If you were planning to hire a highly qualified candidate to fill a crucial business role, would you hire your company’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.At Graphite, we see the value of this every day. We connect firms, corporations and startups with top-tier business talent and specialized experts who are often asked to tackle some of the toughest and most business-critical projects and initiatives.Since our highly qualified professionals typically have a wealth of industry experience and extensive expertise in finance, strategy or marketing, they will often ask tough, probing questions as part of their interviewing and onboarding process.If you hire them, it’s their job to face challenges head-on, question the status quo, and find solutions to difficult problems. As a result, interviews are usually more about the reality of your business and not about a rose-colored marketing pitch.It’s best to embrace this and not recoil or push back. Ultimately, it’s all in the best interests of your business.

Finding the Right Candidate for Your Business Needs

Whether you’re interviewing one of our professionals or any other job candidate, if you’re having to answer tough questions, there’s a good chance you’ve found the right person for the job.If they’re probing for the biggest problems you’re facing and the difficulties and obstacles they might face in their role, they have the right mindset. If their questions expose gaps, deficiencies or weaknesses you’re unaware of or unable to address, that’s another good sign.As Christian Bonilla points out, the ideal candidate should be questioning “everything that doesn’t make sense” and “eager to join the team and dying to fix things that you’re not doing well.”“If you find someone like that,” he says, “give them what they need and let them get to work.”We couldn’t agree more, and that’s why we’re here to help.If you’re looking for highly qualified professionals who can get to work tackling your biggest business challenges and opportunities, visit us at Graphite to start your search.We offer access to over 4,000 independent business professionals with big-firm consulting experience, extensive industry and educational qualifications, and specialized expertise in finance, strategy, marketing and more.Visit us at www.graphite.com to get started.