Questions Not Asked

Posted by Kevin Merritt on January 26th, 2009

Being a successful entrepreneur requires the ability to ask hard and sometimes awkward questions. It’s the Colombo factor. The ability to ask the socially awkward question if necessary. I haven’t met a successful entrepreneur lacking the ability to ask the tough questions.

  • What do you think about the two of us starting a company together, as co-founders?
  • Would you accept the risk and challenge of being our first hire?
  • Can you afford to work for a lower salary if we make up for it with stock?
  • Why did your last business fail and what did you learn?
  • Do you still want to work here or have you lost the passion?
  • Why didn’t you finish your degree?
  • Do you believe in our vision enough to submit a term sheet?
  • Will you buy our software?
  • How much will you pay us to make that modification?
  • Is there any way I can ask you to give up your Saturday and help me meet this deadline?
  • Hun, what do you think about me quitting my job and starting a company?

What questions are you afraid to ask? What is it keeping you from achieving? The answers are irrelevant if you’re afraid to ask the questions in the first place.

photo credit: Wikipedia

One Response to “Questions Not Asked”

  1. David says:

    Wow, those hit home. Nice touch with the Columbo pic.


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