How to Ask Good Questions: Why vs. How

One of the key lessons I’ve learned during my career (to date) and through conversations on the podcast is the importance of asking good questions. Some may view asking questions as a sign of weakness. This could not be further from the truth.

First, there is truth to the phrase “knowledge is power.” Second, asking questions shows insight into understanding an issue or problem. Third, asking questions also demonstrates leadership; there may be several people that have the same question, but are afraid to ask.

While I believe that generally there is no such thing as a dumb question, I do believe that some questions will yield higher quality answers than others. Is it really hard to ask a good question? How do you ask good questions? It’s important to understand what type of information you seek and what you want to do with the information. To demonstrate, this I will highlight the subtle yet powerful differences between questions that start with “why” versus “how”?

Both words are short, yet crucial in shaping our thoughts and actions. I’ve probably asked dozens of “why” conversations during podcast interviews. Answers to “why” questions provide an explanation and context, but it does not provide a path forward. In other words, asking why is reactionary — it does not put you in control of the situation or the information you receive. It also allows someone else to anchor the conversation.  

Asking “how” places oneself into a more proactive mindset. It leads to a more active understanding of a situation. Answers  to “how” question provide a template for action. The questioner anchors the conversation by shaping the type of information they want to receive in response to their question.

There is nothing wrong with “why” questions, but perhaps the best approach is to ask a “why” question followed by a “how” question to get the most complete answer. To see the differences in response to the two types of questions, let’s look at an example of each.

Joe Sarcinella is preparing to run a 100 mile race. As if that is not impressive enough, Joe is doing this after losing more than 80 pounds. I interviewed Joe and had several questions for him about his adventure and life story. Why did you decide to start losing weight? How/what did you do to exercise? Why are you running the race? How are you training for the race?

The why questions are much more contextual. By asking Joe why he decided to lose weight I learned about the unhealthy habits that led to his size prior to his training. By asking how he was losing weight, I learned what steps he took to start exercising (short walks on a treadmill) and the evolution of his diet. The how information provides a path for others (including me) to follow if we want to eat healthier or begin exercising after finding ourselves out of shape.

The same holds true for the 100 mile race. I asked Joe why he was doing it. Joe explained that as a child he made a promise to his dad to complete a 100 mile race after his did was unable to finish one. However, the question about how he is training for the race gave me a template for training to run long distances. It led to follow up questions about whether anyone could run longer than a marathon (Joe’s answer was anyone could run 40 miles).

If I wanted to learn how I could also run long distances asking “why” alone does not get me where I want to be. Joe’s story may seem a straightforward contrast in the two questions. But many people, including me, ask why questions when I think we want to ask how questions. There is a difference between “why am I not getting good grades?” and “how can I improve my grades?” The second question generates action items, while the first question provides context.

Overall, it’s important to ask questions. However, if you are trying to take action in your life, ask more “how” questions. It’s not always easy — even for me —  but it makes a difference. Over time it becomes easier not simply to ask questions, but to ask the right questions. And your life will be better for it.



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