Ask Better Questions

Lots of people ask the question, “can I..,” to their Managing Broker.  Before that question is asked, the planning is done.  Now, it’s a matter of determining if license law and the brokerage will allow it.  Problem is, license law and brokerages allow most things.  In other words, I can justify all kinds of dumb choices if “the rules” are my only guide. 

I love the way Keith Cunnigham frames this in his book The Road Less Stupid.  He says, “All my problems started out as a good idea and all those “good” ideas were emotionally justifiable at the time. Not only that, my current financial condition represents my very best “thinking.” Yours does too.”

In other words, asking “can I” questions enables us to reinforce our emotional justification, which means that we will probably move forward with our “good idea.”  While it sounds like progress, it probably will not lead us to a better financial condition. Rather, we will end up in the same place, just older. To get somewhere new, we need to ask better questions.

A huge risk in attempting to ask better questions is shifting from “could I” to “should I.”  Unfortunately, “should I” questions elicit the same emotional responses and results that Cunnigham is talking about. Why?  Because they do not identify a problem. 

Think about it.  You are attempting to shift your business strategy to create a better result, but the underlying problem is still there.  Until you get crystal clear about your problem, no amount of creativity or strategy will help.  After a couple of months, you will find yourself stalled, again. Rather than repeat this cycle one more time, answer this one question first:

What is the problem you need to solve?

With that clarity, you will develop real solutions that solve the real problem and thus producing better results. This is what leads to A Career Worth Having, A Business Worth Owning, and A Life Worth Living.


Cunningham, Keith J.. The Road Less Stupid: Advice from the Chairman of the Board (p. 8). Keys to the Vault. Kindle Edition.

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