How to Ask Good Questions

Asking is harder than answering. But we’re only taught how to answer, not how to ask.

Good questions are rare, good answers abundant.

But a right answer to a wrong question will be more harmful than no answer at all. Which is why it’s important to learn another evergreen skill: how to ask good questions. 

Of late, folks ask me about business school and career advice. But I find it hard to help those who ask broad questions, and quite engaged with those who ask specific questions. Often I find myself replying to the questioner with a “Do you have a specific question” when they write “Could you tell me your key takeaways” or “Could you give me advice on how to do X”. 

This is enlightening to me.

In our quest to find answers, we don’t seek the right questions. Perhaps the right question is not “Could you give me advice on how to do X”, but “Is X even worth doing?”

We don’t ask good questions because asking good questions requires clarity of thought. This, in turn, requires three things: (1) Independent thinking, (2) Comfort in ambiguity, and (3) A scout mindset. 

To ask one good question, then, may require you to spend hours thinking independently about one thing and failing at even scoping the problem. It may require you to forgo validating your beliefs and instead challenging even existing ones; that’s what a scout does, as opposed to a soldier.

But we’re not trained this way. We spend hours looking for the answer, when, in fact, we may have to just ask the right question. A few examples of good and bad questions are below. Bad questions are the unexamined, unconfronted questions that we inadvertently seek answers to; they’re the default questions we quickly want to solve. 

Bad question: How to get into a top business school? 
Good question: In my context, does business school make sense?

Bad question: How do I build wealth? 
Good question: Do I seek wealth for its own sake, or ancillary benefits (social status, relevance, and power)? 

Bad question: Could you give me some life advice? 
Good question: I understand that I have to figure out my own path but I’m gathering context, and it would be helpful if you could share what you think worked for you, and why. 

Bad questions can also masquerade as good ones. Think complex, wordy, long questions that the answerer does not understand. For example, consider these bad questions that Congress fielded to Zuck: 

• How many data categories does Facebook store on the categories that you collect?
• Are you willing to change your business model in the interest of protecting individual privacy?
• If I choose to terminate my Facebook account, can I bar Facebook or any third parties from using the data…?
• Even if Facebook doesn't earn money from selling data, doesn't Facebook earn money from advertising based on that data?

It’s funny, in hindsight, but I’d wager that many thought of these questions as good questions. And that’s because Congress representatives asked these (bad) questions in a serious tone. 

Which begs the (good) question: How do you detect bad questions? I take three steps. 

First, ask yourself: Have you thought enough about what problem you have, and the axes / dimensions of said problem? “Enough” is the keyword here. To come up with a good question on any problem, it’s worth having spent at least one hour thinking about that problem. For example: Is it an emotional problem masquerading as an interpersonal one? Self-awareness problem masquerading as a financial one? And more. 

Second, ask yourself: What specific part of the problem are you unable to solve? For example: Are you unable to move on part X of problem P because of X’s dependency on Y? 

Third, answer this question for yourself: If I get the best answer to my question, what will I do with it? Do you expect a prescriptive answer or an exposition? Are you just gathering context on the answerer’s life or are you pattern-matching their context with yours? Would you implement exactly what the answerer tells you?

I find this three-step process useful because it makes me think, twice, before, I, ask, a, question. And I find this pause to be a superpower in detecting a bad question. Many a time, then, I don’t ask a bad question. 

The other route to ask good questions is the shotgun way: Ask as many questions as you can, and keep refining them along the way. I used this strategy during my undergrad in Berkeley. In a lecture of 1000+ students, I would unabashedly ask 3 - 5 questions per lecture. At times, I asked stupid ones; the ones that evoked “ughs” in unison. But more often than not, I’d find friends walk up to me after lecture and thank me for the question I asked. 

This makes sense. Good questions are hard to come by. We’re afraid to ask bad questions publicly. Ergo, we either don’t ask questions or ask bad questions privately. This compounds. Soon enough, you’re old and you don’t know how to write a cold email, ask a good question, or work on the right problem. 

But the good part about wanting to ask good questions is that it’s easy once you make up your mind. You’ve done all the work already (through asking bad questions or finding wrong answers). It’s akin to you having explored the non-solution-space to the problem space you’re dealing with. So all you need to do is to actively reject this non-solution-space. What’s left will be the space of asking good questions. 

Years ago, I met folks at an executive coaching company. This company teaches ‘Precision Q+A’, a skillset to ask precise questions, and answer precisely. While I’ve forgotten the theory part of this workshop, I’ve retained the essence: A good question is a precise question. 

Ask good questions; you won’t have to hunt for answers. 

Until next time,

Abhinav