The Art of the Question

When navigating unknown territory, as we often do in marketing, it’s important to ask the right questions to arrive at the type of answers necessary to make better decisions.

Recently I came across an article from entitled “10 Marketers Come Clean About Their Biggest Challenges,” where the top issue mentioned had to do with questions. As summarized by Grammy’s CMO Evan Greene::

I think the biggest challenge is determining what the right questions are to ask because the market is changing so quickly. Communication is changing so quickly among fans, among brands, and just in general across so many different formats. It’s no longer a simple question of how many Facebook friends you have. It gets far deeper and more sophisticated, into areas like, “What is the pass-along value? What is sentiment? What specific audience is talking about you? What specific audience is engaging?” There are so many different choices these days … and the target is always shifting. You always have to try and stay one step ahead, one step in front, because platforms are changing, conversations are changing, the rules of engagement are changing.

Cultivate the Art of Asking Good Questions

What I believe Greene was getting at when he made this statement, is that no longer can we just ask the simple questions of “who, what, when, where, why, and how.” Rather, thoughtful, productive questioning is a process that takes time, considerable thought, and often hands-on experimentation. It’s the reason why great questioners in business, such as Steve Jobs or Jeff Bezos, were able to move beyond assumptions and conventional wisdom and dig deeper into the process of question asking to arrive at greater truths and untapped opportunities.

According to a Wall Street Journal article entitled “How to Cultivate the Art of Asking Good Questions,” asking the best questions stems from a sense of curiosity and willingness to go beyond the conventional answers. Warren Berger, author of the book A More Beautiful Question summarizes it in this way:

Asking “why” is a great start, but we’ve all seen the questioning child who goes ’round and ’round in a circle of endless “whys.” To question productively and “beautifully” is to inquire with direction and purpose—progressing from “Why” to “What if” to “How.” A questioner can move forward on almost any problem or challenge by first trying to understand it (Why is this a problem?); then imagining possible solutions (What if I came at the problem this way, or that way?); and finally trying to figure out practical ways to turn those what-if ideas and possibilities into realities (How might I actually begin to make this happen?)

Upon reading this article, I was instantly reminded of a TEDx talk I once watched about “asking the right questions.” According to Rachael Herrscher, “there are so many corners of our life where asking the right questions are important.” Learn why asking the right questions became personally important to her in the video below:

What Makes a Good Question?

To summarize Rachel’s talk, a good question is one that gets you the best information necessary. In the video, Rachel talked about asking people from various  professions what it is that they think makes a good question. Below is a summary of their answers:

  • CSI Investigator: “Keep questions open-ended and introspective.”
  • Designer: “Gets more out of listening than try to lead the discussion.”
  • Doctor: “Ask an unscripted question.”
  • Investor: “If you ask a question and get an answer to a question other than you asked, then you already have your answer. It’s the answer that you didn’t want to hear.”
  • TV Show Producer: Oprah asks “what is your intention” whenever someone goes to pitch a show idea; get past the “this is what happened” and get to the connection.

In short, depending on the outcome you are looking for, consider asking questions in a different style or format so that you can arrive at the best answers.

Asking the Right Questions

For those interesting in learning how to think more critically when asking questions, there was a book I once read entitled Asking the Right Questions that served as a great resource for working through complex information to arrive at the real issue. In short, the authors challenge one to take a piece of information, identify the issue/conclusion, locate the reasons, determine if there are fallacies, examine the evidence, consider omitted information, and think about the reasonable conclusions that are possible before engaging with responding to an issue. The book delivers a process for working through complexity from a scientific standpoint, and its learnings can be applied across disciplines.


While most people are too busy or too unwilling to set aside the time to critically think through a problem, there is a way to ask questions that will take you to the very heart of an issue. Asking questions is a process that takes critical thinking and patience to work through, but with a little curiosity and passion, anything can become possible. In doing so, you can set yourself apart by seeing the “big picture” and where all the little pieces fit in. Don’t be afraid to ask the types of questions that will lead you from “why?” to “what if?” to “how?”

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