Early on in my career, I learned that when someone asks you a question, it helps to find out why they want to know before you start to answer. That gives you the context you need to provide the best possible response.

This is especially true when you consider college application essays. Why does a college want to know about a time you faced a challenge, setback, or failure? 

The answer, of course, is that they want to know how you’ll respond to challenges, setbacks, or failures when you get to college. 

I think of it as an unasked question hanging in the air around every prompt: “… and why does that make you someone we want to have on campus?” 

Why would Stanford want to see a letter you write to your imagined roommate? They’re looking for students who can live well with other people.

Why would Princeton want to know about a new skill you want to learn in college? They’re looking for students with concrete and specific personal growth goals. 

That’s not to say that you should just try to tell the admissions office what you think they want to hear. Far from it. 

Instead, when you’re brainstorming, keep that unasked question in mind to help you identify good topics. If you want to learn how to type, how to do a new TikTok dance, and how to meditate, which one is going to be more interesting to admissions? If you have ten ideas for things to tell someone you’ve just met, which of them are likely to lead to a polite and fruitful conversation?