Tag: professional

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.

Fire 30% and Call It Innovation

The interview was going well until it wasn’t.

I was sitting across from a VP who was clearly proud of the company’s multi-year financial transformation project. They were upgrading the ERP (Enterprise Resource Planning) system and adding new tools, including some with AI functionality. It all sounded exciting, and I told her so.

This is when the tone of the conversation changed.

She said that the downside of it all was that six months after go-live, whoever got this position (I was interviewing for a Controller position) was going to have to let go of 30% of the accounting department. I asked where these metrics came from.

A 30% layoff in six months seemed extreme to me.

From her response, it became clear that there was nothing behind the number, just the familiar logic that technology should always mean fewer people. She assumed six months was enough time to work out all the bugs after implementation, and that 30% seemed like a big, round number that would show a nice return on the project investment.

I pushed back. In my experience, automation implementations don’t lead to less work. Yes, the simple repetitive tasks go away, but they get replaced with review and control work. Plus, accounting always has a long list of “nice to haves” that can now be addressed.

The VP didn’t seem to like being challenged. She argued that even if the work didn’t go away, I would still have to fire people and replace them with others who had the “right skill sets.”

I challenged her again: “Why don’t we simply upskill the current staff?” It would be easier, and cheaper, since those people already understood the business and the workflows.

She didn’t have a response and quickly changed the subject. She got off the Zoom shortly after, and I knew I was not going to get this job.

And I was okay with it. This was clearly not a company run by executives who value their people.

To quote Ethan Mollick, almost no one is showing any ‘imagination’ when it comes to what AI could actually build.

Business leaders are almost exclusively focused on how AI can help them lower costs by replacing humans. Reducing headcount is the oldest and most basic way to make your numbers look better for a few quarters. But it doesn’t create a foundation for growth.

Why aren’t leaders focused on doing more? Going into new businesses. Creating entirely new categories. Helping their people become capable of work that didn’t exist two years ago. The VP I interviewed with had a chance to build something. She had a team that already knew the business. She could have invested in them. She chose to cut instead.