Most Effective Questions To Ask On One-On-Ones

 Perhaps the CEO's most important operational responsibility is designing and implementing the communication architecture for your company. The architecture includes organizational design, meetings, process, email, and one-on-one meetings with managers and employees. 

The key to a good one-on-one meeting is the understanding that it is the employees meeting rather than the manager's meeting. This is the free form meetings for all the pressing issues, brilliant ideas, and chronic frustrations that do not fit neatly into status reports, email, and other less personal and intimate mechanisms. 

Some questions to ask in one-on-ones: 

• If we could improve in any way, how would we do it?
• What's the number one problem with our organization? Why?
• WHat's not fun about working here?
• Who is really kicking ass in the company? Whom do you admire? 
• If you were me, what changes would you make?
• What don't you like about the product?
• What's the biggest opportunity that we're missing out on?
• What are we not doing that we should be doing?
• Are you happy working here? 

General Check In Questions

• What's are your plans and priorities this week?
• What's one thing you feel you learned this week?
• Do you feel confident in how you/the team are progressing? 
• How is everything going with the people you are working with on your team?
• What is the primary thing you would like me to help you on from now until our next meeting? 

Career Aspirational Questions

• When you think about yourself in two years time, what comes to mind?
• What two or three new skills would you like to learn on the job?
• Is there someone at the company our outside of the company that you would like to learn from?
• What progress have you made on your career goals this week?