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What Questions Should You Be Asking And To Who?

Have you ever heard this saying “Great Leaders always ask questions”.

Now this question for many, ‘you feel’ only applies to you if you are involved in the corporate world in some way shape or form, but have you ever considered that you might actually be a leader without the title or mantel given to you. We are all leaders in our everyday lives and I’m sure that you probably have one or two people watching you right now, maybe at work, on the train to work or home, at home with your family, in that meeting, when you accidentally kicked your big toe on that concrete curb “ouch” or “F…K”.

Where ever you are right now you are potentially a leader leading someone for good or for bad.

I’m a person who truly believes in the law of ‘give and it shall be given back to you pressed down shaken together and running over’.

I’m not trying to make light of the matter but over the many years I’ve lived on the earth I have seen time and time again the miracle process well not a miracle really but one of the laws of life that when you go out of your way to give a word of encouragement or motivation, a seat in a crowed train, your service for free to that struggling new business start-up, your friendship and listening ear and even maybe your money. I tend to find opportunities opening up for me that I could not find or open up for myself

But How do we really know what questions to be asking as leaders, who should we be asking those questions to and finally what should we be asking once we find that person or group.

Here are some great questions I found online that might help you in getting started.

I’ve just had a session with my husband going through the questions and we had some moments of tears and laughter and moments of silence and profoundness.

Important Things Learned

  • “What’s the most unexpected thing you’ve learned along the way?”
  • “If you could call yourself five years ago and had 30 seconds, what would you say?”
  • What is the best piece of advice you have been given?
  • What is the first moment you remember in your Life?
  • What is the best question anyone has ever asked you? …and how did you answer?

How You Would Spend Your Time

  • “On a scale of 1 to 10, how happy are you with your life?” Then, after I answered, I was asked, “What would make it a 10?”
  • “How will you make this world a better place than when you came into it?”
  • “When you die, what do you want to be remembered for?”
  • What would you do with your time if you could afford to quit your job?
  • If all jobs paid the same, what would you be doing?
  • What would you do if you knew you could not fail?
  • Are you doing what you thought you would be doing when you were growing up?
  • What are your greatest regrets, and what might you change about them if you could?

About You

  • Someone gets a text message from you, and for whatever reason they’re not sure it’s actually you. They’re worried that someone may have stolen your phone. What could they ask to make sure it’s really you?
  • What is the craziest belief (the one that fewest educated people will agree with) that you hold?  Why do you believe it?
  • Make a request where the “right thing to do” is for the other person to say no to you.
  • Are you lucky?
  • What would you do if you were homeless?
  • Who are you when no one’s watching?
  • What are you pretending not to know?
  • What has been your main motivation in life so far?
  • Would you like yourself if you meet you?
  • What does being successful mean to you?


Author: Rachael Aprill Phillips

Bio: Rachael Aprill Phillips is the CEO and founder of The Richible Group a collective of companies whose vision is to help over a million people launch, run and grow a highly successful business. She was also named Top Global Marketing Expert by Huffington Post.

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  1. Just what I need as we come into the new year. I didn’t think about asking myself these reflective questions. It was an eye opener thanks for sharing more posts like this pls.

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