Master your questioning skills

My new years resolution for 2018 was to "ask more/better/crazier questions."

To realize this resolution, I knew I needed to implement it as a system. So I committed to "ask at least a couple of MAD questions in each blog post." After close to 12 months and 70 posts, these are what I learned from this exercise.

1. Questioning is very useful

Adding the MAD questions section significantly extended/complemented my posts, and with little effort. Just by adding this section, I went for another 15-20 minutes, forcing myself out of my default mode. Sometimes I grudgingly did it, just because I had committed to it, but almost always I was surprised by how useful it was.

Many times the MAD questions section got longer than the main post body. And on average it was about 25% of the main body. Questioning also improved the main content, and I had incorporated the findings/leads from some of the MAD questions in the main body of the post. I keep many half-baked posts in my file, and had it not been for the questioning that extended the content, I might not have published many of those posts.

2. Questioning is a frame of mind

I found that questioning delivered those good results with relatively little effort.

I think the reason for this is because our default mode is to not question things. We have been implicitly taught this at our family, school, and work. Asking too many questions, especially hard ones, is frowned upon in polite company. Moreover, the human brain is programmed to save energy and go easy on itself, so it prefers shallow tasks and tries to avoid intense thinking sessions required for many creative tasks. By asking questions it is possible to prime the pump and keep the brain more engaged.

Coming up with the questions is not difficult, once you get out of your default mode and give yourself the license to indulge in the questioning frame of mind.

3. To ask better questions, make it a MAD question

By calling these questions MAD questions, I gave myself the license/protection to go wild, uninhibited by traditional assumptions/constraints. This gave rise to reducing the bar, and approaching the topic with a beginner mind, as an outsider. This made it easier to ask more original questions.

By detaching and discarding the baggage of tradition, you can start working from the first principles. You should remember that questioning is the beginning, not the end. There is a separation of concerns: you first focus on what needs to be done, and not how it needs to be done. So, initially, you don't need to be afraid of the difficulty of the answers as it is not your concern for now.

So, don't feel intimidated to question the basic assumptions that people in your field take as granted. They may as well be due for replacement anyway.

4. To get to the good questions, get over with the bad questions

Bad questions lead to good questions. So roll with them and exhaust them to get to the good questions. Don't quit prematurely, as good things will happen if you go a bit deeper. And do this in a stress-free manner being assured that something will eventually come if you persist a bit more.

You should approach this like brainstorming and freewriting.

5. A good question often involves a perspective change 

A good question is like a good joke. It has an unexpected element and provides a perspective change.  After I get through some questions and I eventually arrive to a good question, I have a visceral reaction similar to that of hearing a good joke.

A good question gives you a perspective change that is productive. It opens a new area to explore. It creates new relations/connections.

After following the above suggestions for asking questions, the why and what if questions can help you get to the perspective-changing questions.

A change in perspective is worth 80 IQ points. --Alan Kay

MAD questions

1. Is questioning how we think? If so, can we think better by questioning better?
I feel like my thinking is done mostly via asking questions. But of course I also need to be thinking to ask those questions in the first place, don't I? So I don't know who is the real hero here. (This reminds me of the joke: "My belt holds my pants up, but the belt loops hold my belt up. I don't really know what's happening down there. Who is the real hero?" ---Mitch Hedberg)

To be fair, let's call questioning as a catalyst for thinking. It seems like they bootstrap each other.

Questions also serve as an interrupt for sanity check, self-inspection, and going meta on the task.

Finally, questions also play an important role in the way we master/internalize things. I relate very close to Barry Diller's approach to learning by deconstructing and understanding from the fundamental elements.
DILLER:​ ​By purpose or by temperament, I'm only interested in those things where I haven’t figured it out, and I really do think that however it happened, that when I was presented endlessly with things I didn’t understand, the only thing I could do—because my brain is slower, and therefore is more literal—and therefore my process is, I have to get it down to its tiniest particle, or else... I can’t come in and understand an equation, if you can put it in equation terms, unless I de-equation it—I can’t pick it up. So I’m forced – by a lack of brain matter, I am forced to – no I’m not saying it – it’s true! To break it down as hardly low as I can get it, and only then—and that’s learning. That’s real – that is joyous work to me, is getting through those layers, down to something, and then once I’m down there, once I’m actually at the very, very base of it, I can actually start to do something good.

2. Can we treat questioning as a tool?
I think questioning can be viewed as a tool, and we will increasingly start to treat it as a valuable tool in the age of big data and machine learning information technology markets. The information is already out there, we just need to ask the right questions to the search engines, expert systems, and machine learning based digital assistants. The easy/usual questions will already be asked by the machine learning systems. To differentiate we should learn how to ask the good questions. In Synthetic Serendipity, Vernor Vinge short sci-fi story, the highschool had a course called "Search and Analysis" that aims to teach students to ask the right questions to the search engines and expert systems.

Even when the information is not there, if you ask the right question, find the right perspective to approach to it, the solution bit is not that hard. Questioning acts as a tool for framing/reframing. This is what the master of gedankenexperiment has to say on questioning.
If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask... for once I know the proper question, I could solve the problem in less than five minutes. --Albert Einstein

So, going forward, shouldn't we have more tools/support for questioning as a tool? What are some tools (mindmaps, etc.) you know that are designed to help support questioning/framing?

3. Is it possible to teach how to ask great questions?
Answers are teachable, so we teach answers. But we don't teach how to question. In kindergarten and primary school, the kids are already pretty good at questioning, but come middle school most kids stop asking questions. I don't know maybe students that ask questions come across hard to manage and contrarian, and get discouraged by teachers and adults.

We (academicians) try to teach questioning during PhD by way of examples/apprenticeship. I am not aware of any organized/formal way that asking better questions is being taught. There is no course or good book on it, as far as I can see.

However, I still believe questioning is a skill and can be teachable. What if we could create a course on this? It will likely be a hands-on learn-by-case-studies class, but at least we can provide more support and material than saying "watch me ask questions and start imitating".


gliush said…
Very interesting idea! Thanks for sharing it!
I'm going to use it everywhere! :)
Unknown said…
So my first question is what is MAD question. What MAD stand for
Varro said…
Re MAD question #3: Precision Q & A is the one framework I've discovered, but haven't found anything else yet. I've been searching for something like this for years.

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