What generic AI gets wrong with this prompt
Leadership essays are the most over-represented genre in any model’s training data, which is why generic AI sounds most confident and most interchangeable right here.
It answers “how you lead” and ignores “invest in others”
The question has two halves, and generic AI only has training data for one. “How you lead” pattern-matches to a million leadership essays; “how you invest in others” is HBS’s own phrasing, and the model quietly folds it into the first half. The result answers a generic prompt instead of this one — and the investment half is where the committee learns whether people grow around you.
Ask your AI — “Which sentences in my draft are about what I did for someone else’s growth, not the project’s outcome? If there are none, what does that say the draft is answering?”
It equates leading with being in charge
Generic AI reaches for your job titles — led a team of five, managed the rollout — because your inputs arrive role-shaped. But holding authority isn’t the question. The committee is asking what shaped the way you use it, and a draft built on titles retells the resume they’ve already read.
Ask your AI — “Strip every title and retelling of a project from my draft. What’s left that shows how I actually lead?”
It gives the essay to the leader who inspired you
Asked what experiences shaped you, generic AI narrates the shaper — the boss or parent you admired — scene by scene. Models expand the story they’re given, and admiration stories are easy to write. But the committee is admitting you. A mentor can open the essay; they can’t carry it.
Ask your AI — “Count the sentences where someone other than me is the actor. At what point does the essay hand the stage back to me?”
It declares a leadership style instead of demonstrating one
“I’m a servant leader who empowers teams” — generic AI compresses you into a label because labels are defined in general training data. Any applicant can paste the same sentence. What can’t be pasted is the moment you did the unglamorous thing for someone on your team.
Ask your AI — “For each adjective about my leadership in this draft, where is the specific moment that proves it? List the adjectives left standing alone.”