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6 Questions You Must Ask Yourself to be a Better Leader

You have to ask yourself these hard questions in order to grow.

Looking for a handful of questions to ask yourself in order to become a better leader is looking for that roadmap or magic wand. There’s no set number of questions, either, because the point of Rebooting is to consistently and continuously ask yourself the tough questions in order to grow.

That said, there are a few questions that I usually ask my clients when we begin working together (remember, this is not a magic formula for success).

While not an exhaustive list by any means, those questions are:

  1. What kind of company do I want to work for?
  2. Would I let my child work at my company?
  3. What kind of adult do I want to be?
  4. In what ways has my old programming helped me become the adult I am today?
  5. In what ways might my old habits be transformed?
  6. How are the things that shaped my childhood forming my current decisions?

The real beauty in rebooting is that you get to start over. So often we are convinced that we are stuck where we are in life. We believe that we have no control over where we are (good or bad) and that we can do little to change it. We forget that we were all born perfect. Just as our environments shape us as children, we can also shape who we are now—and we can begin at any time.

Answering these questions will not turn you into the person you want to be, but it’s a solid start. However, Rebooting can only happen if you answer yourself honestly. This is why I recommend that my clients sit alone with these questions and really try to find the truth. We are all excellent storytellers and tend to tell the tallest tales to ourselves.

Rebooting means removing the mask you regularly wear so that you have nowhere left to hide. This requires letting go of an image of who you think you should be and instead, deciding who you really are. The process is transformative, but it can also be painful. Few of us want to admit who we really are, because that image rarely matches the image of who we think we should be.

Once you have the courage to strip away your mask, answer the hard questions truthfully, and become who you really are, you will be able to sit back and handle things as they come without falling victim to circumstance. I encourage you to take this journey with my book, Reboot: Leadership and the Art of Growing Up. It’s a comfortable place to be; it’s also a place of certainty and confidence. It’s impossible to grow without knowing who you are, where you came from, and where you want to be.

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