job search – Real Thoughts

Impossible Questions

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.

The Questions That Were Never Asked

I could tell something was wrong the moment my friend picked up the phone. She had just spent a “ton of money” paying someone to rewrite her LinkedIn profile and they had done a terrible job. A bad, no good, horrible job whose only use would be as kindling for a fire (I’m paraphrasing here).

I was surprised since she had used a professional. Let me take a look, I said. Maybe I could help.

The package included a resume, executive bio, and a LinkedIn profile with instructions about how to populate the site. I read it all and thought… it was perfectly okay. It was professional and well written, easy to read, full of the buzzy keywords. I started to wonder what the real problem was.

I decided it was an issue of misaligned goals. I asked my friend some questions to find out.

Questions like: What is the main purpose of this profile? What do you want people to take away when looking at it? What kind of tone do you want to convey? Who is your main audience? Besides company names and titles, what do you want to communicate about your career?

She was surprised by the questions because her LinkedIn profile writer never asked them. But more importantly, she herself had not thought about them. She asked for a couple of days to sit with it.

Once she came back with answers, I had the clarity I needed to do a rewrite. I sent it to her a few days later, and she loved it. This was finally what she wanted. What she wanted all along.

She thanked me for all my hard work. What she didn’t know was how little work I had done. I pretty much changed the point of view and did some surgical rewrites, but overall, the foundation was the same package she had paid for.

This made me think about how many projects and pieces of work get tossed every day because we don’t ask simple questions about the end goal at the beginning. About how we discard good work just because it doesn’t match the fuzzy picture we have in our minds.

The professional who helped my friend never asked about the ultimate goal. She assumed it was the same as everyone’s: maximize recruiter engagement. And she delivered exactly that. A well-put-together yet generic result.

My friend failed to see the potential in what she already had. A few strategic questions and a few precise rewrites were all it took to get to the desired outcome.

Good work gets thrown away every day. Not because it’s wrong, but because nobody asks what “right” is supposed to look like.