31 Examples of Deep Conversation Starters

deep conversation starters

 

Have you ever tried getting to know someone on a deeper level; however, the conversation never seems to go anywhere? I think it’s safe to say, we have all encountered this at least once or twice throughout our lives. And while this isn’t necessarily a negative thing, it can be disappointing when the person you are trying to get to know better is closed off. On the other hand, you may have difficulties getting deep conversations to start in the first place. Luckily, we’ve put together a complete list of deep conversation starters that you can use to get to know others better. Therefore, keep reading to learn more.

Key Takeaways

  • Deep conversations are a great way to learn more about other people.
  • If you are going to have a deep conversation with someone, make sure you are in a comfortable and safe environment.
  • Ensure you are actively listening and using body language to show you are listening to others when they are speaking.

Deep Conversation Starters and Questions

Deep conversation starters usually begin by asking a question. Therefore, we’ve separated these questions into different categories so you can find the types of topics you’re looking for with ease. Further, one thing to remember is that when having a deep conversation with someone, you want to make sure it is in the appropriate environment. A lot of the time, these questions can be quite emotionally heavy. Therefore, make sure all parties involved feel comfortable and safe.

Additionally, you should pay attention to your body language to ensure you are actively listening to responses so you can meaningfully contribute to the overall conversation. Naturally, once the exchange has begun, you should be able to continue it pretty easily by asking further questions about the topic you have chosen. With that being said, let’s take a closer look at some of these deep conversation starters and topics below.

Want to take a free personality test? Take our free DISC personality assessment!

Watch this video to learn more about DISC and how it can help you improve your communication in the workplace:

Personal Questions for Deep Conversation Starters

  1. What is the hardest decision you have ever had to make?
  2. If you found out you had 24 hours to live, what would you do?
  3. What is your biggest regret?
  4. How would the people closest to you describe you as a person?
  5. What is your greatest goal in life?
  6. What makes you smile most in life?
  7. If you could live anywhere in the world, where would it be and why?
  8. When you die, would you somewhat be forgotten by others or hated? Why?
  9. If you could change one thing in your life, what would it be and why?
  10. What are three things you cannot live without?
  11. If you could spend one day with someone either living or not, who would it be and why?
  12. What do you value most in other people?
  13. Do you think money can buy happiness?
  14. What is your love language?
  15. What is the one thing you think you need to forgive yourself for?
  16. Do you believe in karma?
  17. How is your perfect day spent?
  18. What is the most valuable lesson in life you have learned this far?
  19. If you could say something to your younger self, what would it be and why?
  20. What is your favourite memory from your childhood?
  21. What makes you feel proud?
  22. If you won 10 million dollars, what would you do with it?
  23. Describe yourself in less than 10 words.
  24. What are you passionate about in life?
  25. What impression do you think you give to people when you first meet them?
  26. If you could be famous, what would you be famous for?
  27. What is the earliest memory you have?
  28. Who do you trust most in life?
  29. What is the best piece of advice you have gotten?
  30. What is one thing you miss about being a kid?
  31. Who do you aspire to be most like in life?

Questions About Emotions for Deep Conversation Starters

  1. Do you think having emotions are required for the human race to survive?
  2. What emotion is the most beneficial, and which is the least useful?
  3. Do you think that animals have emotions, and do you believe their experiences can dictate their feelings?

Questions About Life and Death 

  1. What do you think the purpose of human life is?
  2. Where do you think we go when we die?
  3. If you were to die tomorrow, what are some things you would wish you would have done?
  4. Would you rather know how you are going to die or when you are going to die?
  5. What does it mean to live your life to the fullest?
  6. What is a day in life worth?
  7. Do you believe in a higher spiritual power?
  8. Is taking a life justified under the right circumstances?
  9. If you could trade your life to save another, would you do it? Why or why not?

Other Questions

  1. Do you think artificial intelligence will help or hinder society?
  2. What is one conspiracy theory you wholeheartedly believe is true?
  3. Do you think our dreams have alternative meanings?
  4. What is something you believe should be taught in school that isn’t already?
  5. What is the most challenging aspect of your job?
  6. If you could change one thing about society, what would you change or why?
  7. Do you think people can really change for the better?
  8. What is your favourite quote, and why?

