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https://www.cultureamp.com/blog/great-one-on-one-meeting-questions/
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General check-in questions
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Start each one-on-one meeting with a personal check-in. Knowing the mental state of your team is valuable context for how to proceed in the rest of the meeting.  These questions are important to ask every time, so you can understand how people are doing as far as work-life balance, wellbeing, and personal life. If something has come up for the individual, allow space to discuss it further. This is where flexibility is key – if you are too focused on getting through a rigid agenda then you might miss cues when your direct reports need support or guidance.
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1. How is everything going today? Tell me about this last week?
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2. What’s on your mind this week?
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3. Last time we spoke you said X was a challenge for you, how is that going?
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4. What are your plans and priorities this week?
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Alignment questions
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This is where you want to discuss company confidence, and how connected or aligned an individual feels to the organization. These are particularly important following an engagement survey, or any big change in your organization.
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5. Do you have any questions about the recent change involving X? (e.g. announcement from CEO, merger, teams).
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6. How confident do you feel with where the company is going?
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7. How aligned do you feel with where the company is going?
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Progress questions
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It’s important to understand how people feel they are progressing and where they are experiencing growth. This can relate to what they’re learning on the job and whether they are feeling a sense of achievement or momentum.
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8. What has energized you in your role [over a period of time]?
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9. What has challenged you [over a period of time]?
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10. What has gone well/not so well for you [over a period of time]?
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11. What’s one thing (or a few) you learned this week?
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12. Do you feel confident in how you/your team are progressing?
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13. How are you/your team progressing towards established goals?
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Relationship-based questions
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Interpersonal interactions are often a missed topic when it comes to one-on-ones, but they can have a huge impact on someone’s experience at work. Managers have a great opportunity to coach their team members when it comes to relationships at work.  You can also take this opportunity to ask for feedback on you as a manager and how your relationship is tracking.
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14. How is everything going with people you work with/on your team?
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15. Any interactions you’d like to discuss?
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16. What feedback do you have for me?
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Career aspiration questions
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Often career conversations are reserved for once a year when a review of some sort is done, or completely ignored if a manager doesn’t feel confident in leading the conversation. Career aspirations and goals are important to discuss much more frequently – you can even check-in weekly (i.e. what progress have you made on your career goals this week?).
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17. When you think about yourself in two years time, what comes to mind?
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18. What are two or three new skills you’d like to learn on the job?
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19. How are you progressing towards your bigger career and life goals?
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20. Is there someone at the company (or outside) that you’d like to learn from?
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21. What progress have you made on your career goals this week?
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Questions to close your one-on-one
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Ending your one-on-one meeting on an actionable question keeps the loop of feedback open.
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22. What are you committing to between now and the next time we meet?
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23. What can I help you with between now and the next time we meet?
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24. Is there anything we didn’t cover that you’d like to discuss next time?
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