Surviving the HBS ‘Answer a Question You Wish We’d Asked’ Question

Following the various HBS applications I’m seeing, it’s clear my post today should be about how to approach the HBS “Wished-We’d-Asked” question.

The first thing, which I hope is obvious, is there are two tests here: (1) can you find a question that is appropriate and important, and ask it in an interesting way – a way that piques your reader’s interest; and (2) can you answer it in a way that advances your admissions prospects?

The two are of course related – you want to choose the single question that most allows you to advance your admissions value. As this essay comes at the end of the set, you will be looking to address a topic or factor that you have not spoken of yet (or not enough.)

The steps to a good question are as follows:

  • What is there left, that is really important to say, that hasn’t been said in my other essays?
  • What question will best let me address that?
  • How can I formulate the question in a really interesting way?

An appropriate question, in Adcom’s eyes, is one that opens a channel of insight into who you are, what you stand for, what formative experiences in your past matter and why, how you have derived your values or motivations or ambitions, or other similar important stuff about you.

In other words, the right kind of question is one where the answer will leave the reader significantly more knowledgeable about you.

The right kind of question will be hard to answer. If you ask a question you feel you can knock off “no sweat,” then the question is probably betraying your admissions prospects.

Finally, it’s important (if you want to stand out, and you most surely do) that you ask the question in an interesting way. You could say, “I wish you had asked me what my favorite TV show is,” but that’s a yawn. It would be more flavorful to say, “I wish you’d asked me why I own the full 7 season DVD box set of ‘The West Wing.’”

You could say, “I wish you’d asked me about my community service,” but that’s like a road sign “beware, extreme dullness ahead,” when you could say everything you need to say about your volunteering in a soup kitchen and beyond under a question like: “I wished you’d asked me how cook soup for 400, in the dark, with one onion.”