7 Questions Every CEO Should Ask Themselves Every 30 Days

My Favorite "Thinking Time" Questions

When it comes to leadership, I firmly believe that having the right question is more valuable than having the right answers…

What follows is a list of questions I like to ask my teams during meetings, and myself during solo “Thinking Time” sessions. I hope it will inspire you to start your own list of go-to questions:

  1. The Great Question: What is the one big thing that, if accomplished, would have the most significant impact in my business and render the need for other seemingly-important projects unnecessary? (NOTE: This question was inspired by one of my favorite business books of all time, The One Thing.)
  2. The Gut-Punch Question: Why are our ideal prospects, the ones who already know about us and our product, NOT buying from us? Is the offer unclear or unappealing? Is it undesirable or uncompetitive? Are we trying to sell it to the wrong person?
  3. The Intensity Question: In what areas of my life can I double my intensity? What about 10X?
  4. The Procrastination Question: What are three things I haven’t started because I’m pursuing perfection? What are a few steps I could take today to get the process started? 
  5. The Enemy Question: If I was competing against myself, what chinks in the armor would I exploit? How would I put a massive dent in my own brand?
  6. The Pragmatic Question: Is our strategy not working because the strategy is bad, or is it not working because we are incapable of executing this strategy due to constraints we cannot resolve at this time? What are those unresolvable constraints? What is a strategy we can consistently execute upon today?
  7. The Zero-Base Question: Knowing what I know now, if I could start all over again, what changes would I make to my business model? What is preventing me from making those changes today?

NOTE: The questions, above, and the idea of “Thinking Time” was inspired by this book.

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