Why Choosing a Skeptical Job Seeker is sometimes the Best Choice for the Job

If you were planning to hire a highly qualified candidate to fill a crucial business role, would you hire your any’s biggest skeptic? How would you react if a job candidate asked you some extremely tough questions and challenged your startup’s business model or even your future solvency?

The first instinct for many executives and entrepreneurs is to get defensive.

Business is often personal, especially if you’ve invested your career, time and money in building up a successful company. However, the best job candidates often ask the toughest questions, including some you might be unable to answer.

That’s what happened in the case of UserMuse, a market research startup founded by Christian Bonilla.

A Startup Interviews Its Biggest Skeptic

UserMuse was looking to hire its first employee since launching, and one of the candidates was Bonilla’s former colleague, Tommy. The two had discussed UserMuse in the past, but Bonilla soon discovered that Tommy was one of his startup’s biggest skeptics.

Among the questions he asked were:

• “What percentage of buyers do you think will never come back?”

• “What are the biggest challenges you’re hiding behind your user growth?”

As the interview proceeded, Tommy continued to ask probing, blunt questions. He challenged each metric and the insights that Bonilla offered up.

As the latter describes the exchange, “It felt more like an investor pitch than interviewing a potential hire.”

The recurring theme was, “Tell me why this isn’t going to fail” and “Tell me why you aren’t going to give up when things go sideways.”

While the interview challenged Bonilla on a number of levels, it also convinced him that he had found the right candidate for the job.

Why It Makes Sense to Hire a Doubter

A good hire doesn’t care about your personal pride and accomplishments in building up a business. The right candidate focuses on your company’s strengths and weaknesses, your future, and the toughest challenges you face.

It’s not about what got you here but where you’re headed and whether you’ll succeed.

Healthy skepticism is precisely what most companies and crucial business initiatives need. They need highly qualified candidates who will ask the tough questions, identify potential problems, and help solve them with tenacity.