Is it true that, "It never hurts to ask"?

"It never hurts to ask."  I'm not so sure that's true. 

I think whether or not it hurts to ask depends on the question, and even more importantly, it depends on the way you ask.

Imagine you approach your teacher ten days before college application deadlines and blurt out, "Can you write me a letter of recommendation for college?"  What are the chances that your teacher is going to feel good about that question?  You're obviously not very organized.  You're making your teacher pay for your disorganization by asking so late, and you don't seem to feel badly about it at all.  What if you've also never seemed too interested in the subject matter and you spent a lot of time yawning in her class?  What if this is the first time you've ever tried to have a conversation with this teacher?  Doesn't it hurt to ask now?

What would have made that question a better one?

You could have spent the duration of the course earning the right to ask.  You could have been an engaged student who didn't just work hard, but also seemed genuinely interested in the subject matter.  You could have said, "Hi" to that teacher in the hallway.  You could have given a lot of thought as to why your work in this teacher's class is worthy of a recommendation.  You could have respected the teacher's time by approaching her earlier, and by asking if it would be OK to schedule an appointment at a time that would be convenient for her to discuss your college applications. 

And instead of blurting out the question, you could have had a real conversation with the teacher about your work in the class, what you hope to study in college, and why you were hoping she could share your story with the colleges in a recommendation.   

It takes a lot of work to earn the right to ask, to invest the time and energy to build a connection like that.  But whether you're asking for a favor, a raise, some assistance, an opportunity, or some advice, putting the work in ahead of time makes it a mutually beneficial exchange.

It never hurts to ask right.