In school we’re taught to provide the right answers to given questions. We’re instructed to assume that the questions we’re asked are the right ones. As a result, school doesn’t provide us sufficient training in the skill of asking the right questions.
However, much of our happiness and success later in life comes from asking the right questions. Some of these right questions are universal for a given domain and some vary from individual to individual.
For example, in the field of happiness, I used to think that the right question is “what makes you happy?” I then discovered that, at least for me, the right question is “what’s meaningful without taking away too much of your happiness?”
In the field of success, asking yourself “how can I best apply my skills in the context of market realities to produce something that others want?” is a better question than asking “what am I passionate about?”
In the context of venture capital investments, the right question is not “is this a good idea?” but “what will this team do with this idea?”
In the context of building startups, the right question is not “how much money do we need?” but “what do we want to achieve before hitting profitability or raising more money, and how much money will it take to get there?”
You can make substantial progress in asking the right questions by consciously reminding yourself to do so. However, sometimes the only way to get there is to first ask the wrong question, arrive at the right answer but for the wrong question, and then learn from your experiences.