What is the toughest decision you had to make in the last year? How did you make it? Please walk me through your process.

The particular situation and eventual decision don’t matter here. It’s the process that’s most telling. Insist that the interviewee literally walk you through the process step by step. Are they more analytical? Did they write out pros and cons on a piece of paper? Are they more emotional? Did they have confidence in a gut feeling and go with it? Are they more relational? Did they call up a trusted mentor? Did they own the ultimate decision? And are they able to communicate all of this lucidly to you? Love this question.

Source: This great list of unconventional interview questions from On Startups by Dharmesh Shah.

Have you asked this question? How did it go? Do you have advice for how best to ask it? PLEASE RATE! AND WRITE A REVIEW (in the comment box below)!

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One thought on “What is the toughest decision you had to make in the last year? How did you make it? Please walk me through your process.”

  1. I really like this question because if forces people to think through the answer before blurting something random out. I like that you can take it much deeper, simply by asking ‘why’?

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