I once worked for a start-up that got acquired. The CEO of the acquiring company introduced himself, his company and his vision for the future at an all-hands meeting. He was ambitious yet gracious and was kind enough to open the floor up to questions. I raised my hand, suddenly, all eyes in the room shifted towards me in quiet anticipation as if all of the air had been sucked out of the room. I had asked a question regarding maintaining our top position in our niche. The eyes of the audience grew cartoonishly large; it was the best question asked at that internal all-hands meeting. To his credit, the acquiring CEO gave a thoughtful answer. The all-hands adjourned soon after and the crowd dispersed, the acquiring CEO needed to leave, but we had a brief moment of eye contact as he paced towards the door; he gave me a silent head nod as he did so. I had earned his respect, that much was undeniable. Moreso, I had cemented my status for having the special sauce when it came to asking questions.
What if I told you that you have been lied to your whole life, that there is such a thing as a stupid question, and you have likely asked them numerous times without realizing it? You undoubtedly will not believe me, but I am here to speak the truth. Take this unlabeled pill from my linty pocket in the middle of the club, and I’ll show you how far this rabbit hole goes. After all, nothing bad has ever happened in human history when someone has ingested a pill from a stranger in a crowded nightclub…
Ah, my child, I see you have decided to take me up on my no-strings-attached offer of free psychoactive drugs. Now, time to start dispensing the promised truth. One thing that separates a good question from a bad one is how readily available the answer is. For example, if the answer is available on the first page of a Google search or is listed in a document that you are supposed to be referencing, like a list of instructions or a textbook, then it is a stupid question. I learned this lesson the hard way at the most toxic job I’ve ever had; an elder statesman absolutely tore into me for calling to ask about something that was codified in the procedure. His overly vitriolic response drove home the point that asking questions like that was not okay, and he was absolutely right. Furthermore, asking a question that you are culturally expected to know the answer to is a stupid question. For example, a recent STEM grad not understanding something covered in Freshman Physics is a stupid question. Is it fair? No. Will it happen anyways? Yes. By the way, it’s normal for your eyes to hurt.
Another factor that determines if something is a good question or not is how well-intended it is. Despite this being more qualitative than quantitative, it’s no secret that most people can sniff out a gotcha question from a mile away. Asking a question with a sincere desire to learn is far better than asking a question in order to create a sizzle reel for the Chinese Communist Party. Admittedly, part of this is delivery, as the tone used in the delivery can easily sway a question into either camp. Hence, those who are not naturally charismatic will have to work on their delivery just as much as they work on the content of their questions. Again, is it fair? No. Life is tough, learn Kung Fu.
Realm of control is another part of the criteria in what determines a good question from a bad one. By that, I mean that the recipient of the question should have ample opportunity to the information necessary to answer the question, and the authority to act on the answer. For example, going into your workplace and asking the maintenance manager on how the company plans to capture more market share (Aww shit, Dan’s being a capitalist again) is a bad question. However, that same question asked to the CEO of your company is a great question; the CEO has a large amount of control over the company’s market share and has the knowledge necessary to answer that question.
Moving onto our next training module is understanding who you are interacting with in the first place. Yes, this will mean that you’ll have to understand the incentives, tendencies and biases that your conversational partner has; how they view the world is absolutely going to impact their answer. While not everyone needs to become NostradAmish, asking a question with a predictable answer is a bad question. Thus, asking questions whose answers cannot easily be predicted is a much better question. Again, this builds off of asking questions that aren’t an easy Google search away and being genuine (and not playing stump the chump). One of my favorite questions to ask people is If you had one magic wish, but you could only use it to benefit society, what do you wish for and why? This is because almost nobody will have a canned response for it. Therefore, their response will tell you a lot about who they are (I once received hookers and cocaine as an answer!).
While this isn’t about questions directly, being time-efficient and optimizing for good questions (as per the criteria that I’ve graciously shared with you, my drug fueled apprentice) is an absolute must. Time is limited, thus nobody will willingly sit through an endless stream of terrible questions if they can at all avoid it. Truthfully, you may only get a handful of questions to ask in any one interaction, so making them count is an absolute necessity. I’ve been fortunate enough in my previous job to have an hour-plus long group sit-down with two consecutive CEOs, and even then, I had to prioritize what questions to ask. This isn’t a 007 game; you do not get unlimited ammo. Furthermore, ask enough pointed questions and you’ll develop a reputation for asking good questions; it’ll be like you’re moving double-speed compared to everyone else.
The rest you must learn on your own, young Neo.
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