My favorite random 1-1 questions

If the organic conversation dies down and we still have time left in a 1-1 meeting, I like to toss out an open ended question and see what happens.

Here are a few of my favorites:

• Who at the company do you wish you could work with more and why?
• Who at the company do you wish you could trade places with and why?
• Where have you failed recently?
• What’s your stress level, one to ten? What would need to change for it to be one less?
• What’s the next thing you’d be excited to learn about?
• What part of your job do you wish you didn’t have to do?
• What’s slowing you down the most right now?
• Is this job what you expected when you accepted it?
• What’s the first thing you’d do if you were CEO?
• What’s the first thing you’d do if you were me?
• What are your superpowers?
• Do you feel like you’re getting enough feedback?
• What’s the least valuable meeting you have regularly and why?
• What’s something you do that you feel is undervalued?
• What do you think is your greatest accomplishment here?