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Business School Application Failure Essays Series – Part III: Disappointed Others

May 10, 2019 :: Alex Collazo

[Don’t forget to dig into Part II of this series! Wahoo!]

Dartmouth Tuck used to ask applicants to “tell us about a time you: received tough feedback, experienced failure, or disappointed yourself or others. How did you respond, and what did you learn about yourself as a result?”

The multi-part question is a lot to bite off, but the idea behind each of these sub-topics is the same: how do you handle failure? Do you give up, do you blame others, or do you take responsibility and improve? This topic is absolutely worth taking the time to think through, because it contains basically every version of the “failure story” question all in one prompt. If this type of question doesn’t come up on any of your application essays, it almost certainly WILL come up in the interview, and folks, this one is a biggie.

Think of this as a drill you run in football practice. The exercise may seem like it has nothing to do with the game, but when you’re at the season playoffs and you complete the game-winning pass you’ll realize all that prep you did WAS relevant: you were building muscle memory. In this series, we’ll break down this question and address each piece, building that muscle memory so that when you come across a “failure” question either in an essay or in an interview, you can make like Tom Brady and bring home the ring. Here, we dig into Part III.

Part III: Tell us about a time you…disappointed yourself or others.

Again, if you haven’t read the first two articles in this series, take a moment to give those a read; a lot of the principles apply here as well!

This essay topic follows much the same theme—you thought one way about something, but you were WRONG, you fell short, or you suffered the consequences of a weakness. As a result of that failure, you learned ABC and grew in XYZ ways, becoming harder, better, faster, stronger, as Kanye put it.  The twist here is in the measure of failure: rather than the classic business metrics of not hitting a pre-established target, or simply screwing something up in such a way that money was lost, this is all about what you or others EXPECTED of you.

This emphasizes a much more personal note in an essay that already demands a deep level of vulnerability. For example, let’s say you’re responsible for hitting a revenue target, and you miss it by 10%, disappointing yourself, your team, your boss, or all of the above. The key in this essay is recognizing that the disappointed expectations have little to do with the actual revenue target (or whatever the goal is) and EVERYTHING to do with the choices you made along the way, and why THAT was your chosen course of action, one that would prove to be “incorrect” or “misguided.”

Here’s how you KNOW it’s all about the decisions you made and the path you took. In another version of this story, you could have exceeded the revenue target by 20%, and still have chosen a course of action that disappointed yourself or those around you. Even though the outcome may LOOK like a success, those expectations about HOW you achieved that outcome trump the outcome itself—now what does THAT reckoning feel like?

Recommended Reading: Discussing Humble Leadership in MBA Essays

The magic here lies in exposing that disconnect between what you DID and what was expected of you, remembering that you are measuring yourself against EXPECTATIONS (yours or others’), and not concrete results. Was there a moment you realized you had let down yourself or someone else? Was it pointed out to you? Take us to THAT moment, following the same principles we’ve explained before, where you show us your thinking BEFORE the mistake in order to really demonstrate that contrast with your thinking AFTER you realize your failure.

A good indication that you are telling a solid story here is that this moment of realization should be a SURPRISE. If you made choices that you KNEW would disappoint your own standards or others’, then that’s not a very exciting essay. “Well, I knew that not speaking up when my boss asked who forgot to submit that grant application by the deadline was wrong, but I just really didn’t want to face my mistake.” If you KNEW you were acting in a disappoint way AS you were doing it, then that doesn’t make for an interesting moment of growth. Far more effective is the story in which you didn’t even realize until later how you were falling short. Then, when someone called you out on it, or you had an “aha!” moment, THAT’S when it hits you, and you realize how you’ve disappointed your own or other people’s expectations. Queue growth.

Following this surprise reveal of disappointed expectations, we should see some fundamental shift. Similar to the other failure essays, we need to see you identify how you got BETTER after this incident. One cool aspect of this particular version of the failure essay is it gives you greater latitude to delve into the personal, especially if you choose a story in which you disappointed YOURSELF. Expose the ways in which your own expectations for yourself have deepened, and through that, how your aspirations for yourself have grown.

A great measure here is to ask yourself, “who do I want to be; the guy who chose X easily achievable outcome, or the guy who chose Y hard path?” This is where you can really show the adcom what you are MADE of—not just by what you’ve done but by what you EXPECT of yourself, and how you respond when you fall short of those expectations. This is a deeper level to the failure essay than we’ve yet seen, and if done well, can really amp up your essay.


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