Do your conversations seem artificial and meaningless? Do you find it difficult to go beyond niceties and connect with your employees? What do you do when the answers you get are rote, scripted, and hide the “real” stuff underneath them?

The innocuous “How are you?” at the start of a conversation often begets a rote and scripted response like “I am fine,” or “I am doing good.” which is more of a conversation stopper than a conversation starter. Let us get serious and ask deeper conversation questions that prompt reflection and make space for deeper connections with people we care about. We must always ask a question out of curiosity and care, and never out of obligation and norm.

Every 2 weeks I share my most valuable learnings from living life fully in my Deploy Yourself Newsletter. Sign up now to download a workbook with 164 Powerful Questions which I use daily in my work and coaching. Allow these questions to transform your life and leadership.

Research has shown that people with deep relationships are healthier, happier, and live longer. Conversely, a lack of good relationships is associated with worse physical and mental health. The famous author Brene Brown says, “A deep sense of love and belonging is an irresistible need of all people. We are biologically, cognitively, physically, and spiritually wired to love, to be loved, and to belong. When those needs are not met, we don’t function as we were meant to.”

How Well Do You Really Know Your Colleague?
How Well Do You Really Know Your Employee?

You owe it to yourself to break the logjam of meaningless conversations and connect with employees on a deeper level. You can do that by asking some powerful connection questions – that will add meaning, purpose, and joy to your relationships. The below questions will reveal something real about a person’s life, character, and beliefs. These questions can’t be answered with a one-word response (good, yes, busy, fine) and will spark a deep conversation and build strong connections and relationships.

  1. Would you like to be famous? How?
  2. Define what your perfect day would look like?
  3. What are you most grateful for?
  4. If you could have one ability, which ability would you choose to have?
  5. What have you been waiting to do? Is there an unfulfilled dream? What are you waiting for?
  6. What do you value most in a friend?
  7. What is your best experience in life so far? What is your worst?
  8. Share an embarrassing moment from your life?
  9. If your house is burning, and the firefighter can only get one item out for you, what would you ask him to salvage? Why?
  10. If you can have lunch with anyone, whom would you like to have lunch with?

“The most important single ingredient in the formula of success is knowing how to get along with people.”―

Theodore Roosevelt

Life’s biggest lessons and opportunities often come out of deep relationships with others. We interact with many people daily, and isn’t it a wasted opportunity if we never get to know them deeply?

Bonus – More Connection Questions To Build Strong Relationships

If you liked the questions above, please find a more larger list of questions which I have collected from different people and sources over time.

  1. What’s your biggest struggle?
  2. What are you good at doing? What do you believe you are the best you? What have you gotten noticed for throughout your career?
  3. What do you enjoy? What do you look forward to doing? What energises you? What do you love about your work?
  4. What feels most useful? What kind of work makes you proud? Which of your tasks are most critical? What are your highest priorities in life? Where does work fit in?
  5. How has your life turned out differently than you expected it to?
  6. What do you feel most guilty about?
  7. How do you want to be remembered?
  8. What advice would you give yourself ten years ago?
  9. Where are you making a contribution to something bigger than yourself?
  10. What did you love to do most when you were 6 years old?
  11. Are you living a meaningful life?
  12. What’s the one thing you cannot live without?
  13. What inspires you the most?
  14. What is one dream you have yet to accomplish?
  15. What is your greatest fear?
  16. If you could change one thing about yourself what would it be?
  17. If you could tell your former self one thing right now what would it be?
  18. What did you really love doing as a kid but don’t really do anymore?
  19. What is stopping you from doing it now, and what would happen if you did?
  20. If you could, what is the one thing you would change about your past?
  21. What in your life has been on hold? What have you been waiting for?

We all know the warm feeling of human embrace and connection when we feel heard and understood by another human being. Deeply connecting with another person builds trust and inspires us. Asking powerful questions (and sharing our own answers to them) helps to understand what people value and to glimpse life from someone else’s perspective. On various occasions, I have been surprised on finding out how someone I thought was very different shares his or her deepest values with me. And vice-versa.

Asking these questions and listening to the answers often require practice and empathetic listening. But it can be very rewarding to establish deep connections with friends or colleagues. It makes working with them easier, joyful and leads to long-lasting relationships.