How to cultivate habit of asking good/smart questions?

A few good resources worth consuming on Taro:

• "Asking Effective Questions That Get Great Answers Quickly"
• "The Breakdown Of A Good Technical Question"

Another thing that will help is to categorize types of questions that your colleagues are asking -- are they strategy questions, technical questions, debugging questions, something else? Making notes about this and writing down things like phrasing, length, and format will be very valuable.

Rahul which resources would you recommend for strategy questions? and how can I gauge the best mentors in my org who can assist me with it.

When Rahul is referring to "strategy" questions, I assume he means the strategy and overall direction of the team. There isn't a good dedicated resource for that, but the process should be as follows:

1. Figure out the goals of the team - You want to get as concrete as possible, which generally means metrics (KPIs) in a massive company like Amazon. For example, our goal at Instagram Ads was to increase a certain revenue metric (duh). However, you may be working at an earlier org where the goals are more build-oriented. This was the case for me back at Portal.
2. Understand what's holding the team back from those goals - Generally a team will execute some collection of projects in an attempt to meet the goal. This sounds simple enough, but it can be held back in many ways:
   1. Unable to come up with projects that move the goal sufficiently
   2. Not enough headcount to execute all projects
   3. System is unstable and constantly breaking, reducing team velocity too much

In terms of who to talk to for understanding this entire space, it will be a combination of these 3 people:

1. Your manager (obviously)
2. Your product manager (if applicable)
3. Your tech lead and other senior engineers (SDE 3s and Principal SDE if your team has any)

To gauge who's best equipped to help you with this big picture stuff, the easiest thing to observe is their presence in team meetings. Anybody who is confident in their opinions and driving the team meetings clearly has a big impact on the direction of the team.

After you have identified the best potential mentors though, there is another thing to figure out: How to make those people want to mentor you. We have 2 resources where we talk about that:

• "How do I find a proper mentor within my company?"
• Session #5 - Mentoring Junior SWEs [E3] to Senior [E5] In Just 2.5 Years At Meta