I knew better, but I did it anyway. I clicked on a clickbait article about hiring red flags.
Some of the advice was basic. Never hire someone who badmouths their former employer. Never hire someone who asks no questions. Never hire someone who doesn’t show curiosity about the company or the role. Fair enough.
But there was one that didn’t sit well with me. The author argued that you should never hire someone who can’t answer the question: “Tell me about your biggest failure.”
The argument was that someone who couldn’t answer this question didn’t have enough self-awareness to be a good performer.
I disagree.
Not because this is untrue, but because this is what I call an impossible question.
If you answer truthfully, you are highlighting your shortcomings to the hiring manager. And you don’t know what that manager considers a disqualifier. You try something relatively safe, only to find out you’re sitting across from someone who sees that particular issue as unforgivable.
If on the other hand you try to be strategic and answer with a non-answer, or a strength disguised as a weakness, you look disingenuous. Your application moves to the rejection pile.
Heads you lose, tails you also lose.
People know what their biggest failures are. They probably lie awake at night reliving every moment. They just won’t tell you. It’s not a lack of self-awareness. It’s self-preservation.
“What is your biggest weakness” is another question in this category. It gets asked less and less these days because people have realized it doesn’t tell you anything about a candidate’s ability; other than their storytelling and spin abilities.
By asking impossible questions, interviewers aren’t being clever or fishing for red flags. They are setting people up for failure.
And the interview process doesn’t need more help at being terrible. It’s already broken and getting worse by the minute, with algorithms removing qualified candidates automatically and recruiters who can’t be bothered to close the loop after taking up someone’s time for weeks.
As interviewers, we can do better. Ask what the candidate has built. Ask how they think through problems. Ask what they would do in the first 90 days. Those questions tell you something real.
Or better yet, ask them to ask you questions. See how they think and what they care about. That will tell you more in five minutes than any rehearsed failure story ever will.
Real Thoughts 