The Power and Magic of Questions

The first time Scott asked me out, I had planned on saying no.

He, my friend (Paula), and I were all eating dinner out, and Paula got up to go to the bathroom. Purely based on the principle that women could use the facilities completely on their own without assistance, I intentionally remained at the table with Scott. The only downside was that I intuitively knew that he would take this opportunity to ask me out on a date.

As he built up his courage to ask the all-important question, I built up my courage to turn him down gently. But then something strange happened.

Scott asked the question in the perfect way. It could’ve been a friend thing, or it could’ve been a date. There was just that infinitesimally small sliver of differing interpretation that could’ve meant something else, and if I said no, I would not only look like an idiot, but it would probably be kind of mean. So I said yes.

I’ve long since forgotten the words he used in phrasing his question, but I now believe they had to be divinely inspired. If not for that perfect question in that perfect moment, we probably never would’ve gone out or become the amazing partners that we are in marriage, business, and life.
Now that I have some life experience behind me, I’ve learned that it wasn’t just that moment. It seems to me that people are focused entirely too much on knowing the answers when really, all the brilliance and power naturally exist in the questions themselves.

Questions build connection and help you understand the other person’s frame of mind, reasoning, and goals. It is often the case that the person who has asked you a question isn’t asking the question they should be asking, and usually it’s because they don’t realize there’s a deeper question to ask. I mean, you don’t know what you don’t know. Questions help you bridge that gap.

Instead of, “How much do you charge,” the real question should be, “Can you solve my problem?” (Pricing should always be the follow-up question, not the lead question.)

Or someone may ask, “Do you work with my accounting software,” when the real question they should be asking is, “Do you know how to help me streamline my processes, get me the information I need to make good decisions, and make my systems more effective so I can accomplish my goals and still have time to watch my kids play soccer?”

The best consultants and entrepreneurs I know spend the bulk of their day learning. They don’t take the questions at face value; they pivot and ask the real questions that haven’t been asked yet. They bombard people with questions all day long in their perpetual quest for the underlying “truth.” They’re seeking the “ah ha” light bulb that can bring everything together into business nirvana.

  • Why do you do what you do?
  • Where do you want to be?
  • What do you want to achieve?
  • Why do your customers buy from you?
  • What have you tried already, and why didn’t it work?
  • How can you make your product better?

Why, why, why, why, why?

And my personal favorite that comes up in our company over and over and over again… “Is there a better way?”

And here’s the thing, when you ask the right questions, you get magic.



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