Asking the right questions of your data and knowing what you are looking to find is a critical  component for gaining insights from your data that drive specific actions. Data is not black  and white; there is so much you can do with it. Accordingly, two people with the same data  can come up with very different insights. This is because so much depends on the specific  problem to be solved and the approach you take to solve it. 

Perhaps, counter-intuitively, this process starts with questions, not answers. We don’t actually learn  anything unless we truly question it. Most schools use a paradigm where they teach kids to answer  questions asked by their teachers, but they don’t teach them how to question. The outcome of this is it  forces kids to learn only facts. 

There are two things that are wrong with that approach. First, we live in a world today where facts and  other information are in abundance and are immediately accessible. We no longer have to find the  nearest encyclopaedia to look something up. We have this at our fingertips. In fact, we have much  more information available at our fingertips, from many more sources, and some of those sources are  either missing critical context or are not accurate. If we do not have the skills to question the  information, we end up believing the information and insights are true when they are not. This is exactly what we are seeing play out in the world today with massive amounts of misinformation  being treated as a truth. Many people are not questioning it. Second, the world is continuing to evolve  and change at a rapid rate. The half-life of facts and information is shorter than it’s ever been. We  don’t really know what information we need in the future. A better skill to teach kids is the ability to find  their own insights when they need them, by asking the right questions. This is not just a problem  related to teaching kids. As we grow up and join the workforce, it sometimes is even harder to teach  and apply questioning, as there are many cultural reasons why this is perceived as a negative. 

What then are some key things we can do to help people ask the right questions when they are  looking to gain insights from data? 

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Start With the Problem – Not the Data 

Most people work with data backwards. They begin with the data they have available, then leverage a  set of tools and analytic techniques, and come out with some insights. The problem with this is they  end up using very simple, closed and leading questions, which then leads to uninteresting insights.  When you build a house, you don’t start building before you think about the requirements for the  house, and then build a blueprint. Starting with the data, without doing much preliminary questioning  and thinking, will give you the same results as building a house without any requirements. This is one  reason why people who are good at questioning use systems thinking. The starting point has to be  the full problem from a systems perspective – not the tools or what transformations to apply to the  data. 

Identify the Right Key Performance Indicators (KPIs) Ahead of Time 

Ideally, organizations have already established a measurement framework with the proper objectives  and KPIs before they even look at the data. If they haven’t, they won’t be able to ask the right  questions, as they will be too focused on metrics, which may be irrelevant or not important to the  situation or the organization. 

Question Not Just the Data, But Also the Assumptions 

Proper questioning to achieve the best insights requires the ability to not just question the data, but  also the assumptions and other information (i.e., context) related to it. Data can provide us different  insights when we have different assumptions. Asking open-ended questions is a great way to make  

hidden assumptions visible. This is akin to how kids are asked to write out their work when solving  math problems, as it provides an opportunity to understand the thought process and see where there  may be assumptions that will impact the insights. 

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Use a Questioning Framework 

There are multiple questioning frameworks available on the internet that help with asking the right  questions. One in particular is introduced by Max Shron in his book “Thinking With Data.” Start by  asking questions related to the context, such as what is the problem or situation, who are the  stakeholders, are there any related projects or dependencies. Then ask questions related to the need,  such as what will this give us that we did not have before, and why is this important to the  organization. Then ask questions related to the vision, such as what will the results look like and how 

is the logic related to the insight. Finally, ask questions related to the outcome, such as what does  success look like, who will use these insights, and what will they do with them. Although there are certainly plenty of wrong answers, there are not nearly as many wrong questions.  Be inquisitive, approach problems with a 360-view in mind, continually ask why, what, who and how – simply producing something by rote or formulaic command won’t get you to the insight you need.  Embrace the art of questioning.