⚠️ A small disclaimer before we begin:
I'm going to say something quite obvious. But it still surprises me as to how many people fail to practice such an obvious thing. If the following is too obvious to you, I apologize for wasting your time in advance. Perhaps, this isn't for you.
Okay, now that this is out of the way...
We often look up to successful people and want them to be our mentors. And we often message them asking for advice. So, here's a tip that will help you avoid making a bad first impression and actually get the advice you need:
Before asking a question, think about what the other person’s answer would be.
Then respond to that question.
Then think of their reply.
Then respond back.
Carry this conversation out in your head for two-three more rounds till you actually have a better question — or even better — have managed to answer it for yourself.
Here's an example of a real-life scenario where you can use this principle:
Let's say you message a founder asking for advice around your career.
"What should I pursue?"
Their natural response would be to know more about your context — where you're coming from, what challenges you're facing, where your interests lie, etc. So, answer this in your head.
Then, lead with what you've answered as your first message. Save them an unnecessary question. Come across as more thoughtful, more precise. People love it when you have provided them all the necesssary context they would need to answer your question. And it is generally the case with experienced people that their answer to most questions with missing context is:
They aren't wrong for saying this. But of course you want a better answer than "It depends." To ensure that you get it, supply them with the context around all the variables you think the answer depends on.
If there are more variables that you aren't considering, that is okay. But at least do your due diligence when it comes to thinking about the problem yourself.
Here's another example in a workplace context:
Imagine you wanted to tell your manager that you can't execute a certain task within a specified deadline due to so and so constraints.
Now think about what your manager's response to it will be. Will your argument hold?
Usually, you will realise that your manager will suggest an option that's actually reasonable, making your argument null and void.
So, why don't you assume the conversation has already happened and do what your manager would've suggested you do anyway?
In life, it's always the more thoughtful who people love to work with. They have empathy and consideration for the other person and can think two steps in advance.
Be more thoughtful. Ask only when the question and the problem are clear to you yourself to begin with.
Also, it is often the case that we write to others to only seek validation for the decisions we have already made for ourselves in our heads.
In such cases, what happens is:
You ask someone experienced for their opinion. And when they state it, you try to fight their opinion and nudge them to the answer you want out of them.
When people do this, it is often extremely obvious to the mentor figure the question is being posed to.
Hence, only ask questions when you're genuinely interested in finding out the answer or are genuinely confused. Do not ask them if you already have an answer you'd love to be true and now just want to get it validated by someone of repute.
In any case, you will only do what you feel is right for you, regardless of the reasons you state to others. Experienced people can only help you understand a problem better, they cannot convince you to take any decision. That is ultimately up to you and your intent.
So, when you approach someone for advice, aim to understand the real problem, its constraints, and its trade-offs better.
And the only way you do this well is by asking detailed and precise questions that not only show your willingness to understand more but also signal your sincerity to the person you're asking the question to.
Instead of asking, "What should I do?",
ask, "How can I think about this problem better, given the constraints I have?"
and, "What is a mistake an amateur would make here that an experienced person wouldn't?"
Approach with an intent to understand, not with an intent to validate your existing beliefs.