A simple list of questions that I've found to be effective or find interesting to ask.

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.

  1. What are your long-term goals?

  2. How can I make your days more fulfilling?

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

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

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

  6. What do you like the least?

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

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

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

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

  11. What are you most excited about?

  12. 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.

  1. How is your family?

  2. How was your weekend?

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

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

  5. 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?

  6. What does your ideal weekday look like?

1: “Are you afraid of anything at work?”

2: “Have you seen something recently and thought to yourself ‘I wish we’d done that’?”

3: “Is there something we should measure in the company that we currently don’t?”

4: “Is there any part of the company you wish you were able to interact with more?”

5: “Are there any benefits we don’t offer that you’d like to see us offer?”

6: “Is there an area outside your current role where you feel you could be contributing?”

7: “Is there anyone at the company you wish you could apprentice under for a few weeks?”

8: “Have you seen someone here do great work that’s gone unnoticed?”

9: “Are there things you don’t know about the company that you feel you should know?”