“What If?” And Other Terrific Questions

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Entrepreneurs have to ask a lot of questions to get further. But they often don't ask the right things. What if there was a way to ask terrific questions?

A writer friend of mind told me that when she is considering her next novel, she starts with one question: “What if?” What if a Southern Belle played flirty with a handsome Southern gentleman during the Civil War? Or, what if a widower found a letter in a bottle from his long lost love? And, from that, classics are born.

Asking simple questions can lead to big things.

This came to me recently when working with clients who had difficulty understanding and answering the right questions about starting a business.

Entrepreneurs will frequently say, for example, that they have no competition. Yet, the investors that I know say that when an entrepreneur says that, it’s the biggest red flag and instantly turn down the request for capital. Hence, it’s worth asking: “Who is and who may become my competition?”

Entrepreneurs don’t ask the right things.

Despite the amount of information in books, and on the internet, why do entrepreneurs fail to ask the right questions? Here is my take:

  • Clients are overwhelmed in this new world, and it’s understandable that they can’t even consider the questions to ask.
  • Entrepreneurs, frankly, don’t like or are uncomfortable doing the research to develop these questions. In addition, the process can be difficult, time consuming and even expensive.
  • Entrepreneurs are afraid they won’t like the answers and avoid the subject.
  • Entrepreneurs are so excited with their idea they can’t believe there could ever be something to question.
  • It’s a combination of fear, and the lack of skills and experience; the idealistic notion of “If I build it, they will come,” has no place here.

Consultants and businesses coaches need to take some of the blame because they assume too much, and believe the client when they nod when asked if they understand.

Maybe just being open and honest, like they do at support groups, and say: “Hi, my name is ____, and I am starting a business and have no clue what the hell I am doing.”

How to ask the right questions:

But, seriously, here’s what I suggest:

  • Relax, and know that you’ll make mistakes. Mitigate the damage by being vigilant. Ask that difficult concepts be explained in simpler terms.
  • Get to know your business inside and out, make friends with financial statements and the internet.
  • Develop reliable resources outside your company. Don’t go to Uncle Buck, or Auntie Em. They love you too much to tell you the truth, nor will they truly understand your business’ needs. Visit places like Google, your library and incubators for networking opportunities.
  • Don’t stress yourself with trying to know or do everything. Some business gurus can’t add to save their lives, so what do they do? Use their wisdom to hire a bookkeeper.



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