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

[Don’t forget to dig into Part I and 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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