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Discussion on: How do you learn to "ask the right questions"...?

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Jonathan Yeong

This is a great question!

Here's how I ask questions. Quick aside, I definitely struggle with "when" to ask questions. I'm starting to lean towards asking the question earlier rather than later. But let's get into the how!

Just ask the question!
This is especially true for an async environment. Rather than asking "hey can you answer this question" and waiting for a reply. Post the question and let others answer it. If you're in an in-person environment, it might be better asking if the person has time to answer a question first. But you'll be able to see if they're focusing hard on something.

Question structure
Try to structure your question with here's where I'm stuck, here's what I did, what do I need to do to get unstuck.

You want to have done some research on the topic before asking the question. The amount of research is very dependent on what you're working on. If you're new to a codebase, it's okay to not have too much detail in the question. You're still trying to figure out how things work. But it's important to try to answer the question yourself beforehand. Doing so will get your brain primed for the answer by your co-worker - which in terms helps you retain that information better.

Also, doing your research could highlight some outdated documentation that you can fix and make an immediate impact to the team!

Rubber duck
I've been in situations where I've wanted to ask the "perfect" question. I felt this way because the team was busy and I didn't want to interrupt them.

First off, you should ask anyway! Getting unblocked is better than being stuck for hours or days on end.

Secondly, it might be worth rubber ducking the question first. Try to explain it to a rubber duck, or dog, or child. Someone who doesn't understand your context. Make the explanation as simple as possible. Slowly step through your problem. Going through this process can help you polish the question you want to ask. Or you might find the solution!

Interview questions
Interview questions are a bit of a different beast. You still want to follow the question structure. But the "what do I need to do to get unstuck" will be replaced by "what am I looking for?". Ask questions that relate to your values. For example, you might care less about the product than you do about teamwork.

There's a bank of generic questions that people ask like "what is your day to day", "what are some challenges you have" etc. While these questions aren't bad, try to put your own spin on it. Pull in supporting evidence if you can. E.g. instead of "what are some challenges", you can say "I looked on linkedin and it looks like you're scaling their engineering team, what have been some of the problems you've had with team growth, and how are you addressing them?"


Hopefully, these tips helped!