Ask Better and More Questions to Solve Problems and Unlock Potential

Kendra, the owner of a specialty pet store with a physical location and a growing e-commerce presence, had a problem with her website that perplexed her team. Whenever an online customer attempted to take a particular action, their transaction would time out and fail. They tried to figure out the problem for a week with no success. “We were really focused on when the problem was occurring in our efforts to figure out what was going on,” she told me. “We were getting nowhere. It wasn’t until I asked the question when wasn’t the problem occurring that we were able to home in on what might be happening. That question led the team to ask more questions that we hadn’t been asking, ultimately leading us to the problem’s source.”

Kendra’s story illustrates a very important and often overlooked point. Asking the right questions can powerfully unlock our ability to solve problems.

Asking questions is a natural ability that we all develop pretty soon after we learn to talk. We’ve all been terrorized by the incessant “but why?” questions of a toddler. It’s why parents invented the “quiet game” (whoever can be quiet the longest wins!). Somewhere along the way, we began asking fewer questions and missed the opportunity to learn to ask better questions.

Asking great questions is a strategic skill that every business owner can and should develop. In my experience, business owners often don’t ask enough questions, let alone the right questions. Research shows that this failure is often attributable to the fear of being seen as incompetent by employees, customers, and others and the assumption that they already know the answer.

I firmly believe that asking questions is a sign of intelligence. Questions open new pathways to problem-solving and add new information to your personal knowledge base. They ultimately make you better, more efficient, and more skilled at what you do. They identify untapped potential and uncover previously unknown issues. They are a powerful strategic tool that every business owner needs to have in their toolkit and to use regularly.

Now, I won’t tell you that there are no dumb questions. There are, and boy, have I asked some dumb ones in my life. But I will tell you that I’ve never asked a dumb question that I later regretted. I may have felt embarrassed in the moment, but I definitely learned something that I needed to know. If you don’t know, you don’t know. If you don’t know, ask. As far as I know, no one has ever died of embarrassment.

There are many techniques you can use to unlock the power of asking questions. I have two in particular that I like to recommend to entrepreneurs. The first is asking questions even when you think you already know the answer. You can start by asking, “what are we assuming” and then, “why are we making these assumptions.”

Second, we all learned the importance of asking and answering the Five Ws and One H questions, probably in third-grade composition writing. This framework is excellent for organizing your approach to asking questions and the information your questions uncover. Utilize these questions when you are problem-solving in your business and add this fantastic twist: the inverse or negative Five W’s and One H questions. Here’s an example of how to pair them when problem-solving:

  • What is happening? What isn’t happening?
  • Who is involved? Who isn’t involved?
  • When is this happening? When isn’t this happening?
  • Why is this happening in this situation? Why isn’t this happening in other situations?
  • Where did this occur? Where didn’t this occur?
  • How did this occur? How can we replicate conditions that may have prevented this from occurring in other situations?

Understanding circumstances, such as when something isn’t happening and who isn’t involved, can provide insight that’s just as valuable as knowing when something is happening and who is involved.

So much more can be said about the art of asking great questions, but I’ll leave you with this: becoming a Master Questioner can significantly improve your decision-making and problem-solving abilities in business and help you to identify new opportunities. It can also profoundly improve your personal relationships and communication. It’s not often that mastering a single skill can improve both your business and personal life. Now you have two great reasons to invest in improving this skill.