The first three are what I call ‘safe’ questions. Meaning, they are more surface level. They aren’t questions that causes them to be vulnerable, but nonetheless will reveal a little bit about them.

  1. Are you an introvert or an extrovert?
Asking this question will tell you a little bit about their personality. Do they like to recharge their energy when they are alone or by being with other people?

  2. What are your hobbies?
This question draws insight to their interests. What do they like to do for fun outside the hustle and bustle of life? This question will show you a bit of their softer side because they get to talk about things they like to do.

  3. If you could choose to do anything for a day, what would it be?
This question lets them reveal aspects of their ideal life. Picturing what they would want to do without limits will show you what’s important to them.

The rest of the questions go deeper beyond surface level. These questions call for the person to do some self-reflection and will show you more of their personal and vulnerable aspects.

  4. What is your biggest fear?
This question can go deep. But asking them this question will take you into their inner world and show you what occupies their mind and what worries them. The benefit of asking this question is that they verbalize it and get it out of their mind and you can assure them that they are not alone, or the only one with those fears.

  5. What would you change about yourself if you could?
There’s a sense of vulnerability in this question. It makes them reflect on what they currently aren’t satisfied within themselves and makes them aware of what they would want to improve on (This question is not referring to physical qualities).

 6. What did you want to be when you were younger?
When you were younger, your aspirations were more likely clear because your desires were reflected by your values and not influenced by other limiting attributes such as money or time.

  7. Where do you see yourself in five years?
This question often invites them to consider what they want to achieve. Asking them will reveal more about their values and motivations.

  8. If you could go back in time to change one thing, what would it be?
This question often reveals some kind of regret they might have. It will most likely show a life lesson that they learned.

  9. What is one thing you will never do again?
This question piggy backs on the previous question. However it’s a little different. They probably needed to do a particular thing but will choose not to do it again. This can reveal what’s not worth their effort and may show their values in a way.

 10. What was your upbringing like?
You can learn so much about a person from hearing about their upbringing. Much of our personality and belief systems are shaped in childhood, and learning about it gives you a window into the person’s true self.

 11. If you had to describe yourself in five words, what would they be?
This question can be a little difficult if the person isn’t self-aware, or they express who they want to be rather than who they really are.

  12. What’s on your bucket list?
This is an fun question that reveals the person’s hopes and dreams, longing for adventure and travel, and life priorities. They usually get excited when answering this question.

  13. What is one of your best memories from childhood?
Everyone most likely has a favorite memory from childhood. It reveals the simplicity, freedom, and joy of being a child. This question often exposes the tender, vulnerable side of a person.

  14. If you could change something in the world, what would it be?
This question gives you a window into the person’s personal values and sense of justice. You learn what makes them frustrated, offended, or impassioned.

  15. What would you most like to learn and why?
Asking this question will reveal the person’s interests and curiosity. It also will show what they might see gaps in their own abilities or knowledge.

 16.  When do you feel the most confident and why?
The answer to this question tells you where the person feels most self-assured about their abilities and talents. We usually feel the most confident about things we’re good at and what we enjoy.

  17. What big life changes have you recently experienced?
Everyone has a different view of what a big life change is for them. For one person, it could be the loss of a job or a divorce. For another, it might mean buying a new car or getting a dog. See what has been shaking their world a bit.

 18.  How did those changes impact you?
This follows the previous question. Everyone goes through change and some people respond to it better than others. See how recent changes have affected them.

  19. What do you feel passionate about?
It’s one thing to be interested in something or simply enjoy it. It’s another to feel passionate about it. Having a passion means you are “called” to some endeavor. Not everyone has found their passion, but for those who have, you’ll sense their inner fire when they discuss it.

20.  What will be your legacy?
With this question, you’re asking the person how they want to be remembered. What impact do they want to make on their family, community, or the world?

​

We made it to the end!

​

Don't forget about the bonus question I gave you in the beginning of this post!

​

Let me know which questions you liked the most! Or what explanations you found the most interesting?

I'd love to know! 

​

See you around,

​

Bibiana