Final Thoughts

As you can see, there are many different deep conversation starters that you can use to get to know people beyond what’s on the surface. Remember, while not a complete list, these questions are meant to get your conversations flowing so you can naturally learn more about each other. Let us know if you have ever asked any of the ones on our list in the comments. Alternatively, comment on a deep conversation question below that we may have missed.

Recommended Resources:
 

Uncover your strengths and weaknesses with our complimentary assessment. Boost your effectiveness at work and with your team.

Free Resource Library
Access our extensive collection of valuable resources for instant support in your personal and professional growth.

Explore Our Course Library
Enhance your leadership skills with our diverse selection of courses. Take your abilities to the next level and become a more effective leader and team player.

Testimonials

Our Clients Love the Professional Leadership Institute

Your team will, too! Check out some reviews from our students.
The PLI program was invaluable to our network.
The range of topics delivered, the open dialogue, experience, and examples that PLI brought to each session were outstanding and provided a path for our Franchisees and Managers to look at leadership, coaching, and connecting with their teams in a new light. Many have implemented these strategies in their bakeries and have seen immediate results.
Michelle C.
COBS Bread
Highly recommend to help your team move forward
We have locations around BC and Alberta, so getting people on the same page can be very difficult... Until now. Our entire management team and location managers take the same great courses and then meet monthly online with our coach to apply it to our situation. People are engaged, the courses are excellent, we love our coach, and we are all learning together!
Jason Fawcett
President, Kelson Group
The result has been a transformation of our culture. 
We decided to implement PLI's strategies across the country in over 150 locations and over 3500 employees.  The result has been a transformation of our culture.  People's lives have been positively impacted - professionally and personally.  Morale is high and sales and profits are up as a result.
Daryl Verbeek
Daryl Verbeek
We’ve learned how to fix ongoing personnel issues once and for all
The roadmap laid out set our business up to quintuple in sales.  We've learned how to fix ongoing personnel issues once and for all, attract top talent, and spend our time focused on results, not internal staffing problems.  I highly recommend PLI to you - it's worked for us!
John DeJong
Satisfied Client
I had no idea that running a business could be this fun!
In less than 18 months of working with Trevor, he has transformed my business from being average to exceptional, where mediocrity is not acceptable, where being great is standard.  Working with PLI has allowed me to realize my dream of not simply owning a job, but owning a business.
Justin Bontkes
Principal, Caliber Projects
Our culture has taken major steps forward this year
Our culture has taken major steps forward this year with Trevor’s help.  He is funny, relatable, and his tools are very very practical and have helped us focus and upgrade our teams throughout our retail network. Trevor recently spoke to an employee group, and one person remarked, “I could listen to Trevor all day.”   We would highly recommend Trevor.
Stan Pridham
Founder, KMS Tools
The results have been remarkable
At first, we resisted, “This just won’t work with a law firm.” But we persisted and the results have been remarkable: our client base and profits have steadily improved, and staff engagement and morale is the healthiest its ever been.
Doug Lester
Partner, RDM Lawyers
Helped our fast-growing business become what it is today
I've experienced PLI's approach first hand and it's been crucial to sustaining our growth.  I can't imagine a business that wouldn't benefit greatly from his help.
Brian Antenbring
Founder, TEEMA
Provided practical ways to make positive changes
Trevor was incredibly well-received by the entire organization. He was able to articulate people issues that many of our franchisees were experiencing and provided them with practical ways to make positive changes. We have implemented the Star Chart tool across the organization and see it as vital to building happy, effective teams.
Aaron Gillespie
President, COBS Bread
Scroll to Top

Start Learning Today

For Individuals

Unlock your potential and accelerate your career with sought-after management and leadership skills.

 

Transform Your Organization

For Teams

Book a consultation to discuss your challenges and discover how we can help you build a winning team.

 

Sign Up For Weekly Tips!

Get Weekly Coaching Tips Straight To Your Inbox Every Monday.