17 Fun questions to ask your new boss

17 Fun questions to ask your new boss: Starting a new job is both exciting and nerve-wracking. As you navigate the uncharted waters of a new workplace, building rapport with your new boss is crucial. While professional conversations are essential, asking fun and engaging questions can help break the ice and create a positive working relationship. In this blog post, we’ll explore 17 fun questions to ask your new boss to foster a friendly and productive atmosphere

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17 Fun questions to ask your new boss.

1. What Inspired You to Pursue a Career in This Industry?

  • Significance: This question demonstrates your interest in your boss’s background and motivations. It’s an excellent conversation starter that can help you understand your boss’s passion for the industry and possibly identify shared interests.

2. Do You Have Any Favorite Team Traditions or Office Rituals I Should Be Aware Of?

  • Significance: Asking about team traditions and rituals shows your eagerness to integrate into the existing workplace culture. It can help you bond with your colleagues and feel like part of the team more quickly.

3. If You Could Travel Back in Time, What Career Advice Would You Give Your Younger Self?

  • Significance: This question can lead to valuable insights into your boss’s career journey. It may reveal lessons learned, mistakes made, and pivotal moments in their professional development.

4. What’s Your Favorite Book or Movie, and Why?

  • Significance: Discovering your boss’s personal interests can help you establish a connection beyond the workplace. You might find common ground for conversations outside of work-related topics.

5. If You Could Swap Jobs for a Day with Anyone in the Company, Who Would It Be and Why?

  • Significance: This question can provide insights into your boss’s perspective on various roles within the organization. It also encourages a dialogue about career aspirations and goals.

6. What Are Your Top Three Tips for Thriving in This Company?

  • Significance: Seeking advice directly from your boss is a proactive approach to excelling in your new role. It shows your commitment to learning and growing within the company.

7. Have You Had Any Memorable Team-Building Experiences in Your Career?

  • Significance: Sharing stories of team-building experiences can create a sense of camaraderie within your new team. It also helps you learn about your boss’s past collaborations and leadership style.

8. What’s Your Go-To Coffee Order or Favorite Snack for Long Days at the Office?

  • Significance: Understanding your boss’s preferences for coffee or snacks can be a practical icebreaker. It might lead to friendly gestures like bringing them their favorite beverage or snack.

9. If You Could Add One Fun Activity to Our Workplace, What Would It Be?

  • Significance: This question shows your interest in contributing to a positive office environment. It can spark discussions about team-building activities or morale-boosting initiatives.

10. Can You Share Any Amusing Office Anecdotes or Funny Moments from Your Career? 

– Significance: Sharing humorous stories from the workplace can lighten the atmosphere and create a more relaxed and enjoyable work environment. It also allows you to connect on a human level.

11. What’s Your Favorite Way to Decompress After a Busy Workday or Week? – 

Significance: Learning how your boss relaxes outside of work can provide insights into their work-life balance and help you discover shared interests or hobbies.

12. Do You Have Any Pets?

 If So, Tell Me About Them! – Significance: Many people love to talk about their pets, and this question can lead to heartwarming and friendly conversations. It’s an excellent way to create a personal connection.

13. What’s the Most Unexpected or Unique Skill You Possess Outside of Work? – 

Significance: Uncovering your boss’s hidden talents can be both intriguing and entertaining. It’s an opportunity to learn something unexpected about them and possibly share similar interests.

14. If You Could Invite Anyone (Dead or Alive) to Dinner, Who Would It Be and Why? – 

Significance: This question can lead to thoughtful and engaging discussions. It helps you understand your boss’s interests, values, and even their role models.

15. What’s the Most Unusual or Funniest Request You’ve Received from an Employee or Colleague? –

 Significance: Sharing amusing workplace stories can create a positive and friendly atmosphere. It’s a chance to bond over shared workplace experiences.

16. Are There Any Fun Team Challenges or Competitions You’d Like to Organize in the Future? –

 Significance: Expressing interest in team activities demonstrates your enthusiasm for team bonding and collaboration. It can also lead to brainstorming fun ideas for team-building events.

17. What’s Your Favorite Motivational Quote or Saying That Keeps You Inspired? – 

Significance: Learning about your boss’s sources of inspiration can provide you with shared motivation. It can also help you understand their leadership style and principles.


Building a positive and productive relationship with your new boss is essential for your success and job satisfaction. While professional conversations are vital, incorporating fun questions into your interactions can help you connect on a personal level. These 17 fun questions are just a starting point; feel free to adapt and expand upon them to suit your specific workplace and relationship with your boss. Remember that building a positive relationship takes time, so be patient and genuine in your interactions. By fostering a friendly and open atmosphere, you’ll likely find that your work experience is more enjoyable and rewarding.

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