The 5 questions you don’t want to be asked

“A prudent question is one half of wisdom.” –Francis Bacon

A big part of my job as an executive coach and executive recruiter is helping my clients and candidates prepare for interviews. C level executive assessments typically involve four or more rounds of interviews across a representative selection of leaders from the enterprise. Each succeeding round typically requires more and more preparation as the finalist candidates are siphoned through the selection funnel.

Preparation and the comfort zone

During the selection process my job is to help each side derive the most value from each interaction. Even those companies with great cultures and well honed interview processes expect me to help them fine tune their interactions with their favorite candidates. And even the most poised, accomplished and confident executives can develop a nasty case of the jitters before a working meeting with the Board or the CEO or, in some cases, the company psychologist.

As a search consultant I always tried to learn everything I could about my client companies and candidates. If I was coaching an executive through a job search, my process included the same type of mindset. My mantra for all concerned was: “Do everything in your power to learn everything you can about the other side and try to eliminate the possibility of surprise as much as possible!” Each side would approach the next round of interviews feeling comfortable, armed with information and great questions. (Good executives have good answers but great executives ask great questions.)

Successful executives are able to reach the C level, at least in part, because of their near obsessive attention to preparation and detail. In meetings and interviews they command the room because their prospective employer or employee trusts that nothing will fall through the cracks, regardless of the circumstances. So, you can’t spend as much time as I have with these people without learning to respect their focus and discipline. As a consequence, I learned to align my executive search and coaching practices with their mindset.

Are you ‘Anti-Fragile’?

But I was doing everyone a disservice – in fact a big disservice – by encouraging my clients to feel as comfortable as possible. I came to this realization while reading Nassim Nicholas Taleb’s Anti-Fragile. To give you an idea of the book’s thesis and the foundation of my epiphany I’ll quote from the book’s introduction: “Some things benefit from shocks; they thrive and grow when exposed to volatility, randomness, disorder and stressors and love adventure, risk and uncertainty.”

Hmmm. I realized that in my well-intentioned zeal to eliminate surprise, discomfort and stress during the interview process I was in fact playing the part of the ‘Helicopter Parent’ (or Helicopter Consultant?!?). Was there another level in the preparation process that could help my clients and candidates reach and surpass their previous ability to succeed in interviews, regardless of which side of the table they were sitting on? The answer required a bit of counter-intuitive thinking on my part…and theirs.

Getting comfortable with being uncomfortable

Before you walk into an interview, ask yourself: What are the five questions I don’t want to be asked? Let that sink in for a minute. I’m asking you to intentionally make yourself uncomfortable. Start thinking about the questions you don’t want to be asked and you’ll start visualizing those past events where you didn’t perform as well as you would have liked or areas of knowledge that you don’t feel as confident with as you think you should. But you won’t stop there. You’ll start thinking about how you’d answer those questions and visualizing success (because that’s who you are) in an uncomfortable situation.

Your mind may push back. No one likes to intentionally disrupt their sense of well being. It’s a big part of your survival mechanism. But I think we’re one of those things that “benefit from shocks;” who “thrive and grow when exposed to volatility, randomness, disorder, and stressors and love adventure, risk and uncertainty.” If, during your intense preparation before an important interview or meeting – both of which share many common features – you ask yourself the five or 10 questions that you don’t want to be asked, then you accustom your mind and emotions to live with discomfort and eventually you will enter interviews able to “love adventure, risk and uncertainty.”

“Uncertainty is an uncomfortable position. But certainty is an absurd one.” –Voltaire