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The deeply uncomfortable questions fearless leaders ask themselves

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Robert Lentz

by on
in Best-Practices Leadership,Leaders & Managers

So you want everything that comes with making the big time in the working world? That includes the kind of introspection that makes a lot of people nervous. But it's what keeps the great ones grounded and true to the course they always imagined for themselves.

Pour yourself a glass of something nice right now and find a comfortable chair in a quiet place—no matter how close you are to the top, you need to ask yourself each of these questions. And no one but you can tell you what the right answers are ...

  • Have I reached a standard of financial comfort that I would compromise my principles to hold onto?
  • Do I secretly like it when others around me fail?
  • What do my kids think of what I do?
  • When was the last time I used my power to make something great happen for someone?
  • What would my 20-year-old self think of what I’ve become?
  • Has the pressure to maintain my position made me treat people in ways I wish they would forgive?
  • What are the things I haven’t accomplished that might haunt me when I get old?
  • How would I start my career over if I were bounced out of my job?
  • What is it that’s keeping me from getting to know my staff on a more personal level?
  • In order to stay on top and keep the organization profitable, do I keep redefining what is acceptable behavior?
  • Is telling a lie easier than it used to be? Does it happen more often than it used to?        
  • Are there people who look up to me for reasons I wish they wouldn’t?

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