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Please Stop Asking Stupid Questions
stop asking stupid sales questions | JBarrows
By John Barrows | April 28, 2015

I was watching the NBA playoffs last week and happened to catch the post-game press conference with the coach of the San Antonio Spurs, Greg Popovich, after his team had lost the first game of the playoffs. For those of you who don’t know, Papovich is notorious for speaking his mind and having little patience with the media and interviews (which I love by the way). Needless to say, what I witnessed was pure gold. Watch the 2 minute Q&A with reporters and you’ll see what I mean.

All the questions the reporters ask are terrible and get exactly the answer they deserve. I was going to write a blog post about my thoughts as they relate to business but then I came across the article in the link above written by Justin Block (@JBlock49). Justin’s article is spot-on so instead of restating it i recommend reading it.  My view has a slight business angle to it.

The parallel or connection to business is pretty obvious. We tend to ask stupid questions to executives and get exactly what we deserve – nothing. Here’s one I used in the past and still hear all the time: “Tell me about your business.” First of all, it’s not even a question. Second of all, you should know about my damn business before you walk in the door. Clients spend a lot of money on their website and marketing to tell the world about their business. To ask that question/statement not only shows your ignorance but is somewhat insulting.

Questioning is a skill that needs to be continuously developed and improved. We need to ask better questions so we can get better information and align ourselves more directly with the priorities of the business and executives. Here are some small tips on improving your questioning skills:

  • Instead of asking about the weather to try and build rapport in the beginning of the meeting, do some research the account prior to your call to see if there is anything recent in their “news and events” to make reference to and use as small talk.
  • Ask open ended questions, early in discovery phase. Ask close ended questions towards the end.
  • Ask “layering” questions to uncover the details of whatever it is: Tell me more about….; explain to me how….; give me an example of…
  • Ask “pain” (challenges) and “pleasure” (opportunities) questions
  • Educate yourself on the executive priorities of the title/industry you’re meeting with. For example, type into google: “CIOs priorities, manufacturing, 2015”
  • Ask higher level questions about the direction of the business and executive priorities when speaking to executives. Ask lower level, more detailed questions to people below the “power line.”


There are tons of tips and books written about questioning skills. These are tips I’ve picked up along the way and help me. Go find more and get better. Good luck and happy selling.

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