how can I protect that time?Copy
• How do you prefer to hear from me: chat, email, or a quick call?Copy
• What did your best manager do that you would like me to keep doing?Copy
• What did a manager do that you never want to experience again?Copy

The job and the team

• What is going well in your role right now?Copy
• What is getting in your way that I might be able to remove?Copy
• If you were in my seat, what is the first thing you would change?Copy
• Is there anything I should know about the team that nobody will tell me?Copy

Agreeing how you will work

• How often should we meet, and for how long?Copy
• What would make these one-on-ones useful for you?Copy

How to run it

• Tell them what the meeting is for at the start: "This is about getting to know how you work, not about checking up on you."
• Share something about how you work too. A short manager user guide makes this easy.
• End by agreeing when you will meet next and one thing you will each do before then.

What to avoid

• Turning it into a project status update.
• Promising changes you cannot deliver yet.
• Asking all 15 questions. Pick five.