How to answer a challenge question for college supplements

college admissions Common Application supplements

The challenge question is a rare written supplement but is actually a very common interview question. Every college applicant should be prepared to discuss a failure (or something that did not go as they had intended) whether that discussion comes in the application itself or in an interview situation. While, on the surface, challenge questions seem to invite students to share non-flattering moments, a well written challenge question can be a wonderful way to showcase your resilience, grit, and ability to thrive in a difficult environment.

Example Challenge Questions:

  • MIT: Tell us about a significant challenge you’ve faced or something that didn’t go according to plan that you feel comfortable sharing. How did you manage the situation? 
  • Cal Tech: Tell us about a time or experience in which you encountered failure.


While it is essential to discuss the failure or challenge itself, it is equally important to discuss how you managed the situation and adapted in response to it. A challenge question will only work if it becomes an opportunity to learn more about you and how you respond when things don’t go according to plan. Therefore, devote equal time to the challenge and then to the aftermath (the “management” of the lessons learned).

Reflection is critical here! Therefore, it is essential that you select a challenge that has either happened long ago (giving you time to reflect) or is of minimal impact (giving you capacity to reflect). Do not discuss a huge, recent, devastating event in this essay as you will not have the capacity to be reflective.

If possible, keep your answer in the academic realm. This is a wonderful question for a discussion of your first foray into computer programming where you worked hard to craft a code, pressed “enter” and saw a flashing “error” message, or to talk about the biology experiment that you had spent weeks setting up only to walk into the lab one morning to find all of your worms/fruit flies had died.

If academics really don’t provide you with a topic, keep it to your most cerebral extracurriculars. You could discuss sitting down to perform a piece of music and your mind going blank to the notes, getting up to make a speech at debate/mock trial and completely losing the thread of your argument. You get the idea!

Lastly: don’t be afraid to be vulnerable! If a great college essay provides moments to share your humanity and vulnerability, what better place to do so than with an essay about failure or challenge? If you were upset/sad/frustrated/angry when all of your fruit flies died, say so! 


Do not write about a challenge that had a consequence you would regret sharing with a stranger. This is not the moment to talk about the time you were arrested.

Similarly, this is not your discipline/suspension essay. Should you need to describe a discipline situation, you have a separate essay to do this.

Do not talk about a challenge in a way to say anything critical about your classmates, lab mates, peers, or teachers. Do not put the ownership for the mistake or problem onto someone else! Own your own failures.

Do not pretend you’ve never faced failure. Dig deep. It is not an effective essay to write about how the challenge you have faced is that you have never faced a challenge. Your privileges as a human do not protect you from all forms of challenge.

Additional Tips and Tricks:

Keep it little. The smaller the problem, the more time you have to discuss the reflection, the management of the situation, and the growth you have experienced. Can you tell your story of failure in 3 sentences? Do so.

Keep it real. Don’t make up a problem or a failure just to have something to say. Find a moment and expand upon it.

Remember that you will likely face a lot of failures and challenges as an adult – and colleges want to welcome students into their communities who have faced challenges but who know how to grow in response to those challenges. It is ok to have made a mistake. It’s how you grow from that mistake that matters.

Elise holds a BA in Political Philosophy from Williams College and an MEd in Administration & Social Policy from Harvard. She has spent the past twenty years working in top-tier independent schools.


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