What Your Biggest Weakness Really Is

Aakash Gupta
13 min readOct 22, 2024

One of the most important things to do in the job search is to:

  1. Correctly identify what your weakness for that job is
  2. Flip that weakness into a strength by selling them on your work on it

In coaching PMs through questions like ‘Tell me about yourself’ and ‘Why this company,’ the number one piece of advice I gave PMs was:

You need to do a better job of identifying your weaknesses.

You see, the thing most people get wrong is: they don’t identify the right weaknesses.

So, today we’re going to go super deep on this important job skill.

Weaknesses Really Matter

Let’s talk another minute here to double-down on this point.

The reason you’re not getting a job you want is because of a weakness.

Yes, there’s the rare case where someone is just a bit more qualified than you. But why?

  1. “They have more e-commerce experience”
    -
    You can also flip this: you had relatively weak e-commerce experience
  2. They have managed larger teams.”
    -
    You can also flip this: you demonstrated a relatively weaker ability to manage large teams

You can generally reframe anyone else’s victory in getting a job as something that you could have demonstrated better.

So it’s crucially important to get good at this skill — whether you are job

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Aakash Gupta
Aakash Gupta

Written by Aakash Gupta

Helping PMs, product leaders, and product aspirants succeed

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