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Are you asking the right questions?

I took part in an interesting exchange in a Facebook group last night, in which a trader was asking “should I buy puts or calls for the spy or qqq?” This trader, by his own admission, was a consistently losing trader. The question began with something like “I’m going to try depositing money one more time because options are a gamble, but…”

I just happened to see the question and tried to help this struggling trader. My point was that he was asking the wrong question. “Do I buy puts or calls for an index?” I was surprised at the gap in communication that followed; this trader was completely unable to understand that he couldn’t hope to get a good answer because he was asking the wrong question.

Of course, the conversation devolved (as online interactions so often do) and no real progress was made. In reflecting upon my 15 minutes wasted, I had a few thoughts: First, every stereotype about guys whose profile pictures feature a sports car was reinforced. Second, the applicable wisdom from Mr. Franklin about trying to teach a pig to sing.

But, there was also something very important that came out of that conversation—the quality of the questions we ask is vitally important. And that’s probably something we don’t think enough about.

Questions matter

There’s a Voltaire quote that goes, roughly, “you will know a man more by his questions than his answers.” (In reality, I think this is misattributed: “Il est encore plus facile de juger de l’esprit d’un homme par ses questions que par ses réponses.”, seems to have actually come from Pierre-Marc-Gaston ca. 1800.)

Richard Feynman said something like “I’d rather have many questions I can’t answer than answers I can’t question.”

Two people who I think are supremely skilled at asking questions are Tim Ferriss and Joe Rogan. No matter what you think about either of those guys, it’s worth listening to them interview someone. Two very different approaches: Tim researches deeply and tries to ask questions the person has never been asked before.

Joe, however, approaches everything with eagerness and an almost childlike sense of wonder. With absolutely no presumption (as you’d expect from a guy who can publicly say “I am a dumbass”) he will ask anyone questions that might seem naïve or elementary. But, driven on by “tell me more about that” and “I don’t understand that”, sometimes repeated almost obsessively—these simple questions end up driving right to the heart of extremely complex issues.

Ask better questions

As I think about this, I realize that good questions are a portal through which we can see the universe, bring in new understandings, and widen our horizons. In the best cases, they are essential tools on our question for truth.

But our questions can easily become prisons, and we have no idea. Perhaps this is the most insidious bondage: if we ask the wrong questions, pursue the answers with dogged persistence and fidelity, we might be worse off than if we’d done nothing.

I don’t pretend to have answers, but let me share some thoughts about how we can drive toward better questions:

  • First, assume (rather, know) that some of what you think you know is wrong, and maybe even the most important parts. Once we gain some expertise in a subject, we become subject to a whole new set of pitfalls—expertise can be its own prison. Remembering this first truth is important.
  • Check the assumptions that are built into your question. While we can’t always eliminate these assumptions, articulating them and understanding them can sometimes point out errors.
  • Is your question too narrow? A classic example would be a question that has an A or B answer—is it really only A or B? Is there a C, D, or E? Is there an A and B answer?
  • Ask the question from different perspectives.
  • Are you seeking answers or confirmation bias? Careful—the answer to this one might be more elusive than you think. Sometimes, we don’t really want knowledge; we just want to be told we are right.
  • Check your source. If you’re asking someone or a group of people, do they have the answer? Is their answer relevant to you? Are you certain?
  • Go deeper. This is the equivalent of saying “tell me more”. When you have the answer, look deeper into that answer and ask questions about the answer.

I think all of this boils down to building an awareness of the questions we ask and understanding the place those questions have in our knowledge. In some sense, asking questions about the question might be a good place to start!

I may write more on this topic in the future, and I welcome your thoughts in the comments below.


Adam Grimes has over two decades of experience in the industry as a trader, analyst and system developer. The author of a best-selling trading book, he has traded for his own account, for a top prop firm, and spent several years at the New York Mercantile Exchange. He focuses on the intersection of quantitative analysis and discretionary trading, and has a talent for teaching and helping traders find their own way in the market.