The best one-on-one meetings are those that are 90% focused on the employee.

The best way for any manager to focus on the employee is to actively listen.

And the best way to be an active listener is to get good at asking great questions.

For some people, asking good questions comes naturally. For the rest of us, a little one-on-one prep work is best.

Hence, “The List.”

What follows is a list of questions we either: 1) personally use here at Jell during one-on-one meetings, 2) plan to use soon, 3) heard worked really well at companies we admire, or 4) have seen and thought: “Damn. That’d make for a really great question to ask at next week’s one-on-one.”

Some of these will work well for pre-meeting questionnaires. Others are best saved for the actual meeting. And there are a few that you’ll likely want to keep in your back pocket for the right moment.

If you want an easy way to improve the effectiveness of your one-on-one meetings, I highly encourage you to bookmark this page so you can use it as a quick-reference sheet from week to week.

Culture questions

Ask these questions to keep your finger on the pulse of actual team dynamics and company culture from your employees’ perspectives.

1. Are you happy working here?

2. Who do you admire within the company and why?

3. Who has really been kicking ass lately?

4. What do you like about working here? What’s not fun about working here?

5. If we could improve in any way, how would we do it?

6. What’s the number one problem within our organization? Why?

7. If you were me, what changes would you make?

8. What’s the biggest opportunity we’re missing out on?

9. What are we not doing that we should be doing?

10. Is there anything that’s slowing you down from getting your work done?

Personal productivity questions

These questions can be great for encouraging employees to speak up about some of the tougher issues that may need to be addressed for more productive day-to-day collaboration.

11. What are your long term goals?

12. How can I make your days more fulfilling?

13. What can I be doing better to help you in your job?

14. Are there any obstacles I can remove for you?

15. What do you like most about your job today?

16. What do you like the least?

17. Where do you see your career in the next (2/5/10) years?

18. What work are you doing here that you feel is most in line with your long term goals?

19. What’s one thing about your job that, if we fixed, would make you never want to leave?

20. What would you like to learn more about this year?

21. What are you most excited about?

22. What are you most worried about?

Work-life questions

Sprinkling in a few casual, personalized questions can help spur important discussions around the topic of how work fits into your employees’ overall lives—and what you can do to ensure it’s a welcomed, enjoyable part of each week.

23. How is your family?

24. How was your weekend?

25. How are you planning to balance work and personal life this year?

26. What are you doing for yourself outside of work?

27. Is there anything you’d like to be doing on your own time to relieve stress that you’re not getting to? How can I help you achieve those personal goals?

28. What does your ideal weekday look like?

Sources: Andreessen Horowitz, Lynda, Asana, Groove


Prepare for one-on-one meetings ahead of time with Jell. With Jell reports, you can get key questions answered ahead of time and enter one-on-one meetings prepped and ready to listen. It’s one of many Jell features designed with the goal of helping more managers become the bosses of employees’ dreams. Check out Jell reports here